How to have a 1:1

by Adam Marcus, who would love to work with you

A 1:1 meeting is one of the most basic and important elements of building a relationship between you and a member of your team. In the startup world, you’re thrust into 1:1s with no training other than the experience you received in having them with your own manager. In my first job out of school, I was responsible for a team on day 0, starting to conduct 1:1s with members of my team the same week I had my first 1:1 with my manager. In the spirit of reducing the amount of winging it that the next generation has to undertake, I’ve collected a few suggestions in this guide. Like previous advice I’ve given on grad school and startups, it’s an #1 guide based on my own experiences. Share feedback and criticism, or better yet, write up your own #1 experience!

Show up regularly, avoid skipping

The most important thing you can do for a successful 1:1 is to show up on a regular basis. Set a recurring calendar invite with your mentee, and try to only skip it for vacations or once-every-few-months unavoidable conflicts. If you’re the direct manager of the mentee, schedule the 1:1 every week (for at least 30 minutes) or every two weeks (for at least an hour). I set the frequency and length of 1:1s in concert with my mentee. At one extreme, one of the more senior members of our team largely wants me out of their hair and prefers to actively reach out when they want more frequent counsel, so we meet every 2 weeks for an hour. At the other extreme, I meet one of our newest managers for an hour each week, checking in more often than that to see if and how they need help approaching a particular problem.

Even more important than the length or frequency of the 1:1 is that you show up. If you create a welcoming environment for 1:1s, mentees will often mentally prepare a few topics to discuss in each meeting. If you cancel the 1:1 at the last minute, you’re setting your mentee up for disappointment, and reducing the likelihood that they will mentally allocate the headspace for deeper discussion in the future.

The concept of showing up extends to your mentee as well. For my first time as a manager of 7 years, I recently had a mentee message me that they didn’t have topics for our 1:1, and that we could cancel if I wanted the hour back. I honestly didn’t have too much to talk about either, but had one question I had been meaning to ask them, so I suggested we go for a walk to stretch our legs, and cut it short if we had nothing to talk about. Our walk ended up taking up the full hour: we talked through my question, some upcoming timeline-impacting plans the mentee had, and ended up talking at length about some concerns they had about one of their mentees. This anecdote is a nice reminder: you can always cut 1:1s short, but if you don’t make the space for them to happen, you’re going to miss out on some really important and sometimes unexpected conversations.

Prepare some topics, but don’t steal the show

I like to prepare ahead of time for 1:1s. At a minimum, I spend 5 minutes thinking about three things: follow-ups from our last meeting, new topics or feedback to discuss (keep this short: it’s not your agenda!), and questions I’ve accumulated that I didn’t want to interrupt the mentee with. For certain high-detail roles (e.g., someone who is responsible for a remote office), my mentee and I keep a shared document with agenda items we jot down throughout the week so they don’t slip our minds. For roles where I’ve got plenty of other opportunities to give feedback (e.g., code review), the 5 minutes of preparation is plenty of time given I don’t want to control the entire agenda.

There are plenty of 1:1s where the topics the mentee wants to discuss are more important and valuable than the topics I had in mind. Since 1:1s are ultimately in service of the mentee, you should feel comfortable discarding some of your own topics as the conversation flows. In those situations, I identify the one or two key topics I still want to pursue and save them for the end of the conversation.

Listen more than you speak

1:1s where you speak more than your mentee should be rare. Aside from a few topics you’d like to discuss, your mentee should set the agenda. As a result, your goal should be to ask follow-up questions, dive deeper, and provide advice only after your mentee has said what’s important to them.

Spend some of your speaking time repeating what your mentee just told you in your own words. Whether you think you understand what the mentee has said or not, taking the time to repeat it has several benefits. First, it makes sure you’ve internalized what they said so that you’re not pursuing a solution for the wrong problem. Second, it gives the mentee confidence you’ve heard and understand them. Finally, it gives you time to formulate a useful follow-up or answer.

When you do speak, use examples

Whether you’re giving advice or feedback, use examples. Unless you’re sharing a really common principle (e.g., warning against premature optimization), examples make your points stick by making them concrete. One technique is to use the fact that you’ve likely had a similar experience when you were in your mentee’s shoes (e.g., “At a previous job, we didn’t employ continuous integration, and ran into similar problems in having to repeatedly address uncaught regressions.”) Another technique is to call out a recent work product that the mentee can use as a template (e.g., “Ashley recently did a nice job of breaking the feature down into 10 steps to reduce the size of each pull request on project X. Try replicating that example!”).

