Empathy for the devil

Technical leadership is a weird field to work in. It’s a formidable combination of deep technical insights and a wild variety of people.

The managers who roll into tech have a hard time grasping the overwhelming landscape of frameworks and architectures. Coming from a non-technical background is the hardest path to technical leadership.

But the techies who roll into leadership also struggle. They often find it hard to deal with the variety of people and the lack of clear, hard decisions.

I know I did when I first moved into leadership.

Techies that get into leadership believe their technical background has given them insights that others don’t have. “I understand the software development lifecycle better than this MBA type“. That is 100% the case. They usually fail to understand early on that managers from a people or business background also bring valid experience. And too often, that experience is lacking in the technical profiles.

In my experience, developers underestimate how black-and-white their worldview can be. The thing compiles, or it doesn’t. All tests run, or they don’t. Software development has trained us to think in binary.

But dealing with people is never black and white. It’s an ocean of grey trade-offs. And while developers know that people aren’t machines, the binary thinking often translates into their view of leadership.

The transition from software developer to technical leader requires them to drop some of that binary thinking.

Aspiring leaders who are still in the black-and-white phase of their learning curve stand out like a recruiter at a Java conference. It’s that obvious.

The main tell is how they treat people asking them for estimates and timeframes. Would-be tech leaders treat these questions as dumb, hostile, or plain evil. They ridicule and alienate those that mention deadlines and budgets. They band together on social media and conferences, arrogantly scoff at those who don’t “get” it, and pat each other on the back.

Every deadline is arbitrary.
Every manager is evil.
Every stakeholder is dumb.

The problem is always outside of their area of control. If it’s not a Yes, it’s a Hell No.


The truth these aspiring leaders still need to learn is that these “evil” questions don’t come from a bad place. In fact: difficult questions are the price to pay for being a leader. It comes with the territory. Being able to give an imperfect but adequate answer to those questions is why people choose to follow you in the first place.

When people turn to their leader with difficult questions, the mature reflex should be empathy, not arrogance. Why are they asking this? What problem are they trying to solve? Why are they turning to me?

Experienced leaders have honed the skill of giving imperfect but helpful answers that manage expectations and build trust. These answers don’t need to be right, but good enough.

Being able to put yourself in the shoes of those that ask hard questions is the technical leadership superpower.

Without that, why would anyone follow you?