The 25 Micro-Habits of High-Impact Managers

Management can at times seem like staring down a large block of marble — an intimidating task that requires the right tools. And in our experience, most management advice tends to focus on tackling the biggest chunks: assembling high-performing teams through hiring, delivering tough feedback and checking in regularly. Of course, holding regular 1:1 meetings and honest performance reviews are critical items on your manager checklist to get right — but sculpting a magnificent piece of art also relies on the finer chiseling work of shaping that rock, bit by bit. After all, it’s the smallest movements and the intricate detail work that makes a statue worthy of display in a museum. However, this tends to be overlooked.

The signs that you have a great manager are the actions you don't think about until later.

 Part of a weekly conversation where they stop and listen to the team, waiting until everyone's had a chance to share their thoughts. Or the way they pull you into conversations with support, knowing you might be taking a risk, but they always have your back. Even just the occasional overshare about their own lives to show you're all human,” says 

It got us thinking — what are the little daily habits that often go unnoticed, but when linked together add up to form an incredibly strong chain between manager and direct report? To that end, we spent the past few weeks reaching out to folks all across the First Round community for their take on this question: 

What are the small things a great manager has done that have stood out to you across your career?

What follows is a can’t-miss list of 25 targeted tactics for upping your management game — no rote training sessions required. Some folks spoke from their experience as a direct report under a favorite manager in their career. Other startup leaders we admire with tons of people management experience opened up their own playbooks. Whether you’re a brand-new manager, a seasoned vet, or have goals for taking on a management role in the future, there’s plenty of leadership development tactics for you to jot down.

To make the mega-list easier to digest, we’ve broken it down into eight categories — use the outline on the left to navigate to each section. Each category is defined by a soft skill like vulnerability and building trust, followed by a few tips to put those amorphous traits into practice, like monthly reflections or tactics for delivering feedback with care. We assembled this list with hopes that you’ll find at least a few ideas you’re excited to try out — and a greater appreciation for the micro-actions that set stellar managers apart. 

Most folks don’t intend to micro-manage — but when priorities pile up and your own boss is pinging you for updates on that encroaching deadline, the urge to take the reins from your team is hard to ignore. But breaking this habit is critical to give folks the opportunity to flex muscles that would otherwise atrophy and stop them from reaching their full potential.

“Looking back on my career, my favorite managers allowed me to own decisions, even if they disagreed with me. They couldn't do this for every decision — some were just too expensive or difficult to reverse. But if they spotted an opportunity for me to own a decision, they let me run with it. This would often be preceded by spirited debate, where they challenged my assumptions and forced me to think through various outcomes. Then they gave me the space to decide and room to fail and learn (and to sometimes surprise them),” says 

, suggests managers commit one particular phrase to memory — and use it liberally.

“I trust you, make the call” might be the six most powerful words you can hear from a supervisor.

“The best manager I ever had was gifted at coming up with big ideas. He saw incredible market opportunities and was constantly thinking of programs that would improve our offerings. 

But what made him the best was how he passed these ideas along to the team to bring them to life

. Along with them, he would share his utmost confidence that we would make them better than he ever imagined. This enabled me to do some of the most creative work of my career, and I felt supported and believed in along the way,” says 

3. Think of yourself as the team captain, not the head coach.

“I believe that healthy adults don't derive any pleasure from a ‘waterfall’ power structure.

When a manager understands their role is as a coordinator of priorities and doesn’t act from a place of authority, they typically buy into the broader concept of being part of a team with each team member equally responsible for success, trusted to do their work as adults,” says 

The best managers "ask" more than they "tell."

4. Set the tone with cross-functional partners. 

Giving direct reports the freedom to operate as owners extends beyond your immediate team — weave this thread across the entire company fabric. “Oftentimes other leaders in the company may come to me as a partner in driving a decision or initiative forward. Rather than jump right into it, I try to recommend that they go directly to one of my direct reports. I communicate to both the partner and my direct report that I'm available if needed, but that I trust my direct report to have full decision-making ability,” says 

For years in management circles, there have been larger conversations about bringing our whole selves to work and this went into overdrive once we all started working remotely from our kitchen tables (with kids, pets, and piles of laundry all front-and-center on Zoom). We’re shedding our more stoic “work persona” and 

previously weren’t on display in the office. 

