Better Meetings Make for Better Days — 20 Tactical Ideas to Try Out With Your Team

“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 

 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. (

 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:

Set down your suitcase and revisit your wins to avoid the spillover effect between meetings

“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 

 “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.

Stop yourself from diving into solution mode

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 

“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.

 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?

’s first remote offsite last year, CEO 

 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.

, 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.

Spotlight what good looks like — and more importantly, how it got done

Remote meeting culture has been getting a lot of attention these days, but 

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 

 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.”

Book cameos to give people a window into other parts of the company

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,” 

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:

Switch sides when you’re stuck in a stalemate

Not every meeting goes swimmingly — sometimes 

, 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, 

 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.

Deal with derailments by pinning down the details

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 

 (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 

 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 

 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 

’s thoughts here, first outlined in his now classic article, “

,” 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.”

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.

Break down big hairy goals by putting on your black hat

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:

Focus on learnings and long-term impact, instead of just status reports and milestones

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.

Hold a post-mortem — after a big success

Post-mortem meetings are a startup staple, key to capturing lessons learned and 

 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:

Take a minute to share in-the-moment praise and send kudos up the flagpole

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. 

’s Product Lead for New Product Experimentation 

 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 

. “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.”

Regulate the airwaves to run more inclusive team meetings

“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 

20 Super Tactical Ideas to Try in Your Next Meeting

We're spending more time in meetings than ever. The sharpest folks we've interviewed share their best tips for making sure this time is well spent.

The sharpest folks we've interviewed share put-to-use-right-away tactics for making your next meeting less painful.

Ask Why It Won’t Work, And Other Lessons This Founder Relies on While Building From 0 to 1

 is slightly obsessed with one exercise these days: pre-mortems, or the act of thinking through why a particular strategy, product idea, or candidate might not work out down the line. This isn’t a typical focus area for founders. In our experience, they’re usually an optimistic bunch, the types who spend time dreaming up big ideas and figuring out how to run through the walls that may stand in their way — more the “move fast and break things” school of thought.

 want this?’ is often a far more interesting question than why they would

. When you're working on a product idea, there's a thesis for why you believe you’re right and it's really easy to constantly confirmation bias yourself into believing it’s the optimal decision. But once you can also find the counterpoint, the scenario where you’re wrong, you can start teasing out when it would start to make sense — the point at which it 

Oftentimes the question of why something 

 work uncovers the element that actually 

Song has had plenty of experience with making things work these last few years. Since co-founding 

 in 2018, the CEO has had his hands full with the intricacies of the 0 to 1 phase of company building. 

Prior to starting Persona, Song spent five years at Square as an engineer and early team member at Square Capital. It was here where he first had the insight that led to starting a company. From fraud prevention in lending, to trust and safety with food delivery for Caviar, he gained exposure to the wide range of use cases in identity verification — and saw that one-size-fits-all solutions were falling short. With low- and no-code building blocks, Persona’s platform enables customers to craft a more tailored experience.

As investors in Persona’s seed round, the First Round team has had front-row seats to this early startup journey, and we’ve come to believe Song is one of the most thoughtful founders around. And as 

, Persona is at a particularly interesting inflection point — they’ve raised a $50 million Series B and are looking to double their 50-person team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include some big logos like Square, Postmates, and Gusto.

In this exclusive interview, Song takes time to share what he’s learned on his company building journey so far, diving deep into how he brings the pre-mortem mindset to every aspect of running Persona. 

Starting with recruiting, he shares the lessons he learned — and had to unlearn — from his time at Square. Next, we chatted about why Song believes it’s not about going down to first principles, but rather studying other companies to find unusual moves and experiment with different strategies and frameworks — of course, questioning why they might not fit your business along the way. From the strategy behind Persona’s multi-product approach — including a candid discussion about the risks — to why his engineers sell, Song shares a detailed look at his go-to-market thinking.

In our view, there’s a trove of insights in here for founders or those toying with the idea of starting a company one day, but there’s also plenty for engineering leaders and hiring managers as well. Let’s get to it.

LESSONS ON RECRUITING: HOW TO HANDLE YOUR FIRST 10 HIRES AT AN EARLY-STAGE STARTUP

Much of Song’s hiring philosophy stems from his days at Square. “One key piece of how Square scaled this was setting up an entire ladder of how to progress as an interviewer. They weren’t putting people on the critical path of determining whether someone would get an offer or not on Day 1,” he says. 

