39 Do’s and Don’ts for an Effective One-on-one Meeting

39 Do’s and Don’ts for an Effective One-on-one Meeting _ MediaOne

One-on-one meetings are the lifeblood of any professional relationship. They are a chance to evaluate progress and keep everyone on the same page.

But only when run effectively.

It’s easy to sneak a meeting into your calendar, but how much value can you pull from it?

A lot if you do it right.

But that’s not to say it’s easy. According to a study conducted by Hypercontext, 33% of managers agree one of the biggest challenges with one-on-ones is providing value to their direct reports.

So, how do you turn your one-on-ones from boring check-in meetings to vibrant, productive conversations? 

It all comes down to the 39 Do’s and Don’ts of an effective one-on-one meeting. 


Before Your One-on-One Meeting

A little preparation before the meeting can go a long way. It might appear forced, but it will show your direct report that you value their time and opinion.

Here are a few tips to help you prepare for a one-on-one meeting:

#1. Decide on a Cadence and Time That Works Best for the Meeting

Picking dates that work best for both of you is key. If this is your first one-on-one meeting with an employee, you want to pick a time that’s convenient for both of you.

You also want to pick a cadence you can reliably stick with. It could be once a week, every two weeks, or once a month—whatever works best for your team’s schedule.

#2. Schedule Recurring Meetings

If you can, set up a recurring meeting so that it’s on the calendar and you don’t have to worry about setting up a new meeting every time. It can be weekly, biweekly, or monthly – whatever works best for both of you.

But be sure to leave some flexibility so that you can adjust the date and time if something comes up.

#3. Set Expectations for the Meeting

You probably know what the meeting will be about, so why not make it explicit? Share your expectations with each member beforehand. Let each one of them know which role they’ll play.

Do you expect them to participate or own the meeting? If there are external parties, you must ensure everyone knows who they are and why they’re there.

#4. Get the Right Tech in Place

You don’t want tech issues to be an excuse for a poorly run meeting. Use a reliable, high-quality video conferencing platform. Also, ensure all the participants know how to use it and have a backup plan if something goes wrong.

It would be best if you considered getting a video calling app (such as Zoom, Google Meet, or Skype), a brainstorming tool (such as MindMeister or Mural), a one-on-one meeting software (such as MeetinVR), or any remote collaboration tools that you might find helpful.

Ensuring everyone is comfortable and familiar with the technology will help ensure a smooth and successful meeting.

#5. Add Questions to Your Agenda

Don’t wing it. Come prepared with an agenda for the meeting. To maximise productivity in the one-on-one, include questions or topics you’d like to address during the meeting.

You want to think through the main points you’d like to discuss and come prepared with questions or items you’d like to discuss or resolve.

#6. Use a Shared Agenda

Both you and your direct report can collaboratively add items to the agenda so everyone can come prepared for the meeting. That way, if something needs to be discussed during the one-on-one, you can ensure it gets addressed. 

Make sure you both agree on the agenda beforehand. That way, neither of you will be surprised by what’s being discussed during the meeting.

#7. Make Time for Laughs 

A one-on-one is an excellent opportunity to build a connection with your direct report. So, don’t be afraid to make time for a bit of humour. Whether sharing funny stories from your past work experiences or talking about the latest rafting adventure you went on, a good joke can bring some levity and strengthen your bond.

Just make sure you’re both comfortable with the joke and that it doesn’t make anyone uncomfortable. 

#8. When Sharing the Agenda, Ask Your Direct Report to Contribute

Don’t hog the microphone. Invite your direct report to contribute and share their ideas on how to utilise your meeting time best. It will also give you a good idea of what they’re interested in discussing and which areas they’d like to focus on. It will also help you both stay focused on the most critical topics. It’s a win-win.

#9. Corral All Your Meeting Agendas and Materials in One Place

Do your part to help your direct report stay on top of things and organised by corralling all meeting agendas, materials, notes, and other materials in one place. Not only will it make your own life easier, but it’ll also show you care and help ensure that your direct report is well-prepared for the meeting.

