Last week I met with an old colleague of mine who was one of the more talented people I've worked with in my career. They left Fundera as we were scaling (and went on to accomplish great things) because I was going to hire someone above them. We started working together when they were still in college and they did pretty much everything to help us get off the ground and reach product-market fit: operations, marketing, product, etc. They were a true high-potential generalist who was good at anything and everything they needed to do - likely better than even some of the best specialists in those functions. I think about them leaving as one of my biggest leadership mistakes and hardest lessons learned.
There is a lot of literature out there about how founders should always bet on their up-and-coming talent. It’s a common refrain, but we seem to regularly screw this up. We think it’s a safe move to hire the pedigreed external executive. Advisors and boards will push for it even if they don’t personally know the talent on your team. Everyone, not just founders, is predisposed to go after the “silver bullet” I’ve written about before. I think it’s important for founders to recognize this shortcoming - that our natural inclination is to wishfully believe someone out there can do magic for our company. But it's also advantageous to young and talented employees if they can recognize and expect this flaw in their founders, and I’ve been thinking about what a hungry, high-potential person can do to make it clear as day that a founder should be betting on them with more responsibility and not a trophy external hire.
This may seem like a preposterous concept. Why should it be on the employee to help a founder recognize their talent? Shouldn’t good founders always know who is good and deserves to take on more responsibility? The sooner people realize that founders are massively flawed, are largely making things up as they go along, and have a real learning curve when it comes to how to nurture and manage talent, the better - you can use that to your advantage. If you can practice a delicate mix of patience, humility, honesty, and assertiveness, you can, as a young and talented contributor, truly thrive and shoulder more responsibility than most 20-somethings can fathom. This is an extremely difficult combination of traits to express, especially when you are early in your career, think/know you’re good, and likely have an ego. It requires a great deal of maturity.
These are some things I wish I had known when I was starting my career at tumblr when it was very early stage, and things I wish I had known to communicate to high-potential people that were early in their respective careers. They may seem obvious, but they're worth reiterating. The key is you want to understand how founders really feel and think in these types of situations.
Don’t push for title. You do not need to be Chief-Anything-Officer in your early 20’s. Instead, push for responsibility. I don’t want to hear from a 20-something-year-old how they think they should be a “VP” or “Head of” or “C-something.” I will immediately go to an internal dialogue of “Screw this person, who do they think they are?” Even if you’re the messiah, most founders will think this. They want to come to this conclusion on their own. Don’t create a set of biases in the founder’s mind that you have a real sense of entitlement, even if you’re over-delivering. What I want to see is someone who is going above and beyond, delivering terrific outcomes, and yearning to do more.
Don’t imply that you are going to quit if you’re layered. Do people actually do this? All the time. Instead, produce outcomes that make you indispensable and carry yourself like you’re already in the role you want. I want approximately zero veiled threats from someone early in their career. There’s no better way to convince someone you’re not ready for a step up than to be passive-aggressive. Implying you’re going to leave if someone with 15 years more experience than you becomes your manager is just going to give a founder unnecessary anxiety. They’re going to question why you brought this up in the first place and whether they want to deal with the hassle.
Don’t constantly ask for things that don't help you perform better in your role (like more salary, equity, title and reports), but do be honest about what your aspirations are and self-aware enough to know and articulate what you need to get there. I’ve seen high-potential high-performers ask for more money at virtually every review cycle (and in between!) who earnestly believed they were advocating for themselves. Maybe they were, but they were also being annoying. That was the last thing I wanted to constantly deal with. There is a tact to this process that requires real maturity. I am not suggesting to not advocate yourself, I am saying that you need to do it in a way that conveys you are an asset instead of a diva, a leader instead of someone who doesn’t know the ropes, and exhibit some semblance of an understanding of how these decisions are made amongst leaders and founders.
These bullets may sound ridiculous or even condescending because you’re the Talent and you’ve gotta get what’s yours! And sometimes leaders do need a kick in the ass to recognize that they really are working with a superstar (I certainly needed several). But the ability to read the room and navigate it is a soft skill that will truly set you apart. In addition to being terrific at what you do, understanding weird founder psychology and being mature beyond your years can be the distinguishing factor in how much you learn, grow, and are compensated over the course of your journey at an early-stage growing startup. If you’re working with a decent founder you will notice that the people who managed to grow with the company from early on and ended up with the most responsibility and equity are almost always the ones who strategically asked for the least.