The Only One On One Meeting Checklist You Will Ever Need

Date Added
May 21, 2020 8:48 AM

“I’m so sorry, I need to reschedule our one on one meeting again.”

When employees hear that, they will likely either feel relief, frustration, or anger. If they’re relieved, that means you’re missing a major opportunity to discover exactly what it is that employee doesn’t want you to know. If they’re frustrated, that’s because they genuinely need your help to move their work forward. And if they’re angry, it’s because you’re sending the message that they just aren’t worth your attention.

Managers can often shy away from these meetings because they don’t know how to structure them or how to have difficult conversations. More often than not, however, they just don’t have the time. But one on ones are the most high leverage thing a manager can do to directly impact team productivity, morale and engagement.

Take Time to Make Time

It seems counterintuitive that spending time will free up time, but that’s exactly what these meetings can do. One on ones help managers to get out of overwhelm by making sure that every employee 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, a manager’s job is to aid each employee on their personal and professional journey through life as it relates to working at your company. Mentoring and coaching let’s people know that they are supported, which helps to form a strong sense of belonging.

The checklist below is intended to take the guesswork out of the one on one process, so that every manager at your company can execute them with ease. As for how often to have them, there’s no real sweet spot. Some managers hold one half-hour meeting with each employee every month, others do one hour each week. 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 prior to every one on one, especially if you are starting these 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 delve 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 ideal person in this role? What work needs to be done to get them from where they are today to that ideal?

(Note: These first two checklist items are borrowed from a webinar that I did with Jonathan Raymond, CEO of Refound. Watch the entire webinar here.)

3) Set an agenda. You have to know what is happening for your team each week long before the meeting, so that you can use time effectively. One on ones are a collaborative effort, and agenda items will be based on concerns from you and from your employee. Ask one of these question 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. In addition to specific performance issues that you will want to discuss, managers should establish that their role is to help employees to bridge the gap between where they are and where they could be. Think about how you will provide an opportunity to have the employee change behaviors that are standing in the way of excellence.

The Meat of the Meeting

5) Begin with a check-in. How are the both of you feeling? This can be one word or a phrase. If your employee does not feel safe to be honest, they will say what they think you want to hear. If they roll their eyes upwards and take a few seconds, then they are focusing on their thoughts and not their feelings. Build trust by sharing how you feel first. The more authentic and vulnerable, the better.

6) 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 quarterly objectives, and a growth task for development in their role. This might be learning a new software application, or developing public speaking skills by presenting to the whole company.

Use the 15Five system to enhance and streamline your one on ones, and record the most important learnings in one place. Learn More…

7) Get personal (sort of). Check in personally so that employees feel cared for and seen as actual human beings. In his book, Good Authority: How to Become the Leader Your Team Is Waiting For, Jonathan Raymonddescribes 5 types of employee behaviors that managers can safely discuss to open the door to personally relevant, professional one on ones:

– Time management

– Responsive communication

– Taking ownership of a mistake

– Skills gaps

– Not taking enough risks or taking too many

These matters should only be discussed in the context of work, not personally. Let employees make the connections for themselves as to how growth in these areas will also impact their personal lives.

8) Discuss challenges. Address employee concerns about where they are stuck in their work. Effective coaches will allow employees to feel just enough discomfort so that they are growing, but not the stress and frustration that has them shut down completely.

9) Set consequences. Holding people accountable is an art. According to Jonathan, accountability only becomes punitive if you wait. Set clear expectations during a one on one, and follow up with any coaching before the deadline is missed. When failures are discussed in real time instead of weeks later, accountability transforms from punishment into care.


10) Culture check-in. Discuss how people are performing in the context of the culture. Performance should not be about hitting the numbers at any cost, because that could be disastrous for team camaraderie and collaboration in the long run. Ask questions to see how employees are honoring the core company values.

11) Recognize wins. This one is intuitive, since everybody wants to be appreciated for their contributions. Recognition can be useful to lighten up a difficult performance conversation, and is also good for business. According to this study by Bersin & Associates, “companies that provide ample employee recognition have 31% lower voluntary turnover rates than companies that don’t”.

12) Create action items. A necessary part of moving the employee along in their work and growth is to take action. Set clear expectations and timelines.


13) Take coaching notes. Provide coaching notes for employees to look back on when they encounter similar challenges in the future.

14) Take personal notes. Managers may not want to share every detail of these meetings with employees. For example, part of development is letting employees 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 are held regularly and consistently. Keep this commitment and you will create a cadence of feedback and a culture of accountability.

One on ones are more than just meetings. According to Elizabeth Saunders, they are one of your most important productivity tools. So many positive business outcomes are derived from this relatively simple practice. But the best reason to have one on ones is because they are the right thing to do.

As an organization, we believe in conspiring for each other’s greatness. The conversations that take place during one on ones help employees to grow, contribute their gifts, and to live fulfilled lives. What could be more important than that?


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.