One-on-One Meeting Tool – EntreLeadership Help Center

Why One-on-One Meetings Are Important

“One-on-ones are the most important meeting to actually advance your business.”
— Daniel Ramsey, President of Ramsey Solutions

What makes one-on-one meetings so powerful? When you regularly meet face-to-face with the people you lead, you’ll have a prime opportunity to coach them to new heights. Even better, you’ll earn more trust and help keep your team engaged. Both you and your direct reports will benefit in these ways too:

Stronger relationships and deeper trust: Open, consistent communication builds connection.
Personal growth and focused feedback: Help your direct reports develop their skills and thrive.
Better problem-solving and fewer surprises: Address small issues before they get bigger.
Clear priorities and steady progress: Guaranteed time for them to get answers and ensure they’re clear on goals.

Script for One-on-One Meeting Invitation Email

Shortly after your first leader meeting, you’ll roll out one-on-ones. You already told your leaders to expect a follow-up email and calendar invite—this is it. Highlight why these meetings matter and remind them to watch for invites to the meeting series using this email script.

Copy and paste this email to send to your leadership team:

Subject: Let’s get our one-on-one meetings started.

Hi [Name],

Thanks for being part of our first leader meeting.

Like I mentioned, we’re also kicking off weekly one-on-one meetings. The goal is simple: I want to be more available to support you in your role and make sure you have what you need to succeed.

Keep an eye out for an invitation to the series coming soon to your inbox!

In the meantime, if you’re curious about how one-on-one meetings work, here’s a quick read to get you started: The One-on-One Meeting: Your Most Important Business Meeting. Prefer a video? Watch this five-minute lesson on how to have a great one-on-one.

Looking forward to connecting,

[Your Name]

Talking Points for Your First One-on-One:

We call your first leader meeting the buy-in meeting. Your buy-in meeting is crucial for setting the tone for a unified new chapter for your business. But before you ask for buy-in, your leaders need to understand what has to change and why. This is your chance to share honestly about:

What you want for the business
What’s in it for the team
How your current approach is working—or not working

Then you can ask the million-dollar question: If I can show you a path to get what we all want with less cost, how open would you be to exploring it?

Use these talking points to introduce Elite and roll out the new communication rhythms.

Pro tip: Before your meeting, read the ABCs of Alignment for helpful tips on getting commitment from your leaders. Prefer a video? Watch this 30-minute training on team alignment.

First Leader One-on-One Meeting Talking Points:

Meeting length: About 30 minutes

Section 1: Set the Stage (10 minutes)

Take the lead on this meeting and remind your direct report why you’re doing one-on-ones.
Let them know you’ll each guide parts of this meeting based on what you need.
Build rapport. Ask how they’re doing.
Refer to the 1-on-1 Meetings tool inside Elite, and let them know both of you can add talking points there ahead of your meeting.

Section 2: Dive In to the New Communication Rhythms (15 minutes)

Talk through recent changes. Ask if they need clarity on anything.
Remind them again that mutual grace will be needed as you add in the meetings and set new ways of communicating.

Section 3: Leave Room for Final Questions (2–3 minutes)

Ask if there’s anything else they’d like to cover.
Invite regular feedback on your meetings to make sure they get what they need from the meeting.

Section 4: Recap and Action Items (1–2 minutes)

Summarize the key points from your conversation.
Highlight next steps you’ve agreed on.

Talking Points for Your Second One-on-One:

Once your direct report is on board with your new way of working together, your weekly one-on-ones will follow a new format. Start by creating their Key Results Area (KRA) with them. What’s a KRA? A short document that spells out what results every team member is responsible for—what they primarily do in their normal, everyday work and what winning looks like in their role.

Watch this five-minute video on how to build an effective KRA. Intimidated by the dreaded blank page? Use the virtual KRA Assistant inside Elite to get started.

Second Leader One-on-One Meeting (KRAs) Talking Points:

Meeting length: About 30 minutes

Section 1: About the Team Member

Build rapport and connect. Ask how they’re doing overall—but keep an eye on the clock so you don’t accidentally spend 20 minutes laughing about weird neighbor stories.
Transition to KRAs.

Section 2: KRA Building

Agree on their top three to four responsibilities and what winning looks like for each one.
Show them the KRA Assistant in Elite and try it out together.
Ask them to refine their KRA on their own.
Set up a timeline to finish their KRA, aiming for about a month. For example:
- Give them one to two weeks after the meeting to work on it and send it to you.
- Allow one to two weeks for you to give feedback.
- Then give them a week to make their final edits.

Section 3: About Your Notes

Transition to any feedback you have on other work and provide other insights or helpful updates.

Section 4: Action Items and Close

Recap the conversation, confirm next steps, and invite their feedback.

Talking Points for Ongoing One-on-Ones:

After you’ve worked on KRAs in your one-on-one, you’ll let your direct reports steer future meetings. Both of you can add talking points to the meeting agenda using Elite’s 1-on-1 Meetings tool.

Ongoing Leader One-on-Ones Talking Points:

Meeting length: About 30 minutes a week, but it’s okay if you need more or less time

Section 1: About the Team Member

Build rapport and connect. Ask how they’re doing.
Transition to what’s on their mind today and let them take the lead.
The conversation should flow naturally into their work.

Section 2: About Their Work

Get a quick status update on their tasks and projects.
Celebrate their wins, help remove roadblocks, and clear up any confusion.
Once your team is using Weekly Reports, follow up on anything they’ve shared that’s worth diving into. When you click View Agenda in the 1-on-1 Meetings tool, you’ll see your team member’s latest Weekly Report at the top of the screen.

Section 3: About Their Goals and Development

Encourage them to talk about their goals and growth areas. Use their KRA as a guide for their growth and development and ask how you can support them.

Section 4: About Your Notes

Now it’s your time to do more of the talking.
Share feedback on the current discussion, follow up on any action items from previous meetings, and provide other insights or helpful updates.

Section 5: Action Items and Close

Recap the conversation, confirm next steps, and invite their feedback.

BONUS: One-on-One Questions to Ask

Sometimes your team members will walk into a one-on-one with plenty to say. Other times, it might feel like pulling teeth to get them to share openly. So what do you do then? Start with this simple, powerful question: What’s on your mind right now?

From there, try out any of these phrases to dig deeper and keep the conversation going:

Tell me more.
What else?
How does that make you feel?
What do you think?

If you need more inspiration, use this list of questions to guide your conversation.

1. Relationship-Building Questions

What did you do over the weekend?
How are you feeling this week?
What’s been a highlight or low point of your week?
Would you describe last week as red, yellow or green? Why?
Tell me more about what you shared in your Weekly Report about [insert the topic].

2. Accountability and Progress Questions

What are you working on and how’s it going?
What are you most proud of that you’re working on?
Where do you feel the most or least momentum?

3. Clarifying and Problem-Solving Questions

Is there any confusion I can clear up?
What roadblocks are you facing?
Where are you facing a problem? What are some options for solving it?
How can I help you with your current tasks?

4. Coaching and Acceleration Questions

What are some goals you’d like to work on?
Are there any skills you’d like to develop?
How can I support your growth and development?
How can I help you?

5. Feedback and Improvement Questions

Anything else you’d like to talk about today?
Do you have any feedback for me or the team?
Is there anything we could improve as a team?
What topics would you like to focus on in the future?

It might feel a little awkward showing up to your one-on-one with a list of questions, but your team members will appreciate the effort you’re putting in to keep the conversation focused and meaningful.

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