Managers, Take Your 1:1s to the Next Level with These 6 Must Reads
By now, it’s clear to most that 1:1 meetings matter. The pro-tip of setting up a dedicated weekly checkpoint is on virtually every list of best practices for managers these days.
Carving out a corner on your calendar for surfacing issues, nurturing that incredibly important employee-manager relationship, and sharing feedback more consistently is undeniably important. For managers in particular, it’s a chance to maintain a pulse on how your direct reports are doing — and an opportunity to make sure their career ambitions for the years ahead connect back to their more immediate days and weeks.
But while there’s plenty of data on why they matter — and a thicket of meeting templates and agenda tips out there — 1:1s still aren’t easy to get right. Under the pressures and scrambles of early-stage startup life, managers are still juggling several direct reports (although hopefully not more than eight) and wrangling overbooked calendars (but trying to follow that other pro-tip on never cancelling these precious 1:1 slots). Then there’s the issue of what to cover. From less-than-chatty direct reports to those who use the time as more of a therapeutic outlet, managers are often unsure whether 1:1s should be freewheeling coaching sessions or highly structured tactical check-ins.
In putting together our new book for managers and running Manager Track (our program for first-time managers at First Round-backed companies), we’ve found there’s still tons of trepidation on how to approach 1:1s. More specifically, there’s a hunger to make sure these meetings are truly effective.
To that end, we’ve combed through all the pieces we’ve written that include advice for holding better 1:1s. This collection of six impactful articles rounds up helpful habits from some of the most insightful leaders we’ve ever interviewed here on the Review, from Michael Lopp to Julie Zhuo to Lenny Rachitsky.
Unsurprisingly, much of their advice centres around thoughtful question asking and careful listening. But that alone is not enough. Their collective wisdom is connected by a willingness to go the extra mile — an eagerness to avoid turning in a merely perfunctory performance as a manager.
That means putting in additional legwork to prevent your 1:1s from becoming rote rituals where you exchange status updates, wade into the waters of small talk and stick to the shores of safe conversation so you can move on with your day. It requires resisting the easy temptation to see them as a line-items on your managerial checklist, or a chunks of time that clog up your calendar every week.
When it comes to holding more impactful 1:1s, asking better questions is key. But so is an ability — and a willingness — to go the extra mile as a manager.
Instead, the very best managers consider the mindset they want to bring to each 1:1 — the thoughtful questions to posit, the dynamic to cultivate with each direct report, and how to tailor these sessions to their unique needs. We hope these tactics challenge you to probe deeper, shake up your meeting structure, follow up more and make things a little awkward. So in that spirit of rededicating yourself to stepping up your manager game and up-leveling each of your 1:1s, let’s dive in.
We’ve built a question bank to pull together all the 1:1 questions suggested in this article (plus a few other gems we’ve come across) . Check it out here.
1. Figure out which category your 1:1 falls into, and keep three topics at the ready to avoid status update territory.
Michael Lopp (aka Rands) has led engineering teams at Apple, Slack, Pinterest and Palantir — and he’s been writing about leadership and startup topics for more than a decade. Several years back, he shared his thoughts on how to make meetings suck less here on the Review, which was full of evergreen gems on holding 1:1s.
There were tactical pointers, such as his recommendation to hold 30 minute 1:1s each week, but book 45 minutes so you have room if it runs over. And his bucketing of 1:1 meetings into three different categories was particularly insightful. (We’ve outlined a preview below, but see his longer post here for more advice on handling each type.)
The update: These are my projects and these are my people and this is how it’s going down. When a 1:1 starts and is clearly an Update, I start listening twice as hard for a nugget of something that we can discuss, investigate, and explore.
The vent: Essentially a therapy session. This most often comes in the form of your report being pissed off about something. You just have to listen, not actually do anything.
The disaster: They’re freaking out, they’re going to quit, etc. This is the advanced form of the vent. They don’t want a solution, they want to be heard.
Digging into that first bucket, Lopp gives a helpful pointer: “The goal of an effective 1:1 isn’t for an update from your direct report, or for you to lay down some instructions (this tends to happen a lot). It’s a conversation,” he says. “1:1s are a chance to hear about your direct reports’ ideas for your product, their career goals, and potentially their opinion of their performance — it’s their time.”
There are lots of systems for status updates (project management software, bug tracking systems, Google Docs, Wikis) — 1:1s aren’t one of them.
