What I learned about people that scale

Is this person going to scale? If you work at a startup, you’ve certainly heard this question before.

The conventional wisdom says that during periods of hypergrowth, a company will outgrow anyone who hasn’t done the job before. But having seen many of our early leaders scaling through the craziest growth phases of Brex, I was never satisfied with this answer.

Failing to scale is not about lack of will. I haven’t heard of someone who got layered at a startup and wasn’t trying as hard as they could to keep up with the job. So is it simply a matter of skill? I don’t think so. Experience definitely helps, but even experienced leaders have to accept that their past experiences are not perfectly translatable to a new startup. Startups are doing things that haven’t been done before, so experience can only be part of the answer.

Perhaps a better way to think about experience is not as how many times you’ve done a job before, but instead how many times you had to change yourself in order to be successful.

Everyone knows that experienced leaders make a big difference. But this small shift in definition helps understand which types of experience are a good predictor of success. It helps explain, for example, why hiring leaders from fast growing companies is a good idea. It’s not just because they’ve done the job before, but because the company was changing rapidly, causing their jobs to also change rapidly, and these people still managed to be successful. Conversely, hiring an exec who spent twelve years at Google will almost certainly be a disaster for an early stage company.

If ability to change is what it takes to scale, a more interesting question, then, is why changing is hard. Imagine you want to change — what do you do? You start by changing your actions. Stop doing what’s not working, and start doing something else. Think of a first-time manager struggling to adapt to the new role. They know what they have to do: stop doing IC work, and start empowering others.

But forcefully trying to change your actions usually doesn’t last very long. The moment you stop paying close attention to each individual action, you come back to auto-pilot mode. In a matter of time, the manager is back at doing IC work — and struggling at their job again.

There’s a better way to change your actions: change the belief system that generates them instead. My job is not to get a task done, but to help my team win. Once this belief is rewritten in the manager’s brain, the right actions will happen naturally. Being a manager becomes a part of your identity, so you start doing manager things. Going back to your old habits is now a violation of your core beliefs.

Reinventing your core beliefs is the silver bullet of scaling. But it is hard, because the same core beliefs you’re trying to replace were also responsible for your success. The new manager was promoted because they were great at getting tasks done. How could they possibly get rid of this belief? They have to let go of a part of who they are. It’s like breaking up with a partner that you had great memories with, but you know you need to part ways to move forward and ultimately be happier. There’s a certain grief involved in reinventing your core beliefs: a part of you has to cease existing for the new to come in.

But different from a traditional death, this one has agency involved. This is what makes scaling so painful. You have to choose to go through this journey, and most people are not ready for this emotional rollercoaster as part of their jobs. But once the death is accepted and the grief period is over, there’s now fertile ground to nurture new core beliefs. A new version of you. Ready to scale.

The journey of scaling doesn’t end here, though. Scaling is not as simple as other changes in life. Even if someone wants to change, we’re actually not good at teaching people how to scale.

In 1908, the marathon world record was 2 hours and 55 minutes. Today, the qualifying time for the Boston Marathon is 3 hours. Thirty thousand people qualify every year. In the course of a century, we understood what makes a good marathon runner, and created a systematic process that allows anyone, even thousands of amateurs, to become good at it. But if you ask someone how to become a better leader, they will tell you to surround yourself with good leaders and learn from them. Imagine asking a friend how to be a better runner, and hearing that you should spend some time with good runners?

It is frustrating, but learning from good leaders is the safest path we know to become a better one. A big part of the reason is because the hardest parts of a leader’s job can’t be learned by reading a book. You have to feel it in order to develop a sense of what great looks like. You can read all day long about how to run a great meeting, but you only understand what it really means by watching a good leader do it.

Picking the right leaders to learn from is an important step. Here, one tempting mistake is to over-index on a hero. It’s easy to pick a mentor, a previous boss or a successful entrepreneur that you admire, and start trying to emulate them. But you don’t need to be a jerk with your team in order to be a great product leader like Steve Jobs was. While heroes are absolutes, role models are domain-specific. It’s important to learn what to learn from whom. [1] There are probably better role models for people management than Steve Jobs.

The hard part about role modeling, though, is that what we perceive as “good leadership” is often too intertwined with personality traits, and those you can’t easily copy. So it’s important to be authentic too, and lead in a way that is compatible with who you are.