Generally applicable principles that are short and memorable are great, but hard to come by. Luckily, you’ve made or seen many mistakes in the past. Use that vast array of lessons learned to ground the advice you give your mentee.

Ask broad questions and get comfortable with the ensuing silence

While there isn’t always something to talk about, there often is! If I’m halfway through a 1:1 and it looks like the list of topics to discuss is winding down, I borrow from the world of user research and qualitative interviews and ask a broad and open-ended question to give the mentee a shot at bringing up a lingering topic. My go-to question is “What else is on your mind?”

There’s a collection of other questions I use to get at various topics on my mentees’ minds: What mistakes do you think we’re making? What’s B12 doing that confuses you? Where do you want to be in 5 years? How can I help you get to where you’d like to be? Do you have questions or feedback for anyone that you’re afraid to bring up? Ask at most one to two of these questions in any 1:1 — don’t flood your mentee with philosophical questions.

After asking a broad question, I then employ a technique that user researchers and journalists alike embrace: I shut up for a good 10 seconds. I can’t emphasize enough how awkward it is to sit for 10 seconds in silence, but I also can’t emphasize enough how often that broad question and awkward silence results in a conversation that we wouldn’t otherwise have covered.

Give feedback fast, but capture context first

Giving feedback, while not something you will do in every 1:1, is something you should get comfortable doing. At one extreme, if the first time your mentee hears feedback is in a yearly review, you aren’t giving them enough feedback. At the other extreme, if you find yourself giving feedback at every 1:1 or even more frequently between 1:1s, it’s likely that you’re giving feedback too frequently, that you’re not giving feedback effectively enough, or that your mentee is not effectively acting on your feedback.

While it’s important to give feedback fast (ideally in the 1:1 after you’ve thought of or received feedback on your mentee’s work), how you deliver the feedback also matters. Here’s a rough outline I use to give feedback:

• Question: Start by asking your mentee for their thoughts about the topic of your feedback. For example, if a mentee isn’t testing their features well enough before deploying them, ask them “how do you feel about the quality of the software you’re deploying?”

• Context: After asking your question, really pause and understand the mentee’s response and context. You’d be surprised how often the mentee will explain that they already know they’re having an issue. Beyond that, they’ll often have a diagnosis that will surprise you, and offer context you didn’t have going into the conversation. For example, they might explain that they’re feeling pressure because they think they are shipping software too slowly, and as a result they aren’t testing as much as they know they should. A common but unexpected piece of context you’ll get is that the issue has nothing to do with work: perhaps they’ve been distracted by something going on at home, or have oversubscribed themselves to extracurricular activities and need help prioritizing. In the rare case where your mentee isn’t aware they have an issue at all, make sure you identify both the issue and how it affects the team, product, or outcome you’re trying to improve.

• Advice: Based on the context, steer your advice toward something actionable. For example, if the mentee feels internal pressure to ship, explain that you prefer they’d spend more time testing, even if that pushes the deliverable out a bit, or that they shouldn’t gauge their own speed based on the perceived speed of their peers. If the mentee is having issues at home, don’t be tone-deaf in offering performance-oriented advice: identify a solution that gives them space to resolve the core issue while also ensuring the underlying feedback is addressed. For example, while they work through their home issues, have them team up with a peer to test their software, or offer to review their testing checklist.

• Repetition: Regardless of the context, close by repeating the underlying issue you’ve spotted, and how it impacts the company. Explain that you understand their context, and repeat your advice as 1–3 actionable steps they can follow in the next week to improve on the issue.

• Follow-up: At the next 1:1, prepare to follow up on the feedback you gave. If the mentee has addressed the feedback, offer praise for specific actions they took. If the mentee still has room to grow, identify which pieces of advice they heeded and which pieces of advice could use work.

