1:1s — Questions

Alex Aitken
3 min readJun 28, 2019

When I started my 1:1s a few months ago, I kept asking the same questions over and over. In fact, I found that I wasn’t really learning anything new about my team. So, I want to go over some questions that I’ve experimented with and see what questions you may ask during your 1:1s.

Was this 1:1 useful to you?

Now, I’m going to start with a retrospective question that I used to ask after every 1:1. I’ve stopped asking this question now because I’ve found the feedback I get from it doesn’t bring me anything. It’s a closed question with a slightly leading edge to it which doesn’t bring about discussion.

How can I improve?

I normally ask this at the end of every 1:1. I don’t always get responses, but when I do we can have a great discussion on what I’m lacking or even what the team is lacking.

How’s it going?

This was usually an ice-breaker/conversation starter for me. But now I believe this question doesn’t really open the conversation. Almost always the answer is “good”.

I’m experimenting at the moment with using this question as an ice-breaker. I can still get one-word answers, but mostly I’ve been getting slightly more open conversation flowing.

What are you most proud of over the last two weeks?

I’ve been experimenting very recently with this. It’s been catching my team off-guard. Usually they spend some time to think about it. I’m liking the fact that they can retrospect on themselves and come up with one or two things that they believe they’ve done well. It also helps open up conversation with follow up questions about what makes them proud of a certain accomplishment.

What challenges are you facing?

This is a very new focused question for me. It helps me identify where my team is blocked and where they may need help. But I also can get answers that could be brought up in a retrospective.

What are you grateful for over the last two weeks?

I tried experimenting with this question but mostly the team was confused about the question. I may bring it back at a future point when I feel like the team is more mature and I understand them more.

What is your favourite/least favourite thing about working at Careem?

I personally would not ask this every 1:1. But I think it’s a good question to ask occasionally. You can learn a lot about what motivates or demotivates a person. There is one but — and that is — that I found it hard to work this in naturally into conversation. It felt a little awkward.

What have you learnt over the past two weeks?

I don’t ask this question enough. It feels like it encourages the team to think on how they’ve grown and it really helps me to spot places where I might have missed their growth.

There are so many more questions you can ask. You can ask focused mission/value questions that apply specifically to your company to see if the team is aligned with the company values. You can ask for feedback on ideas or where they want to see their career. Let me know if you have other questions you might regularly ask.

Originally published at https://www.alexaitken.nz on June 28, 2019.

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