 — it’s a long-overdue reckoning, and high-impact leaders need to set the tone by modeling authenticity to their team, rather than always plastering on a brave face. “Part of the reason why emotions have such a bad reputation is that we’ve tried to keep them out of the workplace for so long. 

We suppress everything we feel, which means we don’t resolve issues while they’re still manageable.

 Instead, our feelings fester,” she says. 

“Great managers demonstrate self-awareness and empathy by sharing their working style preferences and development areas. I've always appreciated when managers provide an onboarding guide to who they are as a person and a manager. This should include their work styles, expectations of their directs, values and motivations, areas of feedback they are working on and decision-making preferences,” says 

, Chief of Staff and VP of Program Management at

. (If you’re looking to put this one into practice 

outlined the importance of creating a user guide

 right here on The Review— and included plenty of examples to help you get started creating your own.) 

As Product Lead on the New Product Experimentation team at 

 has even experimented with sharing her team’s user manuals during the interview process with top candidates. “This builds psychological safety and trust and can set a clear bar for transparency and honest introspection. As people are considering your team, I’ve found this can be a great way to find alignment with potential team members,” she says.

In addition to sharing her working guide, Mohanty also implements a weekly habit to get folks on her team on steadier footing, even amidst stumbles. “When you set an example of being vulnerable, it makes space for greater psychological safety on the team. As I’ve moved through my career, I’ve learned how it’s okay to show some vulnerability — whether it’s about a personal challenge or something I’m struggling with at work. As a result, it builds deeper relationships with my reports to feel okay expressing 

 or other messy feelings,” she says. To get tactical, Mohanty suggests managers share one high and one low each week, either in a team meeting or in a weekly email, to create an atmosphere of reflection and transparency.

Failure isn’t easy for anyone to talk about — especially for managers who feel like folks are counting on them to get things right. But no one’s infallible, and 

 relies on folks feeling like they can try new ideas and fail fast. “Share a story where you've failed personally or professionally and what you learned as a result. It sheds light that we're all human and on the same level. It allows team members to share their concerns and feel like it's okay to fail,” says 

, Senior Director of Monetization and Pricing Strategy at Pantheon.

And don’t hesitate to open up about the fun stuff, too — especially when workplace stress piles up. “Share a personal update or just a quick anecdote from your life outside of the office — it doesn't have to be big or significant or detailed. Even something as simple as, ‘My son did this today for the first time and it was so cute!’ This makes employees also feel like they can bring their whole selves to work and share with team members. This is especially important in a remote world where it's a lot easier for people to feel isolated and disconnected,” says 

, there are a number of features, marketing campaigns, or sales tactics to tackle. To stay nimble, high-impact managers must strike the balance between excelling at the basics and juggling new ideas that make a splash. 

“A startup doesn’t just move fast — it moves 

, requiring a constant adjustment to how we operate to stay effective. A monthly reflection is the single most valuable tool I’ve found for scaling yourself in a fast-paced environment with continually increasing responsibilities. This is also where we establish a lot of trust and I show care for each team member, which in turn allows me to push the team harder on a daily basis without erosion,” says 

Her frameworks for speeding up your marketing engine

 is a Review must-read for marketing leaders.)

She advises setting up specific 1:1 monthly meetings with each team member, where the report reflects 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. The conversation ends on a buoyant note: What are you most hopeful about as you think about the next month? 

To get started, you can borrow from her template.

When we move too fast, our development areas tend to get amplified and we gloss over our strengths and impact. Without taking time to reflect regularly, we don’t adjust our behavior fast enough — and bad patterns start to emerge and we forget to celebrate our wins.

9. Reserve time for thinking outside the box.

While you’ve likely established some sort of regular weekly check-in with direct reports, these meeting blocks can quickly get eaten up by basic status updates rather than thinking bigger. Carve out time specifically to get creative. 

, recommends setting aside time for dreaming up new ideas: “Providing regular blocks of time for brainstorming and ideating together has been super helpful to bring non-urgent matters to discuss and process and remove ‘thinking or planning’ blocks for kicking off new projects”

As an organization grows, there’s an increasingly heavy burden to 

connect the company’s vital organs together

. The high-impact manager spots opportunities to tie their team’s work with the broader goals all across the org chart. 

