My CTO shared this article with me recently and we had a conversation about it. That’s what prompted this post.
Hiring is one of the most emotionally taxing parts of leadership. Over the years I’ve interviewed many people and my approach has evolved significantly.
I recently joined a company where I invested real effort in shaping the interview process, evaluating candidates and making hiring decisions. It’s been a roller coaster - highs, lows and stretches of deep reflection.
Table of contents
Open Table of contents
The roller coaster begins
You’re in the middle of an interview. It starts well. You and the candidate are talking, laughing, sharing stories about work and life. There’s a genuine connection forming. You start thinking: this might be the one.
Then the technical exercise starts. The cracks begin to show. Despite the pleasant conversation, the candidate struggles with the technical side.
You find yourself encouraging them, supporting them - because you liked them in the first part. They manage to push through the first exercise and you feel a glimmer of hope.
Then comes the second part. That’s when it takes a nosedive.
Performance falters more. I never let my emotions show. I kept encouraging, we kept smiling, we kept going. Underneath, the reality was setting in.
The reality of hiring
Hiring isn’t like software development. In coding, you can iterate, explore dead ends, test your decisions.
Recruiting is binary: yes or no. 1 or 0.
I agree with Matt: you spend weeks or months building a relationship with a candidate, only to make a final decision that will shape both their future and your team’s.
The emotional highs and lows, the pressure of making the right call, the doubts that lingers long after the decision - these are all part of the process.
The principles of hiring
You can’t pause a conversation with a candidate to consider options of what to say. You need to show up and be on. It’s crucial for both parties to have the best information to figure out if this is the right match. It’s particularly brutal because you never get to find out the answer to “what if we’d chosen that candidate who we were uncertain about?”. You can’t A/B test people, you just have to do your best to get to know them and make the best decision.
I couldn’t agree more. Your decision is final and life-altering. You don’t get to go back and change it.
Finding the balance between technical skills and cultural fit is more complicated than building a modern distributed system.
If you feel sick or have a bad day, didn’t sleep well, you better reschedule the interview. You need to be at your best after all you are a face of your company.
To summarize
Hiring is one of the most critical and emotionally charged responsibilities of a leader.
It’s a process full of uncertainty. It’s also an opportunity to shape the future of a team and a company.
A roller coaster. And a journey of growth.