The Secrets Behind Great One-on-One Meetings

Develop Trust

A one-on-one meeting can be a sacred time during which the manager and team member make an individual connection, both as coworkers and as human beings. That doesn’t mean that you’ll become best buddies with everybody you work with, but it sure helps to build rapport.

“The primary focus for the one-on-ones is relationship-building and most importantly, building trust,” says Islin Munisteri, a petroleum engineer. “You’re putting relationship capital in the bank so that you have a wing man (or woman) to back you up in times of crisis. Hint: It’s always a time of crisis.”

The meeting is a personal time to be honest and direct with each other in a safe setting. Only if a team member can talk about what is really worrying her can a manager offer useful advice, or at least an understanding ear.

For one software engineer, the best part of her one-on-ones was that her manager was human and kind when she brought up personal or health concerns. “She cared about me as a person, not just as a worker,” explained the engineer.

If you come to one-on-one meetings from a business culture of sharing—“Aren’t team status meetings enough?”—you might not realize how much this private time matters. Some team members are introverts who don’t like to speak up in public. Or they don’t want to take up others’ time with a discussion that is relevant only to their to-do list. For instance, says Mae Demdam, director of media at Digital Edge, a marketing agency in Jacksonville, Florida, “Individuals won’t speak openly with other people around in an effort not to offend anyone and feel singled out.”

Align Everyone’s Tasks

One-on-ones are not a reiteration of operational status meetings, such as Scrum meetings, during which each team member shares what he accomplished, what he’s currently working on, and what’s blocking his progress. Some of these tasks are bound to come up as discussion items during a one-on-one (not the least of which are obstacles the manager might help the team member to overcome), but the true benefits come from both parties getting a larger view of the situation.

For managers, that may include an early-warning system for problems; for team members, it’s an opportunity to recalibrate to-do lists to ensure everyone is working toward the same goals.

“When done right, one-on-one meetings keep up open communication between manager and worker,” says Elise, who’s been managing professional teams for 20 years. “They align the day-to-day tasks of the worker with the fast-moving shifts in business priorities into which the manager has closest insight. It’s like a dance, and these meetings help adjust the steps.”

Share Business Information Privately

One-on-ones give people a way to share information that helps them move forward. That might be a heads-up on changing initiatives, progress updates about items that affect a single individual (rather than impacting the entire team), or other information that improves relationships with upper management.

“If you’re a fairly competent person, your boss isn’t sitting in meetings with you,” explains Greg, a senior system administrator. The manager is working on her own tasks, such as budgeting, or collaborating with other departments, which means she can’t know everything you’re working on, and you can’t know the other teams’ efforts that could impact you.

“The one-on-one meeting provides two-way communication about those things,” Greg points out. It’s an opportunity for the manager to learn how things are going for the team member, and to pass along anything coming from above that might influence the things you are working on. “At most places I’ve worked, a scheduled communication time, a one-on-one meeting, was the only time one could reliably find one’s manager to get their take on some issue,” says Greg.

Managers have many ways of communicating downstream, and should take advantage of those. For example, use team status meetings to let the group know things everyone should be aware of, such as “We decided to adjust the product launch date” or “The accounting person is going on maternity leave at the beginning of the month, so be sure to send in your expense reports before then.” Sometimes it’s important to share information with just one person, though, such as when a big change is coming, and you want the senior team member to help you deliver the message.

However, one-on-one meetings are a team member’s opportunity to communicate upstream privately. This may be for privacy reasons (“If Heidi is leaving, does that mean we’re going to hire a new senior staff member? I’d like to throw my hat in the ring”) or because the details are irrelevant to the rest of the team (“I’m leaving tomorrow for vacation, so how can I get my expense report done before the accounting person disappears?”).

Provide Mentoring and Feedback

The most rewarding parts of a one-on-one meeting often are those in which the manager and team members learn from one another.

“Listening, being present, and asking questions that prompt deeper insights is super important,” says Zach, a vice president of engineering.

Andrew, a web designer, appreciates that his manager pays attention to Andrew’s mood and work effort. His manager uses those observations to provide encouragement: “Are you having any problems with Suzanne while working on that project?” or “I think you could have done that design more efficiently; what happened?” or “You really crushed it on solving the CSS problem, nice work.”

The meat of a one-on-one meeting usually is collaborative problem solving. Often it goes beyond facts ( “I got that done!”) to motivations, emotional issues, challenges. That might include, “I noticed at Tuesday’s meeting that you were irritated with Todd. What’s up with that?” or “To do a good job on this project, we need Marketing to work with us. Let’s figure out what they need, so they’ll be motivated to help us meet our deadline.”

Feedback goes in both directions. The manager may spend quite a bit of time giving advice based on his own experiences, or coaching the team member on how to deal with a difficult problem (“What do you think you should do?”).

A key part of a manager’s role is to remove the obstacles that prevent their employees from doing their jobs. So the best way for a manager to improve his own skills is to ask team members how he could improve his own skills, such as asking, “How can I help you make this happen?” Ideally, at the end of every one-on-one, the manager has learned something new, too.

