This May, Thoughtworks is proud to celebrate 30 years of helping their clients across the world to build the modern digital businesses of the future through the application of strategy, technology and design. Since launching in 1993, Thoughtworks is now over 12,500 people strong with 50 offices in 18 countries.

Thirty years of leadership in any industry is a remarkable accomplishment. But especially in the rapidly changing technology industry, it demonstrates a relentless, company-wide commitment to innovation and client impact.

“It’s about more than just luck for us,” said Chris Murphy, Thoughtworks’ CEO of North America. “We’ve built into our culture this ability to proactively stay ahead of the industry, by attracting, growing, and retaining the passionate, diverse technologists who want to bring that thought leadership to our industry, to our clients, and to society.”

Murphy, who’s been with Thoughtworks for almost 20 years, has seen much of this growth firsthand. Thoughtworks was an early pioneer of agile software development, and has been fundamental to multiple industry innovations including CI/CD, microservices, evolutionary architectures, infrastructure as code, lean portfolio management, and data-mesh. They have helped hundreds of businesses to use technology to build leaner, more responsive, and more adaptive organizations.

“We’re constantly asking ourselves, ‘Are we still relevant? Are we still innovating? Are we still continuing to bring unique, differentiating value to our clients?’” Murphy said. “And I’m proud to say that as long as we’re asking ourselves those questions, we’ll be able to see over the next 30 years the success we’ve seen over the last 30.”

Most recently, Thoughtworks launched its Engineering Effectiveness solution, which helps businesses empower their software engineering teams to deliver more customer value, more efficiently and more effectively.

“Since the pandemic, many organizations have invested in top-notch engineering talent but they’re seeing dwindling productivity,” Murphy said. “Now, how can they empower and retain that talent while delivering more customer value, more quickly, and with less wasted time? How can they improve the developer experience? These are just a few of the areas where Engineering Effectiveness can help.”

In Thoughtworks’ experience, some organizations utilize as little as 30% of their engineering function’s optimum capacity. Engineering Effectiveness helps developers to spend more of their time delivering value, while reducing friction and waste in their workflows. “This, to me, is really the next evolution of agile,” Murphy said. “It’s this systematic, scalable way of increasing productivity, so you can be nimble and get to market faster.”

Murphy now looks forward to the next 30 years — and beyond — of Thoughtworks industry innovation and thought leadership. As he said, “There’s no room for complacency. With the industry changing so quickly, organizations like Thoughtworks must continue to innovate and adapt.”

Of course, no one can predict exactly what the future will bring. But Thoughtworks plans to be there for it — continuing to innovate and lead technology-led business transformation.

“Thoughtworks has a 30-year history of providing a curated understanding of technological evolutions and applying them in real, practical terms to get real, practical outcomes,” Murphy said. “Our continued focus on that will give us the best opportunity to be at the forefront of embracing new technological changes as they come. And I think that’s very exciting.” Learn more about how to accelerate business-wide transformation with Engineering Effectiveness.

Digital Transformation, Innovation

If there are any eternal truths about emerging technologies, it’s that there are always naysayers. Some who deride the value of the latest ingenuity prove prescient. Others, not so much.

Ken Olson, president, chairman, and founder of Digital Equipment Corp., famously once advised, “There is no reason for any individual to have a computer in his home.” 

Regarding cloud computing, Oracle Chairman and founder Larry Ellison famously complained, “Maybe I’m an idiot, but I have no idea what anyone is talking about. What is it? It’s complete gibberish. It’s insane. When is this idiocy going to stop?”

More recently, Tesla Chairman and founder Elon Musk, Apple co-founder Steve Wozniak, and more than 1,100 people in the industry signed a petition calling for a six-month break from training artificial intelligence systems in order to allow for the development of shared safety protocols. Sensible perhaps, and maybe not exactly naysaying, but certainly a notable detraction about AI.

Of course, for every naysayer there is an evangelist. On the artificial intelligence front, Microsoft founder Bill Gates argues that we have entered the “Age of AI” believing that generative AI is “the most important advance in technology since the graphical user interface” and “as fundamental as the creation of the microprocessor, the personal computer, the Internet, and the mobile phone.”

Mark Cuban, entrepreneur, owner of the Dallas Mavericks, and one of the “sharks” on the venture capital meets game show program Shark Tank,believes “the world’s first trillionaires are going to come from somebody who masters AI.”

