It’s widely recognized that introducing IT teams to the latest technology, business, and security advancements is essential for maximum performance and productivity. What’s not often discussed, however, are the mistakes IT leaders make when establishing and supervising training programs, particularly when training is viewed as little more than an obligatory task.

“Treating training as a checkbox exercise sends the message to your team that you don’t really care all that much about the content they’re learning — and that mindset is contagious,” warns Steve Ryan, a manager at BARR Advisory, a cloud-based security and compliance solutions provider.

Is your organization giving its teams the training they need to keep pace with the latest industry developments? To find the answer, here’s a quick checklist of the seven most common training mistakes you need to steer clear of when upskilling your IT teams.

1. Emphasizing the wrong goals

A big mistake many IT leaders make is relying on a training structure that prioritizes career advancement over skill development.

“This creates a culture of ‘ladder-climbing’ rather than a focus on continuous training, learning, and improvement,” says Nicolás Ávila, CTO for North America at software development firm Globant.

To keep teams engaged and reaching toward goals, Ávila suggests individualizing skill-building while periodically creating skill-focused missions. Experimentation broadens expertise, particularly in a rapidly evolving field like technology where being able to learn many new skills is key to both career and enterprise success, he says. “Creating a culture of development also leads to a happier and more engaged workforce, which can minimize attrition.”

Don’t fear attrition — fear stagnation, Ávila advises. “If you have the right team some members will leave, but if you have the wrong team they might all stay and slowly damage your organization beyond repair.”

2. Neglecting soft skills

Focusing solely on technical skills and ignoring other essential professional abilities, such as business acumen, communication management, and leadership, is a serious mistake, says Sharon Mandell, CIO at Juniper Networks. “Some people call them ‘soft skills,’ but I think these should be thought of as core skills,” she states.

If team members are unable to communicate with and influence both colleagues and stakeholders, it’s unlikely they’ll be able to produce solutions that work for everyone, Mandell says. “A better approach is making sure you’re doing some of both, developing technical and complementary core skills.”

For maximum training effectiveness, Mandell recommends that IT leaders follow a balanced approach. “By focusing on creating well-rounded teams, you’re thinking long term,” she says. You’ll also build a sustainable and resilient organization, not just tech skills for today. “Don’t let urgent things cloud your long-term strategy.”

3. Failing to address change

Commit to continual learning, development, and business alignment to stay ahead of the curve and fulfill larger business goals, advises Dalan Winbush, CIO at code application development platform firm Quickbase.

Because technology is always changing, IT personnel must stay current with new innovations to continue performing their jobs effectively. Prioritizing business alignment at the expense of continuous learning and growth may lead to lack of innovation, stagnation, and an inability to achieve organizational goals, he warns.

Training technology is also rapidly advancing. Intelligence automation (IA)-driven training options — including offerings that utilize artificial intelligence and machine learning — have the potential to boost training results by providing highly focused job- and business-relevant instruction featuring individualized learning experiences.

4. Disregarding diversity

Failing to recognize IT team members as unique individuals leads to uneven training results at best. “Diversity extends to the uniqueness in how we think and process information, and these differences shape the way we learn and interact,” says Ashwin Sadasiva Kumar, senior vice president, learning and campus head, at IT consulting firm Virtusa.

IT leaders and their training colleagues should design training modules that cater to all learning styles. “Some people are visual thinkers, while others are more analytical or creative,” Kumar says. Perspectives matter, he notes. “Therefore, training diversity is important, since it allows team members to approach problems and challenges from different angles, which can lead to more innovative solutions and better decision-making.”

Kumar suggests that CIOs should widen their training perspective and focus on their teams’ needs. “This starts with encouraging employees to be creative and curious, while also cultivating the workplace to prioritize individual growth,” he says. “Employees are looking for leaders to incubate a workplace where they have a seat at the table, whether that’s anticipating the needs of clients, understanding organizational needs and forecasts, identifying and pursuing deals, or feeling motivated.”

5. Instructional irrelevance

IT leaders tend to believe that most staff members understand training’s importance and how it relates to their job, says Orla Daly, CIO at educational technology firm Skillsoft. Yet that’s frequently not true.

IT pros want training relevancy, Daly says. If team members don’t understand why a specific training program or session is necessary, they probably won’t recognize its value. Focusing on topics that are relevant to their job, and may possibly lead to career advancement, will motivate staffers and make them eager to learn.

When lacking context on training’s value, team members are likely to dismiss training as an unnecessary chore. “They either won’t make time for it or will go through the motions without digesting or retaining any of the key messages or insights,” Daly explains. “This not only defeats the purpose of the intended training, but can lead to frustration and disengagement among teams.” IT professionals crave growth and professional development. “If they’re not seeing the value in their current training programs, they may lose motivation or even consider changing jobs.”

Building training relevancy requires IT leaders to recognize and demolish training barriers, such as course sessions that conflict with team members’ hectic work schedules or intruding on their personal time. “It also means connecting training to professional development and career growth,” Daly says.

Leadership development and power-skills training are frequently unfortunate afterthoughts, Daly states. “By showing employees how training can help them achieve their own career goals — in addition to supporting the needs of the business — IT leaders will see greater productivity and engagement from their team members.”

6. Cutting corners

Team education should never be regarded as an afterthought, so training programs should be allocated appropriate resources in terms of money, time, and trainers, says Randall Trzeciak, director of the Masters of Science Information Security Policy and Management program at Carnegie Mellon University.

“Don’t allow resource limitations to deny training to all relevant IT staff members, including secondary support staff,” he advises.

Unlike fine wines or blue jeans, training programs don’t age well. “Make sure that IT skills are keeping pace with change,” Trzeciak recommends. “Ensure there’s an ability to measure training effectiveness during and after the training program’s completion.”

7. Treating training as a discrete entity

Perhaps the best and most effective training approach is educating team members without them even realizing it, BARR Advisory’s Ryan says. Besides providing conventional formal training, a growing number of organizations are making training an integral part of each team member’s everyday work-life.

Ryan points to security training as an example. “This means sending out periodic reminders to employees, conducting regular phishing awareness and reporting exercises, and incentivizing employees to improve by gamifying the learning experience.”

IT Training 

By Chet Kapoor, Chairman & CEO,DataStax

Mistakes: we all make them. Whether it’s screwing up a demo in front of the entire leadership team or hiring the wrong person for a role, I can’t even count how many times I’ve made mistakes throughout my career. These moments are never easy, but they are always learning experiences–and the best leaders are always learning.

Below, I share a few common mistakes leaders and organizations are making today and how they can overcome them to drive lasting success.

Mistake 1: undisciplined growth

Leaders are facing times of uncertainty, magnified recently with the collapse of Silicon Valley Bank and ongoing market turmoil. As companies continue to navigate the current economic headwinds, one thing is clear: growing responsibly is critical both in the good times and the hard times.

Kelly Battles is a seasoned CFO and board member at several Silicon Valley organizations. I recently discussed the biggest mistakes companies make with regard to execution.

“The biggest mistakes that I’ve seen are whiplash overreactions to the fear and greed cycle,” Kelly said.

When times are good, it can be easy to get greedy. Maybe your burn increases, you loosen your controls, or you don’t take discipline as seriously. As a result, you have an organization that’s floating with the tides. The problem is when a tough period hits, now you are unprepared. As we’ve seen over the last several months, irresponsible growth can lead to hiring freezes and limiting investments (at best) or mass layoffs and big risks (at worst).

In Kelly’s words, “The best companies are disciplined during the greedy times and lead with strength during the toughest.”

Growing responsibly requires thinking about where you’re investing resources, the way you’re prioritizing projects, and how you’re tracking progress. It’s a constant balance of patience and impatience–but if you stay disciplined, it will pay off.

