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One-on-One Meeting Checklist: Ten Simple Steps

One-on-One Meeting Checklist: Ten Simple Steps
Rob Lennon
Customer Education Lead at Hugo
Marketer and author with 18 years experience in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

One-on-ones are important, rapport-building meetings between team members and supervisors. Make sure your one-on-one meetings as all the right questions and cover all the bases with this quick and easy checklist:

  • Check in
  • What are the wins?
  • What about roadblocks?
  • Solutions, support, and/or feedback
  • Goals looking forward
  • Support and/or resources
  • Anything else?
  • Summarize
  • Confirm action items
  • Post-meeting reflection

1. Check In

Before diving into the nuts and bolts of recent and upcoming work items, take time to connect with light, open-ended questions such as:

  • How full does your plate feel this week?
  • What have you been up to that balances work with home life?
  • When do you feel most excited about your work?

Getting to know team members’ feelings about their work, as well as checking in to make sure they’re getting enough time away from work to return refreshed, builds understanding and demonstrates that they can be honest with you.

2. What are the wins?

The successes, the great work, the things worth celebrating—what has happened since the last meeting that deserves recognition? Both meeting attendees should be able to list a few, but even wins that have already been announced elsewhere (via email, Slack, a memo, etc.) deserve a little in-person fist-pumping.

Team members may have exciting updates. Leaders may have some good news that’s come down the pipeline. Take some time to exchange, celebrate, and boost employee morale.

3. What about roadblocks?

Once the celebration is complete, it’s time to dig into the challenges. What’s in the way of further success? The possibilities here can cover a broad range, from communication issues to resources, and technological trouble to organizational culture.

Make space for honesty. Listen and ask probing questions to paint a full picture of the issues. Gaining a complete understanding will help with the next step.

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4. Solutions, Support, and/or Feedback

Depending on the roadblocks discussed, team members may need help brainstorming solutions, accessing resources that require more seniority, or simply a sympathetic ear from someone who can offer moral support. (We’ve all been there—whether critical software keeps crashing or simple solutions simply aren’t in the budget, some roadblocks simply have to be tolerated until the situation changes.)

Sometimes, team members express challenges and frustrations that are best addressed by a change in their own outlook or work approach. Good leaders use one-on-one meetings to practice emotional intelligence and offer constructive feedback or reframing as needed. Repeat steps 3 & 4 if there are multiple concerns.

5. Goals Looking Forward

Short-term and long-term, specific projects and overall career trajectories, there are many possible goals to discuss on a one-on-one. Over the course of many meetings, team members and their supervisors will hopefully develop a rapport that allows for discussion of all kinds of goals.

For each meeting, consider what types of goals take priority for discussion. Are there critical items on the agenda that need attention? If so, focus on setting goals that address those items. If things are a bit calmer, take advantage of the opportunity to find out what team member’s long-term and career goals are, and how your organization fits with them.

6. Support and/or Resources

Once team members share their goals in a one-on-one meeting, they’ll need support and/or resources to meet them. Much like step 4, this could mean helping with networking, accessing otherwise out-of-reach resources, or providing insight and encouragement.

Encouraging and supporting team members’ goals is a critical element of relationship and trust building. Don’t miss this opportunity to be a mentor for your team members.

7. Anything else?

Before wrapping up the meeting, make sure that everything that needs to be discussed, has been. Double-check the agenda for items that may have been skipped, and think about whether any of the issues brought up in the meeting opened up a window to new challenges.

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8. Summarize

If there’s nothing else, review the points covered in the one-on-one meeting. Make sure both parties are on the same page about what was discussed, where they stand on approaching issues, and what goals are a priority until the next meeting.

9. Confirm action items

Each person should now have one or more action items they’re responsible for. These may be items that help overcome roadblocks or that move the team member toward their goals. Check to be sure that everyone knows what their tasks are and the deadline to complete them.

10. Post-meeting reflection

Because one-on-one meetings are about more than just getting work done, it makes sense for each attendee to take time for a post-meeting reflection on their own.

How do they feel about the way the meeting was conducted? Could the format of the meeting be improved for future one-on-one meetings? What information wasn’t on hand that should have been? Does it feel like both parties are invested in these meetings, and that they’re useful? Over time, these insights and our quick guide to one-on-one meetings can lead to even better one-on-one meetings.

One-on-One Meeting Templates For Every Need

Depending on the main goal of your one-on-one meeting, we may have just the right agenda template for you. Check out our sample agendas for these meetings:

Catching Up One-on-One

The Upcoming Week

Set expectations and align on near-term priorities for the week ahead.

Review Priorities

Where are we in relation to our goals/plan? Reiterate top priorities to reinforce focus.

Comment on Recent Work

Review recent successes or failures to guide future work.

Status Update and Course Correction

How is x, y, and/or z task going? Offer guidance on work in progress.

New Information

Review new, relevant information.

Follow-Up

Goal Setting One-on-One

Big Picture

Where do you see your career going in the short/long-term? 

Career Growth — Organizational Mandates Alignment 

Where do the organization’s mandates most closely align with your career goals? Discuss how [the direct report’s] job function fits into organizational goals.

Goal-Setting Part 1 - Aspirational

Brainstorm measurable, meaningful short and long-term career goals

Goal-Setting Part 2 - Actionable

Brainstorm measurable, meaningful short and long-term goals to create stepping stones towards achieving specific organizational mandates.

Follow-Up

Do we need solo time to build on this? Should we review our goals again? When will we connect again to measure progress? 

Manager Weekly One-on-One

Intro question

Start with an open-ended question. How was last week? What’s been working well for you lately? 

Celebrate Wins & Lessons Learned

What have we accomplished since our last meeting? Note progress on important initiatives.

How can we be better? Highlight lessons learned from the previous week.

Remove Roadblocks

What (if anything) is stopping—or slowing down—your progress? How can we remove that roadblock? What support do you need? 

Plan to remove specific roadblocks and create action items.

Two-Way Evaluation and Feedback

How are we doing? How can we work together more effectively? 

Open Discussion

Provide time for open discussion. Is there anything else you want to talk about? 

Follow-Up

Should we schedule another one-on-one? Review any action items arising from the one-on-one.

Action items:



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Rob Lennon
Customer Education Lead at Hugo
Marketer and author with 18 years experience in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

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