A Gut Check: How Are We Doing?

Most day-to-day business issues put our attention on current events, how things are right now: How’s this task going? What fires need to be stomped out? What has to be completed this week?

But among the joys of one-on-one meetings is that they can provide an opportunity to look backward and to look forward. When things are going well and there aren’t any big issues to chew over, manager and team member can use the time to measure past successes (yay us!), identify ongoing issues (why do we keep having trouble with that Internet service provider? Should we consider changing vendors?), and think about innovative ideas (including the “dumb ideas” that might not be ready to share with the team). You can ask: “Anything particularly interesting that you’ve learned while you worked with that new tool?” or “Any ideas for things we should change, improve, look at for the future?”

Because not everything is day-to-day. One-on-ones create relationships of trust—and those enable people to think about new possibilities.

This Is Not the Manager’s Meeting

Managers have plenty of opportunity to express what they think is important, and the worker bees who report to them usually have no recourse except to listen. That’s part of what makes a one-on-one special: It’s not primarily to serve the manager.

This is the team member’s meeting. This is time set aside to address whatever the team member thinks is important. The team member should feel confident that the manager is paying attention, giving him his undivided attention, and doing so in utmost confidence.

“One-on-one meetings offer an opportunity for leaders to very specifically address the needs of each person on their teams,” says Jim Rosas, founder of business consulting firm @Revenue. “They give permission to the employee to be open and honest behind closed doors in a way that may put him or her in a vulnerable position with other teammates. Look at it this way: We all have strengths and weaknesses, but do we all want them addressed in public? Of course not.” 

It’s a one-on-one, not a one-on-zero. This is the time for team member to express his views, to share what he thinks is important and that the manager should take note of.

There’s information that a manager can impart to the team member during a one-on-one meeting: “You oughta know” updates, praise, suggestions on how to improve a skill. But under most circumstances, the meeting isn’t about the manager. That shapes the conversation—or it should.

And, as with any relationship, bad things happen when someone feels unvalued and unlistened-to. Phil Stella, a workplace communication consultant, tells a story about Joe (the supervisor) who met with Maria (the production analyst) about problems with a new manufacturing process. Joe should have led a dynamic and creative dialogue to explore possible causes, analyze each different solution, and choose the best one, says Stella. “Instead, Joe shared his thoughts first, barely listened to Maria’s comments, told her how to solve the problem, and then blamed her when it didn’t work. Maria got angry, quit, and took a different job where her new boss wasn’t such an idiot.” That’s not exactly the ideal outcome.

This Is a Conversation: Expect Bumpy Bits

A one-on-one meeting isn’t a report or a presentation. Those belong in many other types of business meeting, where “just the facts, ma’am” is what is wanted, and other issues are tangential distractions. That’s not the case for one-on-one meetings, in which the purpose is to create an atmosphere of trust and personal connection in which you sincerely care about one another.

That doesn’t mean that every one-on-one is a wallow in human emotion—most are not—but the manager, at least, should be ready to respond if the team member lets his feelings show. And really, it’s okay for emotions to flow.

Doing a great one-on-one requires you to exercise your communication skills—whatever those may be. Not everyone is a good listener by nature, particularly when the team member is upset or shy or recalcitrant.

One-on-one meetings can test a manager’s verbal facilitation skills (getting them to talk); listening facilitation (mental and nonverbal); and graphic facilitation skills (recording what they say). Among those—thankfully learnable—skills are displaying interest without judgment, and acknowledging a team member’s viewpoint even when you disagree with it. Don’t worry: You can get better at this. Over time, a manager can learn to ask open-ended “how” or “why” questions such as, “What happened when you asked her about the issue?”

Managers need to be particularly cognizant of each team member’s communication style and what each individual needs. That’s especially true in technology fields, which have a high percentage of introverted workers who are slow to open up.

Team members are not always forthcoming, especially when their previous one-on-one experiences have been disappointing. Trust takes time. However, when people do confide in you, it’s a powerful thing. Do not interrupt them. Let them speak. 

This may make you uncomfortable if you’re new to leading teams—or if you recognize your own weaknesses in this regard. Perhaps that’s something to raise in a one-on-one with your own manager: Can you get a bit of leadership training?

Don’t Be Afraid to Be Personal

You probably don’t need to be told to show a sincere interest in the team member. But some managers, concerned about crossing an “inappropriateness” line, are loath to ask about the team member’s interests outside work.

You don’t have to pry. In fact, you shouldn’t. You can, however, ask friendly questions to learn what team members care about after they leave the office. Your team members’ families probably are pretty important to them; find out (and remember!) the names of spouses, children, siblings. It isn’t an over-personal question to ask about Susie’s kindergarten graduation party.

“Bonus points go to the manager if they pay attention to my life outside of work and ask questions based on those current events,” says Andrew, the web designer. “Such as: I know you’ve been talking about buying a house for a while; any progress on that?”