“The best managers provide context for executive decision-making and rationale that enables me to prioritize with a cross-functional lens,” says 

, Head of Veterinary Translation Medicine at 

. “My manager, from the very beginning, has taken time out of his incredibly busy schedule to answer questions thoroughly and find teaching moments. He doesn't just answer my specific question, he ties it into broader themes and sometimes even goes up to the whiteboard and diagrams things out. Having a CEO take the time to help me personally develop makes me feel valued and supported,” says 

As a startup grows (along with the mountain of work on your plate) regular 1:1s can seem more like rote rituals than effective meetings. But 

the very best managers approach 1:1s with great care

. “My manager listens, always — whether it's about a problem at work, a funny story about a pet, or something I’m excited to learn. In our 1:1's, they are always present and not sidetracked by performing other tasks on the side,” says Laura Percy of Truveris.  

Outside of 1:1s, there’s plenty of questions or issues that crop up — sometimes at what feels like the worst possible time. “The best managers I've worked with always make the time to talk to you, no matter how busy they are. They realize that five or 10 minutes invested immediately not only addresses the topic in question, but it also shows the employee that their needs are a priority,” says 

As an individual contributor, following through on deliverables is core to succeeding in your role. But as you move into the management track and calendars fill up with countless meetings, these good habits can begin to slip. “A small action that has a big impact is just following up and following through consistently,” says

, echoes that this is often undervalued. 

The best managers are incredibly consistent — they’re almost always on time, follow-up, and close the loop on open items. The diligence and consistency seem straightforward but are rare in a leader. 

Whether you’re a first-time manager or have a resume full of leadership positions, like the most-loved knives in a chef’s kit, your people management tools frequently need sharpening. Maybe 

 between members of your team, or your startup is hitting its stride (which comes with growing pains), or you’re 

. Tap into your empathy reserves to clear these hurdles. 

13. Don't forget the humans behind the company's goals.

“When my managers have been great, they’ve looked at my situation with compassion above all, above what they (or the company) need from me. The same goes for when I’ve been my best as a manager. That doesn’t mean the company’s priorities don’t prevail — it just means I feel acknowledged as a human being in whatever the situation is,” says 

“It’s not trivial to pull off because there’s so much pressure on a manager’s shoulders to extract value from a team (to put it in the coldest terms). There’s not often as much pressure to consider those team members in their full humanity. I’ve been fortunate to work for managers who make the experience as human(e) as it can be. I do everything I can to pass that experience on to my directs.”

14. Encourage folks to put themselves first. 

Some reports may wear their heart on their sleeve, and you can quickly decode when something’s awry. Others may have a poker face — but deserve just as much attention. 

, recommends checking in privately when you notice a report is struggling. 

, has seen great managers go a step further and gently nudge folks towards a much-needed break. “If I'm feeling overwhelmed, my manager encourages me to take time off and actively asks how she can lighten my load. These actions help me feel cared for and supported,” she says. 

And when your report is out of the office, resist the urge to ask a quick question over Slack. “If I'm sick or dealing with a personal matter and out on short notice and there's something urgent, my manager handles it. Full stop. My manager doesn't need to ping me or ask a lot of questions, distracting me from my time away — they're just able to take care of it,” says 

 is a key piece of any manager’s role — and also one of the trickiest to get right. There are all sorts of landmines that can blow without warning — even the word “feedback” can cause folks to cover their ears because it’s so rarely done right. But when approached with care, feedback nudge reports closer to their career goals.

Being a supportive manager is easier when the road is well-paved — you’re shipping your deliverables, not missing deadlines, and cross-functional partners are happy. But any startup’s path is littered with potholes and speed bumps that can quickly throw you off course.  

“Early on, my manager told me, ‘I don't want you to mess up. But if you mess up, I will have your back.’ This instilled in me that my manager trusted my decisions, was willing to help me through potential failure, and subtly applied pressure to live up to that trust. He said it once, but it was impactful enough that I still think about it when I face a new decision in my role,” says 

, Associate Director for Division Operations at 

Mistakes happen — if they don’t, it probably means you’re not being ambitious enough. That’s why 

 have become a startup mainstay. “My manager always has my back. Even if I've made a mistake, they explain what went wrong, we work together to devise a plan to keep it from happening again, and then move forward without blame. It may be my mistake, but my manager always lets me know I'm not alone,” says 

16. Create a monthly performance review action plan.

 system that’s chock-full of advice for making the dreaded process more impactful than painful. The key to his approach? Following up those annual reviews with monthly touchpoints. “After the performance review conversation, turn each of the feedback items into a tactical action plan your report can concretely work on. Then, like any project, check in on how they're progressing and share advice, coaching and guidance along the way.” 

