This is a part of my series on one-on-one meetings. For all posts in the series and free downloads to help you start and run the meetings go here: One-on-One Meetings for Leaders

When I finally learned the format for my one-on-one meetings (see part three) I thought that was it. I was prepared to enter a state of leadership nirvana full of magical romps through fields of sunflowers and fairy dust with my team. But so much was still missing.

How to Run a One-on-One MeetingBelow are the remaining steps I took, the results of the meetings over time, and some common questions and answers others have me asked about one-on-ones.

The three hardest things I did to improve one-on-one meetings:

  1. I addressed the elephants in the room. If you remember in part 2, I wrote that I did not address the elephants in the room. “Yeah, you lashed out at Jim yesterday in a meeting and publicly insulted him, but how are we on the Q3 budget?” One of the rare times I changed 15-10-5 format was when I needed to immediately address an elephant in the room. That came first, then we got back on schedule. Elephants can be work-related or personal. If you notice that Larry has been acting withdrawn and quiet lately, that is an elephant. It must be addressed. When I got over my fear of conflict and addressed these issues, the rest of the meeting and the rest of the week changed for the better.
  2. I listened and I took notes. Listening is an active skill. For me it’s like an Olympic…ooh shiny object. I concluded that it’s not because I have ADD but because I am selfish. I really don’t enjoy listening to others. It’s sad, but true. So I forced myself to listen. I forced myself to make at least one note every minute or two. By the end of their 15 minutes, that meant I should have at least eight notes. Which meant I had listened for at least 40 seconds. That was a vast improvement for me. This allowed me to learn about them, ask follow up questions, and show genuine interest. The act of taking notes itself showed that I was listening and withing a few weeks of doing this, my team opened up tremendously.
  3. I followed through. This was made a lot easier by actually listening and by taking notes. One other important change I made was to no longer scheduled back-to-back meetings. This gave me at least 10-15 minutes after the meeting to review my notes and transfer any action items to my list. I then made a point to follow up via email after the meeting, thanking them for the meeting, reminding them of what they agreed to do, and letting them know what I was going to do. During the course of the week, I made sure to let them know my progress in helping them. The over-communication was adored to say the least.
So what were the results of all this effort? Did running better one-on-one meetings really make that much difference? Judge for yourself. Here is what happened:
  1. I began to actually care about my team members. 
  2. I began to take action on that caring. One guy had a son who wanted to learn golf. I knew a golf instructor who specialized in kids. I bought a gift certificate for him. This meant the world to him. (Full story here)
  3. I learned from them. We talked about kids a lot. One guy had 7 kids. My wife was pregnant with our first (and only to date) child. I got more out of those meetings than he did I think. He loved sharing stories and I learned so much about fatherhood from him. That same guy was also a New Testament Greek minor in college. I truly learned what Jesus was saying to Peter at the end of the gospel of John. When you know the Greek, it changes everything.
  4. I laughed with them. 
  5. I cried with them…and gave some hugs. One guy’s dog died and when he told me, there was nothing I could do but sympathize with him and hug him.
  6. I got “inside information.” What was truly going through their minds? What were their fears at work? What skills did they lack? What were some skills that weren’t being leveraged?

one-on-one-download In short, we grew closer, more efficient, and we simply got stuff done.

Common One-on-One Meetings Q & A:

Q: Did you set expectations up front or just lead them that way?

A: I told them up front. The great thing I learned over time with new hires is that when we hit the mark where their time was “up” and I didn’t say anything, they couldn’t believe it. Same thing with how I used to leave my phone (work phone that is) on during meetings in my office and then I would not answer it. I wouldn’t even look at it. They usually asked “aren’t you going to get that?” To which I replied, “No, I am meeting with you right now.”

Q: Did I keep it to 30 minutes?

A: Generally, yes. About 30% of the meetings stayed in the 20-25 minute range, 30% in the 25-30 minute range, 30% right at 30 minutes, and about 10% of them went over, some as much as 15 minutes. It was worth it every time. I budgeted 45 minutes just in case so no one felt rushed and as I said above, I never scheduled them back-to-back.

Q: I don’t have the time for these things. (OK that is not really a question but a regular comment)

A: Yeah that is a load of crap. I know of managers with 20 direct reports that spend 30 minutes with each team member, each week, one-on-one. That’s 10 hours a week, not including prep time and follow up time! Leadership is about getting others to do great work. It honestly took me a few months to understand that my 30 minute investment in a team member was 30 minutes less work from me and probably 3-10 hours in increased productivity from them. That is a pretty good trade off. Plus, I used my time quite often to delegate. It’s simple leadership economics: 30 minutes of my time = 3-10 hours increased work from team. Win.

What objections do you or did you have to doing one-on-ones? What is the biggest way you can improve them?


Matt helps online business owners and brands, small and large leverage the power of partners to grow their businesses. He teaches you how to make money as an affiliate and how to work better with affiliates. Entrepreneurs and companies such as Shark Tank's Kevin Harrington, Zig Ziglar, Ray Edwards, Brian Tracy, Lewis Howes, Shutterfly, Jeff Goins, and Michael Hyatt have trusted Matt to run their affiliate launches.

9 thoughts on “How to Run One-on-One Meetings | Frequently Asked Questions

  1. Jon Stolpe says:

    Matt, this looks like a great series and one that I can use in my own world of team leadership. I’ll be going through the other three posts for sure.

    1. Matt McWilliams says:

      Great Jon. Thanks for the kind words and I do hope they help!

  2. jryan2445 says:

    Matt, good timing on this. I will use it in a management training I am planning.

    1. Matt McWilliams says:

      Awesome Jim. That made my day!

  3. Chance Smith says:

    Keeping meetings to 30 mins is super rough. Either I talk to much, because I love details, or I don’t have set things we are going to talk about inside our specific categories.

    I can see now that when I ask, “OK, so how are the Marketing Plans going?” Which could lead to 15 scenarios or ideas to talk about. Instead I am going to ask about more specific details and anything else we will write down to talk about at the end of the meeting, else it will be added to the next follow up.

    You really have me thing Matt. I really like what I am read!

    1. Matt McWilliams says:

      30 minutes for a one-on-one is a guideline. You should stick to it at least 2/3 of the time. It’s the one meeting that I like to allow for overage on. Which is why I never schedule them up against another meeting unless I absolutely have to.

      Remember if anything should go long, it is THEIR time, especially early on. I would wait no less than 10 weeks before you ever talked more than 8 minutes in you one-on-ones (if you are the leader)

      I am going to write some stuff later on about one-on-ones from the other perspective. 🙂

      1. Chance Smith says:

        I can’t wait to read it! Keep it up and thank you for all the insight!

      2. Chance Smith says:

        Suggestion: Add your One-on-One Email and Notes Template as a free incentive to sign up and subscribe with their email. They are great resources!!!!! You could edit your posts in your series to suggest them to sign up to check out the download. Thoughts? Cheers!

      3. Matt McWilliams says:

        Already in the works actually 😉

        But great idea nonetheless!

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