Human-first 1:1 meetings

Purpose, responsibility, cadence, and continuity

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Sometimes decried as a waste of time or just another layer of management bureaucracy, the one-on-one meeting certainly comes under a fair amount of criticism by managers and employees alike. However, as a Software Engineer and Engineering Manager, I saw it as a necessary and critical component of running or operating inside a healthy, happy, and engaged team. It also establishes accountability on both sides. The key is for the manager to approach this meeting from a human-centered perspective, with the objective of unlocking human potential, rather than seeing it as an opportunity to micromanage or assert one’s own agenda. 

When done right, the one-on-one meeting can be a wellspring of trust and understanding, a powerful channel for the manager to connect with their direct report with the aim of supporting, coaching, and helping them navigate daily work life and guiding them through the various challenges of their career. For the employee, it’s an opportunity to be seen and heard by leadership, to ask questions and raise concerns, and to align their skills and values with the goals and temperament of the company through the wisdom, perspectives, and insights shared by the manager. 

When done poorly, the one-on-one meeting can be a sinkhole of despair for either or both parties: it can be a source of frustration or insecurity for the manager, and for the employee, it can trigger anxiety, paranoia, or resentment. It’s vital that both manager and employee make this meeting work because it forms the backbone of how they perceive each other in the workplace context and builds the foundation for all their other interactions.

In the notes that follow, I tend to write about this topic mostly from the manager’s point of view, but I’ll offer some employee perspectives as well.

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Purpose of the 1:1 Meeting

From the manager’s perspective, a 1:1 meeting should be:

• Most of the time, an enjoyable, rewarding conversation that you have made psychologically safe for your direct report, where you are actively listening and defaulting to trust, and seeking to understand before making any snap judgments.

• An opportunity to build a more layered picture of your direct report as a human being: what motivates them, what aspirations do they have, what do they appreciate in life, what are their priorities outside of work? You should always spend some amount of time just getting to know them as people. You can do this with minimal effort.¹

• A chance to build more layers of trust and mutual respect, which will pay dividends as soon as you and the team encounter a challenging project or unexpected obstacles.

• A conduit for learning about problems on the team, hopefully before they get too unwieldy or perilous.²

• A specific time and place for following up on any previous issues, challenges, or questions that were discussed in another meeting. 

• An opportunity to act as a coach or mentor for a particular type of task, skill, or behavior. 

• Periodically, a time to discuss your direct report’s career aspirations, even beyond the role that they have now. 

• A time to celebrate any recent achievements or to encourage them to reach their goals.

• Sometimes, a good way to gauge interest in upcoming projects, or get early feedback and a different perspective on a strategic, operational, or technological decision you need to make that will affect the team.³

• Occasionally, a chance to offer timely, relevant and nonambiguous, constructive feedback.

From the employee’s perspective, a one-on-one meeting should be:

• Most of the time, a comfortable, safe conversation where you check in with your manager without anxiety or fear of reprisals for anything you might share. You should have the undivided attention of your manager for the duration of the meeting.

• A chance to be seen and heard: ask any questions you have about how you’re being perceived on the team or in the organization. Raise any concerns that you have about life on the team or in the wider organizational context.

• An opportunity to learn from your manager in a coaching or mentoring capacity: this could involve guidance with either hard or soft skills, or help in navigating the politics and social mores of the company.

• A time to seek advice: get your manager’s opinion on work-related topics as a sounding board before making a decision or forging ahead with certain kinds of communication to team members or stakeholders — especially when the stakes might be higher than usual.

• A chance to brag about an accomplishment. Seriously! Managers are not magically aware of everything you do or every piece of work you complete. It’s okay for you to keep your manager in the loop on your wins so they can celebrate with you and be aware of your progress. This will pay dividends come salary appraisal time. 

• A weekly reminder to think about your personal growth and to reflect on your career progress. Ask for a gauge of how you’re doing in your role and what you could do to level up.