“When I go to my manager asking for her to provide feedback on a resource or simply take a look at something, I appreciate that she challenges me to share my intent and clarify what I'm looking for in a response. This helps streamline communication and prevent any misunderstanding, and that clarity of thought is something I always remember when I’m making an ask,” says Lauren Jones of Warby Parker.

18. Take a beat before delivering feedback.

’ may have said it best: A great manager praises in public and reprimands in private,” says 

strongly suggests asking folks how they prefer to receive feedback early in the onboarding process.

Facebook’s Sunita Mohanty recommends prefacing feedback with a simple framing. “My previous manager knew it would be most impactful to give feedback right away on how I could have presented better in a review or ran a meeting more effectively. But there is also the risk of not being in a mental space where I really hear the feedback. He would do a great job of stopping to first ask if I’m open to hearing feedback and then proceeding, which made me way more receptive to whatever came next,” she says.

CELEBRATE AND UP-LEVEL THE SMALL MOMENTS.

, there are all sorts of big milestones that get attention. But for each big achievement, there are dozens of smaller touchpoints along the way worth cheering for. 

19. Look for opportunities to praise in the moment.

“A leader who recognizes and celebrates the smaller milestones on the way to a larger goal helps to keep momentum and motivation. This can be done through something informal like a Slack channel — direct reports can share milestones accomplished or even small wins and get feedback, questions, encouragement, or just a thumbs up,” says 

Jaleh Rezaei, CEO of Mutiny, is another fan of leaning on Slack 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. 

While Sunita Mohanty’s seen a louder approach: “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. Great managers do small things to help their teams have fun and take the work seriously while not taking themselves too seriously,” 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.

20. Spot chances to send kudos up the chain.

A “job well done” can go a long way — and it’s an added bonus if this gets surfaced to folks higher up on the org chart. “I always remember the moments when a manager goes out of their way to up-level you and give you all the credit for the success you achieved,” says 

Edwin Chau of Brex suggests specifically fitting this into the agenda with higher-ups. “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. This next step is key: “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.”

21. Celebrate moments outside of the office, too.

“My manager has twice now sent me a thoughtful gift out of the blue — once over the holidays and once when my son was born. Neither was work-related, but it was a wonderful reminder that he cared enough to remember the important occasions in our lives and it brought us closer together,” says 

 spoke about how he measures his team-building success using a peculiar benchmark that’s stuck with us: “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,’ all Persona alumni would all really look forward to seeing each other. And if that were true, I would think I've done a great job.”

The best leaders understand that great folks will move on from your team or your company for different opportunities — and take key steps to bring those hazy, long-term goals into clearer focus. 

25 Habits of High-Impact Managers

Sharp folks from across the First Round community share the small habits that great managers do, including delivering feedback with care, opening up about failure, and sending praise up the chain.  

We asked a bunch of sharp folks for the small habits that make great managers stand out, including delivering feedback with care, opening up about failure, and sending praise up the chain.

25 Micro-Habits of High-Impact Managers

Counterintuitive Lessons on How to Get Better as You Scale, From Twilio’s Jeff Lawson

, right here on The Review. When you give it a re-read, values like “Draw the owl” and “No shenanigans” stand out as unusual choices.

That unconventional streak paired with a fresh take on oft-overlooked company building processes is something of a theme in Twilio’s story. Consider back in 2008, when it seemed as though the company was swimming against strong currents of accepted startup wisdom. “We got a lot of advice from people saying that developers aren't an audience and nobody knows how to do that go-to-market, we should go build an app instead —  you can always add an API to an app, but APIs can’t be a business,”  says Lawson. 

 — later, Lawson’s seen his bullish bet on developers being influential buyers bear out. Of course, the API economy and 

 have since reached critical mass, but they were still untested waters in Twilio's early days. “Some of our first customers were Intuit and Sony — and it was the developers who had brought us into those relationships very early on,” says Lawson. “If we had waffled on who our customer was or tried to serve multiple different customers, I think we would have had a very different outcome. We knew who we were, we knew what we wanted to be, we had enough evidence that that was correct, and we stuck to our guns.”

