One-on-One 101: A template for better conversations with your employees

by Daniel Hannig

When was the last time you had a frank, one-on-one conversation with your direct manager? Hopefully, it’s not hard to remember the date. While you might think that downplaying roadblocks or minimizing your concerns might impress the boss, it’s easy to forget that a manager’s #1 responsibility is to manage. That means it’s in their interest to have an honest account of what’s working, what isn’t, and what they can use their power to influence.

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If you’re a manager yourself, regular one-on-ones with your employees are an effective way to build a rapport with your team and find out what’s really going on. According to Harvard Business Review, one-on-ones serve two crucial functions:

They are a time to ask strategic questions such as, “are we focused on the right things?” They are a way to show employees that you value them and care about them as people.

By the time performance reviews roll around, you will have already discussed your employees’ key concerns and intervened in areas where they could improve. It’s much less likely that your employees will be blindsided by a performance review if you both have regularly discussed their accomplishments, obstacles, and goals. One-on-ones give employees the opportunity to tell their side of the story and provide context for inefficiencies you might see around the office.

Most importantly, one-on-ones build relationships. In a more personal setting where employees can really be themselves, you might learn something about them that surprises you. In conversation, an employee might reveal themselves to be a more strategic or analytical thinker than you might have previously noticed. You might also learn about skills or interests that they have outside of their job description that could be useful to the team. For instance, an employee with a passion for interior design could help the office manager with requisitioning new furniture.

A minor speed bump, however, is that one-on-ones are an obvious time commitment. While the majority of your other meetings are likely centered on a specific project, one-one-ones can be freewheeling and cover a range of topics. Good planning is crucial to keep these conversations efficient and productive. Otherwise, one-on-ones can run overlong or drift away from relevant topics.

To organize your first one-on-one, here’s a template for what you should do before, during, and after your conversation.

Before your one-on-one

It might seem unnatural to plan out a conversation, but an agenda is a must-have for a one-on-one. Without a list of topics to address, you could wind up 30 minutes into your scheduled meeting talking about the newest lunch hotspot. While a one-on-one might be a good time for you to share company news with an employee, their proposed topics should be given priority. Collaborate on a shared document (like Google Docs or Dropbox Paper), so that you can both add items to the agenda. If an employee is reluctant to share thornier issues, the act of writing them down as topics in the agenda before your meeting could give them the perspective and clarity they need to speak up.

Make sure you stick to your meeting time. While one-on-ones are the easiest meetings to reschedule because only two people are involved, it can quickly become a bad habit. Every time you push back a one-on-one, it sends a signal to your employee that you’ve deprioritized their concerns. How often you have a one-on-one depends on the needs of your employees (new hires will likely need more guidance than experienced veterans), but you should hold one-on-ones at least once a month in order to get any benefit from them. Whether you meet once a week or once a month, be sure that you both commit to your scheduled appointment.

During your one-on-one

When you walk into your one-on-one, remember that it’s an opportunity for your employee to share, and for you to listen. Don’t dominate the conversation or get defensive if you hear something you don’t agree with. A positive, open mindset is necessary to make your employee feel comfortable with being candid.

Start the conversation with some light small talk. Ask your employee how their day has been, where they’re going on their next holiday, and how their family is doing. Opening the conversation with lighter, more personal topics will help to establish trust and show employees that you care about them as individuals, not just as workers.

When you bring the conversation back to professional topics, lead with questions about their most recent accomplishments. Some employees have a hard time patting themselves on the back, but being directly asked about recent successes might alleviate that discomfort. It also starts the meeting on a positive note. No matter what obstacles or issues you have to discuss later, the employee can walk back to their desk knowing that they shared good news, too.

After you’ve started the meeting positively, you can guide the conversation into areas of improvement. Invite your employee to share stories of projects or processes that aren’t moving forward efficiently. Don’t jump in to save the day too quickly–you need to let people vent. While you should always end the meeting with concrete next steps to solve their issues, it’s cathartic to share stories of frustration.