Learn about motivations and identify opportunities

One of the most rewarding aspects of being a manager or mentor is the growth opportunities you can offer your mentee. While you’d be overdoing it to ask about a mentees’ motivations in every 1:1, plan to check in on them at least every few months. Where do they want to be in a year and in five years? Are they looking for more challenging individual contributor projects or new management/mentorship opportunities? Do they want more experience within their track of work or do they want to round themselves out more as a generalist? Are they looking to contribute more to efforts inside the company, or are they looking for external visibility within the community? Where do they think they could grow, and which of these areas are they most looking to grow in?

The challenge and fun in understanding a mentee’s motivations is in identifying opportunities that match those motivations. Sometimes the opportunities are obvious: you know about three projects that are on the horizon, and one of them is a perfect fit for the areas in which the mentee wants to grow. Sometimes, the opportunities require more thought: which conference can you help the mentee submit a talk to so they get that public speaking opportunity?

Don’t overdo the opportunities. For example, if the mentee is a go-getter in finding external speaking opportunities, your best bet is to support them and offer feedback on their practice talks while ensuring that they are on track with their in-the-office deliverables. If the mentee needs a bit more help identifying opportunities, start by identifying one or two and help the mentee set goals against that small set.

Once you’ve identified opportunities, the hard work begins. If a mentee wants to be better at public speaking and you’ve identified a meetup they might target, you haven’t actually helped them improve. Given that they haven’t done this before, offer them a roadmap of achievable goals that you can check in on. To give a talk, they have to make an outline, write an abstract/proposal, submit it, and then put together slides and iterate based on feedback. Help them set goals with deadlines and follow up on those goals at subsequent 1:1s.

If helping your mentee pursue new growth opportunities sounds like hard work, it is! In fairness, many junior employees are just looking for more experience doing things your company already does, so the challenge is more in identifying what they want to learn and helping them find that within the company. As employees grow, they might start looking outside the company for opportunities to contribute back to their community. To the extent that some of their growth opportunities don’t fully align with your company or product roadmap, you’re essentially building a secondary roadmap for the employee’s growth. As a way to avoid burning yourself out, remember that growth is ultimately in the hands of the mentee. If a mentee has a really ambitious external agenda, provide a framework for them to achieve their goal, but expect them to do the heavy lifting, and offer only as much advice and feedback as you’ve got the energy to contribute.

Follow up

The last two sections mentioned follow-up, but the idea of following up deserves its own section. If you’ve given a mentee feedback and actionable advice in a previous 1:1, bring it up in a subsequent 1:1. If your mentee has taken the feedback to heart and employed the actionable advice, offer praise for their improvement. If your mentee hasn’t, ask them how they’ve been working on the feedback and advice you gave last time, and hear what they have to say before re-emphasizing areas they could improve.

Similarly, if you’ve identified a set of goals for a mentee to pursue a new growth opportunity, tastefully bring up any upcoming deadlines or ask them how they are doing against their next goal and hear what they have to say. Management requires iterative measurement and course correction, and follow-ups are the mechanism for reflecting and correcting when necessary.

Where possible, leave tactical discussions out of the 1:1

As a manager, your responsibilities will in some way be a hybrid of two areas of focus: 1) your team’s performance against some goal (e.g., hitting your monthly sales numbers as a sales manager or shipping a new feature as a tech lead), and 2) your performance in motivating and improving your mentee’s output as a people manager. While the two areas are intertwined, your 1:1s should focus more on the individual’s growth than the team’s output.

This advice is hard to follow, and it’s also not perfect advice. Still, it’s important to try. You’ve got so many opportunities to help your team perform tactically against its goal. For example, a tech lead has kickoffs, standups, roadmaps, code reviews, debugging sessions, and impromptu meetings and conversations around how their team should hit its milestones. On the other hand, aside from formal reviews (which happen less frequently and are problematic in other ways), the 1:1 is the one space you have for discussing the performance of the individual. Spend that precious time focusing on systemic ways in which your mentee wants to and should improve, rather than tactically discussing how to complete their next task.

Wrapping up

Every one of my 1:1s is different, and they largely cater to the diverse experiences and motivations of my mentees. While it’s rare for any advice to be one-size-fits-all, this is particularly true of advice that applies to mentorship relationships. Good luck in shaping yours!

Thank you to Nitesh Banta, Meredith Blumenstock, Camille Fournier, and Katelyn Gray for early feedback on this post, and to Matt Martinez for emphasizing examples of broad questions.