To counteract your reports’ likely tendency to go into status update territory (or reluctance to share any topics they’d like to discuss), Lopp recommends keeping a list of three potential topics at the ready for discussion. “That way when they say, ‘Nope — nothing to discuss’ at the beginning of the meeting you can go right to your list to jump start the conversation,” he says. “After a few weeks of doing this, the transition from status to dialog should be well underway.”
Taking on the role of first-time manager naturally presents several “firsts,” but there’s one that stands out in Julie Zhuo’s mind. She still vividly recalls stepping into a conference room for her first 1:1 as a newly-minted manager, trying to hide her faltering voice and unsteady nerves as she faced her direct report — a former teammate who was now sceptically staring back at her.
Of course, she’s now a practiced hand. Before recently striking out on a new venture, Zhuo spent 14 years at Facebook, building out the product design team, hiring designers, and yes, holding more 1:1s. “The most precious resource you have is your own time and energy, and when you spend it on your team, it goes a long way toward building healthy relationships,” she writes in her book, “The Making of a Manager,” a handy manual that belongs on every budding leader’s bookshelf.
In this must read, she recommends spending no less than 30 minutes with each report every week, and she also hands out several other tactical tips for making the most of this 1:1 time. But as we noted when we shared a preview of her book on the Review last year, it was another observation of Zhuo’s that caught our eye: “A coach’s best tool for understanding what’s going on is to ask,” she writes. “Too often, attempts to ‘help’ aren’t actually helpful, even when served with the best of intentions. Your job as a manager isn’t to dole out advice or ‘save the day’ — it’s to empower your report to find the answer herself. She has more context than you on the problems she’s dealing with, so she’s in the best position to uncover the solution. Let her lead the 1:1 while you listen and probe.”
To prepare for that probing, Zhuo makes a habit of scanning her calendar and compiling a list of questions for each person she’s meeting with 1:1. Here are the questions she’s come to rely on to prod the conversation along, organized into three buckets:
Identify: These questions focus on what really matters for your report and what topics are worth spending more time on.
What’s top of mind for you right now?
What priorities are you thinking about this week?
What’s the best use of our time today?
Understand: These get at the root of the problem and what can be done about it.
What does your ideal outcome look like?
What’s hard for you in getting to that outcome?
What do you really care about?
What do you think is the best course of action?
What’s the worst-case scenario you’re worried about?
Support: These questions zero in on how you can be of greatest service to your report.
How can I help you?
What can I do to make you more successful?
What was the most useful part of our conversation today?
Finally, one more tool from Zhuo’s 1:1 question asking arsenal — but this one’s aimed at you managers, not your direct reports. Do all of your 1:1s feel a little awkward? Zhuo picked this tid-bit up from her friend Mark Rabkin, and she finds it to be a worthwhile goal.
The ideal 1:1 leaves your report feeling that it was useful for her. If she thinks that the conversation was pleasant but largely unmemorable, you can do better.
“The most important and meaningful conversations have this characteristic. It isn’t easy to discuss mistakes, confront tensions, or talk about deep fears or secret hopes, but no strong relationship can be built on superficial pleasantries alone,” she says. “There’s no word smithery that gets around the awkwardness of expressing a sentiment like, ‘I don’t feel that you recognise when I’m doing a good job,’ or ‘Last week, when you said X, it made me feel as if you don’t really understand my project.’ But these things need to be said in order to be addressed, and with a bedrock of trust, the conversations become easier.”
“It’s easy to see the symptoms of things — that’s what is actually happening on the surface, but it takes more time to truly understand the underlying cause. Having time set aside with people gives me the opportunity to dig deeper and diagnose the root of a problem. Then we have a shot at fixing it,” says Milinovich, who’s currently building Plato.
For instance, if someone mentions in a 1:1 that they’re feeling particularly stressed or tense and they don’t know why, he goes granular. “I ask them things like what part of the day these feelings are the strongest. Then we can identify triggers, whether they are meetings, or people, or certain types of work.”
This also works on the organisational level, particularly if, like Milinovich, you’re wearing the CEO’s cap. “I get the chance to aggregate all of this information from all of these meetings, and then patterns start to emerge,” he says. “I’ll start hearing the same thing from more than one person. For example, back at URX, three separate people asked me about how we were going to message a product, and I realised that I was repeating myself. It occurred to me that this was something that needed to be broadly communicated to the entire company. Just because only three people asked doesn’t mean they’re the only ones who didn’t know the answer.”
To surface these patterns and make a diagnosis, transparent 1:1 conversations are critical. “A lot of times people just don’t know how to get over a certain hump or out of a rut. If that’s the case, we want them to tell us with zero reservation what’s going on so we can help,” says Milinovich.
