3 Tools to Make Your One on One Meetings More Effective

Woman in one on one meeting


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Laura Berlinsky-Schine2.3k
May 19, 2024 at 5:50PM UTC

When you’re a manager, you’re probably not always aware of the goings-on with your individual team members — their day-to-day activities, their successes, their concerns, their plans and their goals. But it’s important to make the time to check in and stay apprised of their professional and personal lives.

Regular, one-on-one meetings will give you an opportunity to remain up to date with how your employees are doing and progressing. Whether you’re new to the process and deciding if you'd like to hold one on ones or want to hone your existing one-on-one meetings, here’s guidance on how to make the most of your check-ins and make your employees feel supported.

What is a one on one meeting?

A one on one meeting is a sit-down that usually takes place between a manager and their employee, although sometimes mentors, colleagues and others could be involved, too. They are conducted regularly, so both parties can discuss their progress, goals, day-to-day activities, roles, responsibilities and other matters. 

These discussions should be conducted several times throughout the year to give team members a chance to update their managers and keep them apprised of their efforts and concerns. They are separate from more formal performance reviews; in contrast, these conversations are typically more casual and don’t factor into decisions about raises, promotions and so on.

What are the benefits of one on one meetings?

Many managers say that one on one meetings are highly beneficial for both their employees and themselves. Among others, some of the key advantages are:

  1. They allow managers and employees to get to know each other and develop strong relationships.
  2. They encourage employees to voice their concerns and any obstacles they are encountering.
  3. They give managers a chance to ensure that the employee understands the organization’s strategic goals and where they fit into that mission.
  4. They provide a forum for delivering constructive feedback for both the manager and employee.
  5. They enable employees to inform their managers about their personal and professional goals and receive guidance on how to achieve them.
  6. They strengthen collaboration.
  7. They prevent issues from escalating since employees and managers become aware of them early and can work on problem-solving tactics.
  8. They encourage an exchange of ideas.
  9. They support and build teamwork.
  10. They provide the opportunity to have face-to-face time (as opposed to relying solely on digital communication, although one-on-one meetings can be conducted via videoconferencing).
  11. They demonstrate managers’ commitment to helping their colleagues and employees in their careers and professional lives.
  12. They contribute to better-run organizations.

Tools to make one on one meetings more effective

One-on-one meeting checklist

When you’re beginning the one-on-one meeting process, it can be a little intimidating at first. Here’s a checklist to help you out.

1. Establish a schedule.

Make sure your meetings follow an established schedule, one on which both the manager and the employee (or whoever is involved in the meeting) agree. Having a set time every month, every two weeks or other frequency will make it more likely that you’ll both stay on track and not let these meetings fall by the wayside.

2. Get into the right mindset.

Remember: this meeting is meant to be casual. Try not to overthink things. Get into a mindset that will help you set the right tone for the meeting — one that welcomes and encourages sharing. If you’re not in a good headspace, then you risk intimidating or overwhelming or intimidating your employee or team member. You want them to feel comfortable.

3. Come with a set agenda.

Avoid going into the meeting blind. Have an agenda to guide the discussion, even though, as we’ve noted, this should be casual. Casual doesn’t mean it shouldn’t have structure, though. Both the manager and employee should have a voice in setting the agenda so they cover the topics each of you wants to address.

4. Create a plan.

This applies to both the conversation itself and the content. Plan out the meeting itself, but also create a plan with the employee addressing, for example, their professional development, career goals, responsibilities and so on. This will give them a roadmap to guide their career activities and reference in future one-on-one meetings.

5. Prepare resources.

Based on what you know about the employee, come to the meeting prepared with resources that will help them succeed. For example, it might be listings for company-sponsored courses they might find useful in developing their skills and furthering their career. Or, perhaps you think a colleague might be able to mentor them or assist with particular goals.

6. Allow for flexibility.

Even though you have an agenda for the meeting, you don’t have to follow it to the letter. Keep your one-on-one meeting flexible, allowing room for your employee to have a voice in the discussion and guide it according to what they want to talk about. This should be a collaboration between the two of you.

7. Review challenges and obstacles.

In addition to discussing strengths and successes, as well as the overall trajectory of the employee’s career and goals, make sure you touch on any challenges they’re encountering. Listen to what they have to say about these obstacles, and leave room to brainstorm solutions together to help address them.

8. Take notes.

You won’t remember everything your employee says, so make sure to take notes throughout the conversation. You don’t want to come into the next meeting not having a clue about what you discussed last time. Before each meeting, review your notes from the last meeting to make sure you address the most salient points.

9. Leave space for questions.

Make sure the employee has time and room to ask questions at the end of the meeting (and possibly during as well). This is an important step in ensuring you’ve covered all the topics they want to address.

10. Provide alternative venues for check-ins.

Don’t solely rely on one-on-one meetings for check-ins. Make sure your employee knows that they can contact you via other means, such as Slack, email, project-management tools or phone. But these methods of communication shouldn’t replace one-on-ones — they should just give you both the means to discuss issues or concerns that arise, especially if they require an immediate response.

