“With the shift to remote work, most of the interpersonal interactions you have day-to-day are through Slack, email, Google Docs, and Zoom meetings. So it's very possible that for many employees, their only face-to-face human interaction for the day is through a meeting. If that meeting is good, then their day is good. If that meeting is bad, then their day is bad.”
We’ve been mulling over this point ever since HashiCorp’s Kevin Fishner brought it up when he stopped by our podcast earlier this year. Even as some folks are returning back to a physical workspace, this sentiment is still more resonant than ever. Whether they're in person or video conferencing, it’s hard to overstate the impact meetings have on an employee’s day-to-day experience at a startup — and yet lately, many of us seem to be having more bad meetings that are adding up to more bad days.
Whether it’s quips on Twitter about the endless slog of back-to-back Zoom meetings, or well-worn one-liners such as “This could have been an email,” you would be hard-pressed to find another component of the workday that bears the brunt of more jokes, complaints and general discontent. (This recent example from Salesforce’s Bret Taylor is a worthy entry into the canon.)
To help you make more progress toward the elusive goal of running more effective team meetings that don't sap energy or waste time, we’ve combed through our archives to resurface best practices from some of the smartest leaders we've ever interviewed.
Some of their advice offers up incredibly practical pointers around adjusting team meeting agendas or weaving in new questions; others center on reframing your own outlook so you can see these sessions in a new light. A few tidbits focus on how you can make existing meetings more effective, — or, thankfully, revisit and remove them all together. (But fair warning, one or two suggest adding new kinds of meetings that serve a targeted purpose.)
Spanning across team offsites, stand-ups and 1:1s with your direct reports, as well as more specific arenas like product reviews and board meetings, each piece of advice was selected for its focus on helping you approach your regular meetings with more energy and intention. Whether you’re looking for fresh ideas to reinvigorate a meeting that’s gone stale, or are hoping to start a newly recurring session off on the right foot, this roundup of tactical tips has got you covered. Let’s dive right in.
RETHINK HOW YOU CHECK IN WITH OTHERS — AND YOURSELF:
“Whenever someone tells me a meeting was challenging, instead of asking why I’ll ask what happened right beforehand. Usually that’s where the real answer is,” says leadership coach Katia Verresen. “Maybe they saw some discouraging data, or had a rough call. People go from meeting to meeting without thinking that one influences their performance or responses in another. We give ourselves zero transition time, and the result is emotional transference.”
If you’re interested in stopping this spillover effect, get intentional about setting this baggage aside. “I tell my clients to imagine they are carrying suitcases and setting them down,” she says. Another tactic? Bring your brain into a more positive mindset by accessing memories, transporting yourself back to a time when things were running smoothly, when you didn’t feel anxious or overworked.
Returning to a moment you were proud of — whether it’s something you built or a project that went well — will bring on a psychological shift. Especially given our tendency to focus on the negative, celebrating and revisiting recent achievements is one of our best tools for rewiring our brains for clarity, Verresen says.
We delete our wins so easily. No wonder we don't see possibilities for the future.
Checking in on each other has become an essential part of our pandemic routines. That’s why this tip from therapist and mental health advocate Jessmina Archbold (publicly known as Minaa B.) has stayed with us:
“I like to run mental health check-ins at my workshops, asking these questions: ‘On a scale of one to 10, one being the lowest, 10 being the best, how are you feeling today? Who can you ask for help? What do you need to feel supported?’ I have folks ask it of themselves first, and then ask them to pose the same questions to another person,” she says.
For Archbold, this isn’t just about being there for each other — it’s also about boundaries, which she posits are at the center of self-care. “The key is to listen and create space, not to jump in with advice and try to solve their problem. In your 1:1s as a manager, you probably open up by asking your direct report how they’re doing. If their ‘number’ is low, or their response seems muted, ask, ‘Can I support you?’ before diving into solution mode. That gives them the agency and the space to ask for what they need, without getting too probing or positioning yourself as the savior.”
Most folks aren't honest with their feelings because they get unsolicited advice or intrusive questions — you can try to stop that cycle on your team with the culture you create and the micro-actions you take.