To jump start those conversations, he relies on one trusty question at the top of every 1:1 meeting: Where’s your head at?
“You’d be surprised by the range and depth of responses you’ll get from this simple question,” says Milinovich. “Sometimes people want to dive very specifically into what they’ve been working on. Sometimes they’ve had all this angst bottled up about not doing as good of a job recently because of something going on in their lives or with their relationships or health, and we give them a chance to talk about that and be honest.’”
Another way to get people to open up is to model the behaviour yourself, Milinovich says. He’s made a point of being extremely open and honest about his own life, problems he’s facing, and concerns he has about the business, no matter where someone ranks in the organisation. “One of the first lessons I learned when URX was at about nine or 10 people was that the entire organisation tended to reflect my emotions,” he says. “If I was stressed out, people would come up to me and say how they were just as stressed. I get reminded often that how I’m feeling influences everyone else.”
The smallest gestures, ticks or even tone of voice from the founders can cause anxiety, insecurity and turmoil within a fledgling startup. Milinovich views 1:1s as a chance to speak candidly about this, and make sure his words and actions come across clearly. “This is especially important if I don’t have a lot of confidence in something we’re doing,” he says. “It gives me a chance to explain things in a more nuanced way, and to reiterate how excited I am to be here working with everyone on these problems.”
Maggie Leung built Nerdwallet’s content team from scratch (first as a news editor and now as VP of Content), managing a large and critical team of writers and editors. In this capacity, and across her career as a veteran reporter, editor and executive, Leung’s seen her fair share of sticky situations. And there’s one simple habit that’s helped her survive, learn and grow through adversity: asking questions. Not just any questions, though. Over the years, she’s crafted specific lists of inquiries, designed to put herself in other people’s shoes, see all dimensions of a problem, and arrive at the best approach or strategy.
Leung shared 13 of these question sets on the Review a few years ago, giving insight into how to handle a wide range of tough situations (such as managing sideways, handling conflict and letting an employee go). But of course, for our purposes here, we are most interested in the ones she leans on to power up her 1:1s. Here are those lines of questioning, front and centre:
Get past the small talk with specific, yet open-ended questions.
“I have a one on one meeting with everybody on my team on a rotation. Often the conversation starts out with superficial responses. ‘How are things going?’ is followed by ‘I’m fine,’ or ‘Things are going well,’” says Leung. “You let them direct the conversation for a bit and see whether they get to the heart of things. If not, then you nudge them.”
You want to get to the heart of things as quickly as reasonable. With the typical range of 30 to 45 minutes per meeting, that means you need to ask the right kind of questions to get past small talk more quickly. To that end, your questions should be specific but open-ended, says Leung. Here are several examples of that blue sky specificity:
What’s harder than it should be? “It helps you identify patterns when you talk to various people. It helps you smell smoke early. That question could apply to many situations, jobs and companies. And it isn’t judgemental,” she says. As a manager, it’s important to surface issues in a blameless way. The goal is to normality these human moments — not veer into accusation. “If you say, ‘Hey, are you stressed?’ that attempts to force a confession in an awkward way,” says Leung. “Instead, you could say: ‘I know that you’re juggling a lot of work right now. I know you’re doing X and Y. If I were in your position, I might be a little stressed.’ Or, ‘I’m not sure how you’re feeling about this, but if I had to guess, I’d say. …’ It’s OK to be wrong or off, as long as you give the person a chance to set you straight, to be direct with you.”
“What can I do to help?” or “Is there anything you’d like to ask or highlight?” It’s their time to surface things, says Leung. “Sometimes they need to hear that explicitly from us as managers. It’s our job to care. That’s how we help people do their best work and grow. That makes them more valuable to our company and in the job market. That’s a fair trade.” This won’t happen overnight; building trust rarely does. “It’s consistency over time,” says Leung. “If people see consistently that things aren’t punitive or judgey, that you don’t hold things against them or look for the ‘right’ answer, that it’s OK to trust, your interactions will become increasingly open and productive.”
Check your empathy before discussing performance.
Whatever a manager says in a 1:1 meeting can leave a lasting impact. You want to add value, not create cognitive drag that slows productivity. That’s where something that Leung calls “dynamic empathy” comes in. It involves empathising with and sussing out how your direct report feels — and then figure out how to act on it in a swiftly changing startup environment.
As with any other learned skill, you can make considering other people’s motivations an automatic habit if you do it enough. “When I understand and can articulate what someone needs from me, that makes it easier to say, ‘Makes sense. This is what I need from you.’ Then it’s a fair exchange rather than ‘I’m just demanding things from you,’” Leung says.