The key to navigating these extremes is putting emerging technologies in context. The reality is that the AI train is leaving the station. The question is: Do we as a species, do you as a voting participant in a democracy, a consumer, and an IT leader want to be/have to be on that train?

Make no debate: AI is here

I am convinced that the AI train is one IT leaders not only have to be on, but in the lead car. CIOs need to create an environment where the right conversations about the right questions occur guiding preparations for an AI-driven economy. 

Benedict Evans, an independent technology analyst formerly with Andreessen Horowitz, created three possible ways of thinking about AI in the March 27 episode of his popular podcast Another Podcast entitled“GPT-4 Is Here, Now What?

The first possibility is that generative AI is one of those once a decade technology shifts similar to the arrival of the web or the iPhone. The second possibility is that we are witnessing a once every 50-year technology revolution similar to the arrival of PCs or the semiconductor. Evans’ third category is, “Oh my god we have accidentally invented the atom bomb.” And by the way everyone can cobble a generative AI together — in their garage, with household tools using widely available (i.e., not uranium) and affordable raw materials.

What Evans is saying with his classic narrative panache is that AI is not a technology you want to sit on the sidelines and wait to see how it plays out.

You do not want to employ what Gunpei Yokoi, the inventor of the Nintendo Game Boy, called a “lateral thinking with withered technology” strategy. What Yokoi-san meant by this is, whenever possible achieve sought for outcomes with older, cheaper, commodified technologies. You can’t get to the future without AI.

That said, Boston Consulting Group and MIT Sloan Management Review found a “gap between ambition and execution,” with 84% anticipating that AI will be a source of competitive advantage while only 40% have a strategy around AI and about a quarter having adopted any AI into their services or processes.

CIOs need to prepare their organizations for the coming AI era. They need to unambiguously signal to all stakeholders that the enterprise is onboard the AI train. And CIOs will have to manage AI timelines: Generative AI is one of those technologies that is exponentially better now than it was six months ago and will likely be exponentially better in 12 months. The general feeling among technology strategists is that if you have not briefed your board of directors on the opportunities, responsibilities, and liabilities associated with generative AI about six months ago, you are woefully behind.

After all, more than one million users signed up for ChatGPT within five days of its November 30, 2022 release. By February 2023, ChatGPT had reached 100 million users. Meanwhile, venture capitalist firms invested approximately $4.6 billion into generative AI companies globally last year, up from $1.9 billion in 2019, according to PitchBook Data.

Embracing AI leadership

Still, AI has gone beyond fascination and speculation; there are real benefits to be had already. Economists at Goldman Sachs conclude that generative AI could raise labor-productivity growth by almost 1.5 percentage points a year, a de facto doubling from its current rate, and research from Microsoft suggests that developers can perform tasks more than 50% faster when using an AI assistant. 

In practice, however, making good on the promise of AI — without falling prey to its pitfalls — requires leadership. CIOs need to proceed cautiously, recognizing that mistakes will be made and that there will be surprises. AI initiatives should be reviewed quarterly with regards to harms and benefits. At the very least CIOs should familiarize themselves and senior management with the Blueprint for an AI Bill of Rights released by the US Office for Science and Technology Policy.

Some organizations have put “AI ethics” advisory boards in place while others are contemplating creating a new role in the C-suite: the chief AI ethics officer. At the very least CIOs need to signal that AI ethics are being considered.

Artificial Intelligence, Innovation, IT Leadership

The room was abuzz. People were standing, talking intensely, mingling, and meeting new people. This was our first in-person conference in 2023, and it was going exactly as planned: Participants were engaged and networking. In all of our surveys, networking is always one of the top two reasons attendees come to our events (the other is the content), but often we don’t see them doing it. So we’d put a structured networking exercise on the agenda, introduced the session, and presented some sample questions they could use as conversation starters. Voila – off they went. Later, our survey results indicated it was a highlight of the event.

Welcome to FutureIT, our new event brand debuting in five cities in 2023. We’ve focused on leveraging what’s special and important about meeting in person again, with keen attention paid to creating the best – and a memorable — attendee experience. A fresh take on content, networking and experiences means it’s not your father’s IT event – as one attendee enthusiastically told us.

That’s right. Our focus covers three areas: leadership, technology and personal development. The program starts with a workshop to heed the call of deeper learning, networking and personal growth;  features an inspirational, non-endemic keynote, followed by interviews with and panels of exceptional CIOs; and includes not just the aforementioned structured networking but active discussion groups led by our sponsors.