Co-founder and CEO of Mutiny Jaleh Rezaei is a pro at pushing her team to move fast — her framework for speeding up your marketing org is a must-read. But she’s also an advocate for slowing down to build trust and scaling your leadership with intention.
That’s why she recommends dedicating a 1:1 monthly meeting with direct reports to a specific purpose: Getting each team member to reflect on the three things that went well the past month, and three things they’d like to go differently in the next month. Rezaei then shares her own 3x3. “Most of our time at a startup is spent zoomed in. Monthly reflection is when we zoom out,” she says.
Our favorite tidbit is how she ends the dialogue on a buoyant note: What are you most hopeful about as you think about the next month? Grab Rezaei’s template here to try it out in your next meeting.
SHAKE THINGS UP BY TRYING SOMETHING NEW:
When it came time to plan Sitka’s first remote offsite last year, CEO Kelsey Mellard had several goals, from team building exercises that would increase empathy, to strategy sessions that would get everyone on the same page. “Another goal was to examine our existing routines and create new rituals together. I wanted to hold space where we could stay present, reflective and grateful for each other,” says Mellard.
That’s why she enlisted the help of Mike Wang, a skilled designer and facilitator of highly intentional experiences, to craft a more impactful offsite. “As humans, we all hunger for connection — to feel seen, heard, and understood — but often don’t have intentional spaces that encourage these behaviors,” he says.
Here’s how Mellard and Wang created that space within Sitka’s offsite agenda items: “On Friday morning, we all hopped on Zoom, put some music on in the background, and then spent 90 minutes heads down on one exercise: Writing one line about every other person in the company and what we enjoyed about working with them,” says Mellard. “Then, Mike collected all of these notes and rounded it up in one email for each person. So then every person got to open an email with an amazing lineup of points of gratitude from their colleagues. I was really unsure how that was going to go over, to be honest, but it left people in tears.”
Wang agrees. “It hinges on trying to get people to show up in a way they might not even in a normal professional setting, let alone on Zoom. But because we did it in rapid fire — you only had about a minute to spend writing for each person — it felt like a task that you could bite off and be successful at. In the feedback we got afterwards, many said this was their lasting takeaway from the offsite, that they wanted to get better at expressing gratitude for others. It was an incredible high note to end on.”
- Editor’s note: The First Round operating team tried a lightweight version of this exercise at a team meeting and we *highly* recommend it. Here’s our version. With 15 minutes left to go in the meeting, we sent a Typeform link to our 15-person team, with the following prompt: For each meeting participant, write a line or two in response to the following questions: What's something you admire about this individual? What's something this person did recently that you appreciate? Why are you grateful to count this person as a teammate? Answers are anonymous. After they're all in, the meeting owner will round up the lines for each individual and share them in a private email.
Remote meeting culture has been getting a lot of attention these days, but Maggie Leung has spotted a small gap that’s often overlooked: Managers of remote teams tend to miss opportunities to elevate those who excel or highlight strong examples of best practices.
“It’s not just that someone did well, it’s the explanation of how they did it that often goes missing on remote teams,” says the former VP of Content at NerdWallet and current Executive Editor at Andreessen Horowitz.
If you’re only calling out those people by name and not asking them to share their approach, problem-solving chops, challenges and failures with your team, you’re leaving money on the table.
Offering up a specific example from NerdWallet, Leung points to a bimonthly initiative called “What Good Looks Like.” This might require adding a new meeting, but this quick story proves its worth: “We were seeing inconsistent approaches that were creating unnecessary work and wear and tear. So an individual contributor on our team proposed producing a decision tree to help his pod and others make decisions faster and more consistently,” she says.
“He quarterbacked by getting input and buy-in from a few others on our team. Once he was done, he rolled it across our entire 80-person team. So we called out his accomplishment, had him walk our team through how he thought through the problem, worked to get different perspectives and launched it. And we explicitly tell team members that that’s the kind of initiative we value.”
Back when the SoundCloud team numbered in the dozens, it was easy to feel like you were in the fold. “As you grow though, you lose a little bit of connection to things that you’re not directly a part of. I think it’s a very common phase for startups,” David Noël says.
People start to feel this separation anxiety — the sense that if they’re not in a room, they’re not allowed or welcome there.
