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The Startup Guide to 1-on-1's

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If there’s one thing I’ve found to be true over the past year and half of building this company, it’s that I’m completely winging it. Sure, I’ve read articles and books on how to build a company, but I've never actually done this before and I learn best by doing. So, every time I come across something that works for us, it’s a huge win for me. Doing 1-on-1’s has been one of those huge wins.

A few months after I started building our team, I really wanted a regular way to make sure everyone was happy. I pick up on little grumbles and or frustrations in our Slack chat, and would make a mental note or would just talk to that person right away. But I wanted a consistent and predictable opportunity for our team to talk about things.

Enter the 1-on-1.

What is a 1-on-1 and why do them?

Prior to building up the team around Baremetrics, I’d honestly never even heard of a “1-on-1”. I’ve been blissfully self-employed for nearly a decade and never really had a “real” job with a manager, so the concept has just never been a part of my career.

Essentially, a 1-on-1 is a regularly scheduled time for you, as the founder/CEO/manager/person-in-charge, to meet with the individuals on your team to learn more about what’s going well for them, what’s not, what their long term goals are, how you can help them and how you, as their manager, can improve.

After you’ve done a few 1-on-1’s with the same person, you’ll start picking up common themes that are important to them, small frustrations they may be having and ways they want to grow. Plus, it gives you an opportunity to learn more about them as humans and not just employees.

So, how do you do a 1-on-1?

How to do a 1-on-1 with your team

Actually pulling off the 1-on-1 is easy. I mentioned earlier about a 1-on-1 being “regularly scheduled” and that’s very intentional.

How often do you do a 1-on-1?

I do them every 2 weeks. I know some companies that do them every week and others that only do them once a month.

Your team size will likely dictate the frequency, but I find every 2 weeks is the perfect amount of time to keep issues from falling through the cracks while not constantly being in “meeting mode”.

Schedule them, and show up on time

You shouldn’t just drop in or send a message saying, “Hey let’s do our 1-on-1 now!” You need to schedule it and then stick to that scheduled time. Don’t be late. Don’t push it off until later in the day. It’s one of the most important times you’ll have with your team and you need to be clear that it’s important to you.

I automatically send a team-wide message in Slack every 2 weeks with a link to schedule a time that works for them.

Most 1-on-1’s typically last about 30-45 minutes for us.

What to ask and talk about

Okay, so you’ve scheduled your 1-on-1…now what? What do you talk about? I typically ask about 5-8 questions each time when meet. Or rather, I let those drive the conversation.

I try to ask question from a few different topics.

Goals — I want to know what their short term and long term goals are, both professionally and personally. And then I want make sure I help them make those goals a reality.

Business — Even if everyone on your team hasn’t built a business before, they’ve likely got some solid perspective that you don’t, just because they’re not you and don’t think the same as you. Hearing how they think the business could be improved or ways it could grow are always good things to get feedback on.

Happiness — At the end of the day, if your team isn’t happy, what’s the point? If they’re really happy, is it because of recent progress on the product? If they’re unhappy, is it because you’re overworking them? Find out what’s making them happy (or unhappy) and you’ll get a lot of perspective on what makes them tick and how you can help.

Team — Making sure your team is moving along as one cohesive unit is crucial and 1-on-1’s are a great time to find out if there are any issues you can help resolve before they become a real problem.

Management — This one topic is about you. I specifically ask about ways that I can improve as well as things I can do to help them work better.

Performance — Talk about a job well done, or an area that needs improvement.

Each week I try to ask a different set of questions. Here’s a sampling of some I’ve been asking over the past few months.

  1. Is anything in the pipeline unclear or confusing?
  2. What could I do to make your work easier?
  3. How’s your workload?
  4. What are 3 things you would like to see when you show up to work every day?
  5. Do you feel challenged at work? Are you learning new things?
  6. What is something I could do better?
  7. How could we make our weekly stand-ups more effective?
  8. What do you want to be doing in 5 years?
  9. How do you feel your work/life balance is right now?
  10. Do you feel like you’re on the same page with the team as a whole?
  11. How well-received do you feel your opinions are when you offer them up?
  12. What are the top 3 things that you feel waste your time during the day?
  13. Are there any projects you’d really like to work on if you had the chance?
  14. Is everyone pulling their weight on the team?
  15. Are there any big opportunities you think we’re leaving on the table?

More than anything you just want to have a conversation. Try to keep it as laid back as possible and open yourself up as well. This isn’t you grilling them on their performance, it’s you genuinely wanting to understand what they need and how you can support them better.

Follow up on what you’ve talked about

If you ask all of these questions and then never do anything, you’ve missed the point. You need to follow up and take action.

I keep track of all of the questions and answers in Evernote and each week I review what my team has answered and make sure to fix anything that they’re having issues with, or follow up if there were specific things they were having trouble with.

Additional reading & resources

The main thing here is to not overthink it. Just start. You’ll figure out after doing a few 1-on-1’s what works for your team and what doesn’t, but the only way to do that is to actually do them.

That being said, here are a number of resources that can help a lot as you get up and running.

What about you? Do you do 1-on-1’s? What has worked well for you and your team? Share your tips in the comments!