The program also features content aimed at attendees’ careers, by looking at the latest job requirements for senior IT and security executives. This session includes information that will help managers recruit for open positions – a big pain point across so many and IT security teams – as well.

As such, the agenda checks all the boxes regarding what recruiters and our research indicate are the most crucial skills for success in today’s volatile business environment. Sound exciting? We have programs coming up in Washington, D.C.; Toronto; Chicago; New York; and Southern California. Join us.    

Digital Transformation, Events, IT Leadership

Value Stream Management (VSM) is a powerful methodology that not only streamlines value streams and optimizes processes but also promotes sustainability and creates positive impact. As today’s great leaders recognize, true success is not solely measured by the bottom line but also by the impact a business has on its stakeholders, including employees, partners, and the environment. Sustainable leaders understand that making near-term profits at the expense of these other stakeholders and concerns is not sustainable. It’s not sustainable for the business, nor the environment, nor the beings (human and otherwise) that depend on this environment.

Sustainable leaders are clear on a very key reality: they know they have the power to influence the long-term trajectory of the business and much more. Their decisions and actions can shape more than the organization’s future stock price. They can make an outsized impact on the state of the planet that is passed to future generations. They understand this is an opportunity and a responsibility, and they take that responsibility seriously.

A sustainable leader doesn’t just talk a good game; they play one. Through their actions, strategies, and decisions, they make strides in important areas, whether that’s reducing energy consumption, shrinking their carbon footprint, or reducing waste. They make tangible progress and through their words and examples, they inspire others to join the cause.

Here are some ways leadership and sustainability can go hand in hand:

 Setting a vision

A sustainable leader can set a vision for sustainability and ensure that it is integrated into the organization’s top-level strategies and at every level of operations. An effective vision statement sets the direction for an organization and serves as a source of inspiration and motivation for employees. It provides a shared understanding of the company’s purpose, goals, and aspirations and helps align the efforts of all stakeholders around a common objective.

Encouraging employee engagement

Sustainable leaders can create a culture of sustainability by involving employees and promoting eco-friendly practices. In a business context, encouraging employee engagement is about the creation of a workplace culture that fosters motivation, involvement, and commitment among employees. Engaged employees are more productive, innovative, and customer focused, and they contribute to a positive workplace culture. Here are some ways to encourage employee engagement:

Communication. Encourage open, two-way communication between employees and management to foster a sense of transparency and trust.Sustainability ambassadors. Provide employees with the tools and training they need to promote sustainability within the organization and beyond.Set sustainability challenges. Encourage employees to participate in sustainability challenges, such as reducing waste or improving energy efficiency, to spur new ideas and innovative solutions.Recognition and rewards. Acknowledge and reward employees for their contributions, whether it be through bonuses, promotions, or public recognition.Work-life balance. Create a supportive work environment that values employees as people, and helps them maintain a healthy balance between their personal and professional lives.Inclusiveness. Foster an inclusive workplace culture that values diversity, equity, and respect for all employees.

Cultivating innovation

A sustainable leader can encourage and invest in innovative technologies and processes that promote sustainability. Innovation is a critical driver of business success, and leaders play a crucial role in fostering a culture of innovation within their organizations. Here are some ways leaders can cultivate innovation:

Build a culture of experimentation. Create a culture of experimentation and continuous improvement by giving employees the freedom to test new ideas and approaches to sustainability.Invest in technology. Invest in technology and innovation to improve sustainability and reduce the organization’s environmental impact.Provide training and education. Provide training and education to employees on sustainability issues. Encourage individuals to become sustainability experts within the organization.Celebrate successes. Recognize and celebrate sustainability successes, and use them to inspire continued innovation and progress.

Collaborating with stakeholders

Sustainable leaders can engage with stakeholders, including customers, suppliers, and community members, to collaborate and find holistic solutions to sustainability challenges. Here are some ways to effectively collaborate with stakeholders on sustainability:

Foster partnerships. Collaborate with stakeholders to create innovative sustainability solutions.Set shared sustainability goals. Work with stakeholders to set shared sustainability goals and create a joint plan for achieving them.Encourage stakeholder feedback. Encourage stakeholder feedback and engage in regular dialogue to ensure that their concerns and needs are being met.Use data and metrics. Use data and metrics to measure and communicate the progress and impact of sustainability initiatives, and to engage stakeholders in continuous improvement.


