Struggling with the responsibilities of being a new manager, I received encouragement from an unlikely person. This next post is a short one. It's about the power of encouragement at the right time and place.

2014 was my first year as a manager, and it had been brutal. In addition to feeling the (normal) overwhelm of transitioning from technical IC to manager, I was also struggling with performance managing one of my direct reports, who was pushing for a title and compensation bump and running into process and procedural hurdles from the company. I felt trapped and caught in the middle and completely out of my depth, losing sleep night after night wondering how I was going to make this happen.

I worked with senior leadership and our head of HR to work through the logistics of this process (because reasons). This specific case was thorny because things weren’t straightforward on both sides. My report had gone about the process in a way that turned messy, but the company itself hadn’t formally defined a career ladder, so it was kind of on us.

I’d show up multiple days in a row to work with our HR director to push the process forward and keep her apprised of updates in the process. She’d give me input on how I was handling the process, and I’d run that back with engineering leadership to figure out a way forward.

The back and forth was exhausting.

Finally, we got it done. I delivered the news of the promotion and title bump to my direct report, plus the constructive feedback I needed to deliver. I was drained. I walked back to our HR director and let her know the news, expecting a perfunctory acknowledgement.

She thanked me for the news, and on my way out, she stopped me.

“Andrew, you did a good job with this. It wasn’t easy.”

I thanked her for the compliment.

She looked me in the eye. “You’re going to be a CTO one day.”

I nearly laughed in the moment, but thanked her and walked out. What did she know about me? If management was this stressful, no way in hell I wanted to be a CTO.

I thought nothing more of it in the moment, just glad to be done. But in the years to come, I’d go back to that moment in times when I’d doubt myself. The words, “You’re going to be a CTO” wasn’t meant to shoehorn me into a specific vision of the future, but meant to tell me, “I see you have the potential to rise to a level of leadership that you can’t see yourself.”

Truth be told, I didn’t think I was really cut out for leadership. I didn’t think I knew how to handle management, nor handle messy situations well. There was much to critique about how I had handled things. But a few well-placed words at the right time from the right person changed my trajectory and fanned a little ember of self-confidence in years to come.

These days I try to do the same for my mentees and sponsees. I try to have radical candor when giving people feedback. And when I see glimpses of them rising to the occasion, I tell them, I believe in you. You may not know it now, but you will succeed.