Enter Cameos — a way to counteract this creeping feeling. Here’s how Noël described it to us several years ago: Any SoundCloud employee could book time to sit in on another team’s meeting or offsite, the same way Alec Baldwin might pop into a Tom Cruise movie for a few minutes, he says. The only requirement? “You have to bring at least one interesting piece of information about your own team to the meeting, and then you have to bring something relevant back to share with your team from that meeting.”
People don't have to be specifically invited to make a cameo, however. They can request to get some face-time with a team, which will keep them in mind for a meeting that lends itself to having a guest. At one point, this exercise in transparency was even extended to executive team meetings. “I convinced our CEO to allow Cameos at their quarterly offsite — their flagship meeting every year,” he says. “This was really something, because leadership offsites always generate a certain amount of curiosity, anxiety, uncertainty with what's going to come out of it or what they are actually talking about.”
Here’s how it worked: Senior managers nominated people they thought would do a great job not only being observant, but also proactively participating. From a pool of 30 nominees, they randomly selected three people to do a Cameo (each person attended a half-day of the 1.5-day offsite). Afterwards, these employees wrote an internal blog post about their experience.
STAY ON TRACK AND AVOID THESE SPEED BUMPS:
Not every meeting goes swimmingly — sometimes conflict bursts out into the open, leading to tense exchanges that seem difficult to resolve. When you and your co-founder or a senior leader can’t agree on a key decision in a meeting, Coa’s Dr. Emily Anhalt offers up a practical pointer: Have the argument again, but switch sides. Here’s how it helps:
- This practice loosens the attachment to being “right.”
- Helps you see the other’s perspective more coherently.
- Brings to light new points, which might make the best choice more clear.
At the core of curiosity is understanding that you see the world through a particular lens of your own experience. By getting others to share their perspective, you’re gathering more data points and arriving at a more accurate view of the truth.
The product review is where a PM presents the team’s work and earns that oft-coveted executive facetime — which can often be a double-edged sword, says First Round’s own Todd Jackson (who was a PM on Gmail during his time at Google, and on News Feed at Facebook).
“Often, you’ll get interrupted right away, and you need to be willing to engage whoever it is in open-ended debate. This is where a lot of good questions or ideas come up,” Jackson shared right here on The Review several years ago. But distinguishing between what leadership actually cares about as opposed to lower priorities or random ideas is a skill that takes practice.
His advice? Let yourself get derailed by big ideas, but not too much. “If they give specific suggestions that you don’t agree with or that sound random, always strive to understand the spirit of the request,” he says. “Sometimes you might disagree strongly with the specifics, but you really do agree on the high-level goals.”
But if those derailments start to coalesce into concrete decisions, Jackson recommends pinning founders down to brass tacks. “Ask them directly: ‘So is that a decision?’” he says. “Then make your next actions clear: ‘We’ll follow up on that point and come back to you.’” This helps ensure stakeholders feel heard.
It’s also important to try to avoid the “yes man” impulse and think it through. “Usually if a founder has a brand new idea in a meeting, everyone will nod their heads. So then you agree to it too hastily and later you realize there’s some big ‘gotcha’ or it wasn’t as high-impact as it seemed at the time,” says Jackson.
You can't leave any chance for misunderstanding, or for even one person to walk away from a meeting with different conclusions.
“Do you remember the last time you were in a meeting and someone said, ‘We’re going to make this decision before we leave the room?’ How great did that feel? Didn’t you just want to hug that person?” We whole-heartedly agree with Upstart’s Dave Girouard’s thoughts here, first outlined in his now classic article, “Speed as a Habit,” which is full of advice on how you can be that hero at your own company. (If you haven’t read it yet or are overdue for a re-read, we recommend popping open a new tab and checking that off the list ASAP.)
“The process of making and remaking decisions wastes an insane amount of time at companies,” he continues. Here’s a specific speed bump that often slows startups down: “I’m always shocked by how many plans and action items come out of meetings without being assigned due dates. Even when dates are assigned, they’re often based on half-baked intuition about how long the task should take. Completion dates and times follow a tribal notion of the sun setting and rising, and too often ‘tomorrow’ is the default answer,” says Girouard. “I’ve seen too many people never question when something will be delivered and assume it will happen immediately. This rarely happens. I’ve also seen ideas float into the ether because they were never anchored in time.”