In conclusion, leaders can play a crucial role in advancing sustainability and ensuring a vibrant, healthy future for the business, and for all. Let’s follow the lead of those who are sustainability champions. Let’s all be eco-warriors and work together to make our world a better place for future generations. Registration is now open for the 2023 Value Stream Management Summit – True North: Achieve Digital Transformation Success with VSM. Join transformation experts from Tyson, Memorial Sloan Kettering, Forrester, and more on April 26, 2023.  Register today.

IT Leadership

The sixth annual report from Tech Talent Charter (TTC) has revealed that while companies in the UK are making progress toward improving diversity in their overall workforce, there is still a significant lack of diversity among senior technology leaders.

The not-for-profit charity, which focuses on tracking diversity in technology, compiled its report using data from 649 signatory companies, including Global, HP, Lloyds Banking Group, Nominet, PwC and CWJobs. The 210,245 employees included in the data set are estimated to represent around 16% of the UK’s technology workforce.

The Tech Talent Charter is free to sign — the only obligation signatories are required to meet is sharing their data with the charity when requested. It is only mandatory for signatories to share gender and ethnicity data but this year’s report represents the first time the TTC has started to track other aspects of diversity, including age, disability, sexual orientation, religion and neurodiversity.

The aim of collecting this data set is to try to understand what is actually happening at the coalface of diversity and inclusion in tech, since not being able to fill shortages in the tech talent market costs the UK economy about  £63 billion a year, according to Tech Talent Charter COO Lexie Papaspyrou.

Commenting on the report’s key takeaways,  Papaspyrou said that while it’s heartening to see that 28% of tech workers are gender minorities and 25% are from minority ethnic backgrounds, when those figures are compared to the percentage currently holding senior leadership positions, the drop-off is  alarming.

The data collected by TTC found that 22% of senior tech roles are held by gender minorities, a figure that is 6% lower when compared to tech roles overall, while ethnic diversity almost halves in senior roles, dropping from 25% to 13%.

There’s a pervasive idea that these figures just highlight the fact that a large percentage of women naturally leave the workforce at certain point to start families, but that doesn’t explain the drop-off experienced by people from an ethnicity minority background,  Papaspyrou said.

“There are no natural barriers that exist for ethnic diversity and senior roles in the same way that maybe you could argue exist with regards to gender,” she said. “There is a gendered societal problem that women are dropping out of the workforce because they need to take parental or career breaks, but that’s not the case when it comes to ethnicity.”

Papaspyrou added that she doesn’t believe it’s a coincidence that, for senior roles, the data for gender parity is more positive than the data for ethnic parity, given that the UK government has made gender pay gap reporting mandatory, but not ethnicity.

When it comes to D&I, data is key

One of the founding tenets of the Tech Talent Charter is the importance of data, so much so that if a company fails to provide TTC with the information required from them, they are removed as a signatory.

One of the ways the charity is helping organizations to have a better understanding of where they are on their D&I journey is through dynamic benchmarking, with a new tool that is freely available and allows companies to input their diversity figures and see how they compare to other organizations of the same size in their region and sector, Papaspyrou said.

“Those are the three areas we are constantly questioned about by companies,” she said. “They say, ‘I don’t know how to contextualize my figures because the publicly available ones are across all UK companies and I’m a small SME in the North East, so that isn’t relevant to me’.”

For TTC, while there is still an amount of churn regarding organizations that refuse to hand over their data, many companies are entering their fifth or sixth year of being signatories to the charter.

As a result, their support and willingness to provide more data has led to TTC being able to ask questions through eight diversity lenses, with neurodiversity emerging as a distinct area of interest, Papaspyrou said. Among current signatories, 53% are now measuring neurodiversity among employees, a figure that has doubled from last year.

Measurement of social mobility lags

However, Papaspyrou  was concerned about the data gap that exists regarding the measurement of social mobility, which lags far behind other areas including age, religion and orientation.

“We need to be looking at these intersections and social mobility is the one that falls across every single other lens and has such massive tangible impact on what works and what doesn’t work,” Papaspyrou said, adding that it was dismaying to see that lack of reporting, particularly in a year where the country is going through such economic hardship.

“When you look at the technology industry and where tech salaries are, in some cases three times the average UK salary, the fact that more organizations are not focusing on this is a big opportunity lost,” she said.

Looking forward to the next 12 months, Papaspyrou said TTC will be working with its signatories so that when the next data set is collected, organizations are ready to tell the truth, whether the data they have is good, bad, or unavailable.

