One-on-ones are my most valuable meetings; here’s how I run them

Mathilde Collin
The Startup
Published in
5 min readMay 3, 2019


Front employees having a one-on-one

Employee engagement & retention at Front is high. We have an employee NPS of 97 and in a recent employee engagement survey, 93% of the team agreed that they know how their work contributes to the goals of Front. We’re far from doing everything perfectly, but there are are few things we’re probably doing right, and when I feel like something is working and having a big impact I like writing about them so other people can benefit from them too.

In recent conversations with the team, I’ve learned that the way we do one-on-ones offers a simple model for demonstrating care and boosting engagement. I also get a ton out of them. So here are the details.

We have three kinds of one-on-one meetings

Weekly, managers and employees meet for a standard one-on-one. They report on progress, unblock issues, and ask and answer questions. The goal is to ensure people are working on the right things and they understand why that work matters to the business. We strive to reserve as much one-on-one time as possible for issues or concerns that can’t be discussed out in the open or shared via email. We keep our one-on-one topics/agendas in a Paper doc so the other person is notified when an edit or addition is made. If during the middle of the week you see something added that needs to be addressed immediately, you can connect sooner.

Monthly, managers and employees meet for a pulse check on general happiness. Ahead of time, managers send six to eight questions for the employee to be prepared to discuss. We always include:

  • In the past month, what have you been happy about?
  • In the past month, what have you been less happy about?
  • Any questions/feedback for me?

And a few out of this list:

  • How do you feel about your goals for this quarter?
  • Any feedback for me?
  • How could I be a better manager for you?
  • What can I do to make your professional life better?
  • What’s the biggest problem of our organization?
  • What don’t you like about our product?
  • What would you like to improve next quarter?
  • What would you like to achieve by the end of the year?
  • What would you like to learn?
  • How is your team doing?
  • What would you like to be better at / in which areas would you like to grow?
  • After X+ month/years at Front, how do you feel overall?
  • If you were me, what would you do differently?
  • What are the things you’ve done since you joined you’re the most proud about?
  • Is there anything I could do to invest more in your growth?
  • In the next month, what would you like to do differently from last month?
  • What’s the split of your time today between X/Y/Z? What would you like to spend more/less time on?

I ask every person to share their responses to these questions with me at least 24 hours before our scheduled check in so I have time to prepare my feedback and work on their questions.

A new program we’re rolling out is every six months, managers and employees meet to discuss career development. Ahead of this meeting, the employee prepares responses to such topics as what he/she likes and dislikes about their current role; careers he/she admires; where he/she wants their career to be in 6 months, 12 months, 2–5 years; and a list of skills, competencies, and experiences that he/she needs to develop. In reviewing this worksheet and identifying growth opportunities, the employee and manager commit to next steps that will help the employee pursue their desired career path. The managers then connect regularly with their direct reports on these plans to give feedback and ensure people are tracking to their development goals.

They take work…

I’ll be honest, these meetings are a lot of work. I have 12 direct reports. It takes a lot of time to prep for and follow through on commitments made in all of these one-on-ones. There are a few things I’m doing to make it easier:

  • Every one-on-one is set up as a recurring event and unless one of us is on PTO or out sick, we never reschedule! It’s critical to demonstrate that this time is important.
  • I have a recurring event on Mondays where I spend 45 minutes prepping for that week’s one-on-ones.
  • My EA helps by making sure I know about all the one-on-ones I have that week and she even drafts emails for me to send to direct reports with the questions I want them to respond to, too (thanks to Front 😉).

… but it’s worth it

If done effectively, these one-on-ones are an opportunity to show my team that I care about them, their professional success, and their overall happiness. It gives them an opportunity to step back and think about what they need to be successful, and to hold me accountable to setting them up for this success.

I also get incredibly valuable feedback from these sessions that has changed the way I lead and manage and even given me new perspectives on business opportunities. A few examples:

  • In Front’s five years, I’ve never been surprised by any employee departures because of the candor in which what’s working and what’s not is discussed in my one-on-ones.
  • My two favorite questions to ask direct reports are “if you were me, what would you do differently” and “what don’t you like about the product?” From the first, I learned to more consistently repeat our vision and strategy for the team to absorb. And from the second, I learned that it was confusing to know if a Front conversation was shared and with whom, which is what inspired product changes we shipped last year.
  • I’ve learned other things as well, like: I’m not great at sharing positive feedback, I can look annoyed when I’m listening to a presentation, and the company needs to do a better job of celebrating all team’s successes, not just the revenue and product teams. I’ve taken action on all of this feedback.

My purpose is to help people be happier at work. It’s why I founded Front and why I care so much about helping my team do their best work. I’ve written before about how we run All Hands and how we practice transparency, but I firmly believe that making sure you’re getting the most out of your one-on-ones is another really efficient way to demonstrate care and boost engagement.

If you have other advice for great one-on-ones, I’d love to hear it.

Update: my team at Front built templates for these meetings. Download if you’d like some help getting started yourself.