Mistake 2: failing to implement AI across the business

The age of AI is here. Leading enterprises like Netflix and Uber have been leveraging AI to drive business outcomes for years, but today these capabilities are within reach for companies of all sizes. It’s not just about building AI products–it’s also about using AI to improve performance and efficiency across the business.

I had the chance to catch up with Hussein Mehanna, who heads up AI and ML at the self-driving car company Cruise. Hussein shared how his team is using AI to improve their operational efficiency. They have a paradigm called the “continuous learning machine,” where engineers use AI to automate their repetitive work tasks and build predictive models to help with productivity. This way, they can focus on high-value tasks and the more creative aspects of their work.

Winning companies of today and of the future will be AI-first:

It starts with data. Focus on finding quality data and building proprietary signals (i.e. unique insights that come from your data)Once you have quality signals, start searching for monetization methods. Usually, you can use the data to improve your apps and productsHave a strong AI execution framework that includes people, process and, technology–and use it across the business

Mistake #3: Treating DEI&B like a “nice-to-have”

Many companies view diversity, equality, inclusion, and belonging (DEI&B) through the numbers, and there’s a common misconception that hiring diverse individuals equates to a more diverse and inclusive culture. But that’s only a small piece of the big picture.

To build a truly inclusive and equitable workplace, leaders need to focus on driving real behavioral change. This starts with each individual looking in the mirror and asking themselves every day: How did I show up? Did I listen actively? Can I identify any implicit or unconscious biases at play? If I made a mistake, did I take accountability, and how can I do better next time?

Alana Mayo is president at Orion Pictures, a division of MGM that’s dedicated to underrepresented voices and authentic storytelling in film. I often refer back to our discussion on the Inspired Execution podcast, where Alana shared tips for holding ourselves accountable and demonstrating inclusivity.

“In meetings, don’t always speak first. Take note of when you are talking more than other people in the room. And the biggest thing to remember is that both active listening and speaking up require vulnerability,” she said. “It ultimately goes back to creating a culture where there’s really good communication and where everybody feels comfortable enough to be vulnerable.”

Today, it’s not enough to treat your DEI efforts as a box on a checklist. Real progress and impact start with each leader, each individual at your company. And in the current economic climate, now is actually the perfect time to double down on investing in your people–it will pay off.

For more insights and stories from world-class leaders, check out Inspired Execution here or wherever you listen to your podcasts. Season 5 is coming soon!

About Chet Kapoor:

Chet is Chairman and CEO of DataStax. He is a proven leader and innovator in the tech industry with more than 20 years in leadership at innovative software and cloud companies, including Google, IBM, BEA Systems, WebMethods, and NeXT. As Chairman and CEO of Apigee, he led company-wide initiatives to build Apigee into a leading technology provider for digital business. Google (Apigee) is the cross-cloud API management platform that operates in a multi- and hybrid-cloud world. Chet successfully took Apigee public before the company was acquired by Google in 2016. Chet earned his B.S. in engineering from Arizona State University.

IT Leadership

You might think that senior-level IT leaders have a lock on the art of landing jobs. After all, that’s partly how they reached such lofty heights, right?

But you’d be wrong. CIOs, vice presidents, directors — all make similar mistakes when they are on a job prowl, executive recruiters say. The two most common, and most fatal, are talking too much during an interview and resumes that are either too braggadocious or that go on and on and on.

“Our record was a 55-page resume,” says Judy Kirby, CEO of Kirby Partners, an executive search firm. “Not even their mother is going to read that.”

Here is a look at a dozen common mistakes even seasoned IT leaders make when looking to land new jobs, according to experts who can help.

Going grandiose

Charley Betzig, managing director of Heller Search Associates, has seen two candidates in the past year lose out on opportunities because of too-grandiose resumes. “These were great candidates, and we did our darndest to try to work with them to rewrite their resumes.” Both refused.

Betzig suggests instead sticking to the facts and keeping your resume “clean” by eschewing trendy design and offbeat type faces.

Finally, save your patents and published papers for the end of your resume and don’t lead with this information, Betzig says. “Employers don’t really care about that stuff,” he adds.

Failing to back up claims

In addition to holding your resume to a reasonable length, make sure it notes specific accomplishments. “I am a visionary innovator” doesn’t mean much to anyone wanting to learn about your credentials. (What did you innovate? In what way was that visionary?) Instead, talk about what your team produced and how, exactly, this helped your company create a new product, save money or time, generate revenue, or enter a new market.

Show, don’t just tell, how you’ve met specific challenges, whether strategic or operational.

Choosing ‘me’ over ‘we’

Similar to going grandiose, too many IT leaders forget that leadership is often more about team accomplishments than personal accolades.

Both on your resume and during interviews, recruiters emphasize focusing on ‘we,’ not ‘me.’ Nobody wants to hire someone who sucks all the oxygen out of the room or doesn’t play well with others. Make sure to share the credit with others on your team, and don’t talk trash about any company or person you’ve worked for.

Misunderstanding what makes a good interview

While you’re interviewing, answer the questions as succinctly as possible. Remember you’re not driving here; the interviewer is. “Be a listener first,” Betzig says. “Make sure it’s a conversation; listen and react.” He says that candidates are often so excited about landing an interview — or want to convey all their experience during the time allotted — that “they’re just bursting.”

Resist that impulse, and keep each of your answers to five minutes, maximum. Recently “we had a guy we thought was a great fit,” Betzig says. He had the qualifications and was a local candidate for the role. But the hiring company reported back that during the hour-plus interview, they were able to ask him only three questions because he talked so much.

“It was tough for them to imagine putting this person in front of their executives,” Betzig explains, and they wouldn’t consider doing another interview with him.

Overlooking the power of practice

If you’re working with an executive recruiter, that firm will likely do at least one mock interview with you and will video you in the process. “That can be a very sobering experience, to see yourself in action,” Kirby says. The recruiter will give you tips about how to improve your interviewing skills and resume because, after all, he or she gets paid if you do land the role, from the company that posted the job. It’s wise to take their advice.

And if you flame out after the first interview, you can often get feedback from the recruiter that you wouldn’t be able to get directly from the hiring manager because of perceived or real legal constraints.

If you’re looking for a job without the help of a recruiter, Kirby suggests you still enlist a trusted friend or peer to do a mock interview — and video it. Check to ensure you show enthusiasm for the job without being over the top, and make sure you answer the questions succinctly and without grandstanding.

Not seeing yourself clearly

Spending 20 years or longer at the same company isn’t necessarily viewed as favorably as it used to be, says Shawn Bannerji, managing partner for the data, digital, and technology leaders practice at Caldwell. Back in the day, it was considered a sign of loyalty to stick it out that long. But these days, staying at the same place for decades can be a negative.

The question is whether a person who’s been immersed in the same culture for so long “can be successful outside the norms of that specific organization,” Bannerji says. Many of the traditional leaders in their respective industries — such as GE, IBM, Morgan Stanley, and P&G — have multiple systems and processes set up to ensure their employees’ success, he explains.

After spending so long in one place, IT leaders can perhaps successfully transfer their expertise and skills to another organization or industry. But some hiring managers feel this category of candidate should “go somewhere else and prove it first, and then I’ll hire them,” Bannerji says.

If you do find yourself wanting to move on after a long stint in one company — anything over seven years — spend time thinking through exactly how your skills are transferrable. And make sure that is reflected on both your resume and in interviews.

Failing to have foresight

IT leaders seeking to build their careers further need to take the approach of successful pool players and think at least two moves ahead. Where are you in your career, and where do you want to be? How do your pay and benefits compare to those of your peers? That’s another strike against staying at one place too long; company lifers tend to miss out on the same pay jumps that more nimble IT leaders generally receive.

