Lead Upwards. Sarah E. Brown
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think through “why” is just as important as “how.” The best startup leaders constantly learn to improve and achieve faster, better results.
DEPARTMENTAL UNDERSTANDING BEYOND ONE NARROW AREA
As an individual contributor or a manager of a small team, you can get away with having depth of expertise in one area without much breadth across the department. Your remit may be narrow. Being an executive comes with an expectation that you understand the fundamentals of many areas of your department, not just one specific area of functional expertise. This includes things like knowing about front‐end engineering vs. full‐stack, and how to manage multiple technical teams running multiple products, etc. While you aren't expected to know everything (that's what hiring your team is all about), you'll need to expand the breadth of your functional area expertise in order to hire, retain, and effectively manage a team of high performers who execute across your function.
RESPONSIBILITY FOR BUILDING AND LEADING A HIGH‐PERFORMING TEAM
You can be a “team of one” as a “head of” at a startup for longer than you'd think. I did it for several quarters before hiring my team in a recent executive role. But you can't reach any kind of scale without growing your organization. If you can't hire a team, that can be a dealbreaker impediment to your success. First‐time executives often fail to attract the best talent, because candidates may feel that their abilities as a leader are yet to be proven.
We'll dig into how first‐time startup executives can succeed at hiring in later chapters, including how to build an inclusive, high‐performing team that will support each other's success. If you want to be an executive (or already are one), be prepared to adopt a “servant leader” mindset and stretch your skills in effective management as one of your highest priorities.
SIMPLY PUT: IT'S A BIGGER COMMITMENT
Startup executive and Diversity and Inclusion (D&I) expert Aubrey Blanche says that while it's possible to live a balanced life as an executive, we shouldn't underplay the lifestyle impact. It really is a bigger commitment than a non‐executive role.
“There is often discussion that you don't have to give up some of your life to be a leader. We do a disservice to people when we're not honest about the big life impact that comes with taking on leadership roles,” says Blanche. “There certainly are unique situations where you can work part‐time and be a VP, but it really does require you to put your job relatively central to your life. I think we should go into that choice with eyes wide open,” says Blanche.
LESS COMPANIONSHIP AND CAMARADERIE WITH OTHER NON‐EXECUTIVE STARTUP EMPLOYEES
While you'll enjoy camaraderie with your fellow executives, don't expect to be chummy with your team in the same way, especially if you were promoted from within the ranks. Being the team leader gives you power and a position of authority that won't allow you to act as you did before, even as a manager. That power is significant. You can't expect to be on “even footing” when you could fire, promote, or give pay rises to your people. Their livelihood is now tied to your decision‐making, and that puts you in a position of power that shifts the dynamics within your relationships.
You're also dependent on your team. No startup executive would be successful if they didn't have a high‐performing team rallied around them, but it's inherently imbalanced and skewed by authority dynamics. It's much harder for a report to get their boss fired than vice versa. If you fail, your team may stay on and you may see the door, but it wouldn't be them making that decision. Because of this power imbalance, you must act accordingly.
We must not abuse this power imbalance or put our direct reports in positions that could hurt them (for example, dating them, or engaging in behavior that's inappropriate for the hierarchy). Some startup executives have too much power over their teams and reports. Unlike at big companies, some startup leaders can get away with a lot without oversight, which is thankfully becoming less the norm thanks to movements to increase equity and inclusion and expose and enforce consequences for bad behavior. The checks and balances within the startup ecosystem have been lacking for too long. Thankfully, many startups are creating opportunities for employees to have a real voice in giving feedback on their managers and supporting a healthy, inclusive culture on teams.
Acknowledging inherent imbalances, we can still create strong, positive relationships with individuals on our teams. Even though we can't be peers while we're managing our reports, we can get to know them as individuals, help them be stewards of their own careers, give them growth opportunities, and support their contributions and productivity. We can do our best to treat everyone with the kindness and respect they deserve and ensure they have a psychologically safe and affirming work environment that honors their individual needs as well as the collective team needs.
If you're signing up for an executive role, embrace the fact that your ability to consistently perform these management responsibilities makes a true difference in people's lives. Aspire to do this well, knowing even with good intentions you can and will make plenty of mistakes along the way. We'll talk about how to deal with this later in the book in the section on team management.
EXECUTIVES HAVE THE MOST CONTEXT OF ANYONE IN THE DEPARTMENT
As an executive, in most situations, you'll have more context about the business than others on your team. I didn't realize how much this context impacted my team's decision‐making until I became an executive. A full schedule of cross‐functional meetings gave me a real‐time understanding of the business that no one else on my team had. It was up to me to regularly communicate these to my team so they could be effective in their roles. It's an executive's job to communicate to their team what's going on outside a department to others. Due to the pace of startup life, this isn't always as expeditious as the speed at which they're garnering new intelligence. Some information can't be shared with the team due to confidentiality or other concerns.
This may sound simple, but it's a powerful concept. As a leader, you'll often know more than others on the team about any given topic. You have to somehow get everyone rowing in the same direction on a regular basis when they can't know all of what you know right away.
While you can't share everything with every team member at all times, with your guidance you can steer your reports towards what they need to be successful in their roles. It helps to build trust so that they will follow you as you make decisions to which they don't have full visibility.
WHO'S QUALIFIED TO BE A STARTUP EXECUTIVE?
There is no minimum number of degrees nor years of experience required to be a startup executive. You read that correctly: None. There are 24‐year‐old CEOs of startups and there are 24‐year‐old VPs of sales at startups. Some startup executives have MBAs from fancy top‐tier business schools and thirty years of business experience. Others didn't graduate from high school. Some don't become startup leaders until they've got two decades of business under their belts and some are promoted after five or six years of startup experience.
No lack of credentials should keep you from aspiring to become a startup executive. Will a twenty‐six‐year‐old who's been working for four years be better suited to be a successful startup executive than someone with two or three times that amount of experience? It depends, just as it depends for founders. According to Harvard Business Review, the average startup founder is 45, even though stereotypes would have us believe it's much younger.1
Here's another stat from Harvard Business Review that motivated the inception of this book: women tend to only apply for jobs that they're 100% qualified for vs. men will apply when they only meet a selection of the criteria