Deciding on when a decision will be made from the start is a profound, powerful change that will speed everything up.
To counteract this tendency, challenge the when in your next meeting. “It’s not that everything needs to be done NOW, but for items on your critical path, it’s always useful to challenge the due date. All it takes is asking the simplest question: ‘Why can't this be done sooner?’ Asking it methodically, reliably and habitually can have a profound impact on the speed of your organization,” he says.
GET BETTER AT GENERATING IDEAS AND CAPTURING LEARNINGS:
At HashiCorp’s executive offsites, there’s a dash of structure to make the process of brainstorming company objectives more effective, says Kevin Fishner. “There's a few Harvard Business Review studies around brainstorming that show when you just bring people together and ask them to put stickies up on a wall or whiteboard, it doesn't work that well. So we give executives two weeks before the offsite to write down what they think the three focuses should be for the upcoming year,” he says.
“Then, each exec gets five minutes at the meeting to talk through their suggestions. Then we put all the suggestions into a list — there's usually quite a bit of overlap so we end up with about 15. Each exec then ranks five initiatives, five being the most important, one being the least, and then we just do a sorted ranking from there.”
Here’s why this approach works: “First, allowing everyone to think about the objectives independently means they won’t get stuck in group think. Second, folks can often be more thoughtful when there's not as much urgency to come up with ideas on the spot. And finally, each leader gets equal airtime and opportunity to have their voice heard.”
Adam Grant agrees that brainwriting is best, pointing to evidence that groups generate fewer and worse ideas while brainstorming than when the very same people are working on their own.
“If you know the group is nervous about ego issues or status hierarchies you should collect the ideas anonymously,” the organizational psychologist and Wharton professor says. “It’s about leveraging the power of the group for idea selection, where people are actually better collectively, but letting individuals be creative first.”
Individuals are great at generating ideas. Groups excel at selecting ideas using the wisdom of the crowd.
We’ve all been in this meeting: The team is toying around with the idea of taking on a big new project. Excitement is running high, creative juices are flowing, and ideas are being batted around at a dizzying speed. “At this stage, everyone will jump in and immediately ask, ‘How do we make this happen?’ But right now, you’re headed for potholes,” warns Mutiny’s Jaleh Rezaei. When it comes to your thesis, there are things you’re right about, and others that may miss the mark, she says.
To uncover the hidden traps ahead, Rezaei relies on the “black hat" technique, where you kick off new initiatives by asking a targeted tough question: “Let’s assume that it’s one year from now and we’ve failed at our goal. What went wrong?”
“This question creates a subtle shift from a very optimistic mindset to triggering the team’s problem-solving neurons. It points them in the direction of trying to articulate the things that we don’t know yet,” Rezaei says. “The aim here is that you want to get to a list of five to 10 major assumptions implicit in achieving the long term goal.”
But it’s not about just dwelling on the negativity. “The next step is flip the negative statements into positive ones and reframe them to include the key levers that will make the program work. These are your core assumptions that must be true for you to hit your long-term goal.” Try out this slide format in your next kickoff meeting:
Back in his founder days, defy.vc’s Brian Rothenberg relied on a smart tactic during SkillSlate’s board meetings. Instead of offering up a status report summary of the last month’s metrics and milestones, the focus was on the month’s learnings. “Start asking questions like, ‘What can you apply from those insights, and what additional questions did they lead to?’” says Rothenberg.
This tactic carried over to his days at TaskRabbit and Eventbrite as well. “Like many other startups, we were in a cycle where we’d ship some buzzy new feature and almost hope for faster growth,” Rothenberg says. While tons of thought went into the features, hypotheses and metrics were sometimes murky — and long-term impact wasn’t always specifically monitored.
“Historically, a team would ship a new feature, we’d cheer the launch, and then that team would immediately shift to a new project,” he says. “People were moving on to the next project before asking questions like ‘What did we learn?’ or ‘Did we have the impact that we expected?’ Or even ‘Should we keep this feature at all?’”
Don’t just ask “What did we do?” Chart your progress by also asking, “What did we learn?” Being driven by questions, rather than achievements, unlocks future impact and further learnings.