Career paths used to be more straight-line; “you’d work hard, get good reviews, and assume that path would lead to recognition, rewards, and promotions,” Bannerji explains. “But we’ve seen a departure of this path,” he says. People who want to rise in their careers need to acquire new skills and competencies, and “develop a portfolio that’s a professional calling card” or else “opportunities can pass them by.”

He advises you to find a mentor who can act as a career sherpa to “advise you how to invest your professional capital” and to help you determine which skills you should be focusing on at any point in time. If, say, you’ve spent a decade in infrastructure, try to develop more direct business acumen and broader management or strategy expertise.

Getting rusty on tech

Conversely, a business degree and strategy proficiency alone won’t cut it as a CIO in today’s world. “The role is evolving to have more substantive technical dimensions,” Bannerji explains. “Cybersecurity, AI, machine learning, the journey to the cloud” are all important on a resume today. Digital supply chains and other areas also require technical chops.

It’s also important to understand product development because IT is expected to help or sometimes even lead in that regard.

Not honoring the job description

It can be tempting, and sometimes okay, to ignore some things on a job description’s checklist that don’t fit. But if you apply for a position that specifies an advanced college degree as a minimum requirement, and you have a bachelor’s, don’t expect to land the interview no matter how much experience you may have.

Also make sure the job is something you really can handle. If the organization wants an implementer, and you’ve been mostly a strategist, “that’s not the same thing,” Kirby says. Even if you force-fit things and you’re lucky enough to be hired, chances are good that the position won’t be sustainable for very long and you’ll be job-hunting again before you know it.

And, if you don’t calculate all the key elements correctly — position, company, pay, and location — you can “throw off the entire equation,” Bannerji adds.

Losing sight of the social-media details

Particularly at the senior or executive level, you and your entire family are on view. Hiring managers routinely check social-media accounts for inappropriate photos or posts, especially regarding you and your spouse, for a clue about how you both might conduct yourselves at corporate events and how you represent yourselves in the broader world.

If you don’t want people snooping, adjust your social accounts’ privacy settings while you’re job hunting — and suggest that all the members of your immediate family do the same. Something that’s ‘cool’ or ‘cute’ or ‘funny’ might not translate the same to anyone who doesn’t already know you.

You might survive an Instagram photo of yourself barbequing in your Speedo, if you insist on keeping that visible online, but make sure your LinkedIn account and other more professional venues don’t show you in sweatpants or risqué clothing, or looking (or acting) inebriated. Vet your videos and invest in some professional photos.

Kirby recalls a situation when one company’s internal candidate was determined to sabotage his closest rival, an external candidate. The internal person found photos of the external guy at a party with drinks in both hands and acting goofy, all while standing next to an X-rated cardboard cutout. Internal Guy emailed the photos to hiring managers, and in the process both candidates were thrown out of contention.

You can still be you, of course; just don’t leave any potentially damaging documentation of your wildest moments in places where recruiters or hiring managers can find it.

Failing to read the room

To survive executive-level interviews, you must hone your emotional quotient (EQ) skills, Kirby advises.

“One of our candidates was showing off his deep knowledge of baseball and failed to notice that one of the other people in the room had her eyes glazed over.” It cost him the job.

Forgoing leveraging your network

Job hunters “often don’t want to be a bother to their contacts,” Heller’s Betzig says. “But that’s a big mistake. Your contacts want to be there for you, to be the person to help you find your next job.” Make time to network; he advises reaching out to five to 10 contacts each day.

Get in touch with everyone you know from your former jobs and those you’ve met in various professional organizations, explain what you’re looking to do and ask if they’ve heard of anything related to that and to let you know if they do. “Chances are that IT leaders’ next jobs will come from their network,” Betzig adds.

Careers, IT Leadership, Resumes

The cloud has changed the IT and business worlds forever, and generally for the better. But when misused or abused the cloud can backfire, leading to a serious business setback or, in a worst-case situation, long-term competitive damage.

Ensuing proper cloud use is essential in today’s high-stakes, fast-paced business environment. Learn from the following 10 mistakes, and do your best not to repeat them.

1. Poor planning

Enterprises risk running into trouble if they lack a detailed cloud strategy. “A pragmatic and structured architectural approach when moving to the cloud is critical,” says William Peldzus, senior director and Center of Excellence head with enterprise consulting firm Capgemini Americas.

It’s imperative to think strategically when moving to the cloud, Peldzus says. “Proper architectural designs and preparations will potentially eliminate days, if not weeks and months, of troubleshooting and debugging issues.”

Even small steps will position an organization for cloud success, Peldzus states. Learning from any missteps made along the way, from planning to migration, is also important. “Those who attempt to jump into the cloud and figure it out on the fly will not be successful,” he warns.

2. Misunderstanding migration

Cloud migration is not a once-and-done process. “It’s a continuous journey with complex interrelated issues,” says Karthik Narain, cloud first lead at enterprise advisory firm Accenture.

Many IT leaders mistakenly view cloud migration as a conventional project, complete with bedrock start and finish dates. Yet recent Accenture research found that 32% of enterprises that view their cloud journey as complete are actually leaving value on the table while placing their organizations at risk. “A narrow focus on cost savings can put organizations at a competitive disadvantage compared to those using the cloud more strategically across its many dynamic forms, including public, private, and edge,” Narain says. “In fact, our … research has shown that those [organizations] that viewed the cloud strategically actually reduced cost more than those focused only on efficiency.”

3. Underestimating cloud costs

It’s a common misconception that cloud migration always leads to immediate cost savings. “In reality, cloud migration is expensive, and not having a full and complete picture of all costs can sink a business,” warns Aref Matin, CTO at publishing firm John Wiley & Sons.

Cloud migration often does lead to cost savings, but careful, detailed planning is essential. Still, as the cloud migration progresses, hidden costs will inevitably appear and multiply. “You must ensure at the start of the project that you have a full, holistic cloud budget,” Matin advises.

Cloud costs appear in various forms. Sometimes they’re in plain sight, such as the cost of walking away from an existing data facility. Yet many expenses aren’t so obvious. “For example, the cost of talent, including reskilling, upskilling, and finding the right cloud talent, or for reorganizing your business structure,” Matin says. “All of these expenses should be considered in your planning.”

4. Cloud complacency

Cloud computing’s first era is drawing to a close. Most enterprises already have some form of cloud infrastructure in place, observes Ronen Schwartz, general manager and senior vice president, cloud storage, at hybrid cloud data services and data management firm NetApp.

The cloud is at an inflection point, Schwartz states. Many organizations still retain significant amounts of data, applications, and workloads on premises, even as they continue migrating to the cloud. Yet he believes that many such enterprises are now entering an evolved cloud — hybrid multicloud environments in which cloud services are fully integrated into the organization’s architecture and operations.

“It breaks down silos to simplify management and deliver observability everywhere,” Schwartz says. “The evolved cloud is just like its name suggests — it’s not an end state.”

Once an enterprise enters the evolved cloud, Schwartz recommends pushing forward to avoid stagnation. “If they migrated applications, now they can refactor them for the cloud,” he says. “If they’ve refactored them, they can now optimize for performance or for cost.” In either case, Schwartz advises pushing forward and evolving along with the cloud.

5. Poor data accessibility

A major challenge facing many larger enterprises is leveraging data spread across disparate systems. “Ensuring that data is accessible and secure across multiple environments, on-premises as well as on applications running in the cloud, is an increasing headache,” says Darlene Williams, CIO of software development firm Rocket Software. She notes that a survey of mainframe technology users revealed that 80% believe that mainframe technology remains critical to business operations.

Abandoning data stored on legacy systems can deprive departments of access to potentially valuable insights. Williams warns that enterprises that tip the scale too far toward the cloud, risk forgetting the inherent value of data locked in legacy hardware.