There will be a lot of activity focused on how to improve progression at higher levels and removing the barriers that are stopping diverse employees from reaching those roles, Papaspyrou said.

“It seems like the entire business community here has really picked up on this idea that you can pack as many people into the tech workforce as soon as you want. And, while it’s great and you’re getting them in, if they’re not getting on, why are we doing it?” she said.

Diversity and Inclusion

MTF Finance Chief Technology Officer Dan Wilkinson on why transformation needs an ignition point, how to change mindsets to embrace doing things differently, and the challenges that lie ahead as MTF acquires new businesses.

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CIO Leadership Live

The ‘broken rung’ has long restricted women from achieving managerial positions in IT, and the latest joint and McKinsey Women in the Workplace report finds underrepresentation in leadership roles is still a problem, and more so for women of color.

Teradyne CIO Shannon Gath, who has a passion for helping women in STEM leadership roles to be successful in their careers, emphasizes education as a vital starting point for understanding the challenges women face in getting ahead in IT. The Boston-based test-equipment manufacturer recently enlisted McKinsey to conduct education sessions with leaders across the company to help them understand specific issues women confront in advancing their careers.

Generate awareness of the nature of the problem within an organization is key, Gath says. “There are still too many people who don’t understand the problem itself and that it’s systemic,” she says. “If they’re not understanding there’s a problem, you’re not moving forward.”

More than simply mentoring

Mentoring programs have often been seen as the solution, but they’re not always effective. Lack of program structure, poor mentor and mentee matching, and inconsistent commitment between participants can impede effectiveness, says Dr. Christie Struckman, a research vice president at Gartner, who argues that these programs often intimate that something needs to be fixed in the women participants. Instead, mentoring programs should be “more about providing space to talk about career aspirations, supporting evaluating options, strategizing how to get opportunities, and providing assurance,” she says.

Gath sponsors a project at Teradyne to learn and adopt successful strategies from organizations leading the charge for diversity, equity, and inclusion (DEI). “We’ve heard of the different programs as we looked at mentorship and sponsorship, and all of them have their pros and cons,” she says.

Shannon Gath, CIO, Teradyne 


But when Gath and her team met with an organization that had been conducting what it called mentoring circles for about five years, something struck a chord. The mentoring circles gather women who are at around the same job level and are interested in growing in a certain area, and pair them with two executives as mentors. The circles meet on a regular basis for six months to do a deep dive on relevant topics.

Teradyne piloted this approach, targeting points at which leadership rungs are broken for women, with the aim of addressing the hurdle, Gath says. The key is using metrics to focus efforts where it’s needed most. “We looked at our data and said, ‘Those are the points,’” she says. “So we sent out invites to the women who fall into that ‘rung’ category with some suggested topics, and asked if they’re interested in any of them and want to participate in a mentoring circle. What’s so special about it is it’s exactly what we need for where we are right now.”

Gath knows that having the right match can make or break the experience of two-way mentoring. And sponsorships help open the door for only one or two women. “You don’t get the broader impact,” she says.

Through Teradyne’s mentoring circles, women are paired with two mentors, providing a better chance of connecting and getting value from the program. This approach also removes the pressure of a one-on-one relationship, and having women circled together with other women extends the benefits by helping them build a support network — something that’s vital to career development. “It’s connecting women who are challenged with the same thing you are,” Gath says. “So even after the mentoring circle is complete, they are your sounding boards going forward, and you should be able to carry that with you for the rest of your career.”

Avoid tokenizing the women in leadership roles

To support women in leadership roles, it’s important to avoid behaviors that marginalize them, according to Gartner’s Struckman, who says it can be a case of death by a thousand cuts, in which many small actions mount up to behaviors that tell women they’re not valued, something that can impact job satisfaction and retention. “Women aren’t going to stay someplace where they’re marginalized when they know they can get hired elsewhere,” she says.

But to address marginalization, you must first be able to recognize it, Struckman says, adding that organizations should work to ensure awareness about behaviors that create an environment where people feel this way. Struckman also advises confronting certain behaviors with clear expectations of what is expected (while not demonizing people), and communicating expectations publicly while supporting marginalized people privately.

For women in senior leadership positions, Struckman says it’s also important to avoid tokenizing them.

“Very often when there’s a woman in leadership, she is the only female,” she says. “She gets asked to lead the ‘Women in IT’ activities, serve as the primary recruiter and interviewer of diverse talent, and asked to mentor or coach a large host of other women.”