Post-mortem meetings are a startup staple, key to capturing lessons learned and moving past blame. But Twilio’s Jeff Lawson is also an advocate for putting these same muscles to use in a different way — when things are going right.
“Usually post-mortems is the word you use to describe analyzing the things that don't go well, but we do post-mortems when things go well, too,” he says. “That is the way in which you continually build this muscle of analyzing the outcome and asking what all of the inputs were that led you there and try to do your best in the moment when everything's fresh in your head to learn and to capture knowledge.”
For example, after Signal (Twilio’s annual customer event) the team pushes past exhaustion to meet and capture what the call “worked, not worked.” “It would be easy for everyone to say, ‘All right, I'm taking the next week off. We just worked our butts off.’ But two weeks later, if we came back and did the post-mortem, they would have forgotten a lot of stuff,” says Lawson.
RALLY TEAM SPIRIT BY BOOSTING RECOGNITION & INCLUSION:
We’ve all heard the importance of giving real-time feedback regularly, especially when it comes to positive comments that give team members a boost and reinforce the right behaviors. But with a full plate of back-to-back meetings, it can be hard to carve out the time to send those notes of encouragement. Instead, try using your time on your next video call as an opportunity to serve up positive feedback.
Mutiny’s Jaleh Rezaei recommends leaning on Slack (or Microsoft Teams perhaps) for quick hits of positivity. “When I see something that I really liked, I usually will send a message to the person with a short heartfelt message like, ‘It was incredible for me to watch you shine in the meeting. Well done,’” she says.
Facebook’s Product Lead for New Product Experimentation Sunita Mohanty has seen a noisier approach, though: “Bang the drum — literally. A friend of mine loves using props to get her team fired up, like a tambourine she shakes when she’s excited about what someone says,” she says.
Each individual person’s strengths are superpowers that lead to an all-star team. Find moments to recognize specific ways that each person’s superpower shines and encourage team practices around sharing gratitude for each other.
Take it a step further by making sure that getting this feedback to folks higher up on the chain has its own slot on the senior leadership’s agenda, says Brex’s Edwin Chau. “Every weekly meeting with his direct reports, my manager (the CTO) has us each share some amazing things that members of our groups have accomplished recently. These team members could be four-plus levels removed from my manager,” he says.
If you’re planning on borrowing this tactic, the follow up step is critical: “My manager then sends a short, but extremely impactful email to all the folks that got mentioned recognizing their accomplishments. It's often a surprise to folks that someone many levels removed has that level of visibility into their work and is aware of their contributions.”
“Extroverted folks, those who've been on the team the longest, and members of dominant identity groups often get their perspectives heard more than others. Leaders need to pay attention to these dynamics, from how women and people of color are often overlooked, to how folks who are remote, newer to the team, ELL (English Language Learners), or more introverted can find it tough to speak up,” says Coa’s Head of Emotional Fitness Vaneeta Sandhu (formerly of LifeLabs).
It’s not enough to make sure everyone has a seat at the table — inclusive leaders make sure everyone gets airtime, too.
Here’s her punch list of more tactical tips:
- Build thinking into meeting time. “That could be as simple as saying, ‘Before we all answer, let's all jot down our thoughts.’ That's great for people who are operating in their non-native language, for introverts, for those who are neurodivergent and so many other groups.”
- Rely on ritual questions. Make a habit of ending key points in a meeting with questions such as, “Who haven’t we heard from yet?” and “What are two additional perspectives we haven’t considered?”
- Return to the interrupted. While preventing interruptions in the midst of an engaged conversation — especially a virtual meeting — can be counterproductive, one thing leaders can do is track completion. “If someone is talked over, go back to them and say, ‘Hey, did you want to finish your thought?’ or ‘I’d love to hear the rest of their point before we move on.’”
GO THE EXTRA MILE TO MAKE YOUR MEETINGS EVEN MORE EFFECTIVE:
“As leaders, we tend to ask very broad feedback questions like ‘How are things?’ You need to get very, very specific,” says Massella Dukuly, Learning and Development Lead at LifeLabs.
Her go-to tactic for surfacing that more specific feedback is what the LifeLabs team calls scaling questions. “A quick example is: ‘On a scale of one to 10, how well do you think I facilitated that meeting? Most of the time, you’ll usually hear seven or eight, because they're uncomfortable saying anything beyond that,” Dukuly says.