6. Platform sprawl

Whenever possible, IT leaders should consolidate and merge cloud-based services to reduce costs and avoid platform sprawl, says Wayne Carter, vice president of engineering, with cloud database technology provider Couchbase. “For example, rather than using multiple databases, a multimodal database can handle different data types and models from a single, integrated backend and prevent … data sprawl and spending unnecessary funds.”

Carter advises IT leaders to look deep within their organizations to understand how software resources are being used. “They may find there’s software that can have multiple licenses added for more than one team to use across the company,” he notes.

7. Inadequate security

Lax security can turn a promising cloud initiative into an IT nightmare. “Avoiding cloud security-related mistakes requires understanding your cloud environment and ensuring that appropriate guardrails are in place to safeguard your infrastructure against external and internal security threats,” says Emmanuel Nnodim, cloud architect at IT consulting firm SPR.

Failing to guard against against external and internal threats can be lethal, because it jeopardizes the organization’s reputation, weakens customer trust, and can lead to significant financial losses. Nnodim recommends that every stage of cloud planning should include a thorough security assessment.

8. Unbridled enthusiasm

Many enterprises view the cloud as a miracle technology, downplaying the amount of planning and work needed to address real-world design and operational challenges. “When firms encounter these challenges, they struggle to find the skills and experience needed to remediate issues,” says Sunil Moorjani, a director with global technology research and advisory firm ISG.

Moorjani observes that the arrival of multicloud environments, combined with a persistent talent shortage, has made cloud deployment and management even more complex. As a result, many adopters have been disappointed by their “cloud first” results. He reports that nearly 70% of respondents to a recent ISG survey have achieved less than 20% of their primary goals, and many have accounted significant budget overruns and missed deadlines.

Even when viewing cloud adoption in realistic terms, many IT leaders fail to understand that cloud adoption isn’t merely a technical exercise. “Firms must also pay attention to contractual obligations,” Moorjani warns. He notes that multiyear contracts can lock unwary clients into expensive, inflexible consumption models.

9. Rushing migration

Overeager cloud migrators tend to favor a “lift and shift” migration approach, underestimating the long-term costs associated with failing to optimize antiquated applications.

“Enterprises driving to digitize without the proper steps in place will be drained by 10% higher-than-average cloud costs, legacy application delivery times lagging by as much as 400%, high-risk security vulnerabilities, and staggering maintenance and compliance requirements,” warns Marco Roman, head of North American field operations at e-Core, a technology consulting and development services provider. “It’s evidently pennywise and pound foolish to cut these early corners.”

10. Not looking forward

The cloud is continuing to evolve, supporting and improving core business operations in an ever-growing number of ways. Enterprises should always be looking forward, aligning their business strategies to accommodate multicloud, cloud edge computing, and other advancements, advises Matthias Loh, financial services technology lead with enterprise consulting firm EY Americas.

As CIOs ponder which cloud strategies to pursue, they will need to consider how to best future-proof and architect their cloud designs to avoid silos, drive new and profitable growth, and maintain efficiency, security, and transparency. “It’s critical to have a clear and deliberate framework on how to best address the risks and costs associated with the cloud,” Loh adds.

Cloud Computing, IT Strategy

CIOs supporting a hybrid mix of in-office and remote workers, and those who float between, need to implement new tools and strategies to get it right. But they will also need to change how they think about hybrid work, which analyst firm Forrester characterizes as “messy” even as it says 51% of organizations are moving in this direction.

Hybrid work is often thought of in terms of location, according to a November Gartner report. “If leaders focus on location alone, they’ll miss much larger benefits … including flexible experiences, intentional collaboration, and empathy-based management,’’ the report cautions.

Adopting a flexible, human-centric approach that puts people at the center of work will lead to better employee performance, lower fatigue, and intent to stay, according to the firm.

“Even if skeptical leaders are less concerned about fatigue and retention of talent in today’s tight economic climate, they care about performance,” says Graham Waller, a distinguished vice president analyst at Gartner. “Leaders too often are making future of work decisions based on instincts and feelings today. This can be a big mistake as the way we used to work won’t anymore.” 

Unfortunately, when it comes to supporting hybrid workforces and anticipating how organizations will conduct work in the future, CIOs will likely make a number of mistakes before they successfully facilitate the optimal workplace for their organizations in 2023 and beyond. Here are the most likely culprits.

Shortchanging your return-to-office strategy

Remote work caused a great deal of Zoom fatigue in 2022, driven by factors such as a lack of manager coaching on how to connect with teams remotely, says Rebecca Wettemann, principal at tech analyst firm Valoir Research, not to mention the exhaustion and burn out of channeling employees’ every interaction through a screen.

But as employees have come back to the office anticipating the benefits of in-person interactions, many have been disappointed, thanks to an organization not fully prepared for their arrival, she says, despite, in many cases, mandates to do so.

“The biggest tech fail was expecting folks to come back to the office without sophisticated scheduling for knowledge workers, who found themselves commuting to the office to find there was no one there they needed/wanted to see,’’ Wettemann says.

Moving forward, leaders need to include “more presence monitoring and prediction so when people do come to the office they can meet with teams in person,’’ she says. They should also incorporate “a more data-driven approach to scheduling that ensures hybrid work supports diversity, equity, and inclusion, and a more line-of-work focused collaboration strategy rather than a one-size-fits-all-job functions approach,’’ Wettemann says.

Kim Huffman, CIO of global travel expense management platform TripActions, learned firsthand that not having a framework for what the return to the office would look like meant employees did not get the benefits of the in-person experience.

“Things get messy … when you don’t have any structure around the return to work,’’ she says, adding that having no formal construct for returning to the office was a “lesson learned’’ for her and other TripActions company leaders, and since then, “we’ve organized ourselves a little bit better.”

Eroding the culture of trust and connectedness

Kim Huffman, CIO, TripActions


Productivity questions were one “bubbling point of tension” Huffman encountered as part of TripActions’ return-to-office experience. On the one hand, workers who came back to the office felt like they were not as productive, while the people leading teams felt the same about people working remotely, Huffman says.

“It has exacerbated this phenomenon of what really is driving productivity: Is it being in the office or being at home?’’ she says. “There are varying points of view that are being hotly contested across tech companies in the Bay Area right now, and it’s going to be a very interesting journey to watch over the course of the next two quarters.”

Because some people have come back to the office, Huffman believes there is still a stubborn perception that the ones who don’t come back are not as productive. IT leaders need to anticipate this tension and get ahead of it, to ensure not only that employees can remain productive wherever they are but that the organization’s culture of trust doesn’t deteriorate.

Here, the key is ensuring a culture of connectedness, Gartner contends. “IT leaders and employees … overwhelmingly feel that culture connectedness is primarily driven by day-to-day work interactions, and not from being in the office,” according to the firm, which found that 58% of IT workers strongly believe that meaningful connections are based on day-to-day interactions, not where they are located, with only 21% of IT workers agreeing that connectedness is driven by being in the office.

Failing to level the playing field

With hybrid meetings on the rise, there’s a delicate balance to maintain between how your organization serves participants attending meetings in person and those who attend remotely.

Jamie Smith, CIO, University of Phoenix

University of Phoenix

University of Phoenix CIO Jamie Smith, for example, has seen that hybrid meetings have “deepened the chasm” between people who have been coming into the office and those who have remained remote. “We found people on the remote end felt they were less than … because they didn’t have the option to come into Phoenix,’’ he says.

To counteract that, for every meeting with an in-person option, leaders will now do a second purely remote meeting “so everyone feels they’re on the same playing field,’’ he says.

The university uses Zoom, Slack, and Microsoft Teams, but plans to deepen its use of whiteboard technology with a tool called Miro that “feels like you’re collaborating in the same room,’’ Smith says.

