How do you keep improving as a technical leader?

At our last CTO Circle gathering in Barcelona, the most voted question during the open discussion came from an engineering leader at Spotify:

“How do you keep improving as a technical leader?”

I loved the first reply, from Andrea at Microsoft: asking the question is already the first step to solving it.

Most technical leaders are so busy with fires, delivery pressure, hiring, stakeholders, and team issues that they rarely stop to think about improving their own craft.

Then the main answer from the room was simple: find people who are a few steps ahead of you, and learn from them.

Not necessarily a formal mentor. Sometimes it is just someone whose work and career you admire. Someone who has already faced the kind of problems you are facing now, and can give you honest perspective.

Personally, that has been huge for me while building Pullpo. I went from being a CS student with almost no idea about companies, sales, enterprise customers, fundraising, or product strategy, to figuring many of those things out through conversations with people who had already been there.

One important lesson: you usually do not need to give equity, pay expensive advisors, or join a mentor program to get help.

When I started my company, some advisors and agencies offered mentoring in exchange for equity. My advice today would be: be careful with that.

Most good mentors help because you are genuinely trying, because you come prepared, and because you ask about a real problem with enough context.

A bad way to ask is: “Can you be my mentor?”

A much better way is: “Hey Josh! I’m [intro]. I’ve been following your work at [background] and really admire it. I’m struggling with [problem that has to do with background]. These are the options I’m considering, and this is where I’m stuck. Would love your perspective.”

That changes everything.

A few practical ways to keep growing as a technical leader:

1. Write down one leadership problem you are currently facing before asking for advice. “I want to become a better leader” is too broad. “My team is missing deadlines because priorities keep changing” is useful.

2. Build a small group of people you can ask for honest feedback. Ideally, some are ahead of you, some are at a similar stage, and some work in different types of companies. You can also ask at #ask-anything and meet new leaders bi-weekly in #virtual-coffee-1-1 or at our in-person events.

3. Don’t look for one perfect mentor. Look for different people for different problems: hiring, architecture, communication, managing up, product strategy, fundraising, and more.

4. After every useful conversation, write down one thing you will actually try. Otherwise, mentoring becomes just another interesting chat.

5. Review your own leadership every few months: what problems keep repeating, what conversations you are avoiding, and what skill you need for the next stage of your team.