Episode #42: How to Have a Truly Valuable One-On-One Meeting – A Guide for Managers

One-on-one meetings can be tricky. The value can feel elusive and the blur of daily life and reacting to constantly changing needs and time pressures. So how can you avoid wasting both your time and the time of your employees?

Management and leadership is a constant balancing act and it often can feel like we put off important connections for the sake of what seem like our top priorities at the time. And hint, often these are urgent things. Not that urgent things aren’t there, but I really want to be here today to explain to you how you can leverage your one-on-one meetings in a way that can actually help you and your employees to better keep up with those tasks and priorities and to expand the value of that employee relationship and that employees value to the organization over time. So there’s kind of these two things. How do we actually get the work done that needs to be happening right now, but also how can we set ourselves up for a future where each of us is actually more valuable to the whole? So how do you actually have a one-on-one meeting that can make a real difference.

Today you will learn some really good ways to make sure that you get the most out of your one-on-one meetings. I really want them to be worth your while, and I want you to look forward to them as one of the most valuable times in the week. I want you to imagine that the one-on-one is the highest leverage hour of your week or month or whatever it is that you decide. If it’s not that high leverage, it is so worth you spending a little bit of creative time now, and really envision a future where this is humming my clockwork and picture the results around you in your organization. That’s a much, much easier life than most managers live, where they’re living moment to moment, week to week, scrambling and just doing status updates all the time. It really weakens your ability to think strategically and to be a great leader when that’s how you’re operating. So do this, not just for them, do it for you. It’s a creative game. How do you design a conversation that can move the needle in the future?

One of the most frequently recommended best practices for managers is the one-on-one meeting. This is a meeting that typically takes place with a very regular cadence, usually weekly, and it’s kind of considered a building block of your normal weekly calendar. However, one-on-one meetings can be tricky. I know that there are many leaders and managers who may have given up on one-on-ones for a time. Perhaps never put them back on the calendar after a busy spell, or maybe you’ve just have trouble keeping up with them and finding a real way to make it worth your while. So how do you actually have a one-on-one meeting that can make a real difference?

I always feel if you’re going to put anything on your calendar, it needs to have a multiplicative effect on your ROI, the ROI of investing in your team. So it better at least pay for itself five fold for it to be worth your time because friction and distraction are the enemy of great leadership.

I do have something to offer you as well. When you go to allowedpodcast.com, you will see there are some free bonus materials to supplement today’s podcast. You can download them there and use them as a reference to go back to or to even guide you through this episode. You can find the link to that also in the show description, which is right there in your podcast player. So go there right now, click through, and you can access these materials. I want to get through a lot of information today. So feel free to reach out to me with further questions and comments. I really love hearing from all of you.

What you’ll find today in the show notes for this episode or at allowedpodcast.com, is a one-on-one meeting checklist. Now this is something that’s been often requested by my one-on-one coaching clients. You can go through this checklist prior to every one-on-one meeting you have, or keep it right there alongside you at your desk, just to make sure that you are prepared and that you’re making the best use of that time with your employee.

Also, at allowedpodcast.com, you will find a complete one-on-one cheat sheet. Now this is the ultimate guide to one-on-ones. It’s basically a mini ebook that you can print out, and it will really help you to understand the ins and outs of a great consciously led one-on-one meeting that will actually move the needle. Not just tactics, mindset, employee growth, engagement, culture, all of the things that at some point in the year are going to be keeping you up at night. Let’s handle those at each and every one-on-one, each and every week. Now let’s get started.

First, I want to talk to you about the true benefits of a consciously led recurring one-on-one meeting. The key benefits are:

One, you can refocus and reconnect to the importance of growth, personal and professional development for your employee, and cultural priorities. They are a great venue for giving and asking for feedback. It’s a great place to get a pulse check, for morale, engagement, and any important challenges, personal professional, cultural that are ahead. This is a great place to spot strategic issues coming a mile away, and they can be key to creating a collaborative, high efficiency culture, and a consciously run organization.

There are some big pitfalls to avoid, and unfortunately, many of these are what the typical status quo is with how one-on-ones look in today’s corporate culture.

