What I learned from my first three years as an executive
Only the juiciest stuff. You'll have to wait for a second post to hear about "baby's first re-org."
There’s an apocryphal Mark Twain quote that goes something like, “When I was 17, my father was so stupid, I didn't want to be seen with him in public. When I was 24, I was amazed at how much the old man had learned in just 7 years.”
When I was a mere 21 year old IC at a tech company, I thought the executives in charge were clueless and got most things wrong. Now, many years and my own management experience under my belt, I realize the level of my naiveté.
I’ve now been an “executive” for about three years across a couple of companies. The “natural” part of work for me was always the product and design sense — I’m not a natural at being a leader, and had to learn every lesson painfully. Here’s five of the most surprising things I learned as I scaled.
Give up getting an “A” on your work, you’re an executive generalist
I started my career as a generalist, and then realized that I’d need to deeply specialize in order to do what I wanted to do. I went from “business operations generalist” to “PM who specializes in B2B low touch products” in six years.
But when I became an exec, one of the most surprising things for me was that I’d have to care about the detailed mechanics of unrelated functional domains more than I ever had before. For example, I had to get really deep on sales. My experience as a PM was jumping into deals when necessary, or selling a couple deals to get the business up and running. But as an executive, I was looking at sales hiring plans and territory divisions on a regular basis. I was jumping into deals every week. This was so surprising to me.
I was back to doing the range of projects I hadn’t done since my earliest days as a “business operations person.” I was writing levels and ladders, thinking about compensation policy, reviewing company wide all-hands slides every week, and diving into the nuances of MQL data anomalies. I was bad at many of these things at first — getting back into the cadence of an enterprise sales deal was challenging. Nevertheless, I never had the time and the focus to polish my skills to perfection, the way I had in my prior role. I couldn’t get an A on anything. I was taking most of my tasks pass/fail, and moving on as soon as I got a pass.
Your greatest value as a good executive is that breadth. It doesn’t excuse you from diving into details – you should still “sample the details to incredible depth” from your teams on occasion, just to keep them on their toes – but you’re much more valuable with the global context than if you deep-dove on only one thing.
My sisters are doctors: their careers look like a triangle, where they get more and more specific over time until their expertise sharpens to a point. My career will look more like an hourglass, with my skills widening back to where they started, just on a higher level.
Don’t overfit your past experience.
Startups mess up by focusing on the wrong things: they focus on execution when they should be thinking hard about strategy, they focus on “scaling” when they should be focused on core product, they focus on core product when they should be focused on technical foundations. I’d argue that the misplaced focus is the result of using the wrong tactics for their stage.
This is very reductive, but there are three stages for startups:
Pre-clear product/PMF. At this stage, vision, clarity, and rigor are important. You’re trying to decide what your strategy should be, and thinking through it carefully matters.
Ex: Segment was very thoughtful on their journey to product market fit — thinking through their user needs, talking to their users, determining their wedge.
Post-clear PMF: When you have PMF with v1, the most important thing actually does become speed: you should be just doing a bunch of things to satisfy users quickly on top of that core vision. The things to do are obvious to the teams: you should find any/all user pain points, stack rank them, and solve them.
Ex: Notion had initial product market fit, but didn’t fix all of the small things fast enough. They didn’t move between “measured strategy” and “go fix things” quickly enough, and everyone complained about the app being slow. They’ve rectified this since!
Building Product #2/V2: You end up having to tack back to a clear direction (otherwise you don’t advance beyond that initial successful product)
Ex: Figma was able to build FigJam/Slides by going back to the strategy well. They had to do two things at once: execute on the core with a deep performance/detail orientation, and build new products with thoughtful strategy.
Execs are the biggest culprits of driving this mismatch. Execs (and even experienced founders) have a Successful Past, and so are likely to bring over their most-recently-applied past job tactics into their new job. But if they’re bringing in the wrong tactics for the stage, it will become more destructive than helpful.
Teams love decisions and love certainty, and the temptation to make a quick decision patterned off your past experience is irresistable at times. But great leaders are thoughtful about the match between the stage of the company, the problem, and the right solution. They don’t pattern match to their last company.
Speak the way they listen
I once gave feedback to a report that just didn’t seem to land: she didn’t grok what I was saying, she thought I was being unfair, and she didn’t understand how it could be actionable. When my boss heard about the situation, he told me that I was delivering the feedback the way I would hear it: too softly. “You mean, I’m not speaking loud enough?” I asked. He shook his head. “You hear feedback very softly – you find feedback in the smallest hints of a comment. But other people don’t. The feedback isn’t being delivered in the way this person will hear it. Say it more directly. It should feel uncomfortably blunt to you.” He was totally right.
I repeat that to myself quite often when I’m delivering feedback, but have started to think about it while hearing it. I am a sensitive listener to feedback, and spend a bit too much time on the psychology and intent of the giver when the feedback feels harsh. But…they just might be loud.
The executive team complementarity matters more than their individual quality.
I was somewhat miffed to realize that a core part of my job was to make friends with the other exec team members. It seemed awfully juvenile, but not that difficult. I am good at forming tight, genuine bonds with a small group of people. I love my colleagues.
