I’ve been a CEO for a long time, but I’m still a student. My area of study? The craft of leadership. It’s a fascinating subject, one that I dove into many years ago while sitting with the leaders of hundreds – perhaps thousands – of companies during my investment banking days.
My job was to determine who would succeed and who would fail, and it often boiled down not to the strength of the product or offering but rather the leadership style of the people involved.
I eventually left investment banking because I wanted to get into the game and play rather than sit on the sidelines. After all this time, I’ve compiled five things that aspiring leaders should add to their playbook right now. Game on!
Be willing to scale with the company.
The way you lead a 50-person company is very different from how you lead a 150, 500, 2,000 or 10,000-person company. And yet, too many leaders become entrenched in their approach and fail to adapt to achieve the exact thing they wanted: growth and scale.
The specifics of these leadership shifts are more than enough fodder for an entirely separate post (stay tuned!). For now, suffice it to say that the decision tree fans out when you expand. You are no longer deeply involved with every element of the business and the goings-on of every person on your team. If you try to retain that prescriptive control, you end up losing control.
Choose to fail instead of getting stuck.
Fear of failure is paralysing. It’s also typically far more damaging than the failure itself. It has become trendy to say ‘fail fast and fail forward,’ but it’s easier to say that than to lean into it – let alone create a culture around it. As a CEO, you get to decide what to reward. Choose to reward risk. Create guardrails and let people fly. And you have to be willing to do it, too.
When you’re in a fear-of-failure mode, your lizard brain takes over, and you’re operating at significantly diminished capacity. You’re also not moving forward. Think of it like a trapeze act: to get to the next bar, you have to let go of the one you’re holding. That means sailing through the air for a minute, but the alternative is clinging to where you were, dangling in perpetuity – or until the inevitable fall. Hear this: being stuck is worse than failing.
Don’t hire people exactly like you.
You’re pretty awesome, right? Definitely. Now shouldn’t that mean you should surround yourself with people exactly like you, to increase the awesomeness exponentially? Nope. Instead, take a moment (or several) to get very self-aware. Where do you shine? Where do you have gaps in either capability or interest?
Hire for those gaps. I tend to go at a thousand miles per hour, so I intentionally seek out team members who cross Ts and dot Is – and, even more importantly, who aren’t afraid to tell me when I’m missing a detail or need attention something. If we all moved super fast, we’d be in trouble. Likewise, I bring things to the table that others might not. Hire for the diversity of thought and capability.
Understand what questions only the CEO can answer – and delegate the rest.
There are some decisions that only a CEO can make. In my case, as in many cases, those decisions center around our brand’s mission, the people moving that mission forward, and how we interface with our board and the associated fiduciary duties. I need to focus on those. If I get distracted away from those and bogged down in minutiae or other drama, I become a bottleneck. That’s why I hire great people who not only balance me out but to whom I can delegate with ease. The best team members see what needs to be done and, without being asked, handle it. If you hired the right people, that’s not scary – it’s freeing.
Ask prospective team members the right questions.
How do you hire those magical unicorns who know what to do and then get it done? It starts by asking the right questions in the hiring process. With everybody on LinkedIn, it’s easy to get lost in someone’s credentials or published persona. And while experience matters, I think it’s critical to focus on these questions:
- What does a candidate love to do? What tasks or responsibilities make their eyes light up?
- What are they exceptionally good at? Not what they’re capable of, or what they studied, but what are they so good at that everyone wants them to handle it?
- What do we need as a company?
- Is there an alignment between 1, 2, and 3?
If yes, there’s your hire. But if even one of the first three is a mismatch, it’s probably not going to work out very well. A person who’s great at making widgets isn’t valuable if you don’t need widgets. A person who is great at making widgets isn’t valuable if they hate making widgets.
And a person who loves making widgets isn’t valuable if they aren’t spectacular at making widgets. If you hire for only two of those things, you’ll exert vast amounts of emotional energy trying to make a role or a person into something it isn’t.
One more thing before we go…
There’s one thing I haven’t mentioned once during this article, and that’s by design – even though it might be the thing people often start asking me about.
What’s my advice as a woman CEO?
Here’s the thing: I am a woman. I am a CEO. But one label doesn’t need to predetermine the other.
The advice in this piece is not only for women CEOs in tech.
It’s not only for women CEOs.
It’s not even only for CEOs.
It’s for anyone who wants to lead.
Why do I make a point of this? It’s so I can offer one more piece of advice: keep learning, and throw away your preconceived ideas of from whom you need to learn. If the ideas in this piece land, great. Try them. If not, great. Don’t try them.
My last piece of advice is to be open to hearing diverse perspectives and opinions. A great idea from someone in an entry-level position is still a great idea. A great idea from someone with a different experience and background can bring a perspective you could never have come up with on your own.
And a great idea from someone with whom you often disagree could be just what you needed to hear, exactly when you needed to hear it.
Here’s to many more great ideas.
Also read: Avoiding leadership missteps in mergers and acquisitions
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