The first one that I hear as a biggest pain point of direct reports is missed meetings. I’ve heard so many disheartened employees say, “My one-on-one keeps getting canceled. Week after week, it gets pushed back, it gets shortened, it gets canceled.” And you may not know it, but even if the one-on-one isn’t that exciting to you right now before this episode, it’s really meaningful to your employees. It’s a touch point they can count on with you and it helps them to feel like they matter to you and you are a proxy for the entire organization. And like it or not, employees often assess their own value based on how much you value them. Now, we want them to be of course, finding their own source of value and perhaps not “needing it”. However, we are all human beings and we’re living in a human system. So it’s really important to keep those one-on-one meetings.

Now, regardless if everything is running really smoothly, or if it’s a total mess at the time and there’s things falling apart all over the place, it’s really important not to cancel a recurring one-on-one meeting. Take that time to focus on individual growth, foster a healthy and engaged employee mindset. And unresolved issue should be addressed on a recurring basis before it’s too late. If you keep canceling the one-on-ones, you will find out usually too late. It’s unlikely to improve on its own. So you want to kind of have that recurring beat so that you can get ahead of things.

The number two thing to avoid is using the one-on-one for a status report. This is not a place for status updates. Instead, it’s a place to discuss where the employee is and where they want to be in terms of their talents, their strengths, their skillset, their mindset. You can take this opportunity to raise their morale and promote a motivated, productive, and proactive mindset by connecting their current role to their future life goals. Yes, I said, life goals. What I mean here is we want to connect their role, which is something that exists in the organization for the organization, to them as an actual individual human being who has a full, whole human life. And we want to help them to identify what are the ways that your life path intersects with what is here and best for the organization? And ultimately when those two are aligned, you’ve just found your sweet spot. So we don’t want to use this for tactical updates. A lot of that stuff could honestly be sent to you in an email or in some kind of an OKR tracking tool or a Slack message. You don’t need what could be read in the document to show up in a one-on-one meeting. That is valuable face-to-face time, let’s use it to build a relationship.

The number three thing to avoid is giving low quality feedback. Please, when you are giving feedback, provide it in a considered, precise, actionable way. A way that is constructive, that recognizes how empowered your employees actually are, whether they currently know it or not. And seeing them as that best self that you know is there. You want to use that feedback to facilitate growth, not just to correct errors. You want to facilitate growth in a positive direction, one that’s proactive and action oriented, not just in a preventative direction. So clearly explaining why a task was successful or why it wasn’t, in a way that is objective, unarguable and clear, that marks the difference between repeated errors and repeated successes.

But really, really key here, again, going back to this point of your employee as a whole person with the whole life, is connecting task performance with their own personal identity, the skills and talents that you know are most important to them. And you know it because you’ve talked about it and every single one-on-one. It’s a big thing that you’re tracking. Is what do you care about employee? So you can always connect the feedback back to that and see how the feedback is related to their desired overall growth trajectory.

This is not a place to get action items done. Sometimes you might be discussing action items that have happened or they’re about to happen. But if you’re trying to use it to tick through a list that really is more like a project related meeting, this is not the purpose of a one-on-one. A one-on-one is there to grow and develop employees. I’ll say it again and again, within their roles and within the team. Action items can stimulate desired growth and they can add real and perceived value to your employees’ roles. So you want to encourage them to engage in those and to succeed, but this is not the place to get them done.

Again, it may be that you’ve been trying to cram a bunch of project meetings into a one-on-one meeting. In that case you may want to look at, “How can we rebalance?” There’s no rule that says you need to have a one-on-one every single week or that it always has to be 50 minutes long. You can shorten it. You can choose to have an every other week cadence. You can have three a month. You might want to have project meetings that are more clearly defined. But I really encourage you, just instead of sloppily using these as a catch off for anything that needs to be discussed and described, just commit, “I’m going to use this to boost the value of this employee and to boost the value of our organization to them.”

Okay, what is the purpose of the one-on-one meeting?

To summarize, it’s to encourage engagement. Engagement of both the employee, both your direct report, and also you as a manager. And if you are a direct report and your manager is not having this one-on-one, you can certainly steer the meeting in that direction and request it. When this is done correctly, one-on-one meetings pay off in both the short and the long term. It cultivates that manager-employee relationship. It establishes a healthy company culture where employees feel both seen and heard, where they feel valued for living in their zone of genius, where they know that this organization is one where they can become even more their best self, and where you are their partner in helping to make that happen.

