The CEO of a startup I worked for as a Product Manager asked me for one last contribution in the last week of my job: a write-up on how to make the team a high-performance one.
For privacy’s sake I won’t get too much into the specifics of this company’s situation, but the gist of it is that they’re a SaaS company that’s been around for several years, dominated their market, and growing steadily, but not innovating. If you’ve seen a few SaaS companies, you know the type: a product that has no competition, whose dominance is cemented by the relationships they have with customers, with customer success and engineering efforts alike devoted to making existing and potential customers happy without higher ambitions.
The CEO and their co-founders, who had launched the startup in college, know what it’s like to be ambitious, fast-moving founders. For all their success, they also know that their team has lost this ambition, their “hunger” as the CEO put it. And, try as they might to introduce new initiatives and activities, they struggle to bring the hunger back.
Joining the team as one of four engineers and the sole designer (under the title of Product Manager), I redesigned the homepage, navigation, and other key product areas. I ushered in modern React development patterns like functional components. I joined leadership meetings and set the company’s 2021 Q1 OKRs. I brought the hunger to build and improve that the CEO so missed. Unfortunately for him, I found the environment unstimulating and quit my job after four months.
After receiving my last work order, I reflected on what this “hunger” really was, and how a founder could create a culture around it. In this post, I’ll share the framework that I created, and some personal leadership examples to illustrate it.
Execution Is Key
I’ll start with a favorite quote of mine:
The success of a startup is determined by the founder’s ability to execute.1
Execution is everything, I frequently remind myself. Idea, problem, experience, and naysayers all pale in comparison to a founder’s willpower to simply get things done.
Ability to execute is easy to recognize when you see it, illustrated by a demonstrated record of success. But what actually is it? Arguably one can be very good at executing on certain things, or even whatever they set their mind to, but still very bad at innovating or leading an ambitious team. So what gives? How can we further break down this concept of execution?
Velocity and Acceleration
There are two kinds of execution: velocity-based and acceleration-based.
Velocity-based execution is the process of reaching a set objective, overcoming all obstacles and uncertainty in the way. Think of engineers who can build any feature or fix any bug, companies who continue to grow through depressions and pandemics, or even pilots who crash-land crippled planes. This is what we typically think of when we talk about ability to execute. It’s obviously crucial to getting anything, especially hard and innovate things, done.
Acceleration-based execution, though, is where the “hunger” comes from. If velocity-based execution is the process of hitting a set objective, acceleration-based execution is the process of breaking free of set objectives and imagining new ones. Acceleration-based execution drives a team not just forwards, but upwards to higher levels. Acceleration-based execution happens when a founder first comes up with a disruptive idea and sets about turning it into an impactful startup, or when a team member comes up with a new initiative that alters the direction of the project.
Acceleration Is Separate From Velocity
Going against the physics of this analogy, acceleration-based execution is initially useful to think of not as a derivative of velocity-based execution, but a process that runs separately and in parallel.
Commercial pilots, for example, are incredibly good at flying airliners, complex systems that require continuous on-the-fly problem-solving and decision-making to operate. Even when things go terribly wrong, as in an engine fire or cabin decompression, pilots are tasked with bringing their passengers as safely as possible to the ground. These pilots are incredible velocity-based executors, yet they’re not doing anything to push forward the standards of aviation or transportation. On the other hand, engineers at Boeing or Airbus don’t have nearly the real-time execution ability of pilots. Instead, they operate in the realm of imagination, finding new problems to tackle as acceleration-based executors.
Neither form of execution is harder or superior to the other. Each is a different mode of operation, requiring their own mindsets and skills.
Ultimately, however, acceleration-based execution only matters if it enters the realm of velocity-based execution. Engineers’ designs must become planes for pilots to fly. Product ideas must go through painstaking coding and selling to become real products. Innovative visions must lead to concrete execution to create an impact.
A Case Study: The Phillipian
The best illustrations I have for this framework come from the year I served as Executive Digital Editor of Andover’s student newspaper, The Phillipian.
For context, The Phillipian is not your average student paper. It’s America’s oldest high school newspaper at 142 years old. It’s financially and editorially independent, with an endowment of several hundred thousand dollars and an annual $20K operating budget. It’s been sued by Andover’s Board of Trustees, and won.
As EDE, I was part of the six-person Upper Management that oversaw our 85-student board and ~100 writers and staff. Every week, we publish a 16–20 page paper, with 60–80 stories across five sections. Each story is written by a writer, edited by the corresponding section editor, edited by a member of Upper Management, edited by a Copy editor, and placed into the paper by Layout staff.
Maintaining this output at high journalistic standards requires relentless execution at all levels. New stories present new circumstances each week, requiring new applications of leadership and problem-solving. No matter what new challenges present themselves or what parts of the process fall through, someone has to pick up the slack to ensure that high quality reporting on the stories that matter are in the paper on Friday.
For all this execution, though, no real innovation is happening. The objectives being pursued are static, the standards set. This is the nature of velocity-based execution.
My mission as EDE, on the other hand, was one of change: transform the paper to a digital-first publication.2 Among other things, I pushed for the creation of a new section, a live broadcast news show called Phillipian Live. I designed the studio, new publishing workflows, new board and staff structure. Velocity-based execution was a side task: I would occassionaly weigh in on an editorial decision or help with the print paper, but for the first half of my tenure, most of my work was separate from the weekly grind. I worked not to pursue existing objectives, but to set new ones. This is the nature of acceleration-based execution.
I finished the core prep for Phillipian Live and recruited the founding team in the spring. When fall arrived, Live was no longer an abstract vision, but a set one that I was leading a team to pursue. I now put all my leadership energy towards the same kind of work my print-based colleagues did: make sure reporters make high-quality segments each week, make sure the show goes live every Friday, no matter what equipment failures, challenging stories, or staff shortcomings occur. The acceleration-based initiaitve of Live had successfully led to concrete velocity-based execution.
