Ah, the one on one (1-1). A sacred meeting in the start-up world to support employees and fuel performance. 

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Yet rarely are you taught how to lead one. New managers and experienced ones alike are expected to pick up managerial duties as if born to them. That’s the nature of fast-moving work environments. 

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But you don’t have to do it alone.

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​​In this guide, we're going to demystify the art of one on one meetings, turning them from a source of anxiety into a powerful tool in your managerial arsenal.

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All so that you can take managing your team in stride, support them in the ways they need, and help them to grow and perform in their roles. 

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Here’s a quick rundown:

• The purpose behind 1-1s
• 7 things you can do to run an effective 1-1 meeting
• How NOT to run your 1-1 meetings
• Topics to cover in your 1-1 meetings
• Questions you can ask in 1-1 to get conversation going, flowing, and fruitful
• Online or in-person? Where should you hold a 1-1 meeting if you're a hybrid company
• How to get your direct report to prepare for a 1-1
• Get more out of 1-1s with YOUR manager
• Use Waggle to make 1-1s more effective (and easier to lead!)
• Frequently asked questions from first-time managers

Why bother? The purpose behind one on ones

One on ones serve as a dedicated time to coach, grow, and support each member of your team so that they can perform in their role. 

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Sarah Watson, Chief Operating Officer at BPTLAB, shared how she views 1 1s:

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They help you do thinks like:

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• Build bonds 
• Develop your managerial skills
• Learn where your team needs support
• Gauge and improve engagement in their role

Let’s look at each one more closely to better understand the benefits of holding regular one on ones with your team.

Building bonds with each direct report

One on ones are a great opportunity to build relationships with your team members. You can get to know them on a personal level, and just as importantly, they can get to know you. 

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It's all about creating an atmosphere of open communication and mutual trust—two essential ingredients of any successful team.

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When you’ve built a good working relationship with your direct reports you’re setting the foundation for them to be honest, which allows you to help them as soon as they need help and solve problems before they escalate into bigger ones. 

Developing and flexing your managerial skills

As a new or developing manager, one on ones are a critical time for you to practice and hone your skills– the ones you didn’t have to pay attention to as an individual contributor.

But now that you’re a manager, they’re paramount to your own performance management and ability to effectively lead your team. 

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These meetings are moments where you can practice coaching, delivering feedback, having difficult conversations, providing support, and more.  

Learning where your support and attention is needed 

When you and your team are bouncing from project to project, focused on deadlines, and measuring your impact, it’s easy to miss signs of burnout, frustrations, disengagement, and conflicts.

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The one on one is a time where you silence the noise, give individual attention, and tune into those feelings and struggles. All so that you can address them through tailored advice and coaching. 

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In 1 1s you can uncover:

• how your report is truly feeling at work and at home
• how they're progressing
• what obstacles they might be facing
• what work is energizing them or draining them
• what tasks they’re struggling with
• what’s holding their growth back

Gauging your direct reports engagement  

One on ones act as a real-time engagement detector. 

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By observing their enthusiasm levels, contribution to discussions, and overall attitude, you can get a fair idea of how engaged your team members are. 

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And, if engagement seems to be dwindling, you're in the perfect position to address it.

7 things you can do to run an effective one on one meeting

Leading one on one meetings can feel daunting but the right approach and mindset can make them effective and impactful for both you and your team. 

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Here are seven ways you can ensure your one on one meetings are supporting your reports in the ways they need most to develop, perform, and progress.

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1. Hold 1-1s regularly

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Regular one on one meetings signal to your team members you’re committed to their development and prioritize them as people.

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It also ensures you stay updated on their career goals and discuss challenges they may be facing.

And having regular one on ones pays off. Gallup reports engagement is highest among employees who meet with their manager at least once per week.

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Ultimately, the cadence of your one on one meetings is up to you and your team. You may find that weekly is too much and bi-weekly meetings are better. Or maybe even monthly. Whatever cadence you decide, make sure they happen.

Deprioritizing, skipping, or canceling them altogether sends a bad message to your team members. 