Be open to personal details, but don’t expect them. “I actively encourage my team to just chat, but I shy away from asking probing personal questions,” one team lead says. “I prefer each person to set the tone they’re comfortable with.”

But part of the point of the meeting is to establish comfortable communication. “That cannot happen if they aren’t open to non-work discussions,” says Greg.

Getting personal sometimes means that the team member complains about a coworker. “The manager needs to permit that without making a capital case of each gripe,” says Greg. “It could be clashing personalities, or it could be the warning signs of a case where the manager needs to step in directly.”

Be transparent. Be honest. The consequence of doing so is that you’ll hear a lot of real concerns, some of which may be uncomfortable to hear. If you can’t answer a question directly, say so. If you hear about a problem, acknowledge it and explain how you’re going to fix it. Above all, be worthy of your colleague’s trust, or you won’t have it for very long.

Schedule the One-on-One as a Recurring Meeting

Those who like to “manage by walking around” sometimes feel that a one-on-one makes sense only when they see something to talk about. But that violates the premise that this is primarily the team member’s meeting. If the manager doesn’t happen to walk by when the team member’s brow is furrowed, she may not know that there’s something bothering him. And for many people, the act of asking the boss, “Um, can we talk?” is a big deal. Asking for a meeting suggests that something is “important”—which means it’s already passed into some level of criticality. Meetings should be held when both parties are comfortable saying, “This might sound like a dumb thing to bother me, but….”—because sometimes they aren’t that dumb.

“Schedule one-on-one meetings in advance,” advises Tim Evanchick, district manager for retail furniture company Yogibo. “Impromptu meetings can often seem adversarial. In contrast, scheduled meetings allow both parties to prepare.”

If one-on-one meetings only happen when there’s something “important” to talk about, the experience is viewed as a negative one. Elise once had a manager who held the meetings only when he had to, such as when bad news was coming from on high. “It resulted in poor morale, and I ultimately left that manager and that company,” she says.

It’s far better for the one-on-one meeting to be part of everyone’s weekly rhythm. Make these recurring meetings (such as every Monday at 2 pm) to establish predictability. Book a regular meeting room; add a dial-in if needed for remote workers. Whatever format the meetings take, keep it consistent so everyone knows what to expect and how to prepare.

Again: The meeting is about the employee. You demonstrate that you are trustworthy by ensuring there is a prioritized, dedicated time every week when you are ready to listen.

Don’t Cancel It. Really, Don’t.

The most damning thing you can do to your managerial reputation is to cancel one-on-one meetings.

Treat these as sacred. If you must, reschedule to later in the day rather than tell the team member, “Let’s just skip it this week.”

Canceling is the easiest way to communicate to an employee that he’s not valued or respected. The one-on-one is an essential time to share what’s on their minds—and if you minimize its importance, the team members feel hurt. Wounded feelings about canceled meetings were the most common complaints I encountered when I asked for advice for doing great one-on-ones.

“Those meetings need to happen,” says Samantha, a software developer. “When your manager is constantly rescheduling them, that’s a sign that your manager isn’t making management her main priority.” Trust is lost, information is not shared, and the team member will lean on another team member for confidences or support.

And the result? “Usually the same things that happen when you aren’t communicating with someone,” says Samantha. “You both build up resentment and assumptions where you don’t give each other the benefit of the doubt.”

“I’d say 75% of my managers in my career held one-on-ones infrequently, cancelled or moved them around the calendar, or were terribly late to each meeting,” says experienced manager Elise. “This resulted in me (as a worker) feeling that I and my work was not a priority.”

And the fix? Just keep the appointment. “I appreciated a recent manager who was religious about one-on-ones and respectful of my time, keeping the weekly time slot, and rescheduling only as a last resort when we mutually agreed,” says Elise. “I modeled that behavior with my own team one-on-ones after that experience.”

Ideally, schedule adjustments should be in the hands of the team member, who has a better idea of how much oversight he needs at the moment. “Tell your boss if you think you’re meeting too frequently or not frequently enough,” suggests Jen, a mid-level manager who’s survived several enterprise management changes. “Discuss this in person (not email). And have a reason for requesting the change other than, ‘I really dread meeting with you and would like to do it never.’”

The one-on-one meetings are important to everyone, at every professional level—but particularly so for those with less experience. “One-on-one meetings with junior people were a lot more important in their eyes,” says Elise. “They were nervous if I cancelled the meetings, as they needed more direction from me weekly. More senior reports often made the mistake that they did not need to meet with their manager as often, but I made sure to use these times to share strategic information that would help them do their job more effectively.” 

That’s not to say that cancellations never make sense. Sometimes, things come up: doctor’s appointments, urgent deadlines, and so on. If the manager and team member have a relationship of trust, an occasional skip isn’t troublesome.

“If you really don’t have anything to discuss, then cancel the meeting,” says Jen. “But note that if you are cancelling every meeting with your employee, you might want to look at the frequency of your meetings (too much?) or your lack of specific goals.”

