How to Hold Better One-on-One Meetings: Tips from Respected Managers

If there’s one thing we’ve learned about managing teams, it’s this: For an entire team to succeed, the productivity and happiness of every individual matters. A lot. In fact, when it comes to reaching goals, many managers will tell you that an effective one-on-one meeting is far more important than daily status updates and water cooler conversations.

These personalized meetings can provide a wealth of insight into team dynamics. When held regularly, one-on-one meetings play a fundamental role in positive manager-employee relationships.

So we decided to ask some highly respected managers: What one suggestion would you give other managers who are looking to make one-on-one meetings more productive and constructive?

Across departments and industries, there were some striking similarities in the answers we received:

  • Remember that it’s the employee’s meeting: The managers we talked to emphasized the importance of active listening. The more attuned you are to individual work styles, preferences and personalities, the more successful you’ll be at one-on-one meetings.
  • Be consistent: Cancelling often or failing to stick to a consistent format, even a loosely-structured one, will prohibit you from getting as much as possible out of one-on-one meetings.
  • Don’t wing it: These managers encourage preparation, whether that means pulling together a list of good questions to ask or collecting agenda items and input ahead of time through digital reporting tools.

Without further ado, here’s what they had to say:

(A big, heartfelt “thank you” to all the fantastic managers who contributed! )

Brett Huff of Trello

Brett Huff
Engineering Manager

“You must have the right perspective. You must sincerely desire to help your employees. Even when they cause problems and they’re struggling, you must see past that to the potential no one sees.”

Juan Montemayor

Juan Montemayor
Senior Manager of Software Development

“Consistency is key. Come up with a format and stick to it. I schedule a 1×1 weekly for 15 to 30 minutes. Short frequency helps keep the change small so we can stay in sync. I find that if they go longer, the 1×1 tends to drag on and become less productive. Some weeks the sync is short and that’s ok. Other times it may require more time. I don’t review project items or status (that’s what planning and Jell updates are for). The 1×1 is my chance to listen and provide feedback. Here’s my format:”

  • Question: How are you feeling (personally)?
  • Question: How are you feeling on the team?
  • Updates: HR and administration, if any
  • Listening: Open topic

Kimberly Hunter of Recruiter

Kimberly Hunter
Director of Operations

“My one suggestion applies to both supervisors and employees — LISTEN. Listen to what the other person is saying and let them get their complete thought spoken before you start crafting a response in your head to what they are saying. We all want to be heard. We have all been talking to someone who looks past us, or says “uh huh” during our talk, and it is obvious they are waiting for a break in the conversation so they can speak. It doesn’t feel good or make us feel valuable to be on the receiving end of that treatment.”

When we engage with someone who is giving us the gift of listening, we are building a stronger bond. Whether your workplace is a brick-and-mortar building or a remote office, strong bonds cannot be overlooked as those bonds feed into employee engagement, company morale and loyalty.”

Santiago Jaramillo of Bluebridge

Santiago Jaramillo
CEO and Co-Founder
Bluebridge and Emplify

“With one-on-one meetings, as in other areas of business, you can try to optimize nuances but many times more consistently executing fundamentals gains the most value. First, I attempt to maintain consistent attendance in order to let direct reports know that my time with them is valuable. To this end, I’ve found it’s more effective to have recurring meetings set so it isn’t a weekly task to find time, which invites user error.”

“Second, you get out of the meeting the amount of thoughtfulness and prep you put toward it. Have a specific agenda to discuss on both ends, with the expectation for the employee to come prepared also.”

“And finally, make sure the 1:1 doesn’t turn into the manager talking for most of the time, leaving 5 minutes for the employee to rush through. The direct report should go first and take half (if not more) time—to make sure you are aligned, set clear expectations and remove blockers.”

Steph Hinds of Growthwise

Steph Hinds
Head Ninja

“Preparation is everything, but I’m not just talking about preparing the morning of or the night before. If you want to have a really productive meeting you need to have an aim: What do you want to happen after this meeting? You also need to have an agenda, such as some questions to keep the meeting on track. The preparation needs to be from both the manager and the employee. It’s so much easier when both people know exactly what they are in the meeting for!”

“It’s also important to leave every meeting with an action list. It shows both people are on the same page in terms of the outcome of the meeting, and it gives you a great starting point for review at the next meeting.”

Jacob Krall of Fog Creek Software
Jacob Krall
Former Tech Team Lead
Fog Creek Software

“Supervisors should be in tune with the peculiarities of each of their employees. Every person has a work style and an intrinsic motivation that is unique. Customize your 1:1s for each employee’s uniqueness, and you will find a deeper understanding of their problems as well as what drives them.”

Jurg van Vliet of 30MHz

Jurg van Vliet

“The one suggestion I have regarding meetings in general is: “Less is more!” Of course it helps to keep meetings short, but that is most of the time a consequence of not meeting too much. And Jell definitely helps us to meet less.”

Chris Byers of Formstack

Chris Byers

“My best 1:1s are a place where the employee leads and feels the ability to direct the conversation. In addition, I try and prep for 1:1s by having status updates come in via online systems beforehand. That leaves us free to speak more strategically and get to working on the open problems.”

James Griffin at Idio

James Griffin
Chief Technology Officer

“My suggestion for managers is to remember it’s the other person’s meeting more than it is yours, so let them set the agenda, and spend more of the meeting listening than you do talking.”

Zach Schmid of YouVersion

Zach Schmid
Software Engineering Manager

“The biggest suggestion that I can give is to allow your direct reports to own their one-on-ones. I don’t mean owning the meeting invite; I mean owning the content of the meeting. Sure, there are always going to be things on your list as a manager that you want to cover, but let their items take the front seat in the meeting. Your team members should be bringing pressing items to the table, walking through yearly goal progress and asking for feedback in areas of development without you needing to probe. If they aren’t doing this, be clear that these are the expectations. At the end of the day, you are the one who owns your role and your development. By empowering your reports to bring items to the conversation, you establish a sense of ownership and encourage preparation for a productive conversation. As a manager, the most important thing I can do is listen—genuinely listen. Do I sometimes up bring items in meetings that aren’t on their lists? Of course. But what I’ve seen is that the majority of the time, the things I want to cover are already being covered.”

“I like to keep these meetings conversational, free-flowing and relatively informal, even allowing time for us to chat about non-work related items. I want to know how each person on my team is doing personally and what’s going on in their lives outside of the office. My employees should feel that they can come and chat at anytime even outside of these scheduled one-on-ones. Nothing is worse than feeling like you can only go talk to your boss during your scheduled meeting time, and that you need to bring a formal agenda to every conversation.”

“Encourage ownership, genuinely listen, be relational and create a conversation; not a meeting.”

Randy Stocklin of One Click

Randy Stocklin
One Click

“Have a collaborative agenda with a standard format that both parties have populated and reviewed prior to the meeting. Then document all action items that come out of the meeting, along with clear expectations on timing with regard to next step(s).”

Additional reading on one-on-one meetings

For more actionable ideas you can use to make your one-on-one meetings as productive as possible, check out these related posts:

What Every Manager Ought To Know About One-On-One Meetings

28 Questions for Insightful One-on-One Meetings

The Science Of Productive Team Meetings: Quality Over Quantity

Unite your team with daily standups, make progress visible, and reach goals faster—all in minutes a day.