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Even if you feel there’s nothing to talk about that week, you should make the time. Plenty can come up once you get talking. You just have to ask the right questions and dig deeper when you spot the need.

2. Ask open-ended questions

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Keep the conversation flowing with open-ended questions. Instead of asking questions that can be answered with a simple "yes" or "no," encourage your team members to share their thoughts, ideas, and feedback. This approach promotes dialogue and can get to the heart of an issue. 

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Let’s look at an example:

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You could ask, ‘Are you okay?’ 

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Or you could ask, ‘How are you feeling this week?’

Most people will say yes to the first question. Even if they’re not okay. Asking how they’re feeling leaves space for them to reflect and genuinely answer. You can always ask follow-up questions to dig further into their mindset. 

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Asking open-ended questions is a skill that can be developed with practice. The more you do it, the easier it will become. And the better your 1 1s will be as a result!

3. Practice active listening

Don’t just hear what your direct reports have to say, really listen to them. 

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What do we mean by that? Active listening requires your full attention so that you can read visual cues alongside the words the person is saying, and respond to the message they’re communicating to you. You need to understand their feelings and perspectives.

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It’s a skill that many managers (and people in general) lack. But it’s invaluable. 

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Listening isn't merely about hearing. It's about understanding and responding to your team members' feelings and perspectives. It involves giving them your full attention and validating their thoughts and emotions. Waggle's AI co-pilot can assist you here with nudges to remind you of active listening practices during your meetings.

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4. Make time for feedback

Feedback can feel… uncomfortable. Both giving and receiving. But it’s essential for growth. 

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Your team culture (and hopefully your company culture) should foster an environment where open feedback is encouraged and demonstrated regularly. 

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And this is a street that goes both ways. 

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Of course, take the time to deliver feedback (positive and constructive) to your direct report, but also ask them where you can improve and what you’ve done that has worked. 

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What they say will help you grow in your role and improve as a manager. 

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Great feedback is:

• Specific
• Objective
• Actionable 

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For example, rather than saying "you're doing a great job," try "I appreciate the way you handled that difficult customer, remaining calm when they were getting annoyed."

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Not only do they know exactly what you’re praising them for, they will be able to repeat the behavior in future. 

 5. Use a meeting agenda

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An agenda keeps the conversation focused, ensures important points are discussed, and makes your meetings more productive. 

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It prevents you from showing up to the meeting, fishing for something to talk about.

And it’s not just on you to fill out the agenda beforehand. Your direct report should add talking points to the agenda that they wish to cover. 

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You can share the agenda with them ahead of the meeting so that they have time to see what you’ve added to it and come up with their own. 

There are plenty of 1-1 templates available to use. In fact, we’re working on a template that you can use in Notion or Google Docs. Sign up to our newsletter to know when it’s live.

Or you can get Waggle. Waggle keeps you on task with 1-1s by nudging you to prepare the agenda ahead of the meeting and reminding you and your reports of any action items they had from the last one. 

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6. Keep track of conversations

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Your one to ones don’t exist in isolation from each other. The concerns, achievements, and development goals from weeks and months ago are still relevant to the conversation you have coming up in your next meeting. 

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That’s why you need to keep track of what you’ve discussed before, how your direct report has been feeling, if there are any trends, and if they’re making progress. Take meeting notes and refer back to them before every meeting.

If your direct report mentioned they were taking a course to learn how to create an email sequence in Hubspot then that’s something you can check in with in subsequent calls. 

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Keeping track of conversations and revisiting them in future meetings allows for consistent follow-ups and shows your team that you're invested in their progress.

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Waggle can help you track conversation history before you join the call so that every 1-1 has your attention and your direct report feels that you really know them and are paying attention. 

7. Be vulnerable and personable

It can be intimidating to share struggles, frustrations, and concerns with the person who judges your performance, helps determine if you should be promoted, and can ultimately fire you. 