This illustrates a classic conundrum — founders and CEOs are threading a delicate needle between approaching problems with first principles thinking and pulling from well-established playbooks. “I’m not a believer that you need to innovate all the things all the time,” he says. “If it matters a great deal to your business, being more inventive is probably more important. If it's a process or something that you do a hundred times a day, that's a good area where you should go optimize and figure it out from first principles. Because it's a repeatable thing that your company does all day every day, and if you get better and better and better at it, you're going to build a stronger company." 

That sentiment also stands out as a theme when you talk to the repeat founder. "One principle we've started talking about quite a bit at Twilio is how we need to get better as we scale," says Lawson. "

Companies should invest energy in this idea because if you don't say it and you don’t make it a goal, chances are things will get worse as they scale because that's just the nature of the universe

As companies get bigger, the natural entropy of the universe wants to make them shittier. There's more chaos. There's more decision-making. There's more politics. But great companies use their scale to their advantage. 

“Being very conscious about that is a goal of ours, both in terms of using software intelligently, organizing into small teams, and putting the customer at the center of what we do,” says Lawson. In this exclusive interview, he reflects on the key unconventional lessons from the past 13 years of Twilio’s journey to do just that — including some of the company’s most critical peaks and valleys and his own evolution as CEO. 

He details some initial wins, like continuing to buck trends by launching a second product in the early days of the company, but also candidly talks about the hard-won lessons, like when one of Twilio’s biggest customers significantly scaled back its investment and they had to reassess their go-to-market efforts. Lawson also makes the case for why executive teams should argue more, why metrics are the least important part of annual planning, and why post-mortems are a helpful tool even when things are running smoothly.

It’s a unique peek behind the curtain at one of the most quietly fascinating companies and CEOs around — company-builders across all industries and growth stages, as well as folks who have hopes to someday occupy these same seats, will find heaps of inspiration to pull from his playbook. Let’s dive in.

For more of Lawson’s thinking on these topics and many more, be sure to pick up a copy of his recent book, “

Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century

LESSON #1: WORRIED IT’S TOO SOON TO LAUNCH A SECOND PRODUCT? FOLLOW YOUR CUSTOMERS OFF THE BEATEN PATH

Twilio Voice launched as the company’s first product in 2008, which enabled customers to make and receive phone calls with API requests — and it was quietly picking up steam with $300K in ARR. And while there were plenty of oft-repeated startup maxims Lawson remembers hearing at the time, like “find a niche, get rich,” the company’s next move swerved off this well-tread course. 

“Very quickly after launching Twilio Voice our customers started saying, ‘Could I also send and receive text messages with this Twilio number?’ So we started researching, and at the time it really wasn’t available in the market,” says Lawson. Instead, large enterprises would get provisioned by a carrier in a lengthy approvals process, followed by spending tens of thousands of dollars each month. 

“While we kept building our voice API, we started working in the very early days — when the company was probably less than 10 people — on product number two. We brought the cost and the barriers of entry for building an app with text messaging from thousands of dollars and months of approvals to 30 seconds and less than a dollar to buy a phone number and send your first text message,” he says. 

It’s a bet that paid off in a big way — Messaging is now the largest product in Twilio’s suite (one that has since expanded to what Lawson estimates today is 60-70 products). “We could have very easily said, ‘Look, we have this brand-new product. It is just getting off the ground. We've got a lot of work to do before we think about product number two,” he says.

We were willing to follow our customers where they took us, even if it meant launching a brand-new product area when the conventional wisdom would have said that was the wrong thing to do.

LESSON #2: THINK IN HORIZONS SO YOU DON’T FOCUS TOO MUCH ON THE CORE BUSINESS — OR SUFFER SHINY OBJECT SYNDROME.

While there are lessons in that experience of launching a second product quickly, there was also a flip side, says Lawson. Now with two products in the product suite grabbing customer attention, Twilio set off to find their next big hit. “We launched our SMS product and it was growing really nicely. The company was 10 or 20 people at the time — still very small — and we had all of our engineers working on a new product after that. And none of our engineers were working on the SMS product, even though it was growing like a weed,” he says.

We should have said, ‘Okay, we got a hit here — we’ve got to double down, we've got to invest in it, we have to resource allocate ourselves well. But we didn't do that

Some early Twilio employees said, “Hey, we keep chasing the shiny things,” which was true. We made some mistakes in not intentionally investing more in the core product that was winning.

