Top 5 challenges of leadership in tech

Top 5 challenges of leadership in tech

A list of perhaps not-so-conventional challenges from my experience

Play this article

#1 The concept of leadership becomes misleading (pun intended)

If you google for leadership and check the pictures page, you will see someone with a flag / in front of the line / standing out from the crowd / being number one in any other form. In practice, leading tech teams is seldom about being in the spotlight.

Leadership in a team of scarce, highly valued, top-paid professionals is more about being able to manage and direct processes and people without using the power of authority. Becoming the process enabler + earning trust and respect + coaching + some servant leadership = best formula to lead a tech team. Never forget to stay away from command and control, micromanagement and any form of coercion.

#2 Building safe environment

Tech people are often fragile. And I’m not implying being nerdy introverts barely walking out from their caves. Although, that happens quite often as well 🙂

The performance of a tech person is maximized when they know there is no penalty for bringing bad news, expressing opinions, disagreement, and all that sort of stuff. The same goes for asking questions, looking for help, and being incompetent outside of the area of own expertise.

Surprisingly, while being vulnerable to the outside world, tech people are often arrogant af and lack any sense of diplomacy between each other. One can check Stackoverflow (or any other resource online) that gathers technology experts and encourages them to communicate. You will see, I’m not even remotely exaggerating.

This is a true leadership challenge to balance opposite sides of the same group. Being a protective proxy for the outside world, building transparent feedback and change management processes helps tremendously.

Meanwhile it is important to focus on process improvement, not develop bureaucratic nonsense. E.g. feedback received in some formalized code reviews is perceived way better than the one provided during a daily meeting.

#3 Keeping momentum while managing complexity

Building complex technology product is complex. And managing this complexity makes another leadership challenge.

Do you know why product managers always worry about backlog, decomposition, sprints, etc.? Not only because of business needs. You simply can’t expect an engineer to work on some 2-month behemoth task and come back with a usable result. Their enthusiasm will be dead somewhere in the middle, focus will drift away to finding shortcuts and premature optimizations. A couple of rounds of such exercise and a very scarce and expensive professional will need a retreat on Bali or, worse, (quietly) quit.

That’s why it’s so critical to break things down into digestible, yet testable / usable / deployable pieces. Sounds like a challenge, right?

While poor complexity management is a master assassin, context switching is a serial killer of productivity. Switching may be caused by many things: afternoon meetings, meaningless reporting routines, chats that never go silent, or product owners pinging the team directly for status updates.

Keeping distractions away from the team is one of the key responsibilities of a tech team leader. That includes organizing internal communications in a non-intrusive way, and keeping business away from the team outside of dedicated contact hours.

#4 Clients (may) have no clue what they want

Or worse, have a rock-solid certainty about the end result, while actually needing something completely different.

Some may argue that this challenge is not about team leadership but think again. What is more demoralizing for the team than to discard some months' worth of work when a client suddenly 'wakes up'?

It's up to the product/project manager to be a facilitator, to coach, educate and guide stakeholders. That includes helping to understand what they want and how to convert expectations into a list of actionable user stories and requirements.

#5 Your project will (most probably) fail

Let's skip the question of why tech projects fail for now. It is as complex, as it is self-explanatory. Yet according to many sources, there is over a 50% chance that any given IT&T project will not deliver the expected value.

How to lead a team that is statistically destined to fail? Certainly not an easy endeavour.

Risk management skills help PM to address this challenge. Breaking projects and products into smaller phases/releases, communicating hard truth in time, and being data-driven are first-aid steps to minimizing the risk of failure.


Those are the Top 5 PM challenges from my practice that appeared in any project or product management job I took. Overcoming those challenges takes nothing else, but developing core PM skills.

Stay tuned for more insights into professional best practices.