Smith’s IT team is always looking for tools to help the university’s employees be asynchronous, he adds, given that they now have employees in more time zones. This means “just having to live with those realities where we didn’t before,’’ which has “forced us in this asynchronous mode,” he says.

Overlooking the innovation factor

And it’s not just the employee experience that can be hindered by poorly conceived hybrid strategies. Innovation efforts can also falter when collaboration experiences are uneven.

Bess Healy, CIO, Synchrony


Early on in hybrid work at consumer finance company Synchrony, CIO Bess Healy says she and other company leaders “quickly learned that hybrid innovation requires a different level of facilitation to succeed.”

Events that had previously been all day in person felt draining to team members on video, Healy says, “so we split them up over multiple days. When we competed in events like hackathons, team members missed the camaraderie of eating together at all hours of the night, so we replicated that with meal credits wherever they are.”

Company leaders also put a higher emphasis on “planned fun” by playing games in person and taking a “brain break during an ideation event.”

“Three years in, these changes have brought more people into our innovation teams than ever before, inspiring new ideas in metaverse, payments, customer experience, and more,’’ Healy says.

Not reimagining the office to fit the new hybrid paradigm

It’s important to give people an incentive to want to come back into an office and be together. One approach some organizations are taking is to design office spaces differently instead of just rows of desks or cubicles.

“One of our offices is new and we’re trying to build space where there’s room for conversations and groups to get together, not just all desks,’’ says Huffman. Leaders should make it a priority to reimagine office layouts this year, she says.

Being slow to experiment with future tech

Virtual reality is one technology that could have an impact on the future of work, and some IT leaders are considering the benefits.

Oculus headsets from Meta, for example, are being rolled out on a trial basis at the University of Phoenix, which has made the decision to go fully remote. This was a big mindset change for Smith, who felt pre-pandemic that “face-to-face collaboration was better and high fidelity for creativity purposes,’’ he says. “Then, when everything shifted to full-time remote, it went against my core beliefs, so personally, I had to lean in.”

Smith has come to realize that staying remote has not affected IT’s ability to collaborate and teams have been able to remain productive and launch “complex new products into the marketplace.” He says that working remotely has increased his ability to access tech talent outside of the Phoenix area.

But when people were working in a hybrid model early on, there would be multiple conversations going on, and “people on the remote end were getting the short end of the stick” because they “couldn’t get a word in edgewise,’’ Smith recalls.

So he hired his first audio engineer who revamped the majority of the university’s meeting technology. The Oculus headsets are being tested by some teams in their daily standup design sessions to see whether they will help the teams work better. The idea is to understand whether “tools get in the way or do they help?’’ he says. “A lot of [collaboration] technologies are still pretty early in terms of capabilities.”

Some initial feedback is that using a physical keyboard in the headset is problematic, but Smith says the experiment will continue in early 2023. “The expense isn’t that much but the question is, Is it a toy or something that fundamentally changes the [remote work] experience?”

Not bringing IT to bear on the office of the future

In addition to rethinking the office and having a sound return-to-office strategy, IT leaders would be wise to invest in technologies tailored to facilitate better hybrid work experiences.

Robin Hamerlinck Lane, SVP and CIO, Shure


At audio electronics company Shure, leaders have “spent a significant amount of time listening to our employees about hybrid work” and subsequently developed a plan called “WorkPlace Now” based on what they learned, says Robin Hamerlinck Lane, senior vice president and CIO.

Employees are free to choose a hybrid work model, and Hamerlinck Lane says company officials have made adjustments for the future workforce by providing different tools for them to adapt.

For example, “we moved to flexible seating in our global offices, so hybrid workers could still have a space to work when they came into the office. With the iOffice app, employees can reserve their workspaces in advance or when they arrive,’’ she says.

IT has developed a ticket system where employees who work remotely can request a remote kit that includes tools to be able to work effectively outside of the office and still remain connected to others, she says.

In 2023, IT will roll out Teams in more conference rooms. “We are especially interested in leveraging camera views and panels that provide equality in our meeting experiences between offsite and onsite associates,’’ Hamerlinck Lane says.

Hybrid work is here to stay, and this also requires looking at adding new layers of security, she says. IT is also thinking about the company’s telecom needs long-term. “Associates have migrated to mobile and/or IP-based telephony, and so we need to look at evolving the traditional desk phone,” she says.

Underestimating the power of low-code/no code

Among several IT initiatives for Shure in 2023 will be prioritizing citizen development with low-code/no-code, Hamerlinck Lane says. Another is building a platform on AWS to enable the company’s development teams as software is migrated to the cloud and to support IoT products. Shure is also investing in Office 365.

“Our entire data program is built to enable data and end-user tools to allow end-user empowerment.”

Kellogg’s Senior Vice President and Global CIO Lesley Salmon agrees, saying that as the demand for apps continues to grow, citizen development will become the norm to help people work more efficiently, and they will soon start using Microsoft’s low-code Power Platform.

“We’ll enable and encourage our organization to develop their own apps by building a community approach to learning and support,” she says.

And what better way to foster the future of work than to empower employees to improve work processes themselves.

Collaboration Software, IT Leadership, Staff Management

Cloud adoption continues its meteoric rise, with IT leaders increasingly going all-in on the platform. But succeeding in the cloud can be complex, and CIOs have continued to fumble their cloud strategies in 2022 in a variety of ways, industry observers say.

Topping the list of typical cloud strategy are three mistakes that fall under the heading of mental blueprint blunders: assuming that a cloud strategy is an IT-only endeavor, that all data must be moved to the cloud, and that a cloud strategy is the same as a data center strategy.

These fundamental issues resonate strongly with Liberty Mutual Executive Vice President and CIO James McGlennon, who admits to having dropped the ball on these strategic priorities while developing the insurance company’s advanced cloud infrastructure.

“These three are still a work in progress,” says McGlennon, adding that every mistake identified and fixed leads to a healthier cloud transformation. “We have continued to evolve our cloud strategy as we gain more insight into the leverage we can gain in engineering, resilience, scaling, security, and market testing.”

Business-IT alignment — pairing the cloud’s technology prowess with an organization’s business business goals — is a top priority for all cloud journeys, but remains a challenging issue for CIOs.

“C-level executives must be involved in assuring that the IT agenda is in line with the business plan. This is their job relative to IT,” says Paul Ingevaldson, a retired CIO based in St Charles, Ill., who says this should be in the rear-view window by now.

“It cannot be delegated, and it certainly should not be the job of the CIO — although she or he has a voice. We should no longer be discussing this issue,” he laments. “It should be a given for any CIO.”

As 2022 ends, CIOs know that business outcomes can only be as good as their cloud strategy is sound. But often they push forward with a blueprint ripe for disappointment, as these common cloud strategy mistakes show.

No way in, no way out

In addition to going it alone, insisting on moving all data to the cloud, and approaching the cloud the way they would a data center, CIOs also often fall prey to flawed thinking about the scope of their digital transformation, either by failing to have an exit strategy if cloud plan 1.0 flops or believing it is too late to implement a cloud strategy at all.

Research firm Gartner notes, for example, that a cloud exit strategy is an essential “insurance policy” that enables CIOs to bail out of a faulty implementation at the lowest cost possible. But this backup plan often slips through the cracks, analysts say.

On the flipside, many CIOs harbor the misconception that it is too late to reap the prime rewards of IT in the cloud. In some cases, however, CIOs just beginning their cloud journeys are better off than early adopters because the related toolsets and services are more plentiful, mature, and far easier to implement. This makes the cloud transformation less expensive and the outcomes better, CIOs say.

“Sometimes, waiting is better than rushing into cloud computing,” claims Dawei Jiang, chief cloud engineer at the US Trade and Patent Office (USPTO). “Everyone has a roadmap. Do not rush; pick the best and smartest solution, and avoid unnecessary work.”