How Often Should You Meet? For How Long?

The accepted wisdom is that a one-on-one meeting should be held weekly, and you should allow 30–60 minutes. Some people have more to say, particularly when a team member holds multiple roles (e.g., someone is both chief architect and member of a corporate advisory board), or the relationship is a new one (thus you need to spend more time getting to know one another).

With experience, you may decide to schedule meetings for 30 minutes—though it’s always a good idea to let the team member suggest that change rather than the manager.

If an hour seems like too much time to give each team member, a manager should consider whether the time crunch is a warning sign. “This is one of the main reasons why it’s typically not good to have more than eight direct reports,” says Lou, an information security manager. “Busy people always make time. This allows a regular cadence for non-urgent issues, which enables a culture that is less interrupt-driven.”

But wait! That means that a manager who supervises eight people is spending eight hours a week in meetings with those team members. That’s a full day of work!

Except: That is your work. “Think you’re too busy and don’t have time to have one-on-ones with every employee every week?” asks Darryl, an experienced network manager. “For this small investment, you get something back. You don’t need to interrupt their work just every time you think of a question; you know you’ll have a meeting with them in less than a week.”

“So now you have more time for your work, and the team members have more time too,” says Darryl. “They really wish you’d stop interrupting them and let them get their work done.”

Once you’re in a rhythm, it’s fine to recalibrate the meeting frequency—but don’t do that too soon. As you work to apply these guidelines in your own organization, make yourself stick to the meeting cadence for a solid month before you decide, “Oh, that’s too often” or “That’s too much time.”

“I have found it helpful to have a regular one-on-one even when there’s ‘nothing to talk about,’” says Liz, a software engineer. “Often, in a recap of the past couple weeks or the work ahead, something comes up that is worth discussing.”

Elise’s experience echoes Liz’s. “I often think I don’t need to meet with a report. I feel like we are aligned because we sit near each other and are in some meetings together. But I go ahead anyway with the meeting, and we surface up a lot of issues to discuss, or do a brainstorm to take a topic further. So, I avoid canceling meetings now and just show up to see what surfaces. These meetings help to go deeper in the relationship as well as with project strategy.”

Choose a Comfortable Place

The usual venue for a one-on-one meeting is in the manager’s office or a company meeting room, and that’s fine. The only thing that really matters is that both people are comfortable.

You can consider alternatives, however. If your company has an open office plan, for example, you may lack a private space—particularly important if the team member needs to throw a hissy fit, or is emotionally distraught enough about a situation that she might burst into tears. Other people can be intimidated by talking in the boss’s office; it doesn’t feel like neutral ground.

One option is to go offsite. Take a walk together (though that presents challenges for taking notes), or go to a nearby coffee shop.

Don’t let technology get in your way. Team members who work remotely need their one-on-one meetings even more than do people who are co-located. Videoconferencing works remarkably well, once you detangle any tech challenges, since much of the “connecting with each other” conversation benefits from visual feedback. Hold the meeting by telephone, if necessary.

Have an Agenda

Whenever and wherever you sit down together, each of you should have some idea of what you want to talk about today. Both manager and team member should write down an agenda, both a “things we gotta cover” and “things we should discuss at some point.”

The team member should create the agenda and email it to the manager an hour before the meeting. The manager can add items, but it starts with the team member.

So, for instance, Bob might create an agenda that looks something like this, and send it to Julie:

• What’s the status on the site navigation project?

• We talked last week about bringing in a contractor to help with the Foobar project. Any update?

• Just to let you know: Manny’s white paper is in Dave’s hands for review. But Dave’s out on vacation this week, so we won’t hear back immediately.

• I need to ask Creative for new signup banners. We need to figure out what the banners should say.

• I had some thoughts about what we might do in our trade show booth, but that’s Hannah’s area. Can I share them with you before I make suggestions?

• Remember, I’m on vacation in two weeks. Who’s going to cover for me while I’m out? What do they need from me?

Some of these are just status updates (though the sort that only Julie needs to be appraised of rather than the entire team). Julie might add an item or two—Bob doesn’t know yet about the project from the new customer, and how that’ll affect Bob’s workload—but in most cases there are fewer of these. Expect 90% of the conversation to be driven by Bob’s agenda.

One reason to put the agenda-creation in the team member’s hands is that it underscores that this is his meeting. If nothing is pressing (“Really, Julie, it’s all the same as last week”) it lets him be the one to suggest that the meeting be canceled.

“It’s their time to surface issues, build rapport, and gain insights from their manager,” says Elise. “I’ve had many team members who looked to me to drive the agenda of these one-on-ones, even writing their own goals. That led to micromanagement and a passive approach on the part of the worker.”

Another reason for the team member to supply the agenda is that it alleviates anxiety: You’re setting the stage for what you’ll talk about. “I had terrible, directionless meetings with one of my bosses until I started sending him agendas beforehand,” says Jen. “He seemed pleased that I did it and the meetings went more smoothly. Plus, he asked me fewer ‘out-the-blue impossible-to-answer-on-the-spot’ questions.”

