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manager shares agenda for one on one meeting with staff
7 Min Read

The Only One-On-One Meeting Checklist You Will Ever Need in 2023

David Hassell, Co-Founder and Executive Chairman of 15Five

Too often, managers shy away from one-on-one meetings because they don’t know how to structure them or how to have difficult conversations. Plus, it’s easy to cut out meetings that you feel aren’t bringing value. But when executed well, one-on-ones have the power to significantly boost team productivity, morale, and engagement.

Below, I’ll share how you can prepare, structure, and make the most out of every one-on-one you have.

Take time to make time

It seems counterintuitive that spending time will free up time, but that’s exactly what one-on-ones can do. You can use smart links to easily schedule online so that there is minimal back and forth to set up the meeting. These meetings help managers avoid overwhelm by ensuring the team is focused on the right task. Taking a few minutes to coach employees frees up your time to focus on your own work with the confidence that you won’t be putting out fires later.

Beyond that, one-on-ones offer dedicated time for mentoring and coaching. Taking this opportunity to help guide your employees on their personalized path to success lets them know that they’re fully supported, which can contribute to a strong sense of belonging.

While there is no single answer for how often you should have one-on-ones; what matters most is creating the cadence and honoring it consistently.

Before the one-on-one meeting

You’ll have to do a bit of homework before every one-on-one, especially if you are starting from scratch.

1) Set the context of human care.  One-on-ones are a space for the growth of each employee with a manager who is personally invested in them. That means that you must meet whether things are good or bad. When things are going poorly, it’s time for a difficult conversation. When things are going well, use the time to appreciate the person’s accomplishments and help guide them into their career trajectory. 

2) Paint a picture of what excellence looks like. Before you get specific about individual performance, depersonalize things. What would excellence look like for the person in this role? What work would equate to success?

3) Set an agenda. You have to understand what’s going on within your team so that you can use one-on-ones effectively. These meetings are a collaborative effort and agenda items will be based on concerns from you and from your employee. Ask one of these questions at least a day before the meeting:

  • “What do you want to discuss in our next one-on-one meeting?”
  • “What challenges are you facing?”

4) Create a plan. Managers, it’s up to you to help employees bridge the gap between where they are and where they could be. Think about the behaviors of your employee and what could be standing in their way of success.

The heart of the meeting

5) Begin with a check-in. How are both of you feeling? This can be one word or a phrase or a conversation. If your employee doesn’t feel safe, they will say what they think you want to hear. Build trust by sharing how you feel first. The more authentic and vulnerable, the better. 

6) Get updates on employee objectives. These are action items that were set in the previous one-on-one. They should include tasks that support the employee’s objectives

7) Get personal (sort of). Your people are so much more valuable than the work they produce. Ask them how they’re doing outside of work and check in with them on a personal level. It’s helpful to take work out of the equation sometimes.

8) Discuss challenges. Address employee concerns by asking them where they feel stuck. Listen to their answers and help them turn it into a learning opportunity. Telling them what to do won’t help them to grow or develop, so instead, commit to solving the problem together.

9) Hold your employees accountable. Set clear expectations of what excellence looks like, and continuously follow up. When it’s time to offer constructive feedback, don’t wait until their next performance review. Giving feedback immediately following an event has the greatest impact on performance.

10) Ask about morale. A “performance over everything” mentality is disastrous for team camaraderie, can lead to employee burnout, and won’t promote healthy collaboration. Ask questions to learn how your employees are honoring the core company values.

11) Recognize wins. High performing organizations are far more supportive and complementary than low performing organizations, and employee recognition can greatly boost performance. Before going into your one-on-one, have several examples of things your employee did well, times when they showed growth, and/or really utilized their strengths.

12) Create action items. Setting clear expectations and timelines will help your employees stay focused on priorities and increase the rate at which they develop.

13) Take coaching notes. Providing coaching notes for employees to look back on will come in handy when an employee faces a familiar challenge that you’ve helped them through before, and when it’s time to reflect on past conversations for performance reviews.

14) Take personal notes. Part of employee development is letting them contemplate a problem on their own. Record your own private thoughts to refer back to when looking at the arc of employee performance and development over time.

15) Follow up. One-on-ones only work when they’re ongoing and consistent. Keep this commitment and you will create effective feedback loops and help build stronger connections with your team.

Many companies are shifting away from outdated once-a-year performance reviews to forward thinking continuous feedback models– a large growth and development strategy that includes real time feedback, check-ins and 1-on-1s, performance reviews (that can include self, manager and 360* feedback), and engagement surveys

15Five provides continuous feedback through our weekly Check-in and 1-on-1 features, recognition through High Fives, as well as more comprehensive development conversations through our quarterly or semi-annual Best-Self Review. Learn more and schedule a demo today.

Co-founder and CEO of 15Five David Hassell

David Hassell is a business columnist, speaker, and serial entrepreneur who believes that when leaders institute cultural practices that support each person in being and becoming their best self, high performance and uncommon loyalty naturally result. As co-founder and CEO of 15Five, David created the science-inspired Best-Self Management methodology that helps leaders and managers address the hidden factors that stimulate sustainable growth and development – things like intrinsic motivation, growth mindset, strengths, and psychological safety in the workplace. David has been featured in The Wall Street Journal, Inc., Entrepreneur, Fast Company, and Wired. Follow him on Twitter @dhassell.

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