Serendipity proved this point for boot and shoe manufacturer Wolverine, which hit pause on its cloud journey during COVID, delaying a hybrid-cloud transformation that has leapt forward of late, given newly available tools and an IT culture better-suited to making the most of the cloud.

Superficial planning — or worse, outsourcing your strategy

CIOs also blow their cloud strategy out of the gate by confusing a cloud strategy with an implementation plan or confusing an “executive mandate” or “cloud first” motto with an actual cloud strategy, according to Gartner. Such superficial approaches to the cloud are certain recipes for remorse, the research firm says.

But worse off may be those who pass the buck on their cloud strategy to partners, Gartner maintains. Relying exclusively on a single cloud vendor, such as Microsoft, Amazon, or Google, or a top IT outsourcing firm, for example, to design an enterprise cloud strategy is a big mistake, Gartner and CIOs agree.

The blueprint for each company’s digital transformation is unique and requires a deep dive into all IT systems by the entire C-suite and IT team to optimize the outcome, analysts note. No third party knows an enterprise better than its executives and employees.

Cloud vendors have created a collection of cookie-cutter blueprints that may be customized for specific purposes, or IT consulting firms can be instrumental helping enterprises implement their cloud strategies, Gartner maintains. But under no circumstances should the cloud vendor nor a consulting firm lead the strategic blueprint, analysts and CIOs say.

“Maybe the biggest blunder is just pushing a strategy but not looking at the management and leadership capabilities,” says Vince Kellen, CIO at the University of California San Diego, who hired two executives from consulting firms as university IT employees to help him build the university’s cloud strategy.

“The way to beat the odds on both cost and quality is for the CIO to have high team IQ within its unit, meaning the IT unit is able to apply local context to the technical solution in a way that either saves money and or builds better quality,” Kellen says.

Major sins of omission

Another top cloud expert points out three additional mistakes CIOs often make when formulating their cloud strategies.

“Not architecting for the cloud,” says IDC analyst Dave McCarthy, when asked where CIOs commonly go wrong when building their cloud strategy. “While it is possible to ‘lift and shift’ existing workloads, enterprises often experience less than desirable costs and performance with this approach. You need to adapt applications to cloud-native concepts to realize the full value.”

CIOs also often make the mistake of “not implementing enough automation,” says McCarthy, who is research vice president of cloud and edge infrastructure services for IDC. “Best practices in cloud include automating everything from the deployment of infrastructure and applications to management and security. Most outages or security breaches are the result of manual misconfigurations.

But perhaps the worst sin CIOs can make, analysts across the spectrum agree, is fail to plan for the shift in culture and skills required to devise and implement a successful cloud strategy. The cloud functions differently than traditional IT systems, and a cloud strategy must not only require new skills but a change in thinking about how to design and manage the environment, McCarthy says.

“When you go to the cloud, it’s like moving from a bicycle to a high-performance vehicle, and you can’t assume that what you did before [in the data center] will work the same; otherwise, you’ll have the same mess on your hands,” says Craig Williams, CIO at Ciena. “It can be worse, too, because your costs can get out of control if you don’t get in front of it.”

Budgeting, Cloud Computing, IT Leadership, IT Strategy

Demand for tech workers remains high, with no signs of easing up.

The proof is in the numbers: 319,652 job postings for IT workers in August, according to CompTIA, a nonprofit trade association issuing IT professional certifications. The month before there were 371,847.

That kind of competition for talent puts pressure on CIOs and their recruitment teams to be strategic in their hiring; they can’t afford to make mistakes if they want to successfully fill open positions.

With that in mind, we asked several leaders experienced in recruiting and hiring IT talent about the mistakes they see that makes hiring harder. Here’s what they say.

1. Always looking to hire externally

“A lot of people in IT default to hiring instead of looking to grow their teams; knowing when and when not to hire is a muscle that has yet to be fully developed,” says Will Markow, vice president of applied research at Lightcast (formerly Emsi Burning Glass), a labor market data analytics firm. Markow notes that his firm’s research shows that hiring external candidates takes more time to fill roles and costs $15,000-plus extra in salary costs. Plus, it signals to your existing staffers that there’s limited growth opportunities, making it more likely they’ll look for new jobs elsewhere.

2. But also promoting internal candidates when you really should hire

Despite his support for hiring from within, Markow says CIOs must be selective about internal promotions. “You can’t upskill for everything; you will have to go out and hire for some things,” he says. “Training in some cases can be faster than hiring, but in some cases, when you need them yesterday, you can’t wait to train up your existing workforce.”

3. Training up when workers have no place to go

Markow says he has seen CIOs with a mismatch between existing training programs and their projected staffing needs, a situation that can leave both managers and workers frustrated. “Sometimes CIOs invest in training their people but don’t have a clear next step for these people,” he says. Moreover, he says, “the CIOs don’t have a good succession plan, so when those people move into the new positions there’s also no one to backfill their [old] roles.”

4. Failing to align IT hiring with business objectives

With IT now thoroughly intertwined with business processes, CIOs need to tightly couple their hiring strategies with their organization’s roadmap, says Seth Robinson, CompTIA’s vice president for industry research. That requires a solid understanding of business objectives, so, for example, if the C-suite talks about their data plans you know whether that means upskilling a SQL developer already on the team or hiring a data scientist.

5. Seeking new hires a bit too late

“We see employers invest in a new technology, and they spend a lot of money for it, before realizing they don’t have anyone with the right skills to operate it,” Markow says. He worked with one company that had invested in data analytics software that sat idle for six months while they identified and trained staff to take on its daily operations.

7. Insisting on brand-name job experiences

Seeking candidates with experiences at big-name companies is another hiring mistake, particularly at companies located in geographic tech hot spots, says Eric Tan, CIO at software maker Coupa. “I see too many of my peers who want people only with those ‘really good resumes,’” he says. Yes, those companies tend to offer stellar training for their workers, but they’re hardly the only places that produce competent talent. Tan points to his company’s veteran program, which has helped him staff about 20% of his team with top-caliber workers with high degrees of perseverance and loyalty.

8. Targeting only top-tier colleges

Similarly, Tan says CIOs should expand their recruitment efforts beyond the well-known tech colleges — something he says he does with great results. His company partners with the University of Nevada, Reno and the training program Year Up to identify and hire candidates coming through their programs.

9. Relying too much on prescreening tech

Technology certainly enables recruiting teams to quickly evaluate resumes, but hiring teams “can lose a lot of people in the prescreening who could be good candidates,” says Ximena Hartsock, CEO and co-founder of BuildWithin, a software platform for creating and managing apprenticeship and employee learning programs. That’s a hard lose in a tight labor market. Hartsock says hiring managers who are overly reliant on such technology, including applicant tracking systems, may miss resumes that don’t fit preset criteria but may still show lots of potential.

10. Overlooking non-IT talent

Tan talks up one of his recent recruits, a former manager at a high-end retail store. That role had exposed her to reams of data and data analysis, which in Tan’s eyes made her a great candidate for a data role he had on his team. He says he was right. “We should be looking for talent beyond the traditional IT profession,” he adds.

11. Not getting specific on skills

You need a programmer, but the job post for the role needs specifics to be successful, says Apratim Purakayastha, chief product and technology officer with Skillsoft, a maker of learning management system software and content. “When hiring for a particular role, you need to be focused on core skills and competencies,” he explains. Hiring managers do better when they list the competencies they actually need in successful candidates and share them in their ads so applicants aren’t guessing about whether they’d be a good fit.

12. Setting unrealistic expectations

It’s great to be clear about what you want, but hiring experts across the board say you also have to be realistic. Don’t go to market for an entry-level programmer and expect candidates to know all sorts of programming languages or have a range of certifications and several years of experience. And don’t expect a candidate to have everything just as you described. An experienced programmer might not know all the languages you want but an otherwise good candidate can learn them.