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But you need your employees to feel they can share those details with you. That takes establishing psychological safety with your team and fostering an environment where being vulnerable, being truthful, and being yourself is not a weakness and will not be punished. 

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One way you can foster that is by demonstrating the behaviors yourself. Your 1-1 is a time where you can share more about yourself so that you build the relationship side of your working relationship. 

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Take it from Tom Sinclair, Chief Technology Officer at Brawn Power. When asked how he approaches 1 1s, he shared this:

How NOT to run your one on one meetings

With management best practice comes bad practice and knowing what not to do can be just as helpful as knowing what to do. 

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Unfortunately, bad practice happens more often than it should. But you’re here because you genuinely want to use 1 1s as an avenue for growth, connection, and productivity.

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So, here’s what not to do. 

Don't treat them as status updates

One on one meetings are not a time for updates on work. Those can be covered in a team meeting or in an async conversation (email, Slack, Teams, etc). 

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These sessions are designed to engage in deeper conversations, help your team members navigate challenges, and build trust and rapport. Using them as a status update dilutes that purpose and makes them ineffective in engaging and supporting your team. 

If you find yourself slipping into a pattern of using this time to run through your direct reports to-do list then you need to press reset and revisit how this time should be spent. 

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Bookmark this article to revisit if needed.

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Avoid cancellations or delays

When work gets chaotic, 1-1s are often the first to get moved because they don’t feel as important as meeting a deadline or delivering a project that will make a dent in your OKRs.

But that’s a huge mistake to make. 

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Regularly canceling or postponing them communicates to your team members that their concerns and development are not your priority. It leaves room for you to miss important developments, conflicts, or achievements that you should be aware of as a manager. 

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Of course, things come up that can’t be avoided, but make it a point to reschedule promptly if you must cancel.

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If your direct report is trying to cancel or push 1-1s regularly, that needs to be addressed too. 

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Are they canceling because they’re disengaged from work? Are they burnt out and not telling you? You need to get to the bottom of it, whatever the reason.

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Don’t see them as isolated events

We hinted at this earlier but it’s worth repeating. Every one to one you hold should be part of a broader dialogue and ongoing relationship with each of your team members. 

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Keep track of discussions, follow up on action points, and ensure there’s continuity in the issues addressed over time.

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The past week should inform the current one. 

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Maybe your report shared something personal that they felt was impacting their performance. You need to check in on that and make sure they’re getting the support they need.

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Don’t dominate the conversation

While you might have a lot to share or advise, remember to give your team members the space to voice their thoughts. Active listening is key here. 

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Aim to spend more time listening than talking, which along with open-ended questions will encourage your team members to open up more.

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Waggle is working on adding real-time coaching to manager calls so that you can improve how you manage in that moment. It will signal to you that your talk:listen ratio is off and will nudge you to adjust. It gives a whole new meaning to ‘on the job training’. Sign up to Waggle here to find out when this feature goes live.

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Avoid gossiping about team members or colleagues

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Keep the conversation focused on feedback, development, and resolving issues. An atmosphere of professionalism and respect will foster a healthier work culture.

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If you gossip or complain about other team members or other colleagues in the company you may influence how your direct report sees and treats others. You also may make them wonder if you gossip about them to others on the team when they’re not around. 

Don't compromise psychological safety

Your one to one meetings should be a safe space for open, honest communication. Make it clear that all thoughts, ideas, and concerns are welcome without judgment. 

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This atmosphere of safety and trust can empower your team members to share more openly, leading to valuable insights and stronger bonds.

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Using something your direct report has said against them could damage psychological safety in your team. For example, if someone shares that they’ve struggled to be productive that week because they have a personal problem at home don’t use that statement against them in an upcoming performance review.

Being dismissive can also damage psychological safety. If someone shares that they’re having conflict with another team member, you should listen and work together to come up with a solution. What you shouldn’t do is blame or ignore them. 

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Don’t lack emotional intelligence

Your emotional intelligence (an often underdeveloped skill for managers) plays a crucial role in your team’s mental health and overall engagement. 