You need a balance of both — and a framework is helpful to ensure you keep investing in your core business, but don’t let that suck up all the resources of the company, says Lawson. “We used a number of frameworks over the years, including the horizons framework. Horizon one is the thing that makes you your dollar tomorrow, horizon two is the thing that'll make you your dollar in a year from now, and horizon three is the thing that might make you a dollar five years from now,” he says.

“So if you don't ring-fence off some amount of resources — conventional wisdom is 5-10% — into investing in the thing that you think might make you money five years from now, then you're probably running the company for too short-term of an outcome,” says Lawson.

There's no shortage of things customers need, and there’s no shortage of wisdom that says you need to invest in keeping your cash-cow core business going — you have to balance both.

LESSON #3: STRIVE FOR EXPERIMENTS, NOT BIG BETS, AND FUND THE BOATS, DESPITE WHAT THE CALENDAR SAYS.

But “the next big bet” is one phrase you won’t hear if you sit in on a meeting at Twilio. “

We don’t think about things as the next big bet, because I think that you need to have five or 10 or 20 bets

Here’s why: “In the early days of those ideas, it's really easy to get married to the next big thing and all run towards it. Instead, you need to think that there are many things that could potentially be the next great thing, but we need to run experiments to figure out if indeed customers want those things,” says Lawson.

“And so as we got more scale at Twilio, we started to think about how to run a number of those experiments at any one time. There's a certain wisdom and discipline in being able to run multiple of those experiments — to be patient and to not expect those things to become giant businesses overnight,” he says.”Treat it as a learning exercise, not yet a business exercise measured in dollars and cents.”

As founders struggle to master the juggling of multiple experiments and shifting their mindset when it comes to outcomes, it’s easy to overlook the part that comes next: what to do when it’s not a swing and a miss, but rather a base hit. In Lawson’s experience, putting more firepower behind the bets that seem to be taking off is trickier than it might sound.

“One of the common mistakes that we, and I'm sure other companies, have made is that you fully allocate your budget at the beginning of the year. You’ve got five people working on one idea, five working on another, and one of those things is just taking off. And when they ask for more resources leaders often say, ‘Well, it’s April, we do budget allocation in December, so we’ll talk to you in December.’ 

What a great way to starve an idea because of an arbitrary budget cycle on your calendar,” 

says. “You need to hold back but be prepared to invest when you see the signs of success and the idea merits that investment.”

You’ve got to send people out in different boats to explore new ideas, but when you see the signs of success, make sure you’ve got the ability to double down in real-time on the winning boat. 

LESSON #4: IF YOUR EXEC TEAM ISN’T ARGUING, YOU’RE NOT PRIORITIZING. 

 that in the early days seemed to be working just fine — but a new exec unlocked an aha moment that deeply altered how Lawson interacted with the C-Suite. “I remember at one point I hired an executive and I gave him our annual plan to review. And this executive read the plan and he said, ‘Okay, a lot of neat ideas in there. But the thing I don't understand is which of these things do we have to get done, which of these are nice to get done, which of these are just ideas? It's not clear.’ And I took that feedback and I thought about something else that had bothered me,” says Lawson.

He came back with a plan to stir up more debate within the walls of the C-Suite. “

As an executive team, we never actually argued — which is a strange thing to bother a CEO

. But in fact, something always felt not quite right to me when we always agreed. Clearly, we must not be 

 if we all agree all the time,” he says.  

“What I came to realize was that the reason why we didn't argue is we weren’t prioritizing. One person says, ‘I like idea A,’ and the other person says, ‘I like idea B,’ and you say, ‘Great, put them both down, we'll do it all!’ And in fact, when you look back on those documents at the end of the year, we rarely got around to very much of anything in those documents,” says Lawson.

He sketches out an example: “Around 2014 we decided that one of the hardest things for companies to do in this environment is hiring engineers. And so we told our R&D group, ‘You have no limits on your budget. You can hire as many engineers as you're able to actually hire and onboard,’ because we thought this was a great way to tell people that recruiting was what they really needed to focus on,” says Lawson.

But the scales quickly fell out of whack. “It turned out the team that got the most budget and the team that was de facto prioritized over everything else was the team that happened to have a hiring manager who was particularly good at hiring,” he says. 