13. Relying on old salary data to plan compensation

The competitive market for tech talent keeps pressure on salaries, which can bump up more quickly than pay for other professions. Paul Wallenberg, senior director for technology recruiting at staffing agency LaSalle Network, says CIOs must be sure to have the most up-to-date data when figuring out compensation. “You have to rely on more dynamic data sources and pooling data that you’re collecting during applications,” he says. “I’m not talking about the amount the applicants are currently making, either. I’m talking about what they expect in a new role.”

14. Not publishing your compensation

Starting in January 2023, California will require employers to disclose their pay ranges with job postings. Others, including Colorado, Washington, and New York City, also have such laws in effect or coming online. But even CIOs hiring outside those jurisdictions should adopt the practice, Wallenberg says. He says his company has collected data that found companies who post such information — whether legally required or not — actually get more candidates and higher-quality ones at that.

15. Lacking diversity on the interview panel

IT leaders continue to focus on diversifying their teams, but too often their interview panels have no diversity and/or don’t even acknowledge the topic. That could lead candidates to think the company’s interest in diversity, equity, and inclusion is all talk, Wallenberg says.

16. Using off-putting language in job descriptions

Certain language can be off-putting to candidates, Robinson says. For example, a job posting looking for a “diverse candidate” (an awkward phrasing, to say the least) when the company is looking to build a diverse team could leave would-be applicants puzzled on what the CIO wants in the individual. Similarly, job descriptions that use “competitive” or “demanding” could turn off potential candidates. There’s proof of this: A 2019 LinkedIn report found that 44% of women and 33% of men would be discouraged from applying to a job if “aggressive” was used in the job description.

17. Putting candidates through onerous interview rounds

Hiring teams often ask candidates to demonstrate their knowledge by developing code or taking tests. Such requests, particularly if they’re time-consuming, can be onerous for candidates. “You could be excluding people who have jobs and don’t have extra time to put into these rounds of interviews or doing homework,” Robinson says.

18. Paying too little attention to the nontechnical stuff

It’s easy when hiring for tech positions to focus only or mostly on a candidate’s technical skills, but Purakayastha warns against overlooking other important skills, such as communication capabilities and the ability to work collaboratively. “I see very competent people being hired but they don’t have enough of the soft skills needed or the skills to adapt to a new culture,” Purakayastha says, adding that his company has a list of 45 values, such as professional integrity, that it seeks in candidates to help them think holistically about applicants.

19. Ignoring next steps for new hires

“Hiring is just the first step,” Purakayastha reminds. Next up: Retaining the new hire and helping them grow. “Change in the technology field is happening much faster than you can hire, so managing your employee’s technical career has significant ROIs that should not be overlooked.”

20. Poaching

It’s a common practice, particularly among tech firms in Silicon Valley and other high-tech corridors. But poaching talent from your competitors drives up salaries without addressing the pipeline issues that are causing such drastic competition. Plus, it doesn’t typically solve staffing challenges over the long term. As Markow points out: “If you’re just offering the highest salary, what’s to stop another company from offering more?”

21. Skipping over what you can offer

Candidates in this market have lots of choices, so CIOs should be selling prospects on what they and their companies offer. “If you don’t have a vested interest in their careers, they won’t have an interest in joining you,” Tan says.

22. Failing to sell what your company offers

“You need to pay competitive salaries for sure, but you also need to make sure you’re hiring for mission and not just money,” Markow says. Research shows that companies who give workers a reason beyond compensation to come and stay, whether that reason is engaging work, a flexible schedule, the actual mission of the organization, or advancement opportunities, do better recruiting and retaining talent.

23. Adding staff when you don’t know what you already have

Markow says he worked with one CIO who, believing his IT team lacked the skills needed to successfully compete, was planning on a significant round of hiring. He then actually assessed and inventoried the skills his staffers had and found that his team was actually market-leading. As a result, he needed to hire for only a fraction of what he had originally planned. “Too many CIOs don’t take time to understand their bench strength and they mistakenly hire for skills they don’t need,” Markow adds.

24. Being biased against the unemployed or underemployed

Hiring managers sometimes still perceive out-of-work individuals as less desirable or less competitive, discounting a range of possible reasons for their unemployed or underemployed status, Hartsock says. But she points out many workers, particularly today, left or scaled back on work for very valid reasons, such as staying safe during COVID. Hartsock says companies may find a boost in their hiring if they stopped chasing passive candidates and put more energy into engaging truly active applicants — including those who are under- or unemployed now seeking to re-enter the workforce. As she notes: “There’s no better worker than somebody needs a job.”


Newly minted CIOs have a wealth of guidebooks, white papers, and blogs to help set themselves up for success from day one, as the first 100 days of a new leadership role are crucial.

But theory can only take a new leader so far. Practice is how leaders are made, and as anyone who has gone through this challenging process knows, those first months on the job as a CIO are likely to be rife with mistakes.

So, to supplement your guiding material on what to do as a new leader, we thought it important to inform you of the missteps most likely to trip you up. To do so, we polled a half-dozen veteran CIOs and researchers to share what they’ve found to be the most common mistakes that rookie CIOs make — and how to avoid them.

Here are their top 10.

Trying to change too much too fast

Change is a top priority for CIOs. According to our 2022 State of the CIO report, 84% of IT leaders say CIOs are increasingly seen as a changemaker and the lead on business and technology initiatives. That, veteran IT leaders say, can put a lot of pressure on new CIOs to come in and shake things up.

Such an approach, however, can be a mistake, says Joel Schwalbe, CIO of Transnetyx, noting that first-time IT leaders are often tempted to take on too much change at one time.

“Rookie CIOs are eager to make a good impression, but this leads to potential challenges. Organizations are only capable of absorbing a certain amount of change. Setting realistic expectations is essential for rookie CIO success,” he says.

Keeping everyone on the payroll

Brian Jackson, research director in the CIO practice at Info-Tech Research Group, has studied how CIOs tackle their first 100 days in the role and has found that many new IT chiefs think there’s no need to clean house.

“They assume that there is no one who deserves to be fired, and sometimes there is,” Jackson says.

He understands the impulse to maintain the status quo when it comes to staff. New executives in general and first-time ones in particular don’t want firings to be among their first moves, he says. But it’s frequently a necessary move that must be made.

“It’s not going in and saying, ‘I’m going to fire someone,’” he says. Rather, it’s recognizing that if there is a toxic personality, they must go. “That’s your job as a leader. And if you let it linger for too long, the situation just gets so much worse and you wish you did it a lot sooner.”

Failing to assess the culture early on

Most CIOs have likely heard that “culture eats strategy for breakfast,” the famous quote from management guru Peter Drucker. But rookie CIOs don’t often take that message to heart, according to both researchers and experienced CIOs.

“One of the rookie mistakes is not truly understanding your business, culture, and organizational fabric,” says Richard A. Hook, executive vice president and CIO of Penske Automotive Group and CIO of Penske. “Everyone is focused on their 100-day plan, but the reality is the pace of that plan and composite will vary between organizations. Get to know your peers, their teams, your team, and the overall organization before taking a too-aggressive approach. In the end, organizations win with the best people, be sure you know your teams and deeply understand the business before acting too harshly.”

Jackson agrees, saying new executives should assess their department’s culture and the organization’s overall culture early on. This, he explains, lets leaders know how to adjust and change so they can be most effective moving forward.

“There are different styles of leadership, and they can all be equally valid, but the culture of your organization is going to dictate what works,” he explains. “And if it’s not the culture you’d prefer, then you have work to do. There are ways to shift culture and get people to behave differently.”