It’s not about just understanding what’s going on with someone else, but actually doing or saying something about it. It’s about moving things forward.
To walk the tightrope of providing continuous feedback that helps people grow while maintaining motivation, Leung recommends reflecting on these types of questions in advance of 1:1 meetings that touch on performance to put yourself in your report’s shoes.
Does the person you’re managing feel invested in your company or team goals? Why should he/she be? Have you clearly explained the vision or goals, and his/her part in achieving them?
Does he/she feel as if you’ve got his/her back?
Do you know what motivates him/her?
In every relationship, both parties must get something out of it. What are you offering vs. what you’re expecting? Is what you’re offering good enough, or can your employee do better elsewhere?
Does your direct report understand what he/she is supposed to do? How to do it?
Does he/she have the right training, right scope, right authority, right resources and enough time to do as you need?
Does he/she know how important your ask is?
What does he/she need from you or other colleagues?
Is he/she encountering bottlenecks? Are those localized or systemic? If they’re systemic, do you need to address this bigger picture?
5. Make performance reviews more impactful by keeping careful notes and actually following up in special 1:1s.
Let’s continue pulling on this thread that connects performance reviews and 1:1s.
Through his weekly newsletter and tactical Twitter threads, Lenny Rachitsky has quickly established himself as one of the sharpest voices on startup topics. Case in point: Last year on the Review, this former Airbnb product lead shared the performance management framework he developed and honed over the years, unpacking why most reviews “suck” and offering up a collection of templates and real-world examples managers can use to take these critically important conversations to the next level.
There’s one story in particular that sticks out. Early on in his tenure as a manager, Rachitsky had a direct report who was under-performing. After hours of preparation for their performance review conversation, he felt that he’d made a real impact and was excited for the progress ahead. But when Rachitsky checked in a month later, things still weren’t trending in the right direction. “My direct report had vague memories of a few points I had mentioned, and a clear desire to improve, but 95% of the message was lost,” he says.
“At that moment I learned two lessons. One, it’s my fault as a manager if my report doesn’t remember what development areas to be focusing on. Two, I was treating the performance conversation as the end, when it’s really only the beginning of the performance development process.”
We want to believe our carefully-chosen words of wisdom are interpreted correctly and seared into the minds of our reports. It’s safer to assume they aren’t.
In other words, failing to formulate a follow-up plan after performance discussions is one of the biggest mistakes you can make as a manager. And if that initial conversation is only the beginning, the rest of the process should play out over the course of the year in the ongoing, regular touch points you have with your direct report.
Here are two targeted tactics from Rachitsky on how managers can use 1:1s as a venue for that important follow-through work:
Keep tabs and take (specific) notes in your 1:1s throughout the year.
When it comes time to fill out evaluations of your direct reports, you want the specifics in the accomplishments and development areas sections to be significant and meaty. “Your reports are hungry for feedback. They’re looking at every morsel of information you share with them to figure where they should spend their time. Don’t waste this opportunity,” says Rachitsky. To ensure you have enough substantive material to draw from, use your 1:1s as an opportunity to keep closer tabs and put in the leg work.
“Keep track of instances where your report did well, didn’t do well, or generally did something noteworthy. Share these things with your report in weekly 1:1s and save them in a running file so you can refer to them come performance season. For example, ‘July 10th – Ran an excellent meeting with senior execs,’ or ‘Sept 3 – Put together a very strong strategy for Q3,’ or even feedback from others such as ‘Jan 4th – Spike shared with me how impressed he is with Jane’s ability to run a meeting,’” says Rachitsky. “I keep a separate Google Doc for each of my reports for this purpose. In addition to Google Docs, there are neat feedback and performance management tools like Matter, Culture Amp, and TINYpulse that can help you keep tabs on performance throughout the year.”
Create a two-sided action plan after a performance review — and turn one of your 1:1s into a monthly career coaching chat.
At the end of your performance review conversation, ask your report to list five to seven concrete actions they want to work on over the next six months and add them into a simple spreadsheet. It’s important to check in regularly on this plan between performance conversations — but don’t use your regular 1:1 time. In Rachitsky’s view, 1:1s are for talking about how a project is going, upcoming deadlines, or blockers. An additional, special session is needed monthly to check in on the performance review action plan and broader career discussions.
“The focus of these meetings is to step back from the day-to-day and focus on career and performance development. Remind your report ahead of each meeting to update their spreadsheet with a status and any new discussion items they’d like to make time for,” says Rachitsky. “The meeting should be mostly you listening, asking questions, and (when really necessary) offering suggestions.”