The one-on-one enhances performance, productivity, and it will help you to tackle roadblocks in real time and see issues coming a mile away. And we all know the issues that destroy companies are not just the tactical, it’s so often the personal. So let’s really commit to doing this together. All right.

Now I want to give you some steps, some clear steps. First start with a kickoff meeting. You could think of this as a role negotiation meeting when we are aligning on purpose. This first meeting is a really critical step in setting a framework and a mental model where you can lead your employee down the road to growth and development and to establish that the one-on-one has that purpose, because this is often just not expected. It can even take an employee back if they’re used to, whether with you or in another team they’ve been on at some point, they’re used to be in a tactical meeting, and suddenly you’re asking questions about their personal life. It is useful to just have a conversation about what the conversation is going to be about and do that first.

First get a clear picture in your mind, what does success look like for this employee in their role and what is the role of the one-on-one in supporting them in being a success in that way? What is the ideal and what work needs to be done for them to get there? The things we’re looking for here are:

Number one, create some clarity. Clearly detail what their job requires and what is expected of them. What role do they play in the big picture of the company? You want to identify with them what are their key responsibilities and how does their work directly impact the work of the rest of the team and the organization as a whole? So seeing how we are part of a greater whole is a big piece of employee engagement, and you want this to be as clear and concrete as possible, not vague, so that they can really make sense of it even in the worst of times.

The number two thing we’re trying to create here is transparency. Even if you know that it was on the website, or maybe mentioned in an HR onboarding at the beginning of an employee’s engagement with your company, it’s very useful in this meeting to review your company’s mission, vision, values, and big picture goals. So this is all of the stuff that relates to strategy and culture like who is this organization? What’s its purpose? You may feel this is really redundant and that you’re just saying it again and again and again. And the truth is, that’s how it should feel. Only when you are repeating it so often that you’re really sick of hearing yourself, are you saying it often enough for all of your direct reports to really solidify it in their head as the number one thing to keep coming back to? And if it’s not worth coming back to you as a number one thing, that’s a bigger question, that’s a bigger issue. That’s an issue for probably another episode.

Just to get really specific into an example here, employees usually know that their organization frowns upon stealing, but they often don’t know that there’s a commitment in that organization to being conscious in relationship. And that means that there’s a no gossiping role. That we’ve all agreed not to gossip. Many employees wouldn’t know that gossip is simply exchanging words about somebody with somebody else that you wouldn’t exchange with them directly, and that you have not exchanged with them directly. That’s gossip. It’s very cut and dry. And many employees may not realize that. And you can imagine that if that’s not translated on a consistent basis, that misperceptions can be the norm and a toxic gossip culture could emerge. So we want to be really, really transparent, clear and concrete about what is it that this company is all about? What does it look like to lead inside of this company? And I mean, leadership that anybody in the organization can do. What does it look like to actually embody and enact this organization’s culture and values? This is a great place to do that.

The third thing we’re trying to get done in this initial meeting is establish what accountability looks like. This is partly, we might want to discuss more like the extrinsic accountability, so rewards, whether they’re monetary or otherwise, growth and development expectations, who’s depending on you for what and why, but it’s also the bigger picture accountability that connects more to personal choice and responsibility. And this is why listening is so, so important. We want to be listening for what are they wanting to hold themselves accountable to? If there’s no choice, there’s no personal responsibility. So we want to be discussing what accountability looks like for them, what’s in it for them, and ask them that question. Don’t just tell them.

And really the orientation is around, “How can accountability help me in growing? How can it help us as a team in growing? What could we contribute if we were accountable for ourselves and how will our success be measured so that we can align on what are we accountable to.” Now, I’ve talked about clarity, transparency, and accountability.

Criteria number four for what this first meeting could look like is to add structure. Whether you are checking in with each team member for 30 minutes, once a week, or for one hour a month, we want to add some structure to the one-on-one so that there’s a habit to it, there’s something to expect. Establishing a structure will ensure that your employees know that they will be getting regular face time with you, and that they’ll be given a chance to give and receive performance feedback and they’ll know what order that’s going to happen in and what are the relative priorities of each of those items.