Underestimating the people (and political) part of the job

C-suite executives and board members now recognize technology as an integral part of business, and they’re increasingly contributing to — and even leading — technology decisions.

Consider, for example, findings from tech research and advisory firm Gartner. It found that 53% of the organizations it surveyed reported that their directors are among the main decision-makers for emerging technology investments, coming in just behind their CIOs and chief technology officers. Gartner also found that 74% of technology purchases are at least partially funded by business units outside of IT, with only 26% of tech investments funded entirely by IT.

This may not be news to most CIOs, who have long talked about partnering with their business unit colleagues to develop the IT roadmap. Yet new CIOs sometimes still underestimate the criticality of building relationships, the importance of persuasion and the art of influence.

“Rookie CIOs underestimate the internal politics involved in a C-level role. There are often hidden agendas and initiatives that do not show up in the official company strategy,” says Jeff Stovall, an industry executive director with Oracle and former CIO for the City of Charlotte, N.C.

Schwalbe makes a similar observation: “The CIO job is a people, PR, and marketing job. Some rookie CIOs might believe it’s a technology job, which it’s not.”

Assessing only the internal landscape

CIOs are executives and must act as such. But there’s a learning curve, and Jackson says his research shows that many first-time CIOs fail to study the external landscape in which their organization operates even though that’s a key responsibility for any C-suite position.

“New CIOs are often so focused they get tunnel vision,” he says. Sure, they’re busy learning about their organization, meeting their C-suite colleagues, assessing their IT team.

“That’s all understandable. But you can get so focused [internally] that the blinders are on to the external environment. But as an executive that’s your job now, too, to know your competitors, to be aware of what they’re doing and what tech differentiators they’re using to create a competitive advantage.”

Jackson recommends CIOs join industry associations, build their professional networks, and attend executive events. That will yield market, industry, and IT strategy insights.

Leaping, without looking and listening first

Similarly, Hillary Ross, managing partner and IT practice leader at WittKieffer, an executive search and leadership advisory firm, says new CIOs may be tempted to jump right into their work without gaining a solid understanding of the waters where they’ll land.

“To be successful, you want to learn what works, what doesn’t, how to influence change in your new organization,” she says. “So it’s important for the new CIO to listen, learn, and then lead.”

Taking the time to do that, Ross explains, lets CIOs uncover pain points within the organization, prioritize projects with confidence, and identify the colleagues and employees who would make strong advocates for the IT agenda.

Building relationships only among the C-Suite

Another mistake some rookie CIOs make: talking only to senior leadership.

Ross says all new executives should be “making the rounds and talking to all levels of the organization. It’s important to get out and talk to everyone so you’re learning what they all need and what they think is really important.”

That includes front-line workers and back-office employees in finance, accounting, marketing, and so on. “They’re your customers, too,” Ross adds.

New CIOs should also prioritize building relationships with their IT vendors and suppliers, Ross says, adding that they may be among the biggest contributors to your IT department (and the IT budget) in the end.

Overlooking process and the technology itself

CIOs know it’s about people, process, and technology. But while they are getting to know their executive colleagues and talking with others throughout their organization, new CIOs should also be studying the processes and technologies that drive both IT and the larger enterprise as a whole.

Yet Ross says that work is sometimes overlooked by new IT chiefs. “It’s important to find out what’s working, how they’re doing things, and if those are the right things to be doing,” she says.

As a new CIO, Ross says it’s imperative to find all that out. Consider, for instance, what happens when a new CIO fails to do a deep dive into the technology stack that he or she inherited.

“Some things may be fragile and working with bubblegum and shoestrings. CIOs need to come in and assess the technology. Some things might seem like they’re working but they’re really not,” Ross says.

New CIOs who miss such problems early on aren’t likely to make a positive impression.

Going it alone

Studies have consistently found that mentors are effective in helping mentees do better and reach their goals. One study of mentorship in the workplace, from Olivet Nazarene University, found that 76% of the 3,000 professionals surveyed considered having a mentor important or very important, yet less than half actually were in engaged in a mentoring relationship at the time.

Ross says individuals moving into a new position can benefit immensely from having a mentor, but — like the survey indicates — too many don’t seek out a mentor. She recommends that new CIOs identify a seasoned IT leader to enlist for the role, giving them “someone to call to get honest advice and lessons learned.”

Flying solo

CIOs not only need mentors; they need allies. So says Greg Layok, who as a managing partner at consulting firm West Monroe and head of its technology practice advises CIOs. “I’ve seen new CIOs miss this one many times,” he says.

Rookie CIOs are often under the impression that they’ll succeed by bringing in the best technology and deploying top-notch solutions, Layok says. But they fail to see that “if they don’t bring everyone on the journey with them, then their good ideas might be perceived as bad ideas and they’re not going to have the business in the boat with them to craft the right solution in a way for the highest value-add.”

He says new CIOs may be bringing great ideas to their new organizations, and those ideas may indeed be truly needed to move those organizations forward. But those CIOs don’t realize that they need to persuade others that their ideas are going to reduce risk, decrease time to market, drive greater profitability, or otherwise bring value to the enterprise.

“CIOs who are in the position for the first time but who grew up in very mature organizations might do this well, but many others may [just] assume that the organization is aware of the value,” Layok says, adding that new CIOs must work at getting colleagues to back their visions.

He notes that all executives want to show their strategic impact on the business, but it’s especially challenging and important for CIOs, “because IT can’t be successful in today’s world being in a silo.”

CIO, IT Leadership

The contact center has traditionally operated through on-premises servers and software, but shifting it to the cloud can help CIOs improve the customer journey. Advances in artificial intelligence (AI) and cloud-based contact center-as-a-service (CCaaS) options now give enterprises more confidence that they can better deliver high-quality customer experiences.

However, there are potential challenges around moving contact center services, especially if the business has spent years cultivating good relationships with its customers. For many organizations, even a 1% drop in the performance of an Intelligent Voice Response (IVR) system can result in a surge of support calls for live agents, who are already under enormous pressure due to workforce shortages.

Here are the top three factors to consider before migrating your contact center to the cloud:

Avoid a rush to the cloud: Contact center software that has been optimized over the years cannot simply be rewritten and moved to a new CCaaS platform. Specific and careful planning must take place to keep optimizations intact and avoid breaking the customer experience. For example, many systems have carefully constructed call flows, routing rules, and natural language libraries featuring customer terminology. Those were refined over time and can’t be immediately replicated in a new system from day one.
Ensure portability to avoid vendor lock-in: Several CCaaS providers offer services that utilize a specific cloud host, making them inflexible. Any cost savings from moving contact center software to the cloud could be negated if an enterprise decides to change cloud providers due to market or technology changes, mergers, or other events. Choosing the right CCaaS provider means looking for options that are cloud-agnostic, as well as nimble enough to move should the need arise.
Enable AI systems that can handle demand spikes or other changes: New technologies that integrate natural language processing and machine learning algorithms can provide flexibility for companies experiencing an influx of new customer interactions. AI software that can learn with each customer engagement helps to ensure that the system recognizes the optimal action for the next customer who inquires about a new topic. For example, early in the pandemic, banking institutions needed to add messages about lobby closures and longer hold times, but many companies began receiving inquiries about stimulus check status that the system couldn’t quickly answer. A solution that can recognize new questions from customers and quickly react with answers is one of the benefits of an AI system that is constantly learning.

Careful planning combined with a strategy that continually prioritizes the customer experience will enable enterprises to achieve a smooth, optimized, and efficient transition to the cloud. IT leaders should partner with well-established experts to guarantee the best experience in that transformation.

To learn more about open, extensible, and collaborative contact center solutions, explore the Microsoft Digital Contact Center Platform powered with Nuance AI, Teams, and Dynamics 365, here.

Cloud Management