I Said Director. I'm Not Sure I Meant It.
I started working with a coach a few months ago. His name is Fred, and we meet every couple of weeks.
I went looking for one because I needed help figuring myself out. Not a specific problem I was stuck on. The bigger question of what my career should actually be.
What I wanted was someone outside of tech. That was deliberate. I didn’t need another engineer to tell me about engineering. I wanted someone who had moved up through a lot of different organizations and understood how that actually works, because that’s the part I never learned.
The first real question he asked was where I saw myself in three to five years.
I said I wasn’t sure. The role is still new, I’m figuring out what it even is, and I need time before I can say where it goes. Then, later in the same conversation, I told him I wanted to get to director.
Both of those came out of my mouth in the same session. I’ve been sitting with that ever since.
I think I want it. I’m not sure yet. And I’ve spent most of my career not having to sit in that gap, because the next step was always obvious. Engineer, then senior, then staff, then senior staff, then architect. I knew what I was and I knew what came next, even when getting there was hard.
Now I’m here, and it stops being a line.
What pulls me toward people leadership is the same thing that pulls me toward teaching. I like training people up. I like pushing younger engineers to get better and helping them figure out what they want. That part I’d do all day.
What pulls me away is the politics. You never fully escape it at any level, I know that. But my read is that it gets worse once you’re a people leader, and I don’t know yet whether that’s a trade I want to make.
That’s the honest state of it. Not a plan. A tension I’m still working through.
The other thing Fred has me thinking about is mentors, and this is the part I’d want anyone reading to actually take with them.
Something he said early on stuck: the thing that got me here is not the thing that moves me forward. Being good at the job was enough to get in the door. It doesn’t get you the next one.
That’s uncomfortable if you came up as an engineer, because being good at the job is the whole identity. You shipped something, people saw it, that was the evidence. It worked for years.
Then at some point the decisions about you start happening in rooms you’re not in. What gets said depends entirely on who knows you well enough to say anything at all. Those are the people who vouch for you to your leadership or to theirs, and who bring your name up when a bigger project comes together and somebody asks who should run it.
I had two mentors who did that for me. Both of them left the company.
I don’t think I understood what I’d lost until Fred made me look straight at it. I’m rebuilding now, inside my company and outside it, and I’m starting later than I should have.
This connects to something I wrote last time about not making enemies. I meant it then as advice for anyone moving into architecture. It’s the same thing from the other direction. Every person you don’t burn is someone who might say your name when you’re not there.
The changes I can actually point to are smaller than I expected.
The first is that I stopped bringing problems. When I see something heading the wrong way now, I don’t just say so. I bring three options with the downstream impact of each one, lay them out, and let people choose. Same information, completely different position in the room. I’m not the guy objecting. I’m the guy who did the work.
The second one is a single word. I’m replacing “but” with “and.”
“That’s a great idea, but” erases everything in front of it, and the person hearing it knows. “That’s a great idea, and here’s what else we might consider” keeps them in it. It sounds like nothing. It is not nothing. It felt awkward for about a week and then it started changing how rooms respond to me.
That’s most of the shift, honestly. Same opinions, same read on the technical problem, delivered in a way that makes people want to build with me instead of brace against me.
About Fred. His full name is Frederick C. Jefferson III, and his practice is Jefferson Leadership. He spent years in leadership development, including running the IDEA Center for Inclusive Leadership at the State Department, and much of his coaching centers on Black executives navigating predominantly white institutions. His site says it better than I can: https://www.jeffersonleadership.com/
I came to him for the outside-of-tech reason. What I got was someone who has spent a career studying how people actually move through organizations, which is the thing nobody teaches you and the thing I needed most. If that’s what you’re missing, he’s worth a conversation.
If you’re at a point where the next step isn’t obvious anymore, go talk to somebody about it. It doesn’t have to be a coach. But find someone outside your field, because the people inside it will only ever describe the path they took.