The agenda also helps the team member prepare. “If you need to approach your boss about a concern, come to the table with whatever information you may need to support your concern, and offer a solution or two to the problem,” says Yogibo’s Evanchick. “Otherwise, you’re just a complainer.”

This process might not come naturally to some team members, so it’s okay to provide an outline to get things started. For example, one manager supplied the team with a list of questions to answer before each meeting:

• What are you proud of in the last month?

• What are you not so proud of in the last month?

• What are you not looking forward to in the next month?

• What are you looking forward to in the next month?

It’s okay to go off script. Don’t worry about covering every item. Most business meetings aim to end with a firm decision, such as choosing the website color scheme. This is more of a laid-back conversation, so both of you should prioritize the issues that must be addressed and which can slide until next time.

Build Follow-Up into the Process

You can create great rapport during the one-on-one, and perhaps brainstorm new ways to tackle ongoing problems. But this is still a business meeting, and someone has to be responsible for taking notes, turning them into actionable items, and making sure the items are acted upon.

In almost all circumstances, it should be the team member who takes notes. She’s the one who is most invested in the outcome, and probably holds the most responsibility for making something happen.

As a practical matter, that usually means the team member sends an email message to the manager right after the meeting. In it, Bob records what he and Julie agreed to, giving both people a paper trail to counter faulty human memory.

It’s also a nicety for Julie to send an acknowledgment of the new to-do items—even when minor—as well as a sincere thank-you to Bob for the meeting. “I appreciated it when things discussed in the one-on-one (i.e., salary request, personal time off, budget requests) were followed up on promptly,” says Elise. “That made me feel recognized and respected.”

A written summary has other advantages, points out Yogibo’s Evanchick, when the one-on-one meeting includes an uncomfortable evaluation or correction. The email thread provides a record of what was said, so it doesn’t become a “he said, she said” situation.

Every week’s agenda should refer back to earlier one-on-ones and what each person committed to. If the team member doesn’t include them on the agenda, the manager should do so.

That all sounds so pretty and easy, doesn’t it? But a lack of follow-up can poison all the good that was accomplished during the meeting. Is it too much to ask for this to be done with empathy and the desire to help the team member accomplish agreed-upon goals? To actually take action on issues?

One developer described her one-on-one meetings as “a kind of ‘gotcha,’ tracking what we talked about in a spreadsheet and pouncing on me if I asked about something twice by saying, ‘We talked about this already on March 26th.’”

The General Start: How Are Things Going?

It’s a deceptively simple management tactic. Ask, “How are you?”

And then wait for an answer.

Really. Wait. Don’t fill the silence.

Sometimes, things are fine, and the team member says so. Or you hear a happy little tidbit, such as the joy of fixing a mysterious bug.

But every so often, a sincere “How’s it going?” causes the team member to launch into a tirade that demonstrates the burning issues that truly do need to be addressed (“I’ve had it with him! Just had it!”). Then you can crumple up your carefully constructed agenda, and chuck it out the window. You likely won’t need to say anything for a solid five minutes, because the team member has been waiting to share this with you.

In which case the manager should quietly celebrate, because it means the one-on-one is achieving its goal: Creating a relationship in which you both feel free to express whatever comes to mind. Because now that you’ve heard about the team member’s real frustrations, you can do something about it.

It might be work-related: the nincompoop in Accounting, or the bozo who decided to upgrade the production systems in the middle of the workday. Or you may hear about personal issues, good or bad: her daughter’s birthday party, or at-home struggles that have affected his work lately.

That “How’s it goin’?” introduction is also a manager’s early warning system. Michael Lopp, author of Being Geek: The Software Developer’s Career Handbook (O’Reilly), writes “As I’m listening to the answer I’m discerning your mood and I’m throwing you into one of three buckets regarding the type of 1:1 we’re about to have:

• The Update (All clear!)

• The Vent (Something’s up…)

• The Disaster (Oh dear…)”

Your Agenda Is Your Friend

As we already discussed, the agenda lays out the items that are top-of-mind and gives the meeting some kind of structure. This prevents surprises and gives each of you an opportunity to prepare for any data-gathering that’s needed. It helps you identify the areas of concern to address immediately, whether minor or major: vacation scheduling, troublesome bugs you need help with, prioritizing work items.

Also, if you’re shy and nervous, it gives you something to consult and helps you get started talking.

Follow-Up from Last Time

It’s a good idea to revisit the items you discussed in the previous one-on-one, particularly if those generated any kind of to-do list.

If the manager made a commitment, discuss where that stands, says Darryl. “If, at the last one-on-one, you said you’d talk to the vendor’s support manager to get the equipment replaced, then share the results at this one-on-one.”

Here’s What’s Happening

Even though the one-on-one is not meant to focus on specific tasks—those fit better in team meetings—it is about the work you’re doing. But don’t let yourself get lost in the details.

