Lifehacker suggests 40 questions to ask your mentor. So that I don’t have to repeat myself, I’m posting the answers here in 4 chunks.
31. What’s the greatest obstacle you’ve overcome?
I was a terrible communicator. Very wordy and imprecise. I started to give presentations, I started writing a blog, forcing me to condense my thoughts into a clearer, simpler form.
32. What’s an obstacle you couldn’t overcome?
I’m terrible at understanding emotions. Working with clients, I can’t tell the cues that help adapt what I’m saying to avoid conflict. I struggle to pitch at the right level of detail. I can communicate a lot clearer than before, but as soon as there’s non-technical issues, I absolutely need an editor. Sometimes that’s a PM, sometimes it’s another technical person. Just another perspective before I put my foot in it.
33. What’s the most unexpected obstacle you’ve had to face?
I’ve done a lot of recruitment over the years, and sometimes I have to reject someone either because someone else was a better fit, or because they failed on some criteria that’s not on the list (such as the guy who, when interviewing with me and 2 female colleagues, only answered questions to me).
Whilst I’ve always been clear that the decision was the right one, explaining that decision is the hardest part about the job. Whilst I want to be direct and honest, I know that my default approach is not appropriate for people who don’t know me well, and so I struggle massively writing, re-editing and phrasing things before talking to the candidate. It’s easily the most stressful thing I have to do.
34. What’s a good thing to be afraid of?
I’ve worked with a lot of people who are motivated by the knowledge that whatever they build will be used and will make people’s lives that little bit easier. But it’s easy to let oversight or acquiescence let in features or bugs that will cause frustration or actual harm, whether by discrimination or universally.
Never underestimate the power you have to make or ruin someone’s day.
35. What’s been the most exciting point in your career?
Becoming a lead. Because letting go of having to do everything freed me up to think about how to make things better outside of the code I was writing. And suddenly everything was new and there were no easy answers, no red-green-refactor and no acceptance criteria for what makes a team work.
And I’m still learning.
36. Do you find any utility in holding onto regrets?
Regrets imply that you don’t like where you are now. And you have the power to change that.
Are there things I wish I’d done differently? Absolutely. And some of them I can’t even blame hindsight. I knew what would happen and I did it anyway for reasons that I couldn’t even justify at the time.
Know thyself. Learn the lessons. And move on. We all have professional as well as technical debt. Acknowledge it. Work with it.
37. Where do you think you could’ve done better, had you known what you know now?
I would have spent more time exploring at the start of my career. I got lots of opportunities, but the switch I made to a product company, which was also a lot smaller, taught me a lot more about myself. If I’d known how much I didn’t know, I would have jumped sooner.
38. Which values got you to where you are today?
“Don’t be irreplaceable. If you can’t be replaced, you can’t be promoted.”
So I document, I simplify. Any call I get out of hours or on holiday is a failure on my part, a bug in the system. If anyone has trouble following me in a project, I make fixing that bug my top priority. Don’t be a gatekeeper, don’t keep it to yourself, don’t be a bottleneck. Remove yourself from the bus factor.
39. When did you know you’d “made it” and were where you wanted to be?
The first time I got paid for writing software. Everything since has been an iteration on that. Review, reflect, improve.
40. Has your definition of success changed over the years?
It’s simplified. When I’m doing consultancy work, which is what seems to suit me best, success consists of 2 things, in this order :
1. Is the customer happy?
2. Did we make money?
The first is how to keep the lights on next year. The second is how to keep the lights on until then.
Everything else is just a way to break those down into smaller chunks.