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#10. Send a Reminder

Give your direct report a little nudge a day before the meeting. Remind them of the date, time, and any other important information. Nothing complicated or intense – just a quick, friendly reminder. That way, they’ll be even more prepared and ready to get the most out of the meeting. Plus, they’ll appreciate the fact that you took the time to remind them.

#11. Block Off 10 Minutes or So Before the Meeting to Collect Your Thoughts

Don’t just go into a one-on-one meeting hot off a flurry of emails or a hurried conversation in the hallway. Instead, take 10 minutes to collect your thoughts before the meeting. Use this time to review your agenda, organise your thoughts, and review any notes you may have. It will help ensure you attend the meeting with a clear head and focused goals.

#12. Treat the One-on-One Meeting as High Priority (Not Just a Checkbox)

Remember that the one-on-one meeting is just as important as any other one. Don’t think of it as something you must do or cross off your list.

One-on-one meetings are an excellent opportunity to deepen relationships, exchange ideas, and ensure everyone is on the same page. So don’t just treat it as a checkbox to be ticked off — show up with the same level of respect and enthusiasm that you would for any high-priority meeting.

#13. Never Cancel

Never cancel a one-on-one meeting. If you have to reschedule, keep it at the same time of day or week. You want to do your best to stick to the schedule, as it shows that you value your team member’s time and efforts.

Cancelling one-on-ones is like saying, “My time is more valuable than yours.” That doesn’t make for a great team atmosphere.

#14. Don’t be Late

Don’t be Late

No matter how busy you are, never show up late for a one-on-one. If unexpected tasks come up and you’re running behind, let your team member know. The least you can do is show respect for their time by letting them know you’ll be running late.

During the One-on-One Meeting

Once the meeting starts, your biggest focus should be creating a psychologically safe space. Psychological safe spaces are free of judgment and fear. It creates a safe and open environment where people can be honest about their thoughts, opinions, successes, and struggles.

Here are a few do’s and don’ts to creating a psychologically safe space:


#15: Start with an Icebreaker

Loosen up the atmosphere with an icebreaker. This could be as simple as asking your direct report about what they’re looking forward to or how their weekend went.

Ask them about their day, their families, or things they’re passionate about. The fact that you’re showing interest in them and getting to know them more personally sets the tone for a comfortable and trusting environment.

#16: Talk less than 50% of the time

Encourage your direct report to talk most of the time. That’s how you get to know their thoughts and feelings.

Let them take the floor and listen to what they have to say — even if it’s something that you disagree with. You don’t have to agree, but you do need to show that you respect your direct report’s opinion. 

A simple trick is to use questions to open up conversations. Ask open-ended questions to get a real conversation going – you’ll be surprised how much you learn.

#17. Listen to Understand

Go slow on talking and go fast on listening. Go beyond listening to respond – listen to understand. Good listening is one of the best gifts to give your direct report.

Take a mental note of every word they say, and be attentive. Show them that you really care about what they have to say by being an active listener – nod, summarise, and ask follow-up questions.

#18. Be Curious

Your direct report may surprise you with their insights and ideas, but only if you are curious enough to encourage them to speak up. Be genuinely interested in their ideas and show that you value them. Also, don’t forget to be surprised with how much you learn. Who knows what hidden gems your direct report may have to offer?

Don’t make assumptions about what they are thinking and feeling. Instead, ask questions to get a better understanding of their perspective. Your curiosity will help foster trust between you and your direct report. 

 While at it, you don’t want to be nosy, either. Be genuinely interested, and don’t go too deep into their personal lives and feelings. Respect their boundaries and give them the space to share.

#19. Avoid Status Updates

Meg Murphy, “Product Manager at Visual Lease,” explains why you should use your agenda for asynchronous status updates. One-on-ones are for feedback, blockers, focus areas, and feelings. 

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Instead of diving into the minutiae of what your direct report is working on, ask how they feel about their work. 

It will help you understand their mindset better and identify if they need additional resources or support to succeed.

