The final part of interviewing for my last job involved coming to Colombia for 3 days and having 21 1:1s. FYI, this is the kind of thing that immigration finds very suspicious and resulted in me being detained and searched for drugs in Canada. But I digress.

I firmly believe that people should interview their boss and have got to the point myself where I will schedule a call and up front say “I’m going to interview you to be my boss now.” – I want to understand things like how they will communicate with me, and what I can expect from them. So when I’m interviewing with people who might report to me I’ll encourage them to ask me anything they want to know – and I think I learn as much from the questions asked as they do from my answers.

The thing is, most people will not ask hard questions in this context. So I wanted people to feel good about me joining, and I wanted to get to know them, so I prepared a set of questions.

The Questions

1) How long have you been at [company]?
2) What were you doing before?
Note: These Qs helped me get a sense of why people joined – e.g. they followed a friend they worked with before.

3) What do you think your biggest contribution to the team is?
Note: This Q (weirdly) helped me discover some things that were happening that I really needed to know about before joining.

4) What do you think the team needs right now?
Note: Hands down the best question I asked from which I got the most useful information. People telling me what solutions they wanted surfaced the problems they were having without asking them to complain at me (which given most of them were at least somewhat trying to sell me on working there I might have got less honest answers to). Most interesting was when people working on the same or nearby things had different views of the problem.

5) What’s your next career goal (if you have one)?
6) What do you most want to learn?
Note: Helped me see where the team wants to grow, and the different approaches people want to take. Helps distinguish between people who go with the flow and people who are more goal-orientated.

7) Did you have a manager you really liked? What kind of things did they do for you?
Note: Reassuringly their current boss (who I reported to) was a pretty common answer to this. I think most people are not very intentional about the kind of manager they want. At least 2 people asked me this question from the opposite perspective – what kind of manager would I be and what could they expect from me?

8) Is there anything you think would make a big difference to your happiness at work?
9) … to your ability to do your job?
Note: Helpful for people who didn’t have a good answer to 4, or who focused on what other people (or teams) needed not their own.

The Process

I had the questions (numbered) on a page, and then I could just number people’s answers in my notes.

I didn’t ask everyone every question – the goal was to start off a conversation, and if they had questions for me then I wanted those to take precedence. I did ask everyone 1, 2, 4 and 5.

We arranged it team by team, most recent joined to oldest. I picked this order for a couple of reasons: building up context is hard, and grouping by team makes understanding that context easier. Newer people will have more a more recent perspective of joining, longer-timers will be better able to explain why things are the way they are.

Unsurprisingly, this many conversations was super exhausting. By day three, between each meeting I was hiding in the bathroom, fantasising about never speaking to another human ever again.

The Results

I learned a lot in these conversations and referred back to my notes as I started working there and even several months in. Question 4 is one that I continue to ask in basically every potential job conversation. It tells me so much about what people think the problems are without asking them to frame things negatively. The ordering worked as well as I hoped it would.

The main thing I would change is to ask more questions about feelings – what do people most like about their job? What are they most proud of? What do they worry about?