The utility of doing this is obvious: you’ll need to ally on important issues to drive the group’s decision making, you’ll need to navigate your reports’ disagreements, you’ll need to use your mutual experience to override the founders’ incorrect intuitions about the way the business should be run. You’ll need to develop shared mental models and skills to overlap on important issues, but be comfortable enough with them to disagree freely when needed.
But I had a hard time doing it in practice. I think it’s way harder than it might seem. If there isn’t an “exec team” structure (Stripe’s PBJCW was an example – they were so explicitly the ruling body and spent more time with each other than their teams), execs like me should make one (that’s why they hired you!)
I didn’t do it successfully, and it had a price. The lack of cohesion led to right-hand-left-hand dynamics in the business and priority scuffles happened at every level of the organization. It ended up happening that the exec team, and then the entire company felt like it was always less than the sum of its parts.
In retrospect, I think you have to create an executive team culture that is stronger than their allegiance to their functional team. It has to be a primary founder priority. On top of that, executives have to bond. As an exec, you can solve this problem in three ways:
“Fraternity Style:” Make your heterogenous executive team invest the time in developing shared understanding. Go bowling. Go on retreats. Have a lot of 1:1s. This is in your control as an exec.
“Jesus and the Apostles Style”: Have a strong CEO share a powerful mental model that unites everyone under the beliefs of the CEO. You can help make this happen (write the “gospels” and distribute them!)
“Captain Planet Style”: Explicitly filter for complementarity when hiring, so that the team comes in with the right balance and shared mental models from the start.
Morale is another form of runway
Your metrics aren’t always going to go up and to the right — every startup goes through hard times, even the best ones. In those cases, you use your dollars in the bank as a way to buy time as you figure it out. The other asset in the bank is your team’s morale. You’ve cultivated morale in good times to spend in the hard times, so that your team can stay together long enough to withstand periods of uncertainty and challenges.
I thought about morale fairly intentionally while I was leading teams within Stripe. My view was that morale comes from outcomes: velocity is the best generator of morale, the team will be happy if we make progress and win. I viewed “losing” as a very temporary state. When my teams were losing, all I cared about was getting on the right path. As a result, I didn’t like what I called “false morale” – efforts to rally the team that were orthogonal from actually making the business work. Whenever I had attempted it in the past (on my own failed startups, in others’ failed startups!) I associated it with being actively destructive by distracting team members from winning or obfuscating the truth.
But there’s a good way of going about cultivating morale during hard times. Cultivating a culture that is positive and non-reactive in a time of crisis is an incredibly worthy investment. The morale can honestly come from other colleagues, from the mission, from the interestingness of the technology, or even the degree of challenge. It doesn’t have to directly drive the business, but it should feel sincere. Dishonest or trivial means are rarely that successful – sugarcoating metrics, having a company soccer team, fancy snacks, famous speakers in the office – because they’re so ephemeral.
The most important thing I learned as an exec is actually something Dee Hock, the founder of Visa, once wrote: the greatest management challenge is management of the self. Your emotions are the hardest thing to regulate as a leader. The job is lonely, you don’t really have many peers, you might not be in love with the founders or the domain, investors are harsh, people will constantly disappoint you, the product isn’t at the quality bar…the list goes on.
At Stripe, I was so emotionally tied to my products, the founders, and my team. My heart would break when I saw issues. I eventually learned how to manage my feelings and channel them the right way. It became my superpower — when I ask folks from my past work for my strengths, they almost always mention sincerity and “really, really caring.” But at Watershed, I had the opposite problem. I sometimes found it hard to be emotional enough.
One of the most helpful ways to manage my emotions was unlocked by my friend E. “Being an executive is being in an arranged marriage,” she said. I know arranged marriages really well, as my parents have been in an arranged marriage since 1991. Like execs looking at a job, they got into the marriage because it ticked a bunch of specific boxes. But “falling in love” had to happen after the moment commitment. My parents are very much in love, but that was an active choice. It’s still an active choice they make every day.
The failure mode of an arranged marriage, of course, is to not fall in love. And the same applies in an executive role where just doing your job and delivering results for your job description isn’t enough. You need that alchemical element of “love” to be great. You can usually inculcate that feeling by loving either the 1) why — “I love this company because I love the mission” or the 2) how — “I love scaling a team, I love this sort of product, I am born for this phase of growth.”1
If you can’t fall in love with the mission or the tactical day to day, it’s not going to work. At Watershed, the challenge was to fall in love with the “sales driven product development”, which was very different from the thing I had previously loved, the Stripe world of “prosumer” individual developers and product-driven sales. It’s possible to convince yourself that your preferences have changed, but it’s extremely difficult to do. It’s all about managing your expectations and emotions — can you make this work? Can you try your best to fall in love? And if not, it’s really hard to limp along in your role. More often than not, it’s time for a divorce.2
It is important to note that loving the who (“I love my team and my colleagues”) is NOT a way to inculcate love for the company. As an executive, when people’s individual interests and the company’s interests are at cross-purposes, you have to make the company-optimal decision. A great executive almost feels like they’re a founder ex officio — they act like a founder and optimize for the company like a founder might, even if they’re not one!
This is, of course, also a big downside of arranged marriages — there should probably be more divorces than there are.
I loved your points around executive team complementarity mattering more than their individual quality, Tara! Thanks for sharing this