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According to a study, 60% of employees worldwide say their job is the biggest factor influencing their mental health. 

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Your reactions to their concerns, struggles, and dips in performance can significantly impact how they 'show up' at work and perform going forward.

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Remember, you are not just a manager; you're a leader. Your role is to foster an environment where your team can thrive. 

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By avoiding these common pitfalls, you can ensure your one on one meetings are a positive experience for both you and your team. 

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Waggle’s real-time coaching and automated nudges can guide you in adopting these best practices, making you not just a good manager, but a great leader.

Want to give it a try? Sign up for Waggle here. 

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Topics to cover in your one on one meetings

Your one on one should should be centered around these topics:

• Career development
• Performance management
• Goals
• Feedback
• Praise and recognition 

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You don’t need to cover each one in every meeting. You might have a 1-1 dedicated to development followed by a 1-1 that focuses on feedback and praise. 

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How you structure your meetings are up to you and your team but these are the topics you should be focusing on. 

Career development

Don't underestimate the value of discussing career paths and development with your team members. Talk about their aspirations, skills they want to develop, or roles they aspire to in the future.

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For example, if a team member is keen on improving their public speaking skills, you could discuss potential training opportunities or chances to present at upcoming team meetings.

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Performance

Conversations about employee performance shouldn’t be left exclusively to annual or bi-annual performance reviews. 

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Having them regularly allows you to know how each member of your team is doing and more importantly, it lets them know how they’re doing. Only then can they make improvements or carry on with the right behaviors.

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Your people want to know, too: 

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So you need to openly discuss performance, but remember to approach it from a supportive angle. 

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Instead of stating, "Your sales numbers are down," you might say, "I noticed a dip in your sales numbers. Let's explore what might be causing this and find solutions together."

Goals 

One on ones are a great time to set and review progress towards goals.

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These goals can be related to career progression and/or personal development.

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For instance, if a team member's objective is to increase customer satisfaction, you could review their key results and brainstorm strategies to achieve them. You could coach them through blockers to goal achievement or even come up with follow-up goals once they achieved them. 

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Feedback

Feedback can be built into every 1-1. It’s a good idea to regularly touch base on what your direct report is doing well, what they could work on, and what progress they’ve made from past feedback.

Keep in mind that you should be getting feedback too. Ask for it and try to get them to be specific when they give it. It can help them and you improve performance. 

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In fact, a Zenger and Folkman survey found 92% of respondents agreed with the statement, “Negative (redirecting) feedback, if delivered appropriately, is effective at improving performance.”

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Praise and recognition

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People thrive when they feel appreciated. Take time in your one on ones to recognize your team members' efforts and achievements. A simple, "Great job on the presentation, your visuals were really engaging!" can go a long way in boosting morale and motivation.

Questions you can ask in one on ones to get conversation going, flowing, and fruitful

Okay, so you know the topics you should cover but how do you cover them? That’s where your open-ended questions come in. 

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Below are example questions you can use in your 1-1s. Think of them as conversation starters. 

We’ve organized them by topic. Take what works, drop what doesn’t, use them to come up with your own. 

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Icebreakers/ Engagement gaugers

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• How are you doing? What’s on your mind this week?
• Are there any particular challenges you would like to discuss?
• How are you progressing with your work this week?
• How are you feeling about your workload and current projects?
• What else would you like to discuss?

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Career development:

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• What areas of your role would you like to develop or improve upon?
• What’s preventing you from taking the next step in your career? 
• What do you want to be spending more time on? Less time on?
• How do you feel about your career growth so far? 

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Performance Management:

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• Can you share any recent feedback you’ve had from your colleagues or clients?
• Is there anything that might be hindering your productivity or motivation?
• How do you feel about your recent projects? Are there any areas you feel you could improve?

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Goals:

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• What’s currently challenging for you and what can I do to help?
•  What has been your biggest accomplishment since our last meeting?
• Are there any resources or support you need to achieve [insert relevant goal]?