As your employee opens up to you about their hurdles, make sure to ask follow-up questions. It’s not enough to just hear their stories. Employees need to know that you are there to help them. You and your employee should collaborate on ways that you can remove their roadblocks together. Once you establish an action plan to eliminate their day-to-day difficulties, you can focus on their long-term personal development. Find out what your employee’s professional goals are and see if there are any upcoming tasks or projects that would be a good fit. And if it feels appropriate, try circling back around to conversational topics or areas of recent accomplishment in order to end the conversation on a friendly note.

Last but not least, remember to jot down notes throughout your meeting (without disrupting the flow of conversation). You can use these as a reference to refresh your memory before the next one-on-one.

After your one-on-one

Once you’ve returned to your desk, take a moment to reflect on your meeting notes. Are there any issues that you can help to resolve? Are there resources you can divert to clear a path for your employee? While some blockers may have causes that are too complex for a simple fix, your employee will appreciate a genuine effort. If an issue can’t be resolved right now, follow up with your employee at your next one-on-one to let them know that it’s still on your radar. It’s better to hear, “I’m sorry, I looked into it, and we don’t have the budget to replace your laptop this quarter” than it is to be left in limbo. It’s essential that employees see results, or at least attempts, from their one-on-ones in order to have faith in the process.

Keep it confidential. Over time, employees might disclose details about their personal lives that are impacting their performance at work. Your discretion is necessary to build trust with your team. Take care not to share anything you’ve learned in a one-on-one that isn’t public knowledge.

30 Questions you can ask in your one-on-one

Below, you’ll find sample questions you can ask during your one-on-one, suitable for a variety of positions and situations. Reading through them might spark a few ideas for your next meeting, or come in handy if you feel the conversation has stalled.

    1. What are some types of projects you enjoy? What motivates you and makes them enjoyable? 2. I know this may be awkward to answer, but is there anything about the way I do my job, or about my management style, that you feel could be improved upon? 3. How can management here help to make your job easier to accomplish? 4. Tell me something you’d like to accomplish within the next year. 5. What do you see as your long-term goals? How do you feel you’re moving towards them? Is there anything I can do to help? 6. Do you feel like you’d benefit if I were more involved in your work, or less? Either way, let’s brainstorm ways we could affect that change. 7. What’s the biggest accomplishment you’ve had since you began working here at _____? 8. Do you have any suggestions for how we could all work better together? 9. How’s your current project going? If there are any roadblocks, how do you think we could help remove them? 10. Do you feel like the team and I provide enough support for you? It doesn’t have to be general; if there’s been a situation wherein we could have done more to help you, let’s talk about it. 11. Who here inspires you to keep up the good work? How do you feel we could let them know? 12. What would you like your next project to be? 13. Have you ever felt underappreciated here? If so, would you mind telling me how and why? 14. Do you feel valued here? 15. Would you prefer it if I provided more, or less direction? 16. What worries you right now? 17. Do you feel like you’d benefit from more coaching? If so, what would you like more coaching on? 18. Are there any rumors that you feel I should hear about? 19. What’s your process when you get stuck on a project? Who do you contact for help? 20. What additional feedback would you appreciate regarding your work? 21. Are you learning enough through your work for your liking? What has your job taught you lately? 22. Do you have any decisions to make that you’re currently having a difficult time with? 23. Take your time, but try giving me three things we could do here to help you get more enjoyment out of your job. 24. Do you feel happy working here in general? Are you pleased with your recent work? 25. What work are you doing here that you feel is contributing to your bigger goals? 26. During what time of day are you most productive? When do you feel you’re at your least productive? Are there any changes you think we could make that would enable you to get the most out of your workday? 27. Where do you see yourself in three years? 28. What do you feel are your biggest wastes of time? 29. Do you feel engaged with your current projects? Daily work? Tell me what helps you to stay engaged, and how I can give some assistance. 30. Is there anyone here who have a difficult time working with, and if so, why?

Getting to know your employees better is a rewarding, refreshing experience that is beneficial beyond its use as a productivity tool. You might also find that you have more in common with your teammates than you think! Plus, developing deeper relationships through one-on-ones with the people you see the most can make it more motivating to come to work in the morning, too.

How do you handle your one-on-ones? Is there any question or method you particularly like to use? Let us know in the comments!


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