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Updated March 23, 2023You’re reading an excerpt of The Holloway Guide to Remote Work, a book by Katie Wilde, Juan Pablo Buriticá, and over 50 other contributors. It is the most comprehensive resource on building, managing, and adapting to working with distributed teams. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, 800 links and references, a library of tools for remote-friendly work, commentary and future updates, and a high-quality PDF download.
A one-on-one meeting (or 1:1, or one-to-one, or one-on-one) is a recurring meeting between a manager and their individual team members. While the format may vary significantly by organization or team, it is typically a time for the manager and employee to discuss how the employee is doing, and may include discussing projects, coaching, mentorship, establishing context, or helping the employee discuss challenging aspects of their work.
One-on-ones were popularized by Andy Grove in High Output Management, where Grove argues that “[ninety] minutes of your time can enhance the quality of your subordinate’s work for two weeks, or for some eighty-plus hours.” This is a compelling return on time invested, and so for good reason, one-on-one meetings have become a management best practice. Grove recommends that the one-on-one meeting be directed not by the manager, but by the employee, and that it is emphatically their time to bring up what is on their mind.
Treat your peers as interesting fellow humans and you might be surprised by what it does for their motivation, dedication, and engagement.Camille Fournier, Managing Director, Two Sigma, and author, The Manager’s Path*
In a remote team, the manager is by default an abstract, distant avatar and not a real live human who interacts socially with their team on a daily basis. Managers can’t see what’s happening by walking around a physical office or by reading faces and body language, so they must have a way to direct and encourage employees to be open and honest if something is wrong. This requires a far higher degree of trust in the manager/direct-report relationship than when you can simply observe their behavior and office dynamics directly. one-on-ones are both the space specifically designated for employees to share any issues, and where managers can connect more deeply with direct reports, form bonds, and establish trust.
The practices for remote one-on-ones are essentially the best practices for one-on-ones in general, but because they’re so critical for remote work, we’ll cover them in detail here. Even in a heavily asynchronous culture such as GitLab, the one-on-one structure is carefully observed. In their remote one-on-one guide, GitLab recommends that managers have seven, and no more than ten, direct reports because “beyond this, proper [remote] one-on-ones are hard to sustain.”
caution The first mistake remote managers make with one-ons is using them as a crutch to replace a lack of overall communication on status, priorities, and work goals. The one-on-one is an ideal time to connect with people who report to you on a human level—if the whole hour or hour and a half is taken up answering questions about projects the report is supposed to be working on, then meetings and documentation need to be improved elsewhere.
To open up the agenda for the direct report to share candidly what’s on their mind with their manager, it’s important to clear out the routine, administrative communication that can take up valuable facetime. This section covers how to do that.
There are a few things you can (not) do to ensure managers and employees get the most out of one-ons:
No status updates. Status updates go in project management software or other forms of documentation. A one-on-one meeting isn’t a status-update setting, so be sure that’s already taken care of elsewhere.
No routine business. Things like scheduling and planning are more appropriately handled in staff or project meetings.
No lectures. Truly one-way communication goes in an email, wiki update, or even recorded video message. It’s not appropriate to lecture your direct report in their one-on-one.
Over time, I’ve learned that getting some particular data during an initial one-on-one can be really helpful, as I can refer back to the answers as I need to give a person feedback, recognize them, and find creative ways to support them.Lara Hogan, management coach; co-founder, Wherewithall*
To ensure one-on-one effectiveness, it’s helpful to make sure you are:
Managing time well. We recommend meeting for one hour, every week.
It’s best to skew timezones in favor of the direct report, and to optimize for the time of day that is comfortable for them to share more easily, where possible.
Keeping the full amount of meeting time signals how much you value these meetings.
Don’t reschedule or cancel: signal how important this time is by showing up.
Having the right environment. This means using video calls, not just audio calls. You want as much information as you can get, including body language and facial expression.
Starting with a baseline. For the first one-on-one, you’ll want to establish a baseline understanding of how your direct report works. Lara Hogan routinely asks the same set of questions in every first one-on-one. (If you’ve already been doing one-on-ones, but not to this degree, you can still do this now!)
Documenting your meetings. It’s wise to use a shared document that you both have access to.
Being prepared. Before the meeting, it helps to scan over your private and shared notes from the previous week so you can follow up. This includes:
Having some questions ready to ask your direct report if the agenda is short.
Mapping out career goals and progress every six weeks (twice per quarter).
Being present. Pay attention! 80% of people admit to surfing the internet or doing unrelated tasks during video calls. Respecting your direct report’s time helps ensure that the one-on-ones don’t become a waste for both of you.
Leaving time at the end. You can use this time to prompt your direct report to share anything they may have been avoiding—good or bad; work-related or not—by asking, “Is there anything else at all that’s been on your mind?”
Relationships don’t have easy metrics to measure, but there are questions that can help managers gauge the depth of understanding they have reached with their direct reports:
Do you know what irritates your direct report?
With whom do they like working the most? And the least?
What are they fundamentally responsible for—what is the point of their role?
How does your direct report like to celebrate wins?
What’s their “tell”—the way you can see that something is wrong?