7 pieces of one-on-one meeting advice, from managers

1. Make the meetings both of your responsibility.

We’ve stressed that this should be a collaborative effort — and managers agree. In fact, Ben Horowitz and Kim Scott even say that employees should be in the driver’s seat for these meetings.

This may sound unusual — after all, managers are there to manage — but the approach can be very effective in ensuring that the meeting is productive and addresses everything the employee and manager want to talk about. 

Of course, managers can provide direction at times, especially if the employee is having trouble coming up with topics to discuss. (This is where those questions above can come in!) Ultimately, however, it shouldn’t be your responsibility alone.

2. Have a regular time slot for the meeting.

According to Elizabeth Grace Saunders, it doesn’t matter how frequently you have the meetings — that depends on factors like the size of the team or company — but it is important to establish a regular time to hold them. “Schedule them on your calendar as a repeating event,” she says. Saunders adds that this will make it less likely for employees to constantly come in with interruptions; instead, they’ll save them for their regular one-on-ones.

She also advises managers to avoid canceling meetings at the last minute or showing up late because that sends the wrong message. (The employee should be showing up on time, too!)

3. Be prepared.

Katelin Holloway reveals that at Reddit, where she is the vice president of People and Culture, employees share their talking points with their managers ahead of time to help direct the conversation. “It allows the employee to guide the conversation in the way that they want,” she said.

While it’s not essential to share your listing of talking points prior to the meeting, you should still make sure that both parties come prepared for the meeting so that it flows as smoothly as possible.

4. Maximize the time invested.

According to Andy Grove, the former CEO of Intel, one-on-one meetings offer 10 times ROI for managers. But too often, these conversations aren’t as valuable as they could be, and time isn’t spent productively.

Saunders suggests maximizing the time investment by having both the employee and manager come up with a list of bullet points ahead of time they’d each like to hit. Then, in the meeting, she encourages them to compare their lists to ensure that they cover the most important ones. Meanwhile, they should also consider which points they might be able to put off for another time.

5. Be fully present.

Even if you’re conducting your one-on-one meetings on Zoom, it’s important to give them your full attention, minimizing distractions — such as turning off your cell phone — and actively paying attention. In fact, this is even more important for remote conversations because distractions are inevitably part of our workspaces.

Jenny Bloom, the CFO of Zapier, says that the company’s distributed team conducts its one-on-ones via video chat so employees and managers can pay attention to nonverbal cues, which are nonexistent in phone calls. This also helps stress the importance of the meetings.

6. Start off on a positive note.

Saunders, for one, encourages participants to share a win. Perhaps your employee delivered an amazing presentation, secured a new client or completed a project well ahead of the due date. Let them know that you’re impressed! This will give them the encouragement they need and start the meeting off on the right foot.

There are other ways you can begin on a positive note. Be creative. Maybe you could pay them a compliment — even as small as “It’s so nice that you’re always smiling. It brightens my day.”

7. Ask open-ended questions.

You’ll notice that none of the questions on the list above solicit a yes/no response. That’s with good reason. CB Insights founder and CEO Anand Sanwal learned from experience that you’ll get more out of your meetings if you go beyond the generic and ask open-ended questions. Now, he puts questions that really make the employees think directly into the meeting invites — questions like “Who do you admire in the organization and why?” or “What is the biggest opportunity we’re missing out on?”

Asking questions like this, he says, really gets the conversation flowing and will help employees and managers alike in developing their relationship and improving their roles and responsibilities.

Are you ready to deepen your connections to employees and help your team members grow within your organization and in their larger careers? One-on-one meetings are a great place to start — as long as you conduct them effectively. The best way to make these meetings successful to follow the advice of others who have been in your shoes — the managers who have had experience honing their own meetings to encourage their employees and help them be the great professionals they know they are.

25 one-on-one meeting questions

You should also prepare questions to ask to guide the conversation. You certainly don’t have to ask all of the prompts listed below — just use them as a reference tool in case lags occur during the discussion.

1. How are you?

2. How’s work going?

3. What would you like to discuss today?

4. What are your concerns?

5. What’s going well?

6. What do you think you could be doing to improve your work?

7. How is [obstacle] going?

8. What are your priorities for the coming week?

9. How well are you working with your team?

10. Where do you picture yourself next year? In five years?

11. What are your main goals right now?

12. How are things going personally?

13. When do you feel the most productive?

14. When do you feel the least productive?

15. What’s holding you back at work?

16. What are your favorite responsibilities or assignments?

17. What are your least favorite responsibilities or assignments?

18. What learning or professional opportunities would you like to have?

19. Who or what gives you inspiration?

20. What feedback would you like to give me?

21. How do you feel that you’re contributing to the overall team/company?

22. What additional contributions do you think you could be making?

23. What’s a new skill you’ve learned or would like to learn?

24. How can I support you?

25. What questions do you have for me?

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