a leadership role, the people who thrive are those who bring curiosity to their own strengths and weaknesses and the strengths and weaknesses of the individuals around them.”
NO ONE IS TRULY QUALIFIED TO BE A STARTUP EXECUTIVE BEFORE THEY'VE DONE IT BEFORE
Another crucial point to let sink in: no one is fully qualified to be a startup executive until they've done it, because there are skills and job requirements you can't master until you've encountered them. This is true whether you're a “big company” person learning to map your skills to the startup arena or a mid‐level manager or director aiming to “scale up” to mature with the business.
Unfortunately, in the past, many members of the dominant group in the startup industry have found a way around this fact by being promoted based on potential, which often translates to “looks like the guy who had the job previously.” According to Kim Scott, executive coach and author of the bestselling business books Radical Candor and Just Work, “Men are more likely to be rewarded for perceived potential, whereas women get promoted purely based on past performance.”3
So how do we help a broader group of people translate the skills and qualifications they have into a startup leadership role? We need to remove the bias of “qualification by association” and break the role down into objective, essential requirements.
WHAT QUALIFICATIONS AND SKILLS ARE ESSENTIAL ON THE JOB AS A STARTUP LEADER
Due to systemic and internalized bias, many qualified people never go for leadership roles in a startup, even if they want them. About ten years into my startup career, I noticed that many startup leaders had backgrounds that looked comparable to mine on paper before going for the executive role. I wondered what their resumes were missing that made them qualified.
It turned out that these individuals were not necessarily more qualified. Once in the roles, they'd learned the skills of the role, which was something I (and many others) were perfectly capable of doing too. If you're comparing your resume to someone else's, you may not see the work they've done or the mentorship they've received outside of their official roles. And, truth be told, many startup executives get their first “shot” based on perceived potential and learn the skills they need on the job. So let's unpack the skills and backgrounds that are necessary to become an effective startup leader.
Here's what you do need to make the leap from mid‐level contributor to startup leader:
Valuable and measurable expertise and track record of success in a key startup functional area (e.g., engineering, marketing, product, sales, customer success, operations).
Some experience in management. If you're a first‐time startup executive and first‐time manager, it will be much harder.
Willingness to learn how to work with financial shareholders. Until you've done a board meeting (we'll talk about how to prepare for these), you won't know what it's really like.
Willingness to learn how to communicate effectively at scale, with multiple stakeholders. Make great slides and write clearly and persuasively.
Be data‐driven. All startups require data to inform their decisions, and today's startup executives are expected to develop data literacy.
Willingness to fail and improve. Startups are built around learning and iterating. You'll need to do this constantly in your role to see which areas of yours are underperforming and need adjustment, using data (see above).
The key element in all of the above is a willingness to learn. If you want to be a startup leader, don't fret if you don't have all of the skills and experience at this very moment in time, because, in reality, no one does before doing the job. You can do it and learn along the way. (We'll talk about the “how” for addressing skill gaps in the next chapters.)
The phrase “growth mindset” coined by Carol Dweck is a Silicon Valley favorite for a reason; it's crucial for people at any role in a startup to learn, adapt, and grow, but the executive especially must grow their abilities as their startup grows.
Empactr co‐founder and CEO Chris Senesi says the key skill he looks for in startup leaders is that they, above all, are initiators.
“I like when an individual is passionate about something and they champion it,” said Senesi. “Taking initiative and ownership in an area builds trust. Leaders then get to create something new and show their skills and expertise. You don't have to be a startup founder to initiate.”
This leads to the next big takeaway for “essential skills and experience” in startup leaders: prior “big‐company” or other scaling startup expertise.
MANY SCALING STARTUPS BRING IN LEADERS FROM BIG COMPANIES
As they mature, it's common for startups to bring in leaders from big companies who've proven they've owned a function or profit and loss statement (P&L) successfully before. Once startups get out of what investor and Harvard Business School professor Jeff Bussgang refers to as “the Jungle” stage of startup growth, they're often compelled by the board to bring in “adults” (the phrase makes me cringe, but it's common parlance) who can steer the ship as trained specialists.
In some ways, it's a catch‐22; often you can't get the startup leadership job until you've proven you can do it, and you can't prove you can do it until you've done it. Where does that leave the contributors who've been mid‐level managers at multiple startups, with valuable expertise, but not necessarily that full executive title?
We'll talk about how to make that transition if you don't bring that “experienced big‐company person” background to your startup leadership journey. For now, let's focus on the startup executive who is a serial “big company” person from a larger organization. If you're coming from a larger company, you may have the expertise your startup needs but will have to learn to adapt to a high‐growth environment.
EXECUTIVE COACH AND FORMER MICROSOFT NORTH AMERICA CFO JOHN REX: ADVICE FOR SCALING STARTUP LEADERS
Executive coach John Rex was a CFO at Microsoft prior to transitioning to a startup and now coaches leaders of all company sizes. He notes that it's a common challenge for scaling startups to help their “big company” leaders adapt and thrive.
“Many people are ideally suited, not to thrive and do a great job at a startup, but a big company,” says Rex.
In large companies, you're incentivized to hone skills primarily around decision‐making without much execution, often in markets that are already established.
“The skill that you really develop is how to decide what's important because there's so much information flowing toward you, so many requests for your time,” says Rex. “You get really good at sifting through large volumes of incoming information. That isn't your remit at a startup that's disrupting a new market,” says Rex.
Leaders coming from larger companies can underestimate the impact of having less structure and fewer resources, which was something Rex himself struggled with coming from Microsoft to a smaller startup.
“I really didn't appreciate the magnitude of how different those cultures are,” says Rex. “For founders I coach, I now tell them, you want to be super careful when you