“There was an entire training process for anyone to become an interviewer and it was very rigorous,” Song says. “Then you'd start off on the interview panels. And once you got your bearings and did a fair number of interviews, you'd become a phone screener, assessing the technical capabilities of candidates on the initial calls. Usually the more senior interviewers were the really good phone screeners. And then for the folks who were incredibly predictive as to whether someone will be successful or not within the organization, they became barometers — the people at the very end of the hiring process who helped determine whether to extend an offer.”

Below, Song delves into his top hiring takeaways from both from his time at Square and building out Persona’s early team.

Lesson #1: Get granular on why a hire won’t work out.

It was from those barometers that Song picked up a critical hiring lesson. “The best hiring advice I received at Square was that when you're about to extend someone an offer, you're thinking to yourself, ‘There’s so many problems this person can help us solve, they’ll be amazing.’ And this almost certainly will be true. But

 it's actually far more helpful to think about all the ways in which this person may 

 work out for your organization — who on the team they might not interface well with, the types of projects they may not succeed in

“The first three months of any new hire is a honeymoon period that masks a lot of otherwise clear problems. Thinking really deeply about all these potential pitfalls can help set you up for success downstream and make sure that this individual is successful as well.”

Of course, every hiring manager weighs the pros and cons of candidates. But Song shares some practical advice on how to spend more time measuring the minuses. Here’s how he operationalizes this “why they might not work” mentality: 

. “In the early days, I used to write a doc, jotting things down for myself as to who would this person work with and how would they do. These days as we’ve scaled, it’s more about coaching hiring managers to think deeply about this,” says Song. 

. “We ask managers to make a really strong pitch to themselves about why this person may not work out and just be heavily aware of the potential pitfalls.” There’s an important distinction here, though. “Externally to the rest of the hiring panel and the team, you should be the absolute champion for the candidate. But internally or in discussions with your own manager, you need to be thinking through what may not go so well,” he says. 

Bias toward no if you’re on the fence. 

“Although saying no may feel harder, it's far better to be a little bit more pessimistic. Hiring is such a big deal when you're only 10 people — it's a 10% incremental difference in terms of the size of your team. That's enormous. So being a little bit more pessimistic can really save a lot of heartache in the early days.” This may seem obvious, but consider the strain that early-stage startups feel as they struggle to stand out in the hiring market. “It often feels so hard to hire folks. In the early days, there's so much difficulty in trying to convince anyone to join. We initially had a tendency to rush decisions and try to hire someone a little bit sooner than we actually needed them. But adjusting to be more cautious and bias toward no has paid off so much for us.”

This approach of course hinges on a crystal-clear understanding of what you’re looking for and a well-developed sense of what a candidate brings to the table. Here, Song shares his criteria:

“This 11th hire has to work well with all of the first 10 people on the team. As companies scale, generally you have more pockets and groups — and problematic relationships can be a little bit more hidden away. But for the earliest stage, there’s no escaping it. Think critically about whether this individual will actually interact well with everyone else here,” says Song. “More specifically, I try to think a lot about how this candidate would interact with the top five people I expect them to work with on a daily basis. And what are core aspects of their working style? Is one person particularly process heavy, whereas the other is much more loose and adaptive? Are the communication styles fundamentally different? Does what they value differ greatly?”

“If this person is more of a big idea type of thinker, could they handle particularly complex projects where there's a lot of nuances? Are they more social? Do they prefer a leading role versus a supporting role?”

“Who are they as an individual and what will really make them feel excited about being here every single day? We want to make sure that we can provide that, that this is a place they can be successful. But especially for non-technical roles, it can be really difficult to assess how a person will actually do the job,” says Song. “For most of my interviews, I actually ask very little about how they would solve a particular problem. When it comes to questions like “What was the hardest challenge you've ever faced?’ often a lot of candidates have canned answers. Instead, I focus on the incentives. What do they care about? What motivates them? What drives them? If it's an hour-long interview, I’ll spend 40 minutes diving very, very deep into what this person wants to do. What is their ideal day to day?”

I'm a big believer that if you can get to the root of someone's motivations, you can sort of work out how they would tackle many problems.