At Sara’s company, she is encouraged to talk about expectations rather than specific tasks underway: What do you expect from me in the next six months? Is working for this company reaching my expectations? “While my one-on-one meetings do tend to at least touch on work from the last two weeks,” Sara says, “I try to keep it to how I’m feeling, what I’m struggling with, and expectations. I’ve had jobs end badly because of mismatched expectations before, so it’s really important to me to make sure things are going ok/not going ok, so I can work on improvements.”

“Make it clear that you’re more interested in outcomes and results,” says Jen. “I don’t want a laundry list of what you did all week. I want to hear about what you accomplished, and how you do it. I don’t care that Person X never called you back, or you couldn’t get the code to work, or whatever. I want to know what you did to fix the problem.”

“Talk about the progress you made around larger initiatives of the business,” says Elise. “The goal of one-on-ones is to stay aligned to business goals and help you be successful against defined goals.”

The manager probably has things to share, too. Don’t rehash the staff meeting, suggests Darryl, but if you’re concerned about an employee’s ability to meet a deadline, bring it up now and ask how he intends to proceed.

That’s when it gets fun: you can consider possible solutions without regard to today’s current emergency-du-jour. In a one-on-one meeting with Kean Graham, CEO of ad tech firm MonetizeMore, a team member suggested a way to improve the performance and efficiency of working with their clients. “We also brainstormed tools we could use to complement the team ad optimization. We implemented the process a few months later, and it turned out to be one of the best innovations of this year,” Graham says. “It wouldn’t have been discussed without having that one-on-one.”

Bidirectional Feedback

In the best one-on-one meetings, both people learn something new. It’s a moment to step back from the daily grind and evaluate progress with a wider view.

The one-on-one’s real goal is to help the team member get the work done—and that includes whatever forces the manager can bring to bear to help that happen. We like to think that the manager can make a difference, since she usually has more experience with the process, the technology, or the company culture.

This is a long-winded way of saying: we’re all here to help one another. That happens through feedback (here’s what I saw) and coaching (here’s a way to do it better). Ideally, feedback is immediate (whether positive or negative), continuous (no one should be surprised by a job performance review), and informed (based on measurable data, not just a gut response).

Some managers imagine that the information flows only one way: I’m the boss, and this is what you should be doing. But the best working relationships are based on both getting and giving feedback, and those are reflected in every one-on-one meeting.

Always do your best to find something to praise. It’s hard to say “Thank you” too often. Few of us resent a compliment, especially if it’s something we’re proud of.

Other resources can teach you how to give feedback effectively, in more depth than is possible here. Keep in mind, though, that the overall goal is to help the person reach his own answers rather than to accept yours. For example, if the team member failed, both of you gain something from that investment if you ask, “What did you learn?” instead of saying, “This is what I would have done instead.”

Career Development

Every so often, take a step back from project discussions, and talk about what the team member wants to accomplish. What long- or short-term goals does he have, and how can they be worked into the day-to-day trajectory?

For example, says a web designer named Jamie, imagine a team member who wants to get better at public speaking. The manager can help set up a few opportunities to speak to the team about a tech topic. “These sorts of goals give you tangible actions that can be followed up on and parlayed into bigger opportunities (like being in on a client pitch),” says Jamie.

Every so often, expect to have—and to encourage—a higher-level discussion about the employee’s career and satisfaction on the team, sometimes called “stay interviews.”

“Find out what their goals are,” says Darryl. “It’s likely that they don’t want to do their current job forever; maybe that next position is something you can help them achieve. Maybe it’s within your own department and you can help them get some experience with and knowledge of their potential future role.”

How Can I Help?

Ultimately, it’s the manager’s job to help the team member succeed. Use this time to learn how to do so.

What is the team member struggling with? If she can’t finish a task because she’s waiting on someone in another department, perhaps you can run interference by talking with the other department manager to remove the roadblock.

“If you’re not hitting your goals, how, as a manager, can I help you remove obstacles to doing so?” asks Jen. “One of my biggest jobs as a manager is helping you clear the way so you can get your job done. I may not always be able to untangle the bureaucracy, but I can try.”

Don’t promise solutions on the spot. This is an opportunity for each of you to raise issues; you don’t have to fix them immediately. But then both of you should go away and think about how to facilitate some solutions.

“Ask about impediments and blocks outside the team,” suggests Esther Derby, an expert in organizational dynamics. You want to know about their dissatisfaction and understand when and how policies get in the way of teamwork and team work. “You can’t fix everything, but you can investigate, look for patterns of blocks mentioned by multiple team members,” she says. “You can create an impediment backlog and post your burndown to the team.”

Lastly, whether you are a company executive or a brand new hire in the mailroom, at the conclusion of every one-on-one you should humbly ask, “Is there anything you would like to see me start doing, stop doing, do more of or less of?” Says @Revenue’s Rosas, “This question almost always exposes a nugget or two that will help your organization.”

Need more questions to ask?

• What could I be doing better as a manager?

• How could the team/the company improve?

• What isn’t fun about working here?

• If you were me, what changes would you make?