These additional responsibilities are rarely acknowledged and considered a ‘side of the desk’ activity, adding additional burdens on time and responsibilities. Instead, Struckman suggests having males serve as allies by acting in these roles where possible. “And where organizations offer things such as flexibility, it should be a talent retention policy that applies across the board, and not just a female retention strategy,” she says.

A positive culture sets the tone

Achieving gender equity takes a multifaceted approach stretching from talent acquisition and retention, to opportunities and promotions that help support women, explains The Hartford CIO Deepa Soni. The insurance company, soon to be recognized with a Catalyst award for its commitment to advancing women and equity, has adopted an organization-wide approach that includes accountability measures, addressing unconscious bias in talent management, and revising other processes. And culture is a vital piece of the puzzle.

Deepa Soni, CIO, The Hartford

The Hartford

Culture at The Hartford is the crown jewel that demonstrates it values equity, “where actions speak for themselves,” Soni says. The company is pursuing an aggressive technology and data agenda, and the plan is to ensure women are a big part of that, she explains.

“We’re strengthening our sponsorship, mentorship, and coaching, and stretch assignments and talent mobility,” she says. “These are all the tactics we’re taking to make sure we advance our women, from hiring them at the intern level to elevating them to the first management level, and getting them to senior leadership roles.”

Soni acknowledges these initiatives, and the results, are years in the making and take consistent commitment, but real progress can be made. “It’s a multidimensional approach coupled with a strong culture that actually amplifies the impact of these strategies,” she says.

Gartner’s Struckman agrees that culture plays a huge role in creating an environment where marginalizing isn’t okay, and where supporting and building each other up is the norm. If, for instance, the expectation is that to progress, you must work over 60 hours a week and at any hour of the day, then women won’t stay.

“Culture tells employees what is expected, accepted, and respected,” Struckman says, adding that we still live in a society where women shoulder most childcare responsibilities, preventing them from being able to drop everything and take care of work unexpectedly. “In some IT organizations, the ‘hero mentality’ is prevalent and rewarded specifically, and thus becomes the definition of what is respected in the workplace,” she says.

She also cautions organizations to pay attention to the managers of women when looking at how they’re faring in relation to promotions and opportunities. “When a woman doesn’t get promoted, most of the focus is on what’s wrong with her and what can be done to improve her,” she says. “But there might not be anything wrong with her. Instead, the lack of promotion is based on a bias of her manager.”

Although we don’t have a systemic way to evaluate bias, leadership needs to look out for it, she says. “If a manager fails to get their women promoted at rates equal to their male employees, that’s more likely a failure of the manager than on the females,” she says. To counter this hurdle, Struckman encourages managers to put more women into new experiences with intention. “When big projects or initiatives come up, we tend to give them to people who have proven themselves already,” she says. “But then we just keep giving the same opportunities to the same people. Women are amazing and competent. We just need to give them the chance.”

CIO, Diversity and Inclusion, IT Leadership, Women in IT

Mandy Simpson, Chief Digital Officer at Z Energy, on why she embraces working for high-change organisations, the need for IT teams to build up trust across the business, and why you should always go for a job that scares you a little.

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CIO Leadership Live

Lekan Olawoye, Founder and CEO, BPTN & Obsidi, talks about the Obsidi platform and building community and networking for Black technology professionals. To learn more about how Obsidi is working with partners to hire incredible Black talent, there’s Obsidi Recruit: To join Obsidi, the URL is or the direct login page is:

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CIO Leadership Live

When you’ve spent your career mastering complex technologies, stepping into a leadership role might not be the first item on your wish list. As a CIO, you’ve already made this transition. But how do you prepare others on your team for this next career step?

This is one of the more challenging steps in any IT career. It requires you to hesitate when you know the answer, let others make mistakes, and convince someone who has spent decades getting to the apex of a technical skillset to let it go and embrace soft skills that may not come easily.

It’s necessary, though. Because if you don’t do the upfront work to prepare your team to take the helm, you won’t have anyone to fill those seats when you want to move up — or step down.

I spoke to IT executives and leadership coaches for tips on how to develop the leaders on your team. Here is their advice.

Stop teaching. Start coaching

You can teach someone to code, manage money, and complete the tasks of being a manager. But teaching is limited. To develop a leader, you have to coach them to become someone who can make decisions on their own, communicate well, and plan strategically. But the transition from teacher to coach can be challenging.

