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12+ Questions to Turbocharge Your One-On-One Meetings

— November 26, 2019

These meetings are about employees. In other words, you need some structure in place to steer the discussion with the right questions, but it’s direct reports who own the agenda.

If you don’t run 1:1s with your team, you’re shooting yourself in the foot.


As someone in a managerial position, you have a lot of plates to spin and many hats to wear.

Worst part?

With never-ending back-to-back meetings, you already feel you’re one step away from a mental institution.


Good news?

You’re a quick scroll-down away from learning how to run effective one-on-ones and enjoy a plethora of benefits that come with them.

Pour Some Rocket Fuel on 1:1s (Part I: Preparation)

I love one-on-ones with my manager.

That’s what you want your team to say. Keep scrolling to learn how to make it a reality.

Get the Frequency Right

First things first:

In an ideal world, you’d meet with each and every report once a week for 45-60 min.


As you chew on the idea, the reality will cut through it like a Swiss Army knife through paper. 


You might have 5-10 people under your wing. How can you humanly carve out 10+ hours a week for one-on-ones?

Here’s a solution:

Take into account your team composition.

With top performers who have more skills on a resume than Elon Musk, you don’t need to meet with them all too often. They are autonomous and would prefer you to stay out.


It’s enough to set up a recurring, once-a-month meeting with top performers for 60 min.

For mid-range performers, it’s OK to meet every two weeks for 45-60 min. You’ll gauge how they are doing in the role without making your calendar overflow.


What about struggling employees? 

With employees who have a hard time keeping their heads above the water, it’s best to meet with them every week for 30-60 minutes to get them up to speed quicker.

As their performance/comfort levels rise from the ashes, change the frequency respectively.

Get Everything ReadSo far so good.

You know how often you need to run 1:1s with your direct reports based on their performance.

Now—it’s time to put 1:1s in your calendar. 


If you set up 1:1s with staffers without explanation, they’ll think they are in trouble. 


It makes sense to give them a heads-up. Best way to do it? Shoot an email around.

Here’s what you can say:

Hi Mike,

I’d like to start running 1:1s with you and all the rest of our content team. 

The idea behind these meetings is to share feedback, discuss potential roadblocks, and talk about whatever else pops up. 

I’d like to start our first meeting on December 6 at 3 PM in room XYZ. 

What do you think?


Set Yourself Some Ground Rules

Here’s some food for thought:

When you take several hours off your busy schedule to run 1:1s with your direct reports, it shoots up a clear message that your team is your top-value asset.


What happens when you’re always 10-15 min late for a 1:1 or cancel it?

The ROI from one-on-ones goes out the window, head-first.

So—make sure you build rapport through being consistent:

  • Always come on time and prepared.
  • Don’t ever cancel a 1:1. 
  • In case of an emergency, reschedule the meeting for a different time but don’t turn it into a habit.

Take 1:1s to the Max (Part II: Running a Meeting)

Break the Ice

With the logistics out of the way, it’s time to run your first one-on-ones with your direct reports.


Nightmare scenario.

When you ask if the direct has anything to discuss, he says, Not really. Everything is fine.

That’s classic.

Don’t stress, though. There are a couple of ways you can kickstart the conversation and break the deadlock.

For starters, you can begin your one-on-one meeting by recognizing the direct report’s recent accomplishment. The key is to be specific and fluff-free.

Need a real-life example?

I know you decided to stay late last Friday to finish up an article before the weekend. I really do appreciate the extra effort you put into this. I’ve read the piece already, and it’s killer. Keep up the good work!


While this conversation starter is great, it falls flat when you’re in a meeting with a low performer. 

Do you say how well-laced his shoes are?


You start with an informal catch-up. Let him share what he’s been working on in the last week. 

It should make the direct report feel comfy before you jump into the meat and potatoes of the 1:1.

Want a pro tip?

Two people meeting with iphone and ipad; image by Alejandro Escamilla, via
Two people meeting with iphone and ipad; image by Alejandro Escamilla, via

Escape the cubicle every now and then. If you go to your local Starbucks or go for a walk, it’ll help your employees feel much comfier to open up about sticky issues.

Go into a Co-Creative Mode

Here comes the juicy part. You’re about to see some killer 1:1 questions.


Keep in mind that one-on-ones aren’t about status updates or laying down instructions.

They are about employees. In other words, you need some structure in place to steer the discussion with the right questions, but it’s direct reports who own the agenda.

Below is a list of 12 lip-smacking one-on-one questions:

Teamwork and Collaboration

  1. In your opinion, is there anything that our team should stop doing? Why?
  2. Do you have any suggestions as to what we could do to improve how we work as a team?
  3. Is there anyone on the team you have a hard time working with?

Work-Life Balance

  1. How are you doing in terms of workload on a scale of one to 10?
  2. Are there any bottlenecks when it comes to your daily work?
  3. In your opinion, is there anything I could do as your manager to make your work life easier or less stressful?

Professional Development

  1. Are there any skills you’d like to pick that would help you be better at your job?
  2. Is it fair to say you’re learning a lot in your role?
  3. Would you like to get mentored, so you could pick some new skills or polish your existing XYZ skillsets?

Managerial Improvement

  1. Is there anything you’d like me to stop doing as a manager?
  2. Do you feel I give you enough actionable feedback?
  3. Is there something I could’ve done recently to help you, but I didn’t?


Do you have to ask all these questions during each and every 1:1?


But make sure you pick one question from each category (feel free to rephrase it) to steer the discussion in the right direction.

So—What Do You Think?

There you have it.

A whopping five tips + 12 questions that will turbocharge your one-on-one meetings.


What’s your experience with 1:1s? What questions do you ask to get honest feedback? 

Let me know in the comments. I’d love to chat!

Join the conversation!