• What’s wrong with our products?

• If you had the time and budget to improve this issue, what would you do?

• What opportunities are we missing out on?

• What do you want to do better that you haven’t had a chance to do yet?

What Not to Talk About

Although the goal is to create an relationship based on trust and openness, some topics are minefields. Don’t go there.

First, eschew gossip. There’s a difference between, “This person is blocking me” and “He is a horrible person.” A good rule of thumb is to pay attention to rants about someone’s behavior (“He said a stupid thing”) versus identity (“He is stupid”).

Avoid talking about people not in the room in a negative way or complaining about leadership. That only leads to poison waters. “Getting in the middle of a feedback between team members when you don’t need to only creates problems and erodes trust on the team,” advises Derby. “When someone comes to you hoping you’ll carry a message for them, coach them on how to offer effective feedback, so the situation gets handled where it lives, between the team members.”

Similarly, you shouldn’t let the conversation get derailed by talking about things that are too personal.

What’s too personal? Where do you cross the line between company information and gossip? Good luck with that. It may help to adopt the attitude: Ranting is okay; it lets people blow off steam. Whining, not so much.

Besides, whining doesn’t move toward a solution. “Don’t let people sit there and complain the whole time. You have to cut that off before it spirals,” says Jamie. “I’ve done this in the past as a supervisor, and it was the worst thing I could possibly do for my team members.” Do listen to the complaints; they’re real to the team member. But move the conversation in the direction of constructive feedback. “Brainstorm solutions that they can follow through on,” says Jamie. “Don’t forget to follow up with them so they know you care about their success and not just your own agenda.”

The only thing you can do is to redirect the conversation to business. When the discussion makes you uncomfortable, say so—and why—and then change the subject.

Secret-keeping is another bad idea. “There is some value in sharing information,” says Elise. “I often found out key office news in one-on-ones, such as people leaving.” But gossip that has no actionable outcome creates problems—particularly for the listener. “One example is my boss telling me someone was to be fired in a few weeks time. There was no reason I needed to know this and then I had to hold that information for a few weeks to myself. Bad idea.”

“Generally, if you wouldn’t say it to your entire team or the company, than it’s probably not appropriate to say to an individual,” says Zach, the VP of engineering. “People are smart. If they get that you may be ‘letting them in’ on something secret, then they are going to also think about what you’re keeping from them and telling others.”

Encountering Bad Attitudes

You’re a warm, well-meaning, devoted person. You’re genuinely interested in the success of the company in general and your coworkers in particular. So the idea of doing a great one-on-one meeting is one you celebrate: see, we can work together even better! We can be productive and innovative! We can make more fun!

And then you bump into someone who thinks that one-on-one meetings suck. Thus, when forced to engage in one, they do so with the enthusiasm suitable for getting a root canal.

It’s not that your team member or manager doesn’t want to succeed. Quite to the contrary. But all of us establish expectations based on our past experiences. Those who have had rotten one-on-ones in the past won’t be joyful about the prospect of a meeting with you.

Happily, these attitudes can be addressed—once you recognize them.

They don’t have reason to trust you.

You, O reader, are a wonderful person. We know that because you have devoted a considerable amount of time to reading this in order to improve the relationship with the people you work with. (And thanks for doing so.)

But your team members and managers may not know that. They may come to the meeting with fear and trepidation, simply because you’re the boss. Or, given past one-on-one meetings, they “know” that the meeting is only for the manager’s benefit, not their own.

That’s in direct contrast to seeing the goal as enabling the manager to make the team member happy and productive—much less treating the individual with respect. One team member encapsulated this attitude when he wrote, “What communication needs to happen in order to make you, as my boss, happy? Let’s start from there.”

“Employee one-on-ones almost always come loaded with hierarchy,” says Annie, a longtime corporate programmer. “You’re usually not treated like the domain expert, even if you are.” Team members don’t trust a meeting with that kind of power play. “It feels like a meeting ‘at their mercy,’ where you’re being sized up again and again, for your productivity, personal health, and optimism,” she says. “It feels as if you’re being sniffed by search dogs, interrogated as a possible suspect of a crime, and evaluated for the quality of your blood by a hungry vampire, all at once—all the while trying to pretend this is a casual discussion that does not directly affect your current career choice.”

The effect is bitterness toward the entire process. “I’ve never seen a one-on-one meeting schedule that was regularly upheld, anyway,” says Evelyn. “They are always postponed or put off as being less important, and eventually we stop having them. I’ve never seen it last more than four months.”

Every organizational weakness is highlighted in the one-on-one meeting.

If the company has troubles, from poor leadership to money woes, they will be reflected in the conversations downstream. Even the best manager can’t fix problems in another department. If the programmers repeatedly complain to their manager about the IT staff messing up the production servers, the manager can try to remedy the situation—but cannot always succeed. If the marketing professional cannot get budget for a project she sees as critical to the company success, frustration is inevitable.