“I started my career as an engineer, as a developer,” explains Andrey Ivashin, CIO at Dyninno Group. “When the business started to grow, I was the smartest guy in the room. I knew everything, every piece of technology and all such things.” Because of his knowledge, he was the one tasked with onboarding new people.

“I would teach them, sharing my knowledge,” he says. Eventually, though, Ivashin began to see that teaching was not enough. “I became a bottleneck. They didn’t learn more than I knew, at that moment.”

This was a revelation, and it is, according to everyone I spoke to, an important one if you hope to develop leaders.

“I switched from teaching to coaching,” he says. “I challenged people by asking questions, not giving them answers.”

Even when he knew the answer, he would guide his team to find it themselves. “I might push them into the right direction,” Ivashin admits. But to teach people to be leaders, coaching them to learn how to discover the answer — and to make decisions — on their own is essential.

Choose your people well

“The biggest piece of advice I can give on transitioning technologists into management is to make sure you’re choosing the right person for the role,” says J.R. Lowry, founder of “The best technologists aren’t necessarily the best managers. Some of them don’t really want to be managers.”

It’s great if these people are, like Ivashin, “the smartest people in the room.” But they should also want the role, be able to acquire the requisite soft skills, and be up for the task of learning skills that might be difficult for them to master.

“These are all probably bright people but also very much focused on left-brain function,” says Gary Mitchell, CEO and founder of OnTrac Coach. “Their personality type, education, training, and work experience, all support that. None of it supports the right-brain functions of creativity, empathy, emotional intelligence — all the soft skills needed for leadership.”

If there are people on your team vying for a leadership role, the first question to answer, then, is why.

“Why does this person want to go into management?” asks George Tsounis, CTO of Stretto. “As a leader, you have to probe there.” Not everyone wants this for the right reasons. In fact, they might not want it at all. They might believe they should want it.

“Sometimes folks believe that leadership is the only way to a title and prestige,” says Tsounis. “But that’s not the motivation you want. You want someone for whom this is about becoming a servant leader and developing a passion for helping people grow.”

There are probably people who love to teach others, who willingly take on a mentorship role and try to make the path easier for new hires or junior staff. Look for those people.

“My first test is to make sure they have an interest and passion in teaching and developing others,” says Jim Chilton, CTO of Cengage Group and general manager for Infosec Institute. “If they don’t, people management will always be a chore, even an inconvenience.”

It’s possible, though, that you won’t have many volunteers. On an IT team, which may be made up of many introverts and people who have worked hard on logic and analytical skills, those who long to communicate and lead can be rare. “I don’t think it’s as high as 80/20 percent of those who don’t want to do it versus those who do,” says Bonnie Davis, executive coach at HuWork. “But it is probably closer to 60/40 percent.”

Make career paths clear

“If you try to force someone to be a leader, it will be a mess,” says OnTrac Coach’s Mitchell. “You will lose them because they will hate it. And you may lose others because they won’t be good at it.”

Avoid this expensive problem by making it clear to everyone that leadership is not the only path to advancement.

“The first step to being a better coach for engineers looking to transition into management is for the organization to provide clearly defined career paths for technical and managerial tracks in engineering,” says Jeremy Schmidt, senior director of talent acquisition at Codility. “Many times, developers feel the only way that they can experience advancement is by going into management. Once in management, they realize that they preferred a more hands-on technical role.”

Developing a leader is costly for you personally because it takes up a great deal of your time and energy. It’s also expensive for the company. And bad or reluctant leadership can do more harm than good.

“To better support your engineers and avoid these issues, leaders need to be able to clearly articulate the different competencies needed to be a successful engineering manager versus staying in a technical track,” says Schmidt.

If the only way to advance in your organization is to seek a management role, reconsider that. You might have to define new roles for people to advance into.

“The practice I’ve always put in place is to established parallel positions, leadership with technology experts,” CTO Tsounis says. “I make it clear that the technology expert is just as important as the director. They get the same pay and bonuses. Of course, this starts with what the company needs. But next is the passion of this person. Because if they are not passionate about it, and are just doing it for title, prestige, or something else, it’s the wrong fit.”

The ask first, tell second coaching method

Once you have identified your people, the first step in your coaching strategy is to have an open conversation, Mitchell says.

“Say, ‘I’ve identified some qualities and abilities in you and want to find out if you are interested in pursuing leadership,” he says, adding that you are looking for two things from this conversation: “The first is willingness. The second is some agreement that they have some skills but could use improvement. In other words, are they coachable?”