Interestingly, when I switched my own leadership over to velocity-based execution, some members of my staff, viewing the objectives I set as static, began their own acceleration-based initiatives. One reporter, for example, pushed to create pre-edited segments rather than completely live ones. Others were continuously suggesting small improvements: changes to our schedule, equipment, or style.
At an individual level, acceleration-based execution is something to train, just like velocity-based execution. I consider myself an especially strong acceleration-based executor, which I attribute to the influence of my parents and other experiences I’ve had.
The conditions for acceleration/innovation at a team level, though, are less straightforward. Why did I enjoy being a changemaker at The Phillipian so much, but not the startup I quit working at? How was Phillipian Live, under my leadership, an environment where my staff constantly pushed for innovation, but my CEO’s team one that lacked this “hunger”?
Creating a Culture of Innovation: Appeal to First Principles and Reject the Status Quo
The most important thing to understand about innovation is that it is fundamentally a break from the status quo. Innovation does not come as a result of good overall execution: intuitively, there’s often more innovation in flawed areas than excellent ones, and as discussed previously, acceleration-based execution requires completely different mindsets and skills compared to velocity-based ones.
As a corollary, the biggest bottleneck to innovation I’ve seen in otherwise well-functioning teams is that they hang on to the status quo too tightly. They view their current objectives as fixed and immovable, basing their decisions on historical precedent rather than original thinking.
At the startup I worked for, the CEO often appealed to the company’s history and promise: “I talked to some investors today, who shared yada yada, which just shows how much we’ve been on the right track!” When new opportunities or innovative initiatives came, they again centered the company and its existing vision: “This makes perfect sense given X existing project!”
These comments, and this kind of thinking, seems innocuous at first. It boosts morale, and what’s wrong with appealing to the company’s previous successes? With my framework of innovation in mind, though, it’s revealed that these comments are actually exactly the stifler of innovation at said company. Through these comments, the CEO creates and continuously reinforces a culture where accumulated knowledge is king, the source from which growth is expected to be derived. Culture is built through action and example, and the CEO’s comments lead team members to think about the company and their own decisions in terms of company knowledge rather than their own creativity.
Parts of The Phillipian are also afflicted by this bottleneck. News writers and editors appeal to a standard “inverted triangle” structure of lede => body => tail, which is effective for pumping out relatively good stories, but leaves little room for creativity or improvement. Analysis of the decisions and projects of past boards precluded new design and experimentation.
The solution to this bottleneck is to strip away reliance on the status quo and instead appeal to the underlying first principles. As Executive Digital Editor, I was free of the literal century of precedent resting on my colleagues’ shoulders. I had only the mission of the paper to work with: serve our readership, our staff, and our community, holding ourselves to the highest ethics and standards of journalism. From these underlying principles, there are endless directions for improvement. I spearheaded a digital-first transformation in pursuit of its various benefits, but my colleagues created new issues of the paper and instituted new workflows for training writers and writing editorials.
Appeal to first principles don’t just happen in the absence of precedent, but are even more important when in-the-moment execution is crucial. Once Phillipian Live started up, making use of templatized segment and show structures was crucial to keeping it going. Editors outside of the section raised constant pushback and proposed direction changes: this is the nature of a precedent vacuum, so it was vital for us to build up a strong and somewhat arbitrary foundation to defend our existing vision.
Yet, with every precedent that I set, I made sure to emphasize the underlying reasons and principles. Segments need to be at least five minutes long because they need to be newsworthy and substantitve, not slip into the silly reaction videos that predated Live. Reporting needs to be live so reporters feel a greater sense of ownership over their work, rather than video editors having the final say in what makes it on air. With the underlying reasoning in mind, even when my decisions become relatively unquestioned tradition, conversation and leadership from my staff is vibrant and improvements continue to be suggested and implemented.
Since coming up with this framework, I’ve noticed that emphasis on first principles is a defining characteristic of my leadership style. In November, I started a series of speaking events called TKS Community Talks. Hosting the first round nearly alone, proving my vision to most community members who doubted the talks’ value, I made a lot of initial decisions that now operate as precedents for the team working around me. When appealing to these precedents, though, I always make sure to share the underlying reason. More than any specific detail, I appeal to the three key objectives of the talks: 1) improve participants’ speaking skills, 2) facilitate knowledge sharing in the community, and 3) strengthen the TKS community. Even though precedents are plentiful and heavily used for the second round, my emphasis on the underlying principles empower my teammates to imagine specific objectives other than the ones I set, driving continuous improvement and innovation.
Emphasis on underlying principles can be as simple as prioritizing a single metric. “The company does what the CEO measures,” former YC president Sam Altman writes in his playbook. “The founders of Airbnb drew a forward-looking graph of the growth they wanted to hit. They posted this everywhere — on their fridge, above their desks, on their bathroom mirror. If they hit the number that week, great. If not, it was all they talked about.” This hyper-focused discussion is much more likely to inspire creativity and innovation than sprawling appeals to higher-order stories and ideas.
Execution (velocity-based execution) and innovation (acceleration-based execution) are fundamentally separate processes. Execution moves a company closer to a set objective, strengthening the status quo, while innovation rejects existing objectives in favor of new ones, disrupting the status quo. Innovation is successful when the innovative initiative becomes the status quo to execute on. A culture of innovation can be built by de-emphasizing accumulated higher-order knowledge and instead prioritizing first principles thinking, such as a set of fundamental objectives or a single key metric.
Originally published on my blog on January 19, 2021