So establishing, “Here’s what we’re going to talk about in every one-on-one and here’s why. It just worked for you. What else might we want to discuss? Any of this seem problematic or concerning? What questions do you have? How can we make it great?” And then you can talk about them in this first meeting. It’s also something that you want to be checking in with them on maybe a quarterly basis or a six month basis, “How’s this one-on-one structure working for you. What can we do to make this even more valuable?”

Okay, now you’ve just had your one time role negotiation meeting. You’ve really set down what’s the role of the employee, what’s the role of the one-on-one meeting, and it’s time to kick off your one-on one-meetings in earnest. Again, whatever cadence that you and your direct reports have agreed to, we are expecting that you’ve blocked these off in your calendar and I really think it is useful to have them be a recurring time and see what time blocks that you’re working with and things aren’t moving around quite so much to the fullest extent possible.

Before your first one-on-one meeting, I want you to reconnect to what is your role as a mentor? Yes, you are a manager, but what’s your role as a mentor. Get into that mindset of being a mentor. This is actually really fulfilling and fun work. Your goal should be to guide your employees on their journey to success. Success, not just for you and for your team and for the company, but success for them. This is your opportunity to get personally invested in your team’s growth and in their development and your employees will follow suit. They will mirror and mimic and feed off of that investment that you have in their growth and they will invest in their growth 10X when they see it and feel it for real. This really means being honest when your expectations are not met, and in praising them to the fullest that is true when those expectations are surpassed. Give yourself that chance to really feel into, “How am I feeling about these expectations? What really matters to me? What matters to them?” And give that direct constructive feedback. That’s your role as a mentor.

The second thing to connect to before your one-on-one meeting is to make sure that you have collaborated on creating the agenda for that meeting. It’s useful to have sort of a boiler plate, a template, a recurring structure for this agenda, but you also probably want to reach out and have a habit of collaborating with your direct report ahead of time, to get some input about what’s going to be on the agenda specifically in each of those big buckets for this particular meeting. That will help both you and your employee prepare. It has a chance to make sure that everybody’s most important items are going to be addressed.

And then lastly, what’s your coaching plan for each of your direct reports? This is something that needs to be top of mind before you begin that meeting. Now, a lot of people, a lot of managers that I’ve asked this question, “What’s your coaching plan for this employee?” They don’t have one. If this is you and you’re scratching your head, “I don’t know. What am I coaching each of my direct reports on?” Awesome, you’ve just uncovered one of the highest leverage possible questions that there is to ask as a manager. What I really recommend is that for each of your direct reports, to have one specific thing that you’re really coaching them on.

I find that there’s actually a lot of leverage in coaching on things that are around mindset and around habits of perception and habits of bringing emotion and personal motivation in. If personal responsibility or personal accountability is an issue, that’s a great high leverage thing to coach someone on, but it also may be that you’re coaching someone on more of a specific skill. So you’re coaching people on influencing up or influencing sideways. You’re coaching them on closing sales. You’re coaching them on being really clear in the way that they present in meetings or present in wireframes and diagrams. It’s important to just have this plan in mind about, what actionable ideas do you have that can help an employee grow in their role in a way that’s personally meaningful to them? And that would be your coaching plan. This can help you in your one-on-one meeting to provide ideas for opportunities where they could improve, ways they could develop, and how they can tackle any current performance issues or roadblocks.

Now your head is in the game. You’re ready to go. Again, once it becomes a habit does not need to take long. You’ve connected to your role as a mentor, you’re excited about giving them some feedback that can really help them grow as a person, you’ve collaborated on creating this specific agenda for that particular one-on-one, and you have reconnected to your coaching plan for each direct report and you’ve looked at how does it relate to their current streams of work? Awesome.

Now it’s time for your one-on-one. Here are 10 steps. You may or may not choose to include each and every one of these in each and every one-on-one meeting. But I want to prevent you from going in and just doing the default, which for so many of us for such a long time, maybe because it’s been role modeled for us is let’s get tactical and let’s just talk about what’s going on now and what needs to get done. You could also get really lost in the weeds on just one particular problem or issue that they bring to you, especially if this is drama based, the one-on-one is actually going to make things worse. So we want to make sure that we’ve got some really strong ideas for what to do in the one-on-one.