What are the names and occupations of the people closest to them in life? Can you draw any insights about their values or passions from this information?
What are their core values in life? (Here’s a list you can pull from if you’re not sure where to start.)
This level of managerial relationship on a remote team is the bar that to aim for. As a manager, it is your job to become an expert in knowing who your direct reports are, how they work, and what you can do to create the optimal environment for them to succeed.
It’s helpful to have a well of options you can turn to regularly to keep your one-on-ones fresh and find new ways to prompt interesting or useful answers from your team. Asking deeper questions leads to greater trust and intimacy than small talk does; a key pattern to foster in developing close relationships is “sustained, escalating, reciprocal personalistic self-disclosure.”*
Rather than ending a one-on-one early when an agenda is light, you can ask your direct report one or two of these questions, ideally getting more personal and reflective over time.
When did you recently get an opportunity to learn and grow? How can we create more of those?
Have you seen someone else doing something you felt worked really well? What was it?
What should I know about you that would help me support you better?
What are you doing here that you feel is most in line with your long-term goals?
What are your biggest time wasters?
If you could be proud of one accomplishment between now and next year, what would it be?
Is anything holding you back from doing the best work you can do right now?
Is there a project or area outside your current role where you feel you could be contributing?
Which areas make you feel like your hands are tied or you are unable to reach your full potential?
If you were to create your ideal position, how would it differ from what you are currently doing?
At what point in the past week were you most frustrated with or discouraged by your work? What can I do to help you manage that?
Would you like more or less direction from me?
Would you like more or less feedback on your work? If more, what additional feedback would you like?
If you were coaching me to have a greater positive impact, what would you tell me?
What can I tell you about myself that might make it easier to understand me and work with me?
Have you seen a product or initiative at another company recently and thought to yourself, ‘I wish we’d done that’?
What vibrations (news, rumors, dynamics) are you picking up that you think I should know about?
What’s our biggest oversight, and how do we resolve it?
What do you feel is our biggest risk right now?
What was the most useful part of our conversation today?
What are you worried about right now?
How’s life?
What’s going on for you these days outside of work?
What is something you’ve done that you’re proud of?
What was something you were scared of as a child? Have you overcome it?
What fictional character do you most identify with?
Would you rather be known or unknown? Why?
What hot topic usually turns into an argument for you?
Do you have a motto or personal mantra?
What’s on your bucket list?
Imagine it’s two years from now, and things have gone well: What has been your role in that? What does your role look like?
What are you worried might happen if you made this transition?
What will happen if you don’t take this step?
What would need to change for you to get to a point of “let’s do this” or “I don’t want this”? What information do you need?
How would you say we’re doing at working together as a team? What makes you say that?
What do you think the rest of the team is most concerned about? (People may also share what they are personally concerned about; this framing makes it easier to share.)
Who on the team is doing really well right now? (Also listen for names that don’t come up.)
Are there any decisions you’re hung up on?
I’ve noticed you’re a little quieter than usual. Is there anything you’d like to talk about?
Do you feel stretched thin? (This wording is useful to measure subjective stress, not objective workload.)
What, if anything, did you used to do that you find you don’t have time for right now?
What is your takeaway from this discussion? (This is especially helpful to get to action steps from a thorny issue.)
In our last one-on-one you mentioned you were frustrated by X and wanted to try Y as a solution. How has that been going?
During this meeting you’ve mentioned that you’d like to pursue X. What steps can you take toward that before our next one-on-one?
What could we change about work that would improve the rest of your life?
What does your ideal outcome look like? (Could be about a specific conflict that’s come up, or approached hypothetically.)
What’s hard for you in getting to that outcome?
What do you really care about?
What’s the worst-case scenario you’re worried about?
Are you afraid of anything at work?
I’ve noticed that our last several one-on-ones have stayed pretty surface. What are your honest impressions of this meeting? What could we be doing differently or better?
What’s something you used to strongly believe in that you no longer do today?
Before making a telephone call, do you ever rehearse what you are going to say? Why?
What are three things you and I appear to have in common?
What do you feel most grateful for in your life?
Take four minutes and tell me your life story in as much detail as possible.
If you could wake up tomorrow having gained any one quality or ability, what would it be?
Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
What do you value most in a friendship?
What, if anything, is too serious to be joked about?
“101 Questions to Ask in One-on-Ones” (Lighthouse)
“The 9 Questions that Uncover the Most Surprising Insights from Employees” (Signal vs. Noise)
“The 8 Best Questions to Ask During a One-on-One Meeting” (Know Your Team)
“These 13 Exercises Will Prepare You for Work’s Toughest Situations” (First Round Review)
“74 Questions to Ask in One-on-Ones with a Manager” (Lighthouse)
“Ultimate Guide to Virtual one-on-ones” (Marcus Wermuth)
Reinventing Organizations: A Guide to Creating Organizations Inspired by the Next Stage of Human Consciousness (Frédéric Laloux)
The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever (Michael Bungay Stanier)
A manager’s work is primarily focused on three major tasks:
setting goals to help employees succeed and grow in their roles;
providing coaching, mentorship (advice on how to improve) and sponsorship (access and advocating for opportunities for them); and