“For example, if someone's incredibly motivated by supporting others, you can usually get a good sense of how they’ll behave when there's a product launch or when a customer challenge arises,” says Song.

uncovering motivations through interview questions

 isn’t easy. “I like to ask, ‘What do you want to do after this role?’ and ‘What are the most important things that you're looking for in your next role?’ For the latter, it’s common for candidates to focus a lot more on the size of the market and impact on the world. But for us at Persona, I’m heavily biased towards people. So if I don't hear that the number one thing that motivates them is people — the folks they work with, or the customers they support — I usually think that this probably isn't the best fit,” he says.

Even when Song does hear that shibboleth in a candidate’s answer, there are still deeper depths to explore. “When you say people are important in your next role, what do you mean by that? Does that mean day-to-day or long-term impact? Is it someone you can joke with or hang out with after work, or is it about being surrounded by people who are similarly motivated? Is it people who you admire versus people who you can learn from?” he says.

Lesson #2: Focus on setting the foundation and finding the glue.

It helps to have an understanding of the pitfalls you’re likely to encounter when hiring, and these lessons were hard won, Song says. “When hires haven't worked out, it usually stemmed from us not understanding the role itself nearly well enough, especially for the first person in a specific role we weren’t that familiar with,” he says. 

“Early on, we had a tendency to hire much more for potential. But requirements of the company often outscaled that potential, which meant that the individual had to grow far faster than they may have even been able to, and in a way that frankly may be toxic towards their own growth trajectory. It was key to spend more time on understanding that role and doing it ourselves for a while to figure out 1) what level seniority we need to hire for and 2) whether we needed to hire someone who already understands this role deeply.”

Song offers up an example: “For our first business hire, we brought in 

, who had a lot of experience leading people and had been at a variety of startups — she knew what she was doing, which was important because she was setting the direction for sales, marketing, customer success, and much more. Whereas on the engineering side, both my co-founder 

 and myself came from engineering backgrounds, so we could really tackle a lot of the foundational pieces and bring in some less experienced folks who could grow with us.”

Part of this comes down to understanding whether it’s a 

. “On the product side, we were still trying to understand what our product is and oftentimes the mistakes that you make are much less costly. Design is also easier to mold and redesign in the early days, and we’re a B2B SaaS company so it wasn’t an absolute pillar initially. Of course, this has evolved and changed, so we’ve started hiring more and more senior folks in these areas as we’ve scaled.”

If you're trying to hire someone to lay the foundation in a function, you can't really bet on potential no matter how much they have — because everyone else will be building off the exact same foundation.

Another frequent pitfall? Missing the mark when assessing the candidate’s motivations. “When it doesn’t work out, I always look back and try to think about what I missed in terms of what this person cared about or wanted to learn. And I think we've had a couple of cases where we felt an immense alignment in terms of core things like people and culture, but we didn't effectively highlight 

what joining a startup for the first-time requires

. There’s an immense amount of pressure, and work-life balance can be very hard to achieve, especially in crunch periods. Painting a picture of what that looks like is important,” he says.

But that’s not to say that Song’s in the “don’t hire anyone from FAANG” camp.“The vast majority of folks here at Persona actually have no startup experience and largely come from big companies. I often joke that we're an entire company of people who have never done startups, but are all trying to learn together at the same time — and I don't know whether that will be a disaster or not,” he laughs. “Hopefully it’s clear that it’s a very friendly learning environment for all of us.”

This runs counter to common wisdom that candidates from top tech companies tend to flounder on a smaller stage with fewer resources. “There are a lot of founders out there who don't have experiences at a larger company, so it can be a bit of a black box in terms of assessing an incredibly specialized candidate and figuring out if they will actually adapt to a startup,” he says. While there are risks, Song sees clear advantages.

“One, you generally have a sense of what this function looks like at scale. Because startups grow unbelievably quickly, knowing what the end result looks like and being able to plan backwards is impactful. If you've only been at startups, you've seen how it works at a smaller operation, but the scaled up portion may be far more challenging and the pace of startup growth makes it very easy to level out.”

The key is finding the big company candidates who have scrappiness in spades. “We're looking for the people who have been the ‘glue’ — the ones who plug all the holes, are maybe a bit less recognized but constantly make it work and tackle problems that no one else was really dealing with,” says Song.

To unearth these hidden gems, ask more about the larger architecture to see how they interfaced with different functions or problem areas. “The utility player type engineers can go so deep on so many different topics of the entire company,” he says. References are also a great place to mine for insights. “If you ever hear things like, ‘If you asked this person anything about the company, they knew how it worked,’ or ‘They will literally run through walls to get something done,’ or ‘They will work with anyone,’ that’s a great sign this candidate could be amazing in a startup setting.”