#20. Talk About Company Goals, Team Goals, Professional Development Goals, and Personal Goals

Talk About Company Goals, Team Goals, Professional Development Goals, and Personal Goals

The purpose of one-on-one is to help your direct report grow both professionally and personally. 

It is also an opportunity to discuss how their goals align with the company’s objectives and to ensure they have a clear path for growth. 

You can even set up a system for tracking progress and celebrating wins. 

And don’t forget to check in on their personal goals too.

Everybody wins when your direct reports are growing and developing.

#21. Share Feedback

Feedbacks aren’t only reserved for quarterly reviews.

Learn to share your feedback with your direct reports as soon as possible. 

Be sure to balance criticism with positive reinforcement so that they can understand what specific behaviours or actions need to be improved.

And a great way to show appreciation for a job well done is by giving rewards and recognition. 

It’s also important to listen to their feedback as well. 

Giving and receiving feedback are two important elements of a successful one-on-one meeting.

#22. Ask for Feedback

Feedbacks are a two-way street. 

You give feedback to your direct reports, and they reciprocate. 

You want to encourage them to voice their opinions, concerns, or suggestions. 

However, it can be difficult to have an open conversation with someone when they feel like their opinion isn’t valued, so make sure you let them know that you’re listening and willing to consider their ideas. 

Moreover, you want to follow up on their ideas and show them you appreciate their input. 

You want to create an atmosphere of trust and respect, so don’t forget to ask for feedback.

It can be as simple as, “Is there anything I can do to make our meetings more efficient or effective?” or something more specific such as, “What do you think of our current system, and how could we make it better?”

#23. Don’t Get Defensive

Don’t Get Defensive

No one likes to be corrected or criticised, so it can be difficult to remain calm when your ideas are challenged.

Learn to listen, digest, and learn from every idea, even if you don’t necessarily agree with it.

Besides, it doesn’t hurt to be flexible. You never know. Maybe your colleague has a better way of doing things! 

At the very least, you’ll gain some valuable insight. So keep an open mind and don’t take feedback too personally.

After all, it’s usually not about you; it’s about creating a better end product. 

You don’t want to be “that guy” who can’t take criticism without getting defensive. That’s a sure-fire way to have your one-on-one meetings become incredibly unproductive. 

You don’t want to be stuck in an endless loop of back and forth, so try to keep things civil and open the lines of communication.

#24. Try the Lettuce Pact

The lettuce pact is a term inspired by Kim Scott’s Radical Candor concept. It’s a simple strategy focusing on two things “challenging directly” while “caring personally.” Scott uses the analogy of someone having spinach on their teeth. She explains that while it’s kind enough to tell them, it’s far better to find a way to approach the situation with kindness and respect. 

The lettuce pact is simple — pair it with something positive when you have something important to say that might come off as challenging or negative. For example: “I know this project has been difficult for you, but I noticed how hard you’ve worked on it, and I really appreciate it.”

#25. Ask the Good, the Bad, and the Ugly

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At one on ones, it’s important to ask not just “What’s going well?” but also “What’s bad or challenging?” and “What do you need to succeed?”. These three questions can help you gut-check how you’re doing as a leader and how your team feels. 

You want to get to the root of the problem and help your team member get to a better place. That’s why when it comes to asking difficult questions, follow up with “How can I help?” or “What do you need from me?”. This will show that you are invested in their success.

#26. Be Vulnerable

Showing you are imperfect and have your own struggles can help build trust. Ask your team member to share their story, but don’t forget to share yours. Being open and honest with each other is critical for a great one-on-one meeting. 

No matter how difficult it may be, admit fallibility and vulnerability. Talk about your struggles, and encourage your team member to do the same. The idea is to create a safe space of understanding and support where both parties can trust and confide in each other.

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#27. Pay Attention to Non-verbal Cues

Your tone and posture say just as much as your words. Pay attention to your body language and ensure you’re conveying the message you want to send. Be mindful of how relaxed or tense you appear, and adjust if necessary. Also, look out for non-verbal cues from your team member; these can be very telling clues about their feelings and opinion on the conversation.