Now, here’s what I feel very strongly about no matter what you choose to do with the rest of the one-on-one, is begin with a check-in. If you have listened to this podcast before, especially when I have a guest on, you have heard me actually in real time having real check-ins with many, many of the guests that have been on this show. The one-on-one meeting needs to be a safe space. It’s one where you hopefully can get really aligned really quickly, where you can feel on the same page, not just intellectually or with agreements about action, but also in terms of your level of presence with each other. You want to be really, really attuned and a check-in helps you do that.

Now, what is a check-in?

A check-in is a simple question that you can use to open up the discussion, where you can just get a sense of, “Where are you coming from as you enter this meeting, where am I coming from?” And it’s more real time. It tends to be not about the meeting itself. It’s usually about, “What was happening right before this?” Or, “How are you feeling today?” Or, “What’s your mindset?” The way that you ask this question matters because it’s really easy to answer the question of, “How are you?” With, “Fine. And then you move on. Or, “Great, great, great,” depending on your culture and then you move on. So we want to ask a question that’s going to… The expectation is we’re going to give an authentic, realtime response. Meaning that the check-in is, I’m not just checking in with you, but when I ask you this question, you’re going to be prompted to really check in with yourself. And so am I, when I answer the very same question. One example would be, “What are you coming in with today?” Or, “What are you leaving behind today?”

And that might be something like, in the meeting right before this, something big happens. I’m noticing like I’ve still got some nervous energy around it, or I’m really excited and I can’t stop thinking about what’s in the future for that. And sometimes even though they’re naming, I’m not quite in the present, I’m already like miles away and I’m planning ahead in the future and I’m excited to get into these next things. Either way it’s grounding them in the present reality of that’s where my head is. And sometimes just naming it helps you to let it go, and then you can be more present.

If you want to hear me doing a checkin, I’ve got lots of episodes to point you to. One in particular that I think is useful is episode number 17, where I was chatting with Diana Chapman. She is the coauthor of The 15 Commitments of Conscious Leadership. And we went through a check-in and we also discussed what a check-in is, how to do one, and why it’s important. So I encourage you to go back and listen to the front end of that episode. After your check-in, now you can pick from this grab bag. Here’s the ideas.

One, follow up on action items. And ideally these are not purely tactical. They are growth oriented. You can discuss action items that were established in a prior one-on-one or ones that have come up in the meantime. And these should include growth and developmental tasks such as learning new skills, using new tools and creating new relationships, as well as specific timeline oriented objectives that connect to bigger projects or goals.

Two, you can talk about behavioral skills. Examples might be clear communication, time management, interpersonal relational skills. And you can talk about these as they relate to that employee’s role within the company. As you’re discussing these, make sure to note where your employee is shining, how it connects to their personal goals, the ones that they’ve shared with you in your initial meeting as you were negotiating the role. So they’re always connecting it back to what really matters to them and who is their best self, what are you seeing from them? You can also then on that strong foundation that is already constructive, you can talk about where expectations have not been met, and you can use this to help direct the employee to finding their own path to success. You can give advice here, but it’s also really useful to ask coaching questions such as, “What could be done differently next time? Or, “If you were to retrace your steps, where do you think was a key decision point where things started going off the rails?”

Number three, this is a great place to give feedback and to receive feedback. Feedback might be performance related. It also might be related to things that are outside of the scope of what you might consider performance. It might be things like, “The other day when we had that team meeting, at the end, I noticed that you checked in with this employee and they left with the big smile on their face. I don’t know what you talked about, but I just want to share I really see that you’re spreading a positive uplifted attitude here, and that makes a really big difference and I really appreciate that in you.” That’s a little piece of feedback that isn’t tactical. It’s more like, “You contribute here in this way.” It may not relate to anything that you guys had on your radar before. That’s great. It’s fine.

This is also a really good place for you to ask for feedback. When employees are encouraged consistently to bring feedback and you are genuinely open to it, you genuinely are interested in their point of view because your desire is to be a great mentor and manager, then they will eventually begin to bring it to you. And this is the best place for them to bring it because real time conversations allow you to ask more questions and get clarity to take ownership and so forth. Ideally, you’re not just getting feedback in your performance review or in a 360 that happens once a year.