They may not be thrilled at the idea. In that case, says Davis, “start by acknowledging that this is a big transition. It’s exciting. But it might be hard.”

Then practice what Davis calls the “ask first, tell second” method of coaching. “Ask them what’s exciting about this. Then ask what’s scary?” And, since the core skill of coaching is listening, “give them the time and space to answer and listen to what they say,” she says.

They might not want to give up the thing they are good at to learn something hard. They might feel jealous of team members who get to keep their hands on the technology. They might fear that others aren’t good enough to do the work they’ve been doing. And they might not yet see the benefits of a leadership role.

In the “tell” portion, point out the influence they will have on larger issue in the company, the essential role of managers on the team, the pleasure of helping people grow into larger careers, and how this will give them a seat at the table.  

“Eventually they will start to explore the new territory and see the benefits of the impact they’re having, enjoy being strategic, making bigger decisions, and having visibility with senior leaders,” says Davis.

Mistakes are teachers

Mistakes are an important part of learning. They are key to making high-level decisions, too. But feeling safe making them at a leadership level can be scary. Helping your potential leaders feel safe making decisions is an important part of coaching them into this role.

“I tell managers that they have to make decisions,” says Tsounis. “It’s part of the job.” But he also makes it clear that everyone sometimes makes the wrong call. “I tell them, ‘If you make nine out of 10 decisions right, you’re killing it. You’re the best manager out there.’ They have to have find comfort with the fact that they can fail.”

Ivashin agrees. “All decisions have pros and cons,” he says. “It is a question of risk. How big a mistake could this potentially be? When people understand that, it gives them the freedom to make decisions. They are not afraid to make a mistake, because they will be mistaken, in any case. The question is only about the size of the mistake.”

Learning the lessons mistakes and bad decisions teach is also important.

“A failure means a learning opportunity,” says Tsounis. “Take it seriously and do a retrospective on it.”

Help them grow their soft skills

Everyone I spoke to told me that technologists tend to be weak at soft skills. They have built up their logical, analytical, and problem-solving skills but haven’t spent the same time beefing up the soft skills needed to lead. They may also be prone — by nature — to neglect their EQ in favor of their IQ. The good news here is that these are people who know how to learn, and communication and empathy can be learned.

“CTOs should encourage their future leaders not to underestimate the power of communication,” says Chilton. “It is important that all technology leaders recognize a key component of their job is to explain business to technology people and explain technology to businesspeople. Leaders are the broker of this conversation and frequent, clear, succinct communication is a critical vehicle to their success.”

Don’t underestimate this challenge, though. Leading a team is not what your new leaders have studied until now, and leading a team can be challenging even for someone with a high EQ.

“The team they’re leading is likely to be different from, say, a sales or customer service team,” notes Lowry. “Technologists are more likely to be introverted. They may be neurodiverse. A manager will need to be able to work well with many different types of people, including those who may learn differently, who may look at interpersonal relationships differently, and who may be harder to coax into communicating what’s on their minds. This requires a manager who puts a particular focus on understanding what makes his or her team tick.”

Tap outside resources

Learning a complex skill is best done with more than one facilitator. Bringing in a leadership coach or encouraging your leaders to take courses or attend seminars on leadership can bring skills to the team you might not have the time or knowledge to convey. A leadership coach can also be a safe place to admit fears or problems your people might hesitate to share with their boss.

“I think a hybrid approach is best,” says Tsounis. Coach your new leader with hands-on leaderships tasks while also encouraging them to enroll in management and leadership learning programs or use a leadership coach to work through mastering more challenging communication skills. “I went to a leadership program at Rice,” he says. “Leadership was way out of my zone, so I went there and learned a lot of concepts. It really does help.”

There are lots of programs available at universities, such Wharton, Berkeley, and others. They may be expensive, but, as Tsounis points out, these are your future leaders. “Do the math and let this person go through that program in parallel their professional work,” he says.

Tapping a leadership coach can also be helpful, even at the new leader level. “Coaching is often reserved for a select few,” says Rashim Mogha, SVP and general manager of Skillsoft’s Leadership & Business Portfolio. “But this mindset is starting to change as leaders understand the importance of scaling coaching company wide.”

“The best times to get coaching with an external coach are when you are at transition points in your career,” says Davis, herself a leadership coach. “People assume executive coaches are only for people at the executive level, but it can be very valuable earlier in your career.”

IT Leadership, IT Training , Mentoring, Staff Management