So how to be authentic? A good place to start is ignoring the preconceived notions of what a leader should look and feel like. We grow up with an idealized version of a leader in our heads — someone who’s eloquent, strong, and always says the right things. If you’re emulating a leadership style of someone else, you’re doing the opposite of being authentic.

Instead, people want to know who you really are. What are your quirks, your passions, your style, and what makes you different? Don’t hide these away; put them at the forefront. I struggled for years trying to be more eloquent in All Hands meetings. The best CEOs I knew were very inspiring in company-wide events, but public speaking just didn’t feel as natural to me. Then, I figured out that writing is a more authentic communication method for who I am. This led me to start writing weekly emails and essays, which became an important part of how I lead.

But the easiest, and best way to be authentic is to be vulnerable. Since every person is going through a unique challenge in life, when you share any details about what you’re struggling with, it is remarkably authentic. You don’t need to start by sharing your deepest fears and insecurities. You can start by just sharing where you are on your journey. What are you struggling with right now? Tell your team. Not only is it authentic, but it also builds an immense amount of trust.

Leaders often push back when I tell them to be vulnerable with their teams, because they think it makes them look weak. But anyone smart around you already knows what you’re struggling with. People can read through the lines much faster than you think. Sharing where you are on your journey is just stating the obvious, but with bonus points for authenticity and trust. Do it.

“Be authentic” is not the most actionable advice, but it is an important thing to figure out. Every great leader does. You just have to try out different things and see what feels good to you.

“What feels good to you.” Many people have an allergic reaction when they hear that in order to be a good leader, you need to feel things. But the best leaders I know are constantly listening to their feelings, because feelings are backdoors to their intuition. Leaders spend their entire lives honing their intuitions like a sophisticated machine learning model, learning correlations between actions and outcomes that are not easily explainable, but still very real. Dismissing your intuition is ignoring valuable data.

Feelings alone can trick us. Logic matters too: a little bit of rigor goes a long way separating feelings from biases. Bias is a case of overfitting: past data is getting in the way of seeing what’s new. Logic can help you understand if you’re dealing with a new manifestation of the same underlying thing, or something new entirely. But the hardest decisions are rarely a manifestation of things you’ve seen before. They can’t be made purely based on logic, otherwise they wouldn’t be hard. This is where the best leaders shine. They learn when it’s time to let their intuition kick in, and they just happen to make the right calls.

So when you’re making a hard decision with no clear answer, but it still feels right, don’t dismiss it just because you can’t explain it. This is still valuable information. But here’s the interesting part: if your decision is correct, you can go back and learn to recognize what it feels like to be right. And this is the essence of good leadership: using all your senses to make the right decisions when there are no easy answers. Scaling is just a matter of how quickly you can get comfortable succeeding at this level of ambiguity.

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Reinventing your core beliefs, picking the right role models, being authentic, and listening to your feelings. That’s a lot of subjectivity. I can’t prove logically why each of these things matter; we just know from experience that they tend to work. In a world where people demand an explanation for everything, this is, perhaps, the hardest part about scaling: taking leaps of faith. Not everything can be rationalized. Sometimes you just need to listen to people who‘ve been through the journey before, even if you don’t fully understand why.

But the biggest leap of faith of all is having faith in yourself. Things will go wrong, and you’ll feel like a failure many times. But don’t assume that you can’t scale just because you haven’t done the job before. The truth about successful startups is that no one really has. This is what makes it hard, but also what makes it fun! Ask someone who’s been at a successful startup about the most extraordinary times in the career, and they won’t think twice. They will tell you about the craziest times, solving the craziest challenges, working the craziest hours, surrounded by the craziest people, but having the time of their lives.

The struggles are what shape us. So regardless of how hard it is, embrace the journey of scaling. Cherish every moment of accomplishing things you didn’t think you would. Remember what it feels like. These are the moments you will never forget.

[1] Interestingly, this may help explain why founder-CEOs have an easier time scaling than executives. There are just more stories out there of successful founder-CEOs to role model, compared to, say, successful CFOs. An easy hack to help leaders scale is to introduce them to great role models to copy (and potentially mentor them). I suspect this is also why great teams are a self-fulfilling prophecy. It’s not just that A players hire A players, but that not-yet-A-players have many good leaders to learn from, across many domains of leadership.