4 Simple Steps for Starting Employee One-on-Ones

Guest Post by Chris Zaugg

Originally posted on uptickapp.com.

So you’ve decided it’s time to start doing one-on-one meetings with your team.


But before you dive in, there are some things you need to consider to make sure you maximize the time and effort.

Just like a good conversation, the best one-on-one meetings are a collaborative effort and go beneath the surface. It’s far too easy to sit down, crack open the laptop (to monitor your internal chat and email), and then just give status updates on the work. 

This is not the one-on-one meeting you OR your team member wants.

I had been doing one on ones for years, because I thought that’s what leaders should do. It was a noble thought, but my execution was all wrong.

I didn’t realize the problem until one of my most productive staff members was feeling lost and requested a regular, weekly one on one. It started me thinking…what does she want from the meeting? What do want from the meeting?

Since you and the person you’re meeting with need to come prepared, it’s best to have a conversation about what you both want to get out of the time together.

So where should you start?

1. Ask them what they hope to get from meeting together

I know that sounds super obvious. But clarifying expectations will save you hours of frustration and will help you build trust with your team member. If you know what their goals are for the meeting, you have a much better chance of having a mutually satisfying one on one.

Here are some things to listen for:

  • They want you to clarify their priorities.
  • They’d like more input on the direction of the company or department.
  • They want you to know what they actually do in their job.
  • They see some important opportunities, and they’d like permission to pounce on them.
  • They want you to help remove some roadblocks they’re facing.
  • They want your honest assessment of their progress.
  • They’d simply like to get to know you better – get some “face time” with the boss.

2. Listen intently to their answers and ask follow-up questions

It’s been my experience that the first answer someone gives me isn’t always the real answer. They might think it is, but if you drill a little deeper you might find they have a different motivation for connecting. If you simply take notes and move on you might never get to the core issues.

When they give you their first answer, follow up with questions like:

  • Can you help me understand a little more about that?
  • What’s the best way for me to share praise with you?
  • What’s the best way for me to give you constructive feedback?
  • When you face a particularly difficult issue, how does it make you feel?
  • Do others on the team feel as you do?

3. Share your objectives for having a one on one meeting

After you have listened thoroughly and intently to your employee it’s time to share with them your goals and expectations. But don’t jump in on those too early. I’ve found if I let someone share everything on their mind I’ll have the opportunity to share whatever I want. So be patient.

Here are some reasons I’ve shared for why I want one on one meetings:

  • I want to get to know them better.
  • I want to serve them according to their unique needs.
  • I want to hear great feedback and collect ideas.
  • I want to collaborate with them on goals and priorities.
  • I want to make sure we’re working on the right things.
  • I want to know what they actually do.
  • I want to know what gets them pumped, and what gets them down.
  • I want to keep my finger on the pulse of my organizational culture.

4. Collaborate on what the meeting should look like

Now that all the cards are on the table, talk about how you can both have your needs met. In our company we use our app, which gives us a structure for the one on one meeting. Within that structure, however, there is a lot of freedom to emphasize certain things that are important to each staff member.

Because it’s important that you come to a mutual understanding, (and you already know what you think), ask your team member a few questions:

  • How are the goals we shared similar?
  • How are they different?
  • How do you think we should handle our different expectations?
  • Once you have walked through these exercises, it’s time to implement your structure.
  • Be clear about what you’ve decided so you both come into the next meeting with the same expectations.

Repeat steps 1-4 which each person you meet with – all check-ins are a little bit unique.

  • Don’t let yourself fall into the “one size fits all” trap. Approach each person as an individual with different needs. It may be more complicated at the outset, but it will pay BIG dividends in the end!
  • And don’t assume that because you asked these questions once that the answers will perpetually be the same. People change. Their motivations will change. Periodically touch base with these questions to ensure you’re on the same page.

Making one on ones mutually beneficial with my staff is the key to ensuring they won’t end up being a frustrating, meaningless “time sucks”. They’ve been a game-changer for me, and I hope these principles will help you get started, too! 

It’s important to ask your team member what they hope to get from meeting together, then listen intently to their answers and ask follow-up questions.

Chris Zaugg


Chris Zaugg is the President of OPIN Systems, where he and his team have created Uptick – an application with a vision to transform businesses one manager/employee relationship at a time. For more helpful articles about how to manage your team, you can check out their blog here. You can also connect with Chris on LinkedIn.


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