Finally, be aware of any lingering awkwardness or tension in the air. If it feels like you’re dancing around a subject and not getting anywhere, take some time to address this head-on.

#28. Avoid Yes or No Questions

Don’t be afraid to ask tough questions – but avoid just getting a yes or no answer. Instead, ask open-ended questions that allow your team member to tell their story and provide more details about their situation. 

If you must ask a yes or no question, try to follow up with something allowing the team member to elaborate on their answer. 

For example, asking, “Did the project go according to plan?” followed by “What challenges did you face?” will provide much more detail than just a yes or no answer.

#29. Get Personal

Your one-on-ones are the perfect opportunity to get to know your team members beyond just work. Ask them about their hobbies, family, and even what they did over the weekend. 

Building a personal connection with each of your team members will make for more productive meetings in the future, so don’t be afraid to go off-topic a bit. 

Who knows, maybe you’ll find out that both of you share an interest in cooking or are huge fans of the same sports team! Besides, it’s always nice to be reminded that your team members are real people too — and finding common ground is a great way to do just that.

#30. Don’t Go Beyond the Scheduled Time

It’s important to respect everyone’s time. So, once you’ve reviewed the scheduled topics, wrap up the meeting and don’t linger longer than necessary. 

That said, if something urgent comes up that needs more immediate attention — like a potential crisis or an emergency project — then it’s okay to discuss it immediately. 

But unless something is of utmost importance, we suggest you save the details for another day.

After the One-on-One Meeting

Once the meeting ends, it’s not time to sit back and relax. You want to follow up on the conversation and identify the action items that must be addressed.

Here are a few tips to help you follow up and stay accountable:

#31. Document the action items and place them in a Central Place

Your to-dos should be tracked in one central place. That could be a shared spreadsheet, a task management system, or any other online tool that makes sense for your team.

Ensure every employee can access the system and, most importantly, knows how to update it.

#32. Schedule Regular Follow-Ups

Follow up with each employee regularly, even if no specific action item is on the agenda task list. Regular check-ins allow for discussing progress, addressing questions or hiccups, and celebrating successes.

#33. Don’t Forget the Small Stuff

It is easy to focus on the big picture during a one-on-one meeting and forget small tasks that still need completion. Schedule time for these smaller tasks separately or include them in the one-on-one meeting agenda.

#34. Assign Next Steps

Hold each other accountable by assigning specific next steps during the one-on-one. That can be done by writing down to-dos in a shared note-taking system or just verbalizing them.

#35. Do Celebrate Achievements

Don’t forget to celebrate successes, whether big or small! Take time to recognize achievements at each meeting and give thanks for the effort that was put in.

#37. Do Leave Time for Reflection

At the end of each meeting, leave a few minutes for reflection. Ask questions that relate to the conversation and allow both people to think about how they can improve or change things in the future.

#38. Follow Up, Follow Up, Follow Up

What’s the point of a one-on-one meeting if you can’t follow up? These meetings’ main goal is to ensure everyone is on the same page and has a clear plan for the future.

So, follow up with an email recap outlining the topics discussed, any action items assigned, and the decisions made during the meeting. 

#39. Ask for Outlook

Create a baseline and set expectations with your employees. Ask them to provide an outlook on what they’re working on, any challenges they are currently facing, or goals for the future.

It will help give you a better understanding on how to support them and build a stronger working relationship.

About the Author

Tom Koh

Tom is the CEO and Principal Consultant of MediaOne, a leading digital marketing agency. He has consulted for MNCs like Canon, Maybank, Capitaland, SingTel, ST Engineering, WWF, Cambridge University, as well as Government organisations like Enterprise Singapore, Ministry of Law, National Galleries, NTUC, e2i, SingHealth. His articles are published and referenced in CNA, Straits Times, MoneyFM, Financial Times, Yahoo! Finance, Hubspot, Zendesk, CIO Advisor.


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