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Giving and receiving feedback:

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• What's one thing you believe is working well for you in your role? What's one thing that's challenging?
• How can I, as your manager, better support your growth and success?
• Is there anything I do that helps and you wish I did more often?
• How do you feel about that piece of feedback? Is there anything you’re unclear on?

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Praise and recognition:

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• What achievement are you most proud of this week/month?
• In which project do you feel you gave your best recently, and why?

Online or in-person? Where to hold a one on one meeting

The hybrid work model presents unique opportunities for one on one meetings. You can opt for in-person meetings, online sessions, or a mix of both, depending on what works best for your team.

In-person meetings: Nothing can fully replicate the connection built through face-to-face interactions. In-person meetings can offer richer communication with non-verbal cues and can sometimes facilitate more candid conversations.

However for some people, especially neurodivergent folks, in-person meetings can be overstimulating. The best thing to do in this situation is to accommodate them in whatever way is best. And to do that, you should simply ask!

Online meetings: Online meetings offer flexibility and convenience, especially for remote team members. They can also be less formal and intimidating, which might lead to more open conversations. Plus, with online meetings, you can take advantage of tools like Waggle to provide real-time coaching, feedback, and meeting notes.

You will lose the opportunity to read body language and other non-verbal cues but Waggle can compensate for that by reading your direct report’s engagement including positive and negative reactions on calls. (All coming soon!)

Making your choice

Both have their strengths but when choosing don’t forget to consider your team's preferences and needs.

If a team member feels more comfortable with online meetings, respect that preference. If another prefers in-person discussions, try to accommodate them where possible. You can also alternate between the two, offering the best of both worlds.

At the end of the day, the goal is to make these meetings as effective and comfortable as possible, fostering open communication and mutual growth. 

Whether you choose to hold them online, in-person, or both, the important part is the quality of the conversation and the progress made. With Waggle, you're equipped with the tools to make these conversations productive, regardless of the meeting location.

How to get your direct report to prepare for a 1-1

Ever show up to a 1-1 faced with nothing but silence and crickets from your direct report? 

They’ve not prepared for it and they didn’t follow up on any action items from the past week?

Here's how you can ensure that your team members are ready and engaged for every one to one you have together.

Clearly communicate the purpose

They should know that these meetings are not just another box to check off their to-do list, but an opportunity to discuss challenges, explore growth opportunities, and build stronger relationships.

Communicate that this time is there for them. Explain the topics you’ll cover in 1-1s and give examples of what it looks like. You can even share this article with them if that will help and make sure to send your meeting agenda with them ahead of time. That way they can add in their talking points too. 

Share a template

Everything’s easier to stick to when there’s a plan in place. A template provides a framework for the meeting, allowing you and your team to structure thoughts and input effectively.

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It’s a trick many managers use to get their direct reports involved in 1-1s and one Mary Kawa uses time and again. 

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In need of a template for your 1-1s? We’re working on a free 1-1 template for Notion (and for Google Docs). Sign up to our newsletter to know when it’s live.

You can also templatize your 1-1s with an agenda in the Waggle platform. Don’t have an account? Set one up today.

Encourage them to block time before and after

Now that you and they have a template to use, you can encourage them to block time in their calendars to fill out the agenda. 

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If they have time in their calendar for 10-15 minutes of prep time before the call, and 10-15 minutes of reflection time after the call, then they are able to prepare for and process the conversation. We’re working on this capability within the Waggle platform so that you can do so automatically as a Waggle user. 

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This not only helps them clarify their thoughts but also ensures you both focus on the issues that matter most. It also keeps your direct report from jumping from one meeting into another and forgetting to prepare. That time will be built in and there’s no excuse not to use it. 

Use a tool like Waggle

Waggle can help direct reports prepare for meetings by providing reminders, suggesting agenda items, and facilitating pre-meeting notes. 

With integrations into your work calendar, your one on one meeting will be synced and prepped from one place. 

You can sign up for an account here.

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Get more out of 1-1 meetings with YOUR manager

As a manager, you both lead one on one meetings and attend them as a direct report.