Those weaknesses can show off (real or imagined) personal imperfections, too. Beth, a senior software developer, complains that in one position, her manager wasted time complaining about other people and parts of the company. “He seemed to want me to ‘mommy’ my manager with sympathy, because I was the only woman who reported to him,” she says.

“In these types of meetings, I’ve never once been asked questions from the perspective of my domain expertise,” says Annie. “Instead, I get questions which feel invasive, judgmental, and make me feel at risk. I answer slowly, carefully, walking on glass. It’s a pretense of a meeting, where nothing gets done but to reinforce the hierarchy and ask the only important question in the mind of most management: Are you getting your work done efficiently?’ There’s nothing productive about this.”

Annie has reason to be upset: she once lost a job after she answered, “How are you doing?” honestly. She says, “How can you tell when one-on-one meetings aren’t search-and-destroy meetings, designed to weed out employees who may raise issues? If you have to be on the defensive, you simply can’t tell the difference.”

Contemplate this: Annie might come to work for you. (After all, she’s a great programmer.) But if she has this kind of emotional baggage, how can you get her to trust that your one-on-one meetings are going to be different?

They see one-on-ones as a distraction from “real work.”

When one-on-one meetings don’t follow the guidelines discussed in this report—they repeat team status updates, the “advice” is only criticism, the manager never follows through—many people conclude that the meetings are a distraction from getting their “real work” done. “Meeting is often the opposite of working,” says Evelyn.

Sometimes, you won’t succeed in changing their minds. But you still do need to impart information to the manager and to let team members know what’s going on.

“I’ve found that bosses fall into two categories: Those who want to hear your problems and issues and help you solve them, and those who don’t,” says Jen. “If they don’t, it’s best to come to the meeting with not only the problem, but your proposed (or already attempted) solution. Show them that you’re proactively attacking it. They may be more willing to help you problem-solve if you aren’t dumping the whole gnarly mess in their laps.”

Don’t feel that you must wait for the manager. Take the initiative and schedule a one-on-one with your manager, says Rudolf, a career coach. “Make a short list of things you want to discuss and keep the one-on-one focused. Your manager will find it just as useful and will appreciate your initiative.”

If that’s more than the manager is willing to do—she keeps canceling meetings—you should still keep the lines of communication open. Send a short email message of what you’ve been working on as well as any ongoing problems or issues. “An unpleasantly surprised boss is not a happy boss,” says Jen.

Understanding Unique Roles

Most one-on-ones take place in an office environment, where one person is the “boss” over the other. Different roles or environmental issues can put a wrinkle in the process, however.

One-on-one meetings are particularly important when employees work remotely or in distant offices—particularly when time zones are a factor. “An open door policy doesn’t suffice for remote employees who specifically have daytime exclusively during my sleeping hours,” says an engineering manager based in Europe. “While I let the team know I’m generally available, the one-on-one is a known time where they can bring things up.”

It’s more than the “devoted time,” however. Managers with remote team workers need to treat one-on-one meetings as even more critical to relationship-building.

As has been demonstrated by plenty of research on remote workers, it’s essential to make them feel part of the team. Everyone else gets “water cooler time,” and hangs out by the coffee machine, during which people catch up on the latest videos, who’s expecting a baby—and the “hall track” during which a casual work conversation turns into a innovative brainstorming session. The one-on-one becomes an important way to connect team members even when there are frequent group meetings.

And for some people, that personal connection occurs only after they meet in person. Varda Meyers Epstein, a parenting expert at Kars4Kids, didn’t meet her current manager until she’d worked at the nonprofit organization for a year. Phone calls and email were awkward, says Epstein. “We couldn’t really forge a relationship. Our correspondence and conversations were always a bit stilted.”

When the organization brought Epstein to spend a month in the office in New Jersey, she and the manager hit it off. “I think [previously] we saw each other as adversarial presences to a certain extent. But when we met we found a place of warm connection.”

Consultants and contractors often have a different relationship with their clients than do regular employees—and it’s always hard to discern in what ways that will be so. There’s no right or wrong way to manage one-on-ones in this circumstance, though it’s a wise idea to talk about the process and expectations early.

The fact that the contributor is active for a short time shouldn’t be a factor. Though, quite often, it is. Many consultants, brought in for “heavy lifting,” aren’t given personal attention, and the managers see no reason to invest in mentoring. After all, the managers assume, this person won’t be around long enough for it to matter. Plus, since the consultant is brought in to solve a specific problem, it’s rare for the individual to participate in the decision-making process; he’s there to address the problem, not to define it, and the one-on-one doesn’t address that “meta” view.

In some cases, however, the one-on-one meetings actually are better for consultants, in part because the manager sees them as experts and grants them additional respect. Also, a clear contract with well-defined deliverables and possible outcomes can set expectations and make the meeting more professional.

Some organizations treat consultants and contractors “just like any other employee” (with the only differences determined by an accounting department), including a regular one-on-one. That’s a good idea, since anyone contributing to the team’s success ought to have the same opportunity to share concerns, provide updates, and to get feedback that adds to project success.