Coaching IT pros for leadership roles

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