The lesson? Be vigorous not just about what makes the list, but the specific order in which priorities fall. “We realized it’s not just about all the things we could do, but the order of importance — which is first, which is second. Now you get disagreements and a lot of vigorous, healthy debate,” he says.  

One of the phrases that comes up at Twilio quite a bit is that your budget is your priorities.

LESSON #5: METRICS ARE THE LEAST IMPORTANT PART OF YOUR ANNUAL PLAN.

With the caveat that he’s “never met a CEO who full loves their planning process,” here’s how Lawson approaches annual planning at Twilio. Each team creates what Twilio calls a BPM — which stands for big picture, priorities and measures. “The big picture is 2-3 sentences about what the team wants to accomplish in the next 5-7 years, aligned to what the leadership team has sketched out in our long-range plan. Below that are the top 5-10 priorities. What do we need to prioritize, in order, over the next 12-18 months in order to get there? And then below that are the measures. The measures just are the markers that tell us if we're making the progress we want to make towards these priorities,” he says.

And while there’s parallels to the traditional OKRs, Lawson points out a few potholes he’s keen to sidestep. “

The thing that I've noticed about OKRs is the objectives aren't prioritized in most companies. At most companies, the energy of OKRs is really around the key results

. Everybody gets very focused on the metrics. And I actually think the most important part of our BPM is not the measures, it's the priorities,” he says. 

Metrics are, in my opinion, the least important part of an annual plan because they’re not very strategic. The metrics tell us if we're on the right path. But charting the right path is actually the hard work.

LESSON #6: EVEN IF YOU’RE PRODUCT-LED, START BUILDING YOUR GO-TO-MARKET MUSCLES BEFORE YOU NEED THEM MOST. 

Between Twilio Voice and Messaging, the company had struck gold twice with what Lawson admits wasn't a particularly strong go-to-market plan. “If you listen to folks giving startup advice, they say the classic mistake that especially engineers make is they assume the thing they've built is so amazing that if you build it, they will come,” he says. “So we got away with what essentially was an anomaly twice in a row, and the company was doing very well. And then we started introducing more products and guess what? People didn't necessarily come and we didn't know what to do because we had never built that muscle.”

The company slowly started bulking up later in life, but their salesforce remained significantly smaller than what you might expect — Lawson estimates that the company went public in 2016 with just a dozen sales reps supporting around $200 million in revenue. “It was very strange, even though we didn’t know it at the time,” he admits.

“It wasn't necessarily that the developer-led go-to-market was so good, it was that we were underinvested in distribution. So that was a challenge we had to quickly fix. And we did over the subsequent years and have since successfully figured out a much better integration between a product- and developer-led motion that is the 

 of how we get into accounts, and then a sales-led motion that cements those accounts and enables us to cross-sell and upsell over time.”

But before that fix came some painful learnings, says Lawson. First, some context to set the scene: In a classic bottoms-up SaaS motion, any developer can adopt Twilio for a dollar and send text messages for pennies. But when they launch a product that's built on top of API and the product starts scaling, the total bill can grow to tens or hundreds of thousands of dollars, especially in some large B2C companies. 

“When we added a dozen quota-carrying reps, we just didn't have enough capacity to go talk to all of our customers. So 

the implicit assumption in that model was that they would just keep buying and they didn't need to talk to us

,” he says. It was a reasonable assumption — developers notoriously would probably prefer not to talk to somebody, and in fact, a lot of customers told them as much, says Lawson. But when the bill begins getting bigger, that dynamic starts to shift.

That was a lesson that “hit us in the face,” says Lawson.  “One of our largest customers was Uber, and they had grown to be a $60 million annual account for us — which is enormous for any software company, let alone one that was relatively young like we were. They were growing like a weed." Twilio was supporting that massive global growth but was disconnected from Uber’s decision-makers. 

“For the longest time, they were basically saying they didn’t need to talk to our salespeople, that the developers were really happy,” says Lawson. “We didn't really have a mature relationship with them. I'll put this into perspective — the rep who was assigned to Uber also had I think 50-60 other accounts. So that rep would go visit Uber maybe once a year for a customer that is paying $60 million annually.”

 may have seemed remarkable at the time, it would introduce plenty of headaches later. “Meanwhile, Uber’s mandate became more about efficiency — and suddenly their priorities became ‘How do we save money?’ as opposed to ‘How do we get into a new country?’” As a result, in just its third quarter as a public company, Twilio had to disclose to investors that Uber was intending to use multiple vendors, not just Twilio, for the same service. 

