How to scale yourself, from founder to leader

All founders need some universal skills to succeed. They need the ability to take bold risks in pursuit of a vision that isn’t self-evident to others. They need the ability to learn (since they’re trying to do something brand-new). And to play a long-term role at their start-up turned scale-up, they need the ability to live with and resolve the inevitable paradoxes of being a founder. When I asked Dropbox founder Drew Houston to look back on his experience, he told me, “I think a lot of entrepreneurs start with a lot of insecurity about what they don’t know. What you want is not to be paralyzed by it, but to harness it—to use that nervous energy to learn and make yourself better. You’ve got to keep your personal learning curve ahead of the company’s growth curve.”

Maintaining a certain humility and a sense of perspective can help you navigate the changes in your role as you blitzscale your company. If you truly want to blitzscale, then speed has to take priority over everything—including your own ego.

There are only three ways to scale yourself: delegation, amplification, and just plain making yourself better.

Can you find, hire, and manage good people, then transfer work over to them so you can tackle the challenges you’re uniquely suited to tackle?

Many founders are so talented that they have a hard time letting go of tasks once they start performing them. They often think things like, “Will someone else be able to do this as well as I can?” The answer is almost certainly, “No, especially not at first, but they’ll probably figure it out over time, just like you did.”

Start-ups get off the ground thanks to the individual talent and hard work of founders like Mark Zuckerberg and Brian Chesky, but they blitzscale into giant companies like Facebook and Airbnb because these founders learn how to delegate.

One of the most important aspects of delegation, and often the most challenging for a founder, is to hire an executive and hand off functional leadership.

For example, a lot of great founders are product people. Initial product/market fit and success are achieved because of their product instincts. But as the company grows, these founders will almost always need to hire an executive to take over leadership of the product organization—it’s too important to be a founder’s part-time job.

A key technique I use to overcome this challenge is to picture the hire as a specific living, breathing person rather than as a role written down on a piece of paper. When you try to picture an abstract “head of product,” for example, you might have a hard time visualizing this faceless entity doing a better job than you are. But when you picture a particular individual (say, Joe Zadeh of Airbnb), all of a sudden your mind shifts to thinking, “Wow, just imagine how awesome it would be to have someone like this running our product team.” It might be difficult to hire this paragon—executives who are that good are hard to pry loose from their current companies—but it doesn’t hurt to try, and at the least, you’ll have a great reference to which you can compare the people you actually consider hiring.

Rather than delegate work you’re doing to others, can you hire people who amplify the work you do? The goal here isn’t to free you up from your work so that you can do other things; it’s to make the things you do much more impactful. This is actually one of the areas I’ve tried to develop and refine in my own life.

Like many founders and executives, I have an amazing executive assistant, Saida Sapieva, to help me with scheduling and logistics. But I’ve discovered that you can take the concept of amplification much further.

For example, I was one of the first start-up leaders in Silicon Valley to borrow the “chief of staff” concept from the realm of politics and established corporations. Unlike a traditional assistant or even a technical assistant, your chief of staff should amplify your business impact: he or she should be a businessperson who can not only make certain decisions for you but also triage the important decisions that you have to make yourself.

A chief of staff can also make sure that all the people who want to meet or interact with you are “briefed” in advance so that your time together can be as efficient and effective as possible.

My first chief of staff, Ben Casnocha, was a successful author and entrepreneur before we began working together; my second, David Sanford, had worked with me at LinkedIn and had also been an entrepreneur (and a restaurateur!). It turned out that Ben and David were better at organizing my own life than I was; I’ve become significantly more productive since they started amplifying my efforts.

To learn more about the role and value of a chief of staff, I recommend that you read Ben’s essay on the topic, “10,000 Hours with Reid Hoffman,”which you can find on his personal website, Casnocha.com.

Once you begin to appreciate the power of amplification, you can find many ways to scale yourself. For example, one of the things you need to do is to process information about your company, your industry, and the world as a whole. I have a freelance researcher on my team, Brett Bolkowy, who helps me learn new things and answer key questions by finding the best information on any particular topic. Another key team member, Ian Alas, helps me with creative projects like the visual summaries I prepare for my books. The slide shows he created for my book The Start‑up of You have been viewed over fifteen million times. Now that’s amplification!

