How To Have Amazing One On One Meetings

February 21, 2018

by Ravi Raman

We are in a culture of meetings run amok. Most upper-level managers I know spend over 50% of their time in meetings. Even worse, research shows that 1/2 of all meetings are considered a waste of time! In spite of an environment where the tyranny of meetings is a new norm, I’m a firm believer that there is a certain type of meeting that is not done often enough, and when it is, it’s done poorly. I’m talking about one-on-one meetings.

Why One On One Meetings Matter

Human connection is the lifeblood of society. Relationships are at the core of what any business is and does. Your company is not a function of your product. Your company is a function of the creativity and productivity of people who choose to work there. One on one meetings are a way of taking care of the human connection in a way that people feel empowered with a clear sense of direction and an unwavering sense of safety and support from their leader.

This blog post is written from the perspective of the reader (you) being the leader. However, the insights apply equally to anyone who is looking to “manage up” and improve the way they relate to their bosses.

Before we get to what you should do in a one on one meeting, let’s talk about what not to do…

Please, Don’t Do This!

The worst use of a one on one meeting is to apply pressure and micromanage team members. No one wants to be micro-managed. If you find yourself issuing a litany of directives and checking in on the status of progress and tasks and other minutiae, you are not only missing a vital opportunity to coach your team, you are pushing them further away from their inner source of creativity and motivation. This is exhausting for everyone, including you!

It’s Not About You (The Manager)

Instead of using a one on one to tick off a checklist or spew directives, approach your one on one meetings with the opposite perspective. In my opinion, the purpose is to support the growth and development of team members.

Take care of project updates and administrative minutiae using email, use one-on-one meeting time to coach your team! If you, as the manager, do not have something to talk about, this doesn’t mean the one on one meeting should be canceled. The time is for your team members, not just yourself! Some of the best conversations happen when there is no “fire to fight” or project to micromanage. With a relaxed perspective and a willingness to explore, you would be amazed at what could emerge from even a short conversation.

One On One Meeting Structure: Three Questions

I like to think of three key questions to frame a one on one meeting. This is how I used to structure my one on ones when I was a team leader. You can be creative with how the questions are phrased, but ensure that each of the three topics are covered. I think you will discover (as I did) that this format of conversation helps team members to feel a strong sense of belonging and commitment to the team. You will also find that they help you (as a manager) to uncover meaningful topics of conversation.

Q1: What is going well?

Start on a positive note. Connect to something meaningful and supportive. Even in the worst times, there is always something positive going on. Encourage your team members to surface the things they are proud of. As a manager, don’t passively listen, but listen intently, to what is being said. If something intrigues you, probe deeply by asking powerful questions. For example:

“Tell me more?”
“What happened next?”
“How did you come up with that?”
“Interesting, should we continue doing more of that?”
“How can we expand the impact of that to other parts of the company/team?”

Q2: What would be even better?

We are all on a learning curve (perhaps several!) and face areas of developmental growth. No one is exempt; even Fortune 500 CEOs stand to improve in specific areas! Encourage your team to surface the things that they see as areas of growth. These may be challenges, missed opportunities or ideas for improvement in the future. If a project just completed and didn’t go according to plan, use this as a chance for your team members to reflect on what could have been better in their approach.

I like the phrasing of “What would be even better?” instead of “What’s wrong?” or “What isn’t working well?”. The former phrasing has a more favorable flare that people will be more receptive to.

As a manager, understand that it’s not natural for team members to want to share things that are not going that well, lest the messenger be criticized. It’s up to you, the team leader, to create a sense of safety in the conversation. Emphasize that you are really interested in hearing what could be even better for the sake of supporting their growth, and also, thinking broadly about how you can also assist in making things even better.

Q3: What, if anything, do you need?

Outdated management models dictate that team members work for bosses, who set goals, plans and allocate resources. Under this model, if things don’t work out, the fault lies with the individuals on the team who supposedly “failed to execute.”

However, flipping the management model makes a lot of sense for dynamic and modern businesses. After all, it’s your team that has a direct line of sign to your business operations, what’s working and where things could be even better. Why not allow your team to tell you what they need? Wouldn’t this both make your job of allocating resources easier and better serve the needs of your team and business?

I’ve discovered that just asking the question, “What, if anything, do you need?” holds remarkable power. It’s a coaching question that gets people thinking about their inner resourcefulness and what is really getting in the way of their taking positive action. Often, you’ll notice that they don’t need much to act on what you discussed, their awareness of what to do is all they needed!

Important: I am not phrasing the question as “How can I help?” Your offering to help might be needed, but should be offered only after your team member has tapped into their inner wisdom to solve their problems. Then, if they are still stuck, you might wish to ask if there is any way you can help. Just be careful not to “play hero” and solve everyone’s problems for them. Sometimes, I’ll let a team member sit with a problem for a while and then jump in only if I see that they are stuck. People can be remarkably resourceful if you allow them the time and space solve problems on their own!

Consistent Frequency

How often should you conduct these meetings?

Only discussing these points during an annual review is the sad truth about how many leaders operate. Consistency is key, though the exact frequency can vary.

When I led teams of 5–8 people working on diverse topics, I would meet with everyone weekly for an hour each. This made sense since each team member worked on radically different problems, and our team was moving at a very fast pace. A lot would happen each week!

If your team is aligned to work on a similar set of problems, or if the pace is slower; bi-weekly or monthly one on ones would make sense. Some global CEOs set aside quarterly one on one meetings with their direct staff members due to the extreme demands on time and travel. Experiment and see what works best for your situation. Whatever you decide, make it a consistent routine. Treat your one on one meetings as sacred time.


I hope that you are now in agreement that one on one meetings are a vital component of your management rhythm. I also hope that you have a clear sense of how to conduct them. The three vital questions I included in this blog post are a fantastic starting point for you. Try them out and let me know how it goes! If you have any further questions, please leave a comment.


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