That’s where the magical second question comes in. “What would it take to increase that score by one point? Then maybe I’ll hear something like, ‘You could have called on people more to include other voices.’ This is important for two reasons. One, giving people greater safety to be able to express themselves increases engagement and commitment. Two, it also gives us micro steps we can then act on to build trust and improve inclusion.” Other follow-ups to consider:
- What could move you from a 8 to an 7?
- How would a 10 look? How about a 1?
- What keeps the score from being worse?
Fidji Simo recently stepped into the top spot at Instacart, but back when she was VP of Product at Facebook, she shared her incredibly intentional playbook for finding focus at work. One of her micro-habits stood out to us as we were giving it a re-read:
“I look at the big meetings that I have during the week, and for each of these meetings, I set a clear agenda of what I'm trying to achieve in that meeting, personally and for the group,” Simo says. “That way when I go from meeting to meeting during the week it's less jarring because I already know what my goals are.”
Having this clarity before the meeting starts — literally a checklist of what she wants to walk out with — and an understanding of her personal priorities ensures that her entire team’s actions and priorities stay aligned.
Being intentional is the ultimate integrity in leadership. It’s stating your values and intentions clearly, then putting your money where your mouth is.
Given her deep experience with board work at companies like Gusto, Patreon and Asana, Anne Raimondi has plenty of thoughts on how to make these oft-dreaded meetings more effective. For founders weighing what to put in the packet of pre-reads and what to slot into the face-to-face meeting agenda, Raimondi offers up some pointers: “From a pre-public company perspective, if you're spending a lot of your board meeting doing just updates and readouts, you're probably not getting the most out of that time. You should be digging in on the decisions that are the messiest ones,” she says.
As for how to craft a pre-read that feels less chore-like, Raimondi’s been impressed when CEOs bring a personal touch to these meeting details. “I’ve worked with many CEOs who write a board letter in advance of the board meeting, which is a narrative just from their perspective. Some are longer than others, but it’s almost like a voiceover for the deck — what's on their mind,” she says.
The best board letters include what the CEO is most proud of and excited about over the last quarter, but most importantly, what’s keeping the CEO up at night. “That in particular is so important for the board to know. What is the most critical issue that's preventing them from getting good sleep?” she says. “Then yes, you still get the deck and pre-read, but it gives you context around where we really need to spend time.”
DITCH THE MEETINGS YOU DON’T NEED TO BE IN:
The tension of a blank page and a blinking cursor is one of the biggest hurdles as we stare down our to-do lists. Nowhere is this more true than with an overflowing inbox. That’s why Tomas Barreto suggests dropping one sentence in a response to quickly regain control over the request and its owner.
“Charles Duhigg talks about responding to invitations to meetings he doesn’t want to attend. He began starting those responses with ‘I can only make it for 15 minutes,’” says the former VP of Eng at Box and current co-founder of Okay. “Immediately, he puts himself back in control. Sure, he’ll ultimately flesh out or explain his response. But he’ll have a foothold to push off from. The page will no longer be blank, and moving through his inbox will feel less onerous.”
Sometimes the most effective meeting is the one that doesn’t happen. For founders and senior leaders who are seriously committed to making meetings suck less, NerdWallet’s Tim Chen shares this lesson from his own experience: Cancel the CEO’s favorite meeting.
“The meeting everyone hates is the large meeting, the one that’s only useful to the meeting owner. This person is often the CEO. And often the meeting consists of going around the room and giving status updates. The meeting owner feels great about it, but everyone else is rolling their eyes, bored to tears thinking about how 'this could have been an email.’ I was running a meeting like this for a long time,” Chen admits.
“I was reading a book about meetings one day and it described exactly this phenomenon and I was like, ‘Oh my God. That's totally my meeting.’ So, I pulled the plug. Don’t waste anyone’s time. Find someone you trust and ask them directly: Are you getting anything out of it or should it be canceled entirely?"
CEOs, kill your most useful meeting. It may be your favorite, but chances are it's the one that everyone else dreads the most.
Image by Getty Images / Emilija Manevska.