Nor am I unique in this. For example, Mark Zuckerberg has a substantial team to help him manage his social media communications so that when he travels and meets people, he can maximize the impact of his interactions.

Trusted employees, freelancers, or even a team of outside consultants can be your amplifiers. The official nature of the relationship is less important than having assistance that you can trust.

Because your company grows and changes so quickly as you blitzscale, it’s crucial for you to figure out how to make yourself better just as quickly so that you don’t become the bottleneck that holds your company back.

As our friend Jerry Chen likes to say, “There are no job descriptions for founders. If the role doesn’t change, there’s something wrong.”

Since you’re going to face new challenges during every stage of blitzscaling, you have to make yourself into a learning machine. My friend Elon Musk is a great example. He dropped out of Stanford’s PhD program in applied physics because he thought he could learn more on his own! He started SpaceX and Tesla by learning literal rocket science and carmaking. So how do you accelerate your learning curve so that you can learn more faster? The key is to stand, as Isaac Newton wrote, “on the shoulders of giants.”

This means talking with other smart people, often, so that you can learn from their successes and failures. It’s usually easier and less painful to learn from another’s mistakes than from your own.

When I need to learn about a new subject, I’ll definitely devour some books on the topic, but I almost always supplement this reading by seeking out dialogue with leading experts in the field.

Brian Chesky at Airbnb, another amazing learning machine, does something similar, seeking advice from mentors like Sheryl Sandberg and Warren Buffett. Brian told our class at Stanford, “If you find the right source, you don’t have to read everything. I’ve had to learn to seek out the experts. I wanted to learn about safety, so I went to George Tenet, the ex‑head of the CIA. Even if you can’t meet the best, you can read about the best.” Brian lives this advice; he got many of his ideas by assiduously poring over biographies of great entrepreneurs like Walt Disney.

Another helpful approach to seeking mentorship is to get help from experts who might be less famous than the Sheryl Sandbergs of the world, but who have faced (and solved) similar issues in the recent past.

In an interview for Reid’s Masters of Scale podcast, Dropbox’s Drew Houston described how he tries to learn from fellow entrepreneurs who are on the same journey:

"Talk with other entrepreneurs. Not just famous entrepreneurs, but people who are one year ahead, two years ahead, five years ahead. You learn very different and important things from those kinds of people. It really helps to have a sense of the longer‑term arc, because the game changes quietly from phase to phase."

In addition to seeking help on an ad hoc basis, I believe it’s a good idea to be systematic about learning from others.

I advise entrepreneurs to have a personal board of advisers or “board of directors” who can proffer advice and help you fill the gaps in your knowledge.

For example, I have a set of informal advisers who help me learn about the areas that matter to me, including very specific topics like virality or people management. If you’re serious about someday blitzscaling a company, you should think of your mentors as a board of directors. Regularly report to them on your progress, and ask them how you can do better. Everyone needs feedback.

Brian Chesky, for example, likes to say, “I’m shameless about getting feedback.”

He and I have a scheduled dinner every month where (among other things) we share what we’ve learned and provide feedback. Leveraging a board like this can help you manage risks and increase the potential upside of your actions.

This may sound like a lot of work, but it’s important to leave yourself time and space for reflection and feedback.

It’s easy to get caught up in an endless to-do list and to lose sight of what is important.

That’s one of the things I learned from Mark Zuckerberg and Sheryl Sandberg. Mark and Sheryl meet first thing every Monday and at the end of every Friday—no matter how busy they are or what else has come up.

The Friday meeting is especially important because it gives them time to look back over the week and reflect on what they’ve learned.

You might feel like you can’t afford to take time out from your busy schedule to make yourself better. After all, you might think, everyone is counting on me.

This feeling, while natural, is counterproductive. Netflix CEO Reed Hastings warned our Stanford class, “[When I was running Pure Software,] I felt like investing in me was selfish. I thought, ‘I should be working.’ I was invited to join YPO [Young Presidents’ Organization], but I thought, ‘I can’t take a day off.’

I was too busy chopping wood to sharpen the axe.

I should have spent more time with other entrepreneurs. I should have done yoga or meditation. I didn’t understand that by making myself better, I was helping the company, even if I was away from work.”

Plus, when you model the behavior of taking the time to improve yourself, you help encourage the rest of the company to develop a culture of learning.

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