The Ultimate One-on-One Meeting Toolkit

When it comes to your one-to-one meetings with your top team, how much training have you received on how to effectively lead them?

If you're like most of the business owners I know, your answer is probably, “None.” As with most things in life, you've simply figured it out—either based on what you think one should look like or what you've observed others doing.

Which is unfortunate, because one-on-one meetings, done right, are one of the most effective, high-leverage tools in your leadership toolbox

Remember, leadership is about producing results through other people. In other words, your success isn't related to what you do; it's related to what your top team does.

Which means that your one-on-one meetings should be the most important 30-minute meetings of your week. They're not a distraction from your real work. They are your real work.

The best part of leading anyone is helping them become a better version of themselves. The better your people get, the more leverage you create, the better your entire company becomes. It's a triple win.

Email, Slack, and quick hallway check-ins all have their place, but none of them gives you the real read on how your people are actually doing than a focused, private 1:1 conversation does.

Run these well and you'll see productivity, retention, morale, and engagement go up, while conflict, misalignment, and procrastination go down, all from one 30-minute meeting each week with each of your direct reports.

The good news is that this toolkit gives you everything you need to run one-on-ones that build a truly high-performing leadership team. Apply it, and you'll end up with a repeatable system for the rest of your career, along with better people and faster growth at the same time. Enjoy!

Part I

I. Master the Essentials

Before I walk you through the tactical parts, let's make sure we're in alignment on what an effective one-on-one meeting looks like.

Your one-on-one meetings should run 30 minutes (or less) and should happen weekly (or, at a minimum, bi-weekly). Monthly is unacceptable.

My personal recommendation is that you should hold all of your one-on-ones back-to-back, on the same day (if at all possible). So, if you have three to five direct reports, that would mean that you have a 90 to 180 minute block reserved every week for these meetings.

Note: if you have more than three direct reports, I recommend a 30-minute break after the first three, hence 180 minutes for five of these meetings.

The goal is not for you to direct or talk. It's to give your direct reports real time with you every week, without anyone else in the room. Yes, you'll discuss projects and KPIs, but the real goal is to foster real conversations between the two of you every week.

In addition, you should see these one-on-ones through the lens of a coach, more than a boss. And you do that by asking more questions than by telling them the answers.

Or, as I like to say, “Your job is to be Socrates.” And how did Socrates teach? He taught by asking questions to draw out of people what was already inside of them.

Note: this doesn't mean you can't teach or tell someone the answer during your 1:1s, it simply means that your default shouldn't be to tell, but to ask and develop because the better they can think, solve and operate, the better their department becomes.

Part II

II. Employ the Do's, While Avoiding the Don'ts

If you want to lead more effective one-on-ones, here's what to follow.

Do

Meet every week (or every other week) and protect it like you'd protect a client deadline. Think 40+ times per year.
Keep it to 30 minutes or less. When 1:1s run past 30 minutes, you'll want to skip them.
Overindex on the relational part of this meeting (i.e., this isn't just status updates and box checking)
Ask more than you tell; be Socrates instead of the expert with all the answers.
Ask open-ended questions instead of closed ones (i.e., less “Did you finish X,” and more “What's the biggest opportunity we're missing?”).
Co-create the agenda a minimum of a day ahead so nobody's walking in cold
Keep detailed notes in real-time on your shared doc
Use your 1:1 meetings to get intel. For example, “What's something that's going on in our company that you think I'm unaware of?”
Always be fully present (i.e., phones down (or away) and no half-listening while answering emails or texts on your laptop).
Continually cast vision for them, their department, the company, etc. Remember, vision leaks every 24 hours.
Hold them accountable, check commitments, don't dodge hard conversations
Encourage them every chance you get (i.e., no one should dread this meeting).
Coach and give feedback in real-time instead of saving it for their annual review
Solve problems before they become major problems
Create an actual development plan and work on it during these meetings
Stay flexible and adjust the conversation to whatever they need that day
Share information so they're never blindsided by news from someone else.
Use AARs (after action reviews) after any big project or event to capture what worked, what didn't and what was learned.
Regularly ask if there's anything they need from you
Keep every promise you make (and fast)
Close with a clear recap of decisions and next steps
Do use a template for your agendas (coming up next)

Don't

Cancel. Reschedule if you have to, but don't cancel
Turn it into an interrogation. Make it feel like a real conversation where you're connecting with them and adding real value, not just “holding them accountable.”
Blindside them with a gotcha they didn't see coming.
Wing it. Showing up unprepared tells them exactly how much this meeting and they matter to you
Make it about you. This is their time.

Part III

III. Utilize a Shared Agenda

Set it up

One of the big mistakes a lot of leaders make is that they don't use an agenda for these 1:1 meetings; they just meet.

From this point forward, that stops. Always use an agenda and I recommend one shared doc per direct report. I like to use Google Docs, but you use whatever system you like.

