Solid career questions to ask team members

Here’s a quick and boring post about career questions. As a lead at Automattic, I think a lot about the career development of my team members. As a lover of questions, I’ve found the following ones to be exceptionally useful and I’ll add a little bit about why below each:

What does job satisfaction mean to you?

Automattic is a company full of folks from all over the world. Just on my team, I have folks from 6 different countries! I’ve learned loads from this including not shoving my Western, Americanized standards of what job satisfaction is onto others. So many factors go into job satisfaction that it’s important to make sure that what it means for your team member is extremely clear from the beginning.

What do you think about your career when you step outside of your current job?

When working somewhere, it’s easy to hyper focus on just the job you have now. By asking this, I’m hoping to prompt folks to think bigger picture. It also clues me in to how I can best help them be successful for that overarching career whether they are or aren’t at Automattic long term. I care about the folks on my team as people not Automatticians – I want them to be successful wherever they go.

If you could have any other automattician’s job (what we call people who work at Automattic), whose would it be? Hat tip Brie!

I’m currently obsessed with this question mainly because it reveals realistic career growth within a specific context (aka the company where you work). It also gives me the chance to talk to that person and connect them with a team member in many cases!

What are your top 3 “bucket list” items for your career or work? Hat tip Brie!

The day to day grind can be overwhelming to the point that you never start work on those Big Projects. By identifying what those things are, I can help hold a team member accountable and create opportunities for them to run after those items. I love when I hear about a new project coming up and I can think of the perfect person for the job because I know it’s in line with what they themselves want to do.

When you think back on your work thus far, what type of work have you really enjoyed the most? 

This often ties directly to job satisfaction and career growth. If someone thinks they want to manage people but really hates when they have to interact with others, it’s likely a good sign it won’t be a good fit. On the flip side, if working closely with others and being a mentor was one of their highlights being a lead might work out really well!

Which type of career growth most resonates with you: moving into people management, leading projects, becoming a subject master, or moving into a new role? 

You can define each of these yourself but these tend to be the main pathways at Automattic. This brings it back to the realistic and practical part of career growth.

Where do you want to be 1 year from now? 5 years from now?

I find this helps me create a career path of sorts for them. I especially like those two different timeframes as I think without having the 5 year it’s hard to know what to do in the next year ahead.

What keeps you working here? 

Plain and simple: this goes back to what is satisfying them about their job.

What makes you most nervous about your career?

I like to know fears to know when I might be able to help. If I can’t, that’s also a great thing to get out of the way too :).


Hope these help – I’ve found them to be particularly useful. Remember the questions are just the beginning. Always try to follow up with clear actions.


Photo by Jungwoo Hong on Unsplash


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