The learning for Lawson? “That wasn’t the right way to approach that account. We accepted it too easily. We were trying, of course, but it was still a relatively laissez-faire attitude. Even if the customer thinks they're fine, it's in our interest and their interest to make sure we've got a mature relationship, that we know what they're thinking and we know what their needs are,” he says. 

“Because we could have easily addressed those problems. We could have become more focused on cost for them, but we didn’t allocate enough bandwidth to be able to hear it nor were we reaching into the right levels of the company for those people to say, ‘Actually, we've got a new priority. Can you help us with this?’ And so that was the big wake-up call for us that somehow we had misallocated the resources of the company to truly support our customers and to do it at scale.”

The company went through the process to right-size the go-to-market machine — starting gradually with upping to 50 sales reps. “The interesting thing about our business model is even though we have really grown our distribution capabilities in the last several years, it hasn't fundamentally changed the economics of our business. Our developer-led go-to-market is still extraordinarily efficient. Last quarter we only spent 23% of sales on sales and marketing to grow the company at more than 50% at $2 billion in ARR,” says Lawson. 

“What we've come to realize is that with a platform and a developer-first product and go-to-market, really the key is building certain products that we know are going to be developer-led, developer-adopted, developer-bought and maybe that's it — maybe that's the whole go-to-market of that product. There are products that may not merit sales, and are more self-serve, easy to use, like infrastructure APIs,” says Lawson.

“But if you're going to get to meaningful revenue with a customer, that's when you need to actually build a mature B2B relationship with the company. And so knowing the full lifecycle of how your product gets adopted, how it gets used, and then who the various stakeholders are as you become more and more strategically important to the customer is key.”

If you've got a large product set as we do, knowing the difference between the products and how they’ll be brought to market — and not treating them all the same — is a key part of the playbook.

LESSON #7: LEAN ON POST-MORTEMS WHEN THINGS GO WELL — NOT JUST WHEN YOU’RE THROWN OFF COURSE.

When lessons are learned the hard way, it’s a good time for introspection and team-wide reflection to fully capture what went wrong. “I talk a lot about this actually in 

 — obviously a lot engineering-minded folks are accustomed to this notion of the ‘five whys’ of blameless post-mortems. If the site has an outage, 

you don't blame the person who wrote the bug

 and deployed it to prod. Instead you ask the question, ‘How do we let a single mistake by a single human being actually take down our website?’” he says.

“And instead of blaming that person for being a human being, you blame the system and you get to the true root cause. The root cause may be the lack of testing. You might ask, ‘Why don't we have testing?’ Well, we don't educate developers on how to write good testing. Or maybe we don't have a good investment in infrastructure to do testing. And when you get to the true root cause, then you can make systemic change,” he says. “When we had that Uber situation, for example, we did a blameless post-mortem and got to the true root cause.”

Lawson’s seen plenty of companies leave post-mortems behind when every piece falls into place — but he’s a big believer in flexing these same muscles, even when things go well. “

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,” he says. 

There are good decisions that net good outcomes and bad decisions that still net good outcomes. People make bad decisions all the time and the results of those decisions are not immediately obvious. So you have to look at the outcomes that you get and not purely ascribe them to the great decisions you've made.

 is our annual customer event and afterwards the whole company is exhausted. But the next day, when we all really want to sleep in, we do one thing — a recap where we capture what we 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,” he says. 

With “worked, not worked,” documented for posterity, it’s a valuable resource to return to again and again. “When we start working on the next year’s conference, we can pull out the ‘worked, not worked’ and we've already documented the outcomes we liked, the outcomes we didn't like, and some of the decisions that went into that. By doing that every year, you just get a little bit better,” says Lawson. 

This approach is perhaps best summarized by one of Twilio’s favorite mottos, which comes from Chief Product Officer 

Every day, our goal is to suck a little bit less

. "It expresses this idea that it’s okay that everything’s not perfect and we suck at certain things, but if we just suck a little bit less every day, then we’re building a stronger company as a result."

This article is a lightly-edited summary of Jeff Lawson’s appearance on our new podcast, "In Depth." If you haven't listened to our show yet, 

. Cover photo by iStock / Getty Images / Jokic.

Series of building blocks with upward and downward arrows

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