The Hidden Challenges of Becoming a Technical Leader

In this second post (first post here), I explore the hidden challenges technical experts face when transitioning into leadership roles. From identity shifts to skills gaps and cultural clashes, I’ll outline the reasons even brilliant people can struggle in this move — and why it’s not a question of capability, but context. In Part 3, I’ll look at how we can better support these transitions — and when promotion might not be the answer at all.

Identity Crisis: From Expert to Leader

None of this is new. Back in 1969, Laurence J. Peter coined the “Peter Principle,” suggesting that people are often promoted to their “level of respective incompetence.” I’ve seen it play out time and time again — not because people aren’t capable, but because leadership is a fundamentally different discipline. I prefer to phrase this more directly: They have the value promoted out of them.

This tension shows up both internally, in how the individual sees themselves, and externally, in how others perceive them.

Until their promotion, this person was a go-to technical expert. They intimately understood some of the most critical systems and tools in the company. In many cases, they’d designed or built them! Their knowledge was deep, practical, and relied upon. They didn’t just succeed in this environment — they loved it. They understood the rules of the game: solve problems, build great tools, go deep. They worked with people who spoke the same language, valued the same goals, and respected expertise above all else.

Then, everything changed.

Internally, they may start to feel unsteady. What once defined their success — clean code, elegant systems, getting things working — is no longer how they’re measured. Their confidence is shaken, not because they’re unqualified, but because they’re suddenly being asked to lead in ways they’ve never been trained for.

Externally, it’s a different story. Now that they’ve got the title, people assume they’re the finished article. They’re expected to stay technically sharp while also making big strategic decisions, leading people, and managing stakeholders — flawlessly. In other words, they’re expected to be two people at once.

That mismatch between internal uncertainty and external expectation is where the pressure really builds.

If the transition to leadership is real — not just a new title — then this person is no longer judged by technical brilliance alone. They're expected to craft vision, communicate across silos, influence up and sideways, and make decisions shaped by compromise and context, not technical purity.

They must learn to delegate the work they love, spend time in stakeholder meetings, align with commercial priorities, and lead teams they may no longer be the smartest member of.

This is where the identity crisis really kicks in. They’ve gone from being the person who does to the person who must enable. From being judged by clean code and elegant architecture to being measured against KPIs, NPS indexes, or PowerPoint slides they didn’t write.

The skills that got them here — deep focus, perfectionism, problem-solving — may not be the ones that carry them forward.

To counter the discomfort of their new role — and to regain a sense of familiarity and control — newly promoted leaders often throw themselves back into the grunt work.

Alongside their new responsibilities and workload, they’ll “keep their hand in,” “support the team,” or offer “a bit of guidance” — one of many justifications that help them feel capable again. It’s comforting to return to what they know.

But more often than not, this leads to burnout.

I’ve been there. Early in my own career, I did exactly this — trying to do it all. It took real work, and a brilliant boss, to help me step back from my old responsibilities and step up into my new ones.

I’ve seen it play out countless times — not because people aren’t capable, but because we fail to acknowledge that leadership is an entirely different discipline. Put simply, their value gets promoted out of them.

Career transitions are never just about a new job title — they’re about stepping into a whole new way of working, thinking, and being seen. For technical experts, this can be especially complex.

The Skills Gaps Most Technical Experts Face

There are a number of skills that make the technical expert a brilliant expert, but sadly, leadership requires an additional set of completely different skills. I’m going to run through a selection of what I think are the most important skills gaps that I have seen in my career, but this list is by no means exhaustive. Nor is it the case that every technical expert is lacking in all of these skills, but there’s certainly enough examples for me to believe this list credible.

Delegation

Delegation is a common challenge for new leaders — but in technical experts, it’s often intensified by habit, pride, and precision. The transition from doing to directing is a very difficult bridge to cross. While new responsibilities move them outside of their comfort zone, technical leaders can often revert to doing, rather than delegating, to seek out comfort and familiarity. Internal conflict also exists owing to the belief that it will be “quicker, more reliable and of a higher quality if I do it myself.”

Leaders must learn that being accountable for tasks is different to being responsible for them, and that their role is that of resource manager, rather than skilled operator. Only by embracing this will they become effective and inspirational leaders.

Supporting this mindset shift from doer to delegator is one of the areas where coaching can have a real impact.

Communication

Technical experts often operate in a language of TLAs (three-letter acronyms), jargon, and shorthand — completely natural in their world, but alien outside it. But it’s not just the content that is different: communication styles vary incredibly between functions like Legal, Finance, Creative, or HR. What the audiences need and expect is also hugely different when they sit in front of an expert versus a leader. Many of the archetypal skills and behaviours that make someone a successful technical expert are the exact opposite of what is required to be a competent communicator.

Leaders need to rise above the detail, tell a story, ignite emotion, take people on a journey — all while remaining clear and concise!

Technical experts often speak to small groups who share a common language, lean on agreed facts, and avoid emotional framing.

All of this advice applies as much to written communication as it does to spoken communication.

Luckily, there are a number of frameworks that can be taught and learnt to develop technical experts into expert communicators.

Emotional Intelligence and Self-Awareness

Often underdeveloped in technical experts, but essential facets of a successful leader, these skills are some of the hardest to learn. The world of the technical expert is one of logic, reasoning, agreed standards and merit-based respect. A leader, on the other hand, must be able to recognise, harness and inspire emotion. They know what they say is only a part of the story. Leaders need to sense team dynamics, navigate office politics, and respond to the unpredictable nature of human relationships — things rarely modelled in technical environments.

In leadership, awareness and mastery of one’s self is an essential skill for success. Technical experts are often forgiven their weaknesses because of their deep strengths. Further, those weaknesses are often underexposed at lower levels. Unlike so-called “soft” skills, technical skills are highly tangible and can be learnt through solo learning using books, blogs and other sources. “Soft” skills, on the other hand, often need at least one other participant on which to practise, in an environment where the learner is highly vulnerable.

Again, coaching is an ideal method of support in the development of these skills, as the coaching relationship provides a safe space to learn about and practise interpersonal, relationship-based skills.

Adapting to Leadership Culture

I remember early in my career I was asked to project manage my first developer. This person didn’t attend any meetings, no matter how far in advance I scheduled them, wouldn’t fill out weekly reports and, tellingly, couldn’t understand why any of this was an issue! Developers get into what is known as “flow” or “the zone,” and leaving it can be very disruptive. The rise of frameworks like AGILE and SCRUM have further contributed to divergence in working styles between technical teams and other corporate business units. Content switching is rarely developed in technical roles. In fact, some people don’t see it as a skill at all — they see it as inefficient and unnecessary.

The world of the leader, on the other hand, is one where focus and context change at least hourly, if not more often! Being able to time-box activities, respect agendas and make the required cognitive and emotional leaps between meetings are all skills a leader must hone.

Work must also fit into the rhythm and flow of the rest of the organisation. This often requires collaboration with other departments, and dealing with ambiguity and uncertainty — conditions less common in engineering or technical roles.

The discussion of what constitutes “real work” came up in a coaching session I had with a newly promoted leader. They were struggling to see their new responsibilities as meaningful. Although neither of us was into sport, I asked: “Do football managers add value to a team?” That landed. They began to see their role not as a player anymore, but as someone setting the conditions for the whole team to succeed.

Closing Thoughts

Let me be clear: many technical experts make this transition successfully, and go on to become exceptional leaders. But being brilliant in one arena doesn’t guarantee success in another. These challenges don’t reflect a lack of capability — they reveal a lack of preparation and support. The career transition for technical experts is rarely straightforward. In Part 3, I’ll explore how we can do better.