Everyone has a different shape to their career. Some people can stay someplace multiple decades, with managers and co-workers flowing around them, while they go on accumulating organizational lore. Some people have an internal timer that goes ding! after 2 years, or five, or ten. Some people follow managers passionately and leave when the vibe is not right. None of these are wrong, and in fact, we need all those kinds of people.
I have long described my job trajectory as being a smokejumper. I am incredibly great at dropping onto a small smoldering problem and digging some fire lines. You can drop me into pretty much any tiny-to-small software company, and I will have the experience to do anything comms-related. Fix the docs? Sure. Ghostwrite talks for the founder? No problem. Sales enablement, conference planning, MC, brand voice, I’ve done it all. And if I don’t know how to do it myself, I know who to call, and I promise they’re good, too.
This week I encountered a new type of interview, and while I can see the intent behind it, you could not design an interview process less advantageous to me, a very senior person with a ton of contracting experience.
The idea is that you go through every job a person has had, chronologically, and ask them the same set of questions about each position. Theoretically, this gives you a good idea of their decision-making processes over time, and whether the same issues keep coming up over and over in their jobs.
However, what this meant for me was trying to decide how someone I worked for 20 years ago felt about a 6 month contract.
1) I have no idea. How they felt about my problem-solving skills was not my problem, as a contractor.
2) I neither remember nor care, nor can you contact them, because that company went under.
3) I left because my contract was up. That’s… how it goes? I’m not here to hang around and replant trees. I unfucked their docs, left them a good template and instructions, and went on to the next tangle.
4) It’s a very boring person who has no career pivots in 30+ years. If you want to know about my current skills, let’s start there and not in the misty past.
I do have times that I settled down and worked longer someplace, and then I usually remember my manager’s name, at least. But that’s usually only for jobs that were interesting enough that I could keep learning, which is a different mode than “expert hired to solve a problem”.
If you want to know how I am at marketing, ask me to contract with you for a week, or get someone who knows how to interview marketers to team-interview with you, or look at my past work.
I don’t blame the interviewer. It’s fiendishly difficult to hire for a role that you yourself don’t understand, and the risks of bad hires at early stage are very high. But as I thought about this interview style, I wondered who would be served by it. Younger people, who wouldn’t be slogging through 30 positions. Less adventurous people, who grow a career at a single org for several years at a time. Men, because who wants to hear the sad tale of “and then I got a sexist boss and had to quit” over and over? White people, ditto ditto, racist.
The concept seems sound – examine a candidate’s decision making in several contexts, derive patterns of behavior. But in practice, it’s probably not going to get you the kind of dynamic, chaos-tolerant, jack-of-all-trades that is so useful in a startup. It was designed for Finance VPs, and that’s who would look good in it.
Excelsior.