Candidates who filled the gaps and served as the “glue” at big companies both know what the future looks like and have the scrappy spirit that makes for a great startup hire.

Lesson #3: Think of hiring as a segmentation exercise.

“One mistake we made in the earliest days was that we tried to create an entire track for interviewing. When it was just my co-founder Charles, myself, and maybe two other people, we prematurely created an entire interview loop, with phone screens, interview problems and onsite interviews, perhaps to make it seem a lot more mature than it actually was,” says Song. “But coming from a large company like Square, often when candidates apply, there's a very high probability that they'll join you. You're an established company. They intentionally came in. And when you're a small startup, it's very different.” 

Startup hiring isn't just about sussing out whether this person's qualified, but actually remembering that every single interview is also a sell.

“If you're trying to attract top talent, a ‘First, let me make sure that you're good enough’ approach creates a weird power dynamic that makes it incredibly hard to hire. You really have to start with a much more back-and-forth approach,” says Song. “Keep the early conversations casual, and make sure the relationship is more of a horizontal-like camaraderie dynamic where you look at the individuals as equal — because for these first 10 hires, it really will be more like that.”

To foster this atmosphere in interviews, Song and his co-founder focused on turning them into conversations where candidates could teach them what they do. “Given that we were so early, we didn't know how half these functions worked. 

 of the things that you aren’t particularly good at as a founder is important,” he says.

Vulnerability also plays a critical role in another aspect of Persona’s recruiting philosophy. “I try to think about hiring almost as an exercise of segmentation. Today it seems as if every single startup out there is talking about hiring for mission, or how they’re going to become the largest company in the world. As a result, 

this ‘You're riding on a rocketship’ segment of recruiting messaging is incredibly crowded. So we’ve taken almost the complete inverse approach

. I often say to candidates something along the lines of:

We're not trying to change the world, we're just hoping to make it slightly better. And hopefully if we succeed, people never think about their personal information being lost or mishandled ever again. It's essentially removing a burden for a lot of people. Whether it's a rocket ship or not, I can't promise you that. I don't know where Persona will be in 10 years — if we are huge, that'd be absolutely amazing, and if we're still alive, frankly, that would also still be amazing

We're just trying to take it step by step, and make sure that this is a great place day-to-day for everyone here. As a founder, all I really try to index for is that 10 years down the line, if we were to suddenly go out and say, ‘Hey, there's going to be a reunion,’ we would all really look forward to seeing each other. And if that were true, I would think I've done a great job.

“And a lot of this hopefully runs a bit counter to traditional startup hiring messaging. In practice, it’s been really helpful for us, not just from standing out in the market and winning candidates over but also in reinforcing a culture of humility, a culture of really wanting to work with other folks and 

 a lot more about the day-to-day experience,” says Song.

Find out what’s uniquely attractive about your company. It doesn't have to be what's traditionally attractive — there will always be a segment of the market that is under-tapped.

LESSONS ON BUILDING THE BUSINESS: FIGURING OUT YOUR MODEL AND GETTING BETTER AT DECISION-MAKING

With a team assembled and a product that’s starting to take shape, the next frontier is fleshing out the strategies that will get it into the hands of customers, help the business run like a well-oiled machine, and set the scene for the company’s next play. 

 tend to be overlooked, and Song highlights another neglected area: whether a popular framework or strategy is actually the right fit for your startup.

At an early-stage startup, you'll be just bombarded with advice. You'll hear that X company did Y and it was so successful, or this strategy works so unbelievably well, whether that be OKRs or frameworks for product decisioning, like 

. All of this advice is correct — given the right context

“What's much more interesting than figuring out how to execute this framework perfectly is discovering when it does 

,” says Song. This concept originally comes from game theory. “It’s the specific spot in which the decision shifts, where you were going to bet and now you’re going to fold.” 

As individuals, we focus way too much on one decision versus another, but not nearly enough on the meta question of the context that would cause that decision to change.

A few variations of this framing to get your gears turning:

•Where's the decision point where suddenly something went from not working to working?

•What are all the criteria that have to be true to flip your decision? 

•What’s the situation in which this strategy wouldn’t be effective? 

•How do we figure out the context in which this situation would be true?

Song takes us through two popular frameworks as examples:

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