Lead Upwards. Sarah E. Brown
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executives because they just don't know what they don't know. They are used to being very successful but it's in a particular context of success. What is required for success in a startup environment is very different from what's required for success in a large corporation.”
“At a big company, I spent most of my time in email and meetings because that's how I processed the vast amount of information that flowed toward me. At a startup, I had to return to practicing skills that I had come to delegate to more junior people in my corporate days,” says Rex.
Leveling down isn't about lack of willingness or a “holier than thou” attitude. Rather, many big company leaders just haven't done it for a long time.
SCALING IS HARD IN BOTH DIRECTIONS
The reason why so many seasoned leaders are brought in as a startup matures is that scalability is hard in both directions. If you've never been a leader at a mature organization, it's a learning curve to get out of the day‐to‐day tactical operations. Many startup leaders struggle with this. (We'll discuss some very practical tips for addressing it.)
Early‐stage startup people develop a skill set that is heavily tactical and geared towards “firefighting.” This involves building functions from scratch and implementing basic processes as well as blocking and tackling, dealing with crises, unexpected challenges, and more.
LEARN TO DELEGATE WITH CAPABLE TALENT AS YOU SCALE
In addition to learning how to delegate, startup leaders need to accurately assess the talent and experience of their teams to understand whether the people they hire have what it takes to mature with the company. The more capable your team, the more you can delegate to them. If they are less capable, you will do more yourself. If you don't have people capable enough, then you're perpetually caught doing everything yourself. Many people burn out due to this (including founders who haven't brought in scalable leaders). You need a team you can truly rely on to do the work now and also help the company grow.
The more successful a leader becomes, the more they need to learn to get things done through others. Leaders can't continue to do everything themselves because that doesn't scale. You have to delegate work to your team.
Just as it's hard for an executive coming from a big company to scale down and do the tactical work, it is difficult for people from startup backgrounds to scale up because they're used to executing and being the ones to solve something. It doesn't come naturally to those of us used to the dopamine rush of being firefighters or those early doers, but it's essential to learn this skill to scale your team and your department's impact alongside you.
EARLY‐STAGE STARTUP VS. SCALE‐UP LEADERSHIP MINDSET
Executive coach and author Gerry Valentine says he often coaches startup leaders from big companies on shifting their mentality and mindset to become comfortable with disruption. Disruption is generally discouraged in those environments but is crucial at startups.
“In big corporations, you are paid specifically not to break things. If you're working for an American Express and you break something, the stock price might shift. You might make the cover of the Wall Street Journal. That's really bad,” says Valentine.
Startup leaders aren't necessarily paid for moving fast and breaking things (a phrase coined in the early days of Facebook), but they are expected to experiment and iterate to drive success.
“In the early days, you're there to learn so your startup can grow faster,” says Valentine. “The mistake I've seen leaders make coming from startups that are scaling up is that they fall in love with disruptive creativity. This matters in early stages, but not in the same way later on.”
STARTUP LEADERS CAN'T GET STUCK AT 30,000 FEET
“We have all seen the leaders who are at 30,000 feet and they're not aware of what's really happening,” says Gainsight CEO Nick Mehta. “I think some people misunderstand that being an executive means we know even more of the details.”
At Apple, every leader is expected to know everything about Apple.4 As a startup executive, you need to understand the details and not lose sight of them while also holding the bigger picture. Being both a tactical, hands‐on builder when necessary and a strategic leader who can empower their team to deliver the next stage of growth is an unbeatable competitive advantage, and in the following chapters we're going to discover how you can make it yours.
NOTES
1 1. Azoulay, P., Jones, B. F., Miranda, J., and Kim, J. D. K. (2021, January 20). “Research: The Average Age of a Successful Startup Founder is 45,” Harvard Business Review. Retrieved November 4, 2021, from: https://hbr.org/2018/07/research-the-average-age-of-a-successful-startup-founder-is-45.
2 2. “Why Women Don't Apply for Jobs Unless They're 100% Qualified,” Harvard Business Review (2021, November 2). Retrieved November 6, 2021, from: https://hbr.org/2014/08/why-women-dont-apply-for-jobs-unless-theyre-100-qualified.
3 3. Scott, K. I. M. (2021). Just Work: Get Sh*t Done, Fast and Fair. Essay, Macmillan, p. 195.
4 4. “How Apple Is Organized for Innovation,” Harvard Business Review (2021, August 27). Retrieved November 6, 2021, from: https://hbr.org/2020/11/how-apple-is-organized-for-innovation.
CHAPTER TWO Bridging the Transition from Manager to Executive: How Leaders Got Their First Role
If you want to be a startup executive, there are several skill and experience gaps you'll likely need to address to make the transition. Here's how some successful startup leaders did it.
The skills and experience gaps you'll need to address to transition to an executive are within your reach. To be a strategic leader who can scale, you'll need to operate differently from how you did in prior roles. In this chapter, we'll discuss how leaders landed their first startup roles and how they successfully bridged the transition.
MAKING THE LEADERSHIP TRANSITION: YOU DON'T HAVE TO BE “FULLY READY” TO GO FOR IT
“I think we have this story that we need to wait to be knighted with a K to be in leadership,” says VC and executive coach Sue Heilbronner. “Instead, just go identify an objective and start working towards it until you're doing it. Deciding to do leadership is that simple.”
HOW THEY GOT THEIR FIRST EXECUTIVE ROLE: REAL STORIES FROM STARTUP EXECUTIVES
Rachel Beisel spent years as a marketing manager in the outdoor industry before pivoting to technology marketing, eventually becoming promoted from Director to VP at her company (she's since become a C‐level executive at another technology company). She credits the help of a mentor in making the leap, including learning how to navigate the startup environment and become an executive.
Samantha McKenna is an accomplished sales leader, former VP of Sales at LinkedIn and On24, and now runs a consulting firm called Sam Sales. In her first executive role, she was promoted from within her organization. She said one of the challenges to making the leap from individual sales contributor to sales executive was, ironically, her high performance as a rep.
“In many organizations