Each week, at least one day before your meeting, each of you should pull up the shared document and add anything you want to it.

Your direct report is responsible for updating any KPIs and wins
You're both responsible for following up on your assigned to-dos, as well as entering any discussion items you'd like to discuss this week, along with any info you think the other person needs to know (especially about upcoming dates of events).
All of this should be completed at least 24 hours before your meeting so both parties can see the agenda ahead of time and prep any materials they may need or answer any questions that were posed by the other person.

Run the meeting

During the meeting, keep it open and document any decisions and action items in real time, including who owns what.

Carry it forward

When it's over, copy the agenda to the top of the doc, update the date, and carry the action items into next week's version. Next week is ready before this meeting even ends.

This simple little practice sets you up for success. You have one document that becomes the definitive artifact of your conversations. No more guessing. Everything agreed to or discussed is in black and white.

Once you build this cadence, you'll never go back

Part IV

IV. Copy This One-on-One Agenda

Here's my recommended agenda for each of your direct reports. Simply copy and paste this into whatever system you want to use and you'll be all set.

One-on-One Agenda

Date:

Time:

I. Wins

· What are one or two good things that have happened over the past week?

II. Status Updates

1. Goals/Plans/KPIs a.

2. Key Projects a.

3. Assignments from last time a.

III. Discussion Items

1. a.

IV. Developmental Items (improvement, education, learning, coaching, feedback, productivity, etc.)

V. Information Items

1. Key upcoming dates a.

2. Other updates a.

VI. Action Items (item, who's responsible, due date)

1. Next meeting date for us:

Get the Google Doc Download the Word version

Part V, Bonus 1

V. 25 Coaching Questions

If you're stuck and need some help generating a handful of better coaching questions, here's a list for you to pull from. Note: this can also keep you from asking the same questions every week.

Wins and recognition

What's something you're proud of from this week that nobody else has acknowledged yet?
What went better than you expected recently?
Who on the team deserves credit for something you haven't mentioned yet?
What's a small win that might not seem like a big deal but actually mattered to you?
What's something you learned this month that you didn't know before?

Performance and accountability

Where are you ahead of where you thought you'd be, and where are you behind?
What's getting in the way of finishing something you committed to?
If you could only fix one thing before our next meeting, what would move the needle most?
What's a decision you've been putting off that you probably need to just make?
Where do you think I'd disagree with how you're handling something right now?

Growth and development

What skill would make the biggest difference for you if you got better at it this quarter?
What part of your role still feels uncomfortable or unfamiliar?
What would you want to be doing a year from now that you're not doing today?
Who do you admire professionally, and what do they do that you'd want to learn?
What feedback have you gotten before that you're still working on?

Team and culture

What's something you think I should know about the team that I might not?
How do you think morale is right now, and why?
Is there a conflict or tension on the team that hasn't been addressed?
What's one thing we could stop doing that would make the team's life easier?
Where do you think communication is breaking down between departments or people?

Strategic and big picture

What's the biggest opportunity we're missing right now?
If you were running this business for a week, what would you change first?
What's a risk you see coming that we're not talking about yet?
What would it take for you to trust the team to handle this without you?
What's one thing you wish I understood better about your part of the business?

Part VI, Bonus 2

VI. AI Prompts for Better One-on-Ones

You don't need to use these, but if you'd like to use your favorite AI to help you build better one-on-one conversations, here are a couple of sample prompts.

Prompt for meeting prep

"I'm about to have a one-on-one with [name], who's responsible for [their role or area]. Here's the agenda for our meeting: [paste the agenda]. Based on this, give me three to five coaching questions I should ask that go beyond the ordinary, along with anything you see that might require a harder conversation."

Prompt for a follow-up note

"Write a short, warm follow-up email to [name] after our one-on-one today. Here's what we covered and agreed to: [paste your notes and action items]. Keep it brief, confirm the commitments we both made, and end on an encouraging note."

Prompt for a development plan

"You are a world-class leadership coach. I want to help [name] grow in [specific skill or area]. Based on what you know about their role and current strengths, suggest three practical ways I could coach or develop them in this area over the next ninety days, including anything I could hand them to read, watch, or practice."

Prompt for spotting patterns over time

"Here are the notes from my last four one-on-ones with [name]: [paste notes or transcripts]. What patterns do you notice in what they're bringing up, what they're avoiding, or how their answers are changing over time? Tell me what I might be missing."

Part VII

VII. What's Next

If having a system for running great one-on-ones feels good to you, imagine what it would be like if your entire business ran like this? If you'd like to build a self-operating business that can scale so you can experience more freedom, wealth and impact, then we ought to talk.

This is exactly what we help service-based business owners build inside the Grow and Scale Accelerator. If you're ready to get out of the day-to-day ops of your business so you can lead it well, check out the Grow and Scale Accelerator here.

Grow and Scale Accelerator >>