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Turning the lens on yourself and becoming an active participant in your own one on ones not only strengthens your relationship with your manager but also provides you with invaluable insights to bring into your own management role. 

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Remember, every one on one is an opportunity to learn, grow, and enhance your managerial skills. Make the most of it.

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Besides following the tips we shared above that help your direct reports prepare, here are a few others:

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Address specific problems

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Use these meetings as an opportunity to bring up specific challenges you're facing in managing your team. Your manager is a valuable source of guidance and resources. 

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So, don't hesitate to ask how they would handle these situations, and seek their advice on how to move forward.

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You can also bring up areas you want to improve in and come up with a plan on how you’ll go about improving them. 

Give feedback

Remember, feedback isn't just for your team members; it's essential for your manager too. 

Though it may seem daunting to give feedback upwards, in a healthy company culture, your manager will welcome your input and the business needs it.

It’s also a time for you to deliver feedback from your team to your manager or to the Leadership team in general.

For example, the company may be placing too many demands on the team that don’t relate to that quarter’s OKRs. You can use your one on one meeting as an opportunity to communicate the impact of that and come up with a solution with your manager. 

Be transparent but don’t compromise confidentiality

When bringing problems to your manager that you’re facing with your team, make sure not to overshare with them things your team has confided in you.

Sensitive information can come up in a one on one meeting. Before you share anything upward, make sure to check with your direct report that they’re comfortable having this information passed on. 

Use Waggle to make 1-1s more effective (and easier to lead!)

Meet Waggle, your AI co-pilot for better one-on-ones and better leadership.

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There’s a whole host of features (and ones yet to come) that help you put management best practice into practice. 

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Here are a few that relate to running effective 1-1s.

Agenda setting:

Waggle is designed to bring structure and purpose to your meetings. 

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With its unique agenda-setting feature, you can predefine discussion points, allowing you and your direct reports to come prepared, making the most of your meeting time.

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It encourages pre-meeting input, ensuring all key topics are covered, making your one-on-ones meaningful and productive.

Real-time coaching:

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Holding a one on one over Zoom, Google Meet, or Microsoft Teams? No problem. Waggle provides real-time coaching to managers during these meetings. 

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This means you can receive immediate feedback and guidance, making your discussions more impactful and efficient. If you’re dominating the conversation, Waggle will let you know and make suggestions to improve your talk:listen ratio. 

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It helps you ask the right questions, listens and learns from the conversation, and provides real-time nudges to guide the conversation.

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*This feature is in development. 

Task automation:

Waggle goes beyond the meeting by automating follow-up tasks. This encourages managers and reports to act on the discussion points and keep track of the progress. 

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Action items are automatically recorded and assigned, ensuring accountability and follow-through.

Ready to become the manager you always wish you’d had–the one your team needs, the one that will wow your business?

Waggle transforms your one on ones from mere discussions to purposeful, action-oriented, and insightful interactions. 

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It's more than just a tool - it's the ally every first-time manager needs to seamlessly navigate through their new role, ensuring every step they take is a stride towards better management practices. 

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With Waggle by your side, you're not just stepping into a managerial role - you're soaring into it. 

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Start your journey today with Waggle and become the stand-out manager we know you can be.

Frequently asked questions from first-time managers

What is a one on one meeting?

A one on one meeting is a dedicated session between a manager and their direct report, providing an opportunity for coaching, goal setting, problem-solving, and open communication.

Why are one on ones so important to have?

One on one meetings foster trust and understanding, provide an opportunity for feedback and growth, and enable managers to gauge their team members' engagement and address any issues promptly. They're key to building a successful and engaged team.

How often should I run one on one meetings?

The frequency can vary depending on your team's needs and your management style, but a good starting point is once every week or two. The important thing is to maintain regularity, demonstrating to your team members that you prioritize these sessions.

How long should a one on one meeting be?

Most one on one meetings last between 30 minutes to an hour. This provides sufficient time to dive into discussions without eating too much into the workday. Remember, it's the quality of the conversation that matters, not the duration.

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