When your direct report asks for advice, Rachitsky recommends turning it around and asking “Before I answer, what do you think?” “This book from David Rock and Julie Zhuo’s writing have taught me a lot about how to be a better manager by asking good questions,” he says.
As the Head of Customer Success and Sales Strategy at Atrium, one of the biggest problems Karen Rhorer sees is that while managers sink tons of time into 1:1s, more often than not they don’t make the best use of it. While the debate over who should “own” the 1:1 meeting is a long-running one, Rhorer is firmly in the camp that managers are on the hook for making this time useful.
“Managers say that they want to loosen the reins because they want the report to take ownership of the meeting. But how can you expect your report to maximise their 1:1 if you don’t set them up for success?” she says. Here’s how she divvies up responsibility: “You prep and set the agenda. Your reports fill in part of the content.”
Unstructured meetings are a waste of time. Remember, time is your most precious resource as a manager — and wasted time harms yourself and your team.
While her advice is tailored for sales leaders, we think managers of all stripes stand to learn from Rhorer’s highly structured and data-driven approach to 1:1s. Here’s a look at two more specific strategies she uses to bake that structure into every meeting:
Remember what you owe your direct reports.
“Leading a sales team is about more than just checking whether reps hit their numbers. Set fair expectations — and make sure reps have a clear pathway to hitting those goals,” says Rhorer.
To do just that, she finds it helpful to view every 1:1 as an opportunity to deliver on the three things she believes that all managers owe to their teams:
Candid, clear expectations: “Frequent feedback, grounded in data, helps strong performers prepare for success in their next role; it gives those who are struggling an opportunity to improve.”
Proactive, rather than reactive, performance management: “Data lets you see into the future. It gives you the ability to understand who is likely to hit or miss quota in advance, so that you can take action — and give that struggling rep an opportunity to catch up before you need to issue a performance improvement plan.”
Opportunity for mastery: “According to Daniel Pink’s “Drive: The Surprising Truth About What Motivates Us,” mastery is one of the main drivers of our professional lives. Your reps want to feel accomplished in the work that they’re doing. If you’re smart with data, you can deliver feedback and performance conversations that empower your reps to attain mastery in their roles.”
Then prep your checklist to make sure you deliver.
That means clear expectations, proactive performance troubleshooting and opportunities for mastery need to be woven into every 1:1 agenda. In Rhorer’s experience, data-laden agendas serve the dual purpose of delivering on managerial responsibilities and designing meetings that maximise everyone’s time. “If you orient your meetings around a set agenda that includes reviewing the relevant numbers, you’ll structure your time in a far more focused way,” she says.
Here’s Rhorer’s prep checklist for helping managers and teams make the most of every 1:1 minute:
1. Identify a success metric for the meeting, and create an agenda that will allow you to meet that purpose. Complete the statements The reason for this meeting is… or This meeting will be successful if… (Rhorer gives an example from the sales world: This meeting will be successful if the manager is aware of the status of deals in a rep’s pipeline, as well as any challenges or roadblocks the rep is encountering.)
2. Craft the items on your agenda and the questions that need to be answered in order to successfully execute on each of those agenda items. For example, an agenda for a sales manager 1:1 may involve discussing the rep’s concerns, completing a pipeline review and identifying next steps. The questions you prepare should help you dig deeper into each of the agenda items. “During the pipeline review portion, you might want to ask: Which deals look like they might be going sideways? Which deals have progressed? What does the overall pipeline look like compared to peers?” says Rhorer.
3. Build appropriate reporting and dashboards to answer those questions. For example, for the pipeline review discussion of a 1:1, a sales manager might have built a dashboard that illustrates metrics such as untouched and stuck opportunities, average age of open opportunities, and opportunities advanced at least a stage.
4. Review relevant data beforehand. Come to the meeting prepared with targeted points of discussion, based on the relevant metrics — and remember that this is your time to dig into the why behind them. “You might infer that a deal’s going sideways if it’s been open for an especially long time, or has a high average number of days between touches,” says Rhorer. “Those are strong indicators that either the rep isn’t actively working on the opportunity, or the prospect isn’t engaging in a way that’s conducive to getting a deal closed. If you have those indicators handy, you have a much clearer idea of how your rep is doing and how you might offer support,” she says.
Better to coach the employee who shows a willingness to learn than turn to external hiring, where you have less context and might even hire someone who just has a different set of improvement areas.
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