Number four, talk about accountability. Are there any unmet goals? Do you need to reestablish expectations? A great coaching manager is able to tactically point out losses as well as encourage and mentor to help team members get back on track.

Five, do a culture check. You can connect back to the greater mission, vision, and values. You can connect to the big picture company goals and the type of culture that’s required to get you there. And this can keep everyone on the same page within the bigger picture, and also within the larger team in which your team is embedded.

Number six, applaud successes. So the one-on-one is a great time to bring the energy up. It’s a great time to recognize your employees’ wins and contributions. It’s a great time to show appreciation for the jobs well done, and this can motivate them and encourage continued growth. It may sound a bit Pollyanna, but it works.

Number seven, create action items. Here’s where you can create some really clear expectations and timelines moving forward. And ideally these are connected not only to OKRs or KPIs, but to tasks that can produce actionable results in a shorter timeframe that are directly connected to that employee’s personal and professional growth goals. We want to make sure to provide space for you guys to kind of hash this out a little bit and for them to ask follow up questions and really help to connect their day-to-day actions to their longterm growth.

All right, take notes as you have the one-on-one. Your coaching notes may seem obvious to you in the moment, just jotting down, “Here are the questions we asked today, and here’s some of the things that came up.” But it’ll be really, really helpful for both you and your employee to look back on when future challenges arise, such as, “This is an issue that we’ve been chatting about since last July. I wonder if there’s real commitment to moving the needle on this one. Maybe we ought to revisit it.” Or, “I’ve seen consistently every single time we’ve been talking about this issue and the ball keeps moving forward and we’re really making progress. And that consistency is what I want to reward.” So lots of good purposes for this. It can also be useful should major performance issues come up later to be able to really trace it back to like what might be your responsibility, what’s their responsibility, and how consistent is this issue really?

Now finally, last tip, please follow up on your one-on-one meetings. Yes, you’re going to have another one soon, but if there are action items, accountability to be had, whether yours or theirs, or some encouragement that you think would be really useful to inject in the week. After the one-on-one happens, close your door, whatever, closer Zoom window, and just make some notes of, “Here’s one or two things I want to do to follow up from this meeting.” A simple, quick reach out by text or Slack can make a huge, huge difference in keeping that employee engaged and in having you an open vehicle for learning, for learning about them and what really is going to help them grow.

I hope that this provides you with some really new ideas for what your one-on-one actually could be for, for how valuable it could be. I want you to imagine that the one-on-one is the highest leverage hour of your week or month or whatever it is that you decide. If it’s not that high leverage, it is so worth you spending a little bit of creative time now to jot down some ideas and really envision a future where this is humming my clockwork and picture the results around you in your organization. That’s a much, much easier life than most managers live, where they’re living moment to moment, week to week, scrambling and just doing status updates all the time. It really weakens your ability to think strategically and to be a great leader when that’s how you’re operating. So do this, not just for them, do it for you.

My final thoughts here are just to remember that you are not alone. Many, many managers struggle with this, and I’ve certainly had seasons where I’m really strong and really great in this. And then the model I was using kind of the needs evolve, and it’s no longer working and I need to go back to the drawing board, but I miss some time there where I didn’t quite realize it wasn’t working. So it’s very, very normal and every company has their own way of doing this. So maybe your company uses a performance management tool like 15Five, which really sets you up for a great one-on-one, or maybe one-on-ones aren’t even part of the culture. By the way, if you wanted to hear more about 15Five, I did have a really great chat with the founders in episode 31, where they talk about best self management. It’s a really cool way of looking at your role as a manager. So I highly encourage you to go back and check that one out. It’ll give you some more inspirational material here.

I hope that you enjoyed today’s summer, short skill-building series on how to maximize the effectiveness of your one-on-one meetings. It’s a creative game. How do you design a conversation that can move the needle in the future? Please let me know what you think and if you would like more skill-building series from me. And don’t forget that the one-on-one meeting checklist and the one-on-one cheat sheet, which is a complete guide to how to have a one-on-one, it’s all available for you at allowedpodcast.com. Open your podcast player right now, and in the description you’ll find a link that will take you right there. I’ll see you next week.