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Responsibility 

Great one-on-one meetings are a two-way street. Both manager and employee have a responsibility to each other and the team to make a genuine effort to establish a healthy, productive relationship. They work best when both parties come with an open mind and are prepared to listen. They also work best when both parties seek first to understand, demonstrate patience, and keep the door open to compromise. Both manager and employee need to care about maintaining an authentic connection. As the employee, at times this may require suspending one’s cynicism carried over from previous experiences. If you had a bad reporting relationship in your last role, it doesn’t necessarily follow that every manager you encounter in your career will be lacking (and if so, you’re working at the wrong company!)

Some things an employee can do to make the one-on-one meeting productive:

• Try not to see it as just another official box to tick in order to collect your paycheck. Suspend your disbelief and at least give your manager a chance to demonstrate their worth before switching off your mind and robotically nodding your head, no matter how much you may be inclined to do so.

• Don’t be afraid to get to know your manager on a human level. Ask them if they had a good weekend or are having a good week. If they were recently out on vacation ask them if they enjoyed the time off. A good manager won’t mind some gentle inquiry into their lives outside of work, at least as an ice breaker at the beginning of the meeting. 

• Come with your own agenda. This is primarily your meeting so make the most of it. Before each meeting, write down what you accomplished last week, what you struggled with, any obstacles you overcame, and any lingering issues or concerns that are affecting your workday, including any communication issues with teammates or stakeholders and anything blocking your ability to make progress on whatever work you’re assigned to. Also, write down anything you’re proud of and want to celebrate.

• If things are going so smoothly that there is little to talk about regarding the present, consider asking your manager some forward-looking questions about how you’re progressing in your role or how you could work towards the next step up in your career.

Some general advice for managers conducting one-on-one meetings:

• If the employee doesn’t come prepared with questions or isn’t very forthcoming with things to talk about, it’s not okay to just cut the meeting short. You should be prepared to prompt your direct report into talking about something that matters if the silence grows too long. Some people are just less verbose or not good at preparing for these meetings at first. Hopefully, with positive encouragement, they will get better, but you should always be ready to take the lead in the conversation to get it back on track and make sure it’s a valuable use of their time. Keep a running list of conversation prompts that you can easily scan and refer to, perhaps categorized into groups like:

  • “Social ice breakers”: when you just need to help your report relax into the flow of talking.

  • “Wellness check”: check how they’re doing physically and mentally.

  • “Career questions”: guide them into thinking more long-term.

  • “Devil's advocate”: probing questions to nudge them into thinking about something on a deeper level, or to provide space for healthy disagreement.

  • “Open-ended questions for pivoting”: eg “Tell me something I don’t already know about you/the team/the project you’re working on.”

• Even though I’ve stated that this is their meeting, there will be times when you need to communicate something important, such as the rationale for a company decision or a critical piece of feedback for your report, and this might need to take priority sometimes. Use your judgment here.

Cadence

A good rule of thumb for the frequency of this meeting is to meet once per week with each direct report for at least thirty minutes. Ideally, both manager and employee should block off an extra thirty minutes on the calendar at the end of the meeting so that the option is there to extend the discussion to an hour if necessary or desired. I’ve heard of managers who only afford their reports ten or fifteen minutes each and blitz through half a dozen meetings on Monday morning just to get it all over with quickly. In my opinion, this is not appropriate and it sends the message to your direct reports that your time is more valuable than theirs, that managing people is not the most important thing you do, and that you don’t really care that much about fostering good working relationships on the team beyond small talk and status updates. Don’t be that manager.

Note: part of getting to know your direct reports is knowing when they do their best focused work and when it’s okay to distract them. Schedules may be hard to wrangle but at least try to ask your employees when they’d prefer to have their 1:1. If nothing else is viable, see if you can let them choose whether you meet in the morning or the afternoon. Empowering people to make even small choices like this can go a long way to establishing good patterns of interaction from the get-go.

Continuity 

Managers: take notes! One of the most powerful ways to establish strong bonds of trust and understanding between you and your direct report is to maintain some semblance of continuity between each one-on-one meeting. It doesn’t matter what method you use (I favor writing on index cards: a different color for each employee so I can easily grab the right stack before each meeting), what matters is that you keep track of important questions and concerns that come up, and record the general gist of the conversation you had. That way, at the beginning of the next meeting you can follow up and either continue the conversation where it left off or ask your employee if they managed to reach that goal/learn that thing/overcome that obstacle/make use of that advice you gave them in last week’s meeting or a meeting you had a few weeks ago. It’s necessary to go over your notes periodically to refresh your memory of what occurred — that way you can be present and mindful each time you meet.

Note: I’ve had some managers who thought that keeping these notes in a Google doc shared only between the manager and employee was a good idea. It might be, and certainly might be convenient. This makes the most sense in a remote work scenario. It could also be a win for transparency. However, I would caution managers to avoid making the assumption that every employee will feel okay with this. Instead, make a point of asking them about their preference and then honor those preferences. For some employees, even though you promise the document isn’t public, the idea of their personal progress or challenges being documented in the company cloud may give the impression that they are being too closely monitored or on some kind of personal improvement plan. Personally, I’ve always found that letting the employee know that I take notes purely on paper and that they are free to keep their own notes too allows everyone to feel comfortable. I also explain why I keep notes: for continuity, not for strict supervision or oversight. 

What a 1:1 isn’t

• The one-on-one meeting is not a status update. There are other meetings where that information can be brought forth, such as a daily or weekly stand-up or an official status meeting. It’s totally okay to talk about the work in progress, work coming up, or work recently completed: but instead of letting the conversation be reduced to a mere status update, dig deeper and discuss something learned, bring up relevant issues, talk about how you and the team overcame challenges or obstacles, and relate it back to the employee.

• The one-on-one meeting is not primarily for the benefit of the manager. It is time and attention extended to direct reports. It is their meeting, and as much as possible they should control the agenda.

• Not just a meeting for average employees. There’s a pervasive myth that ”high-performing” employees don’t need one-on-one meetings. Why would this be true? No matter at what level we perform we all benefit from human connection, guidance, and conversations that promote personal growth and self-reflection. 

• The one-on-one meeting is not just management theater or a waste of time. This is only true if managers don’t understand the purpose and benefits of the meeting, have not worked with their reports to establish the right timing and cadence for the meeting, or have failed to set expectations.

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Location shouldn’t matter

Whether your workplace is fully remote, a hybrid environment, or part of the RTO mandates (unfortunately) sweeping back through the corporate world now that the pandemic is (mostly) behind us, I tried to write these observations and tips agnostic of location. I have experienced 1:1 meetings in-person as well as remote, and if you want to be a great manager or employee you should strive to be attentive, polite, engaged, and fully present in a meeting that is conducted over video chat. 

I empathize with sufferers of ‘Zoom fatigue” and I have certainly experienced days where I have had quite enough of the “weak connection”, visual distortions, sound glitches and just staring at the screen for long periods of time. But it’s important to keep in mind the other side of the equation: staff who are able to work remote really appreciate the extra mobility, freedom, flexibility, and personal autonomy that it brings to their lives. In other words, grin and bear it for the greater good :-) 

Conversely, if you're in a physical office, the one thing you can’t do in a remote scenario that you could occasionally do in-person is to go outside the office to grab a coffee and talk somewhere “off-campus” for a while. This may help nudge an employee to be more candid and open if the situation requires it, or just give both of you an excuse to get some exercise and enjoy some (ideally) good weather. As someone who generally prefers working remote these days, I think the out-of-office excursions to the coffee shop are the only thing about in-person 1:1’s that I genuinely miss.

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Let me know if you have any other good pointers or suggestions in the comments, or if I’m missing anything important.  

Good luck with your next one-on-one meeting!

1. This doesn’t have to be overdone. Ask just one (non-invasive) personal question per meeting and you’ll soon build up a pretty good picture of them and see them as more than just a collection of skills.

2. If you read your direct report’s body language and tone of voice and learn to recognize when an employee is ‘off’ in some way, you might be able to ask them questions to root out larger team problems. (Of course, your mileage will vary depending on how much respect and trust exists between you.)

3. There are going to be some team members who are more comfortable giving their manager feedback or advise than others. Identify who these people are on your team and allow them to offer their two cents, you might be pleasantly surprised and it may help unblock some decision you’ve been wrestling with. In some cases, you may even want to share with the whole team and put something to the vote. Democratic processes can be used in the workplace too, you know. Of course, this isn’t a prescription for every turning point or fork in the road: often it will make more sense to handle the decision on your own or officially delegate.