To Lead at Scale, First Do Things That Don’t

Jake Wilder
Dec 11, 2020 · 6 min read

It’s All About Developing Trust

“Do things that don’t scale,” is some of the common advice that Paul Graham offers to founders and startups. In his experience, the key to a startup taking off is having a founder that makes it take off. Without this first push, companies struggle to gain the traction they need to build momentum in the market.

When Brian Chesky and Joe Gebbia were developing Airbnb, the company had some initial users in New York, but the site hadn’t gained a lot of traction. At that point, Paul Graham offered him this same advice. He told them to go to New York and talk to those first clients. Get to know them. Understand their needs and how Airbnb can deliver an exceptional service.

Brian was skeptical. He said that they’d never be able to keep talking with every client and constantly travel to new cities. To which Paul responded, “That’s exactly why you should do it now.”

What followed was a transformation for Airbnb. Brian and Joe met with Airbnb’s early clients. They talked with people to better understand their concerns. They found out what services they loved. They focused on single stories. Then they worked with these individuals to design perfect experiences.

Only after they had designed extraordinary individual experiences could they see which parts could be scaled to a larger market. And it turns out that once high quality customer service becomes a part of your culture, it scales much better than most people expect, as companies like Disney and Zappos have long established.

By focusing on things that don’t scale, Airbnb was able to build a company that did.

This same principle applies to leadership. The best way to lead at scale is by first learning to lead in areas that don’t.

It’s tempting to try a shortcut. Many people make this very mistake. In their zeal to maximize their influence right away, they’ll try to appeal to everyone through generic leadership problems.

The problem, of course, is that these practices never seem to work. They’re shallow and transparent. Watered down tactics rarely build the trust needed to lead people.

Think about someone you’d consider to be a good leader. Chances are that he or she doesn’t offer hollow buzzwords or grand proclamations without the substance to back them up.

Leadership, at its core, is helping people reach a better place. A good leader helps people see a better version of the future and then inspires them to make that a reality. As David Foster Wallace defined it,

“A real leader can somehow get us to do certain things that deep down we think are good and want to be able to do but usually can’t get ourselves to do on our own.”

All of which brings some level of risk. Before you lead people, you need their consent to go on this journey with you. In order to get them to sign on, you need to show them that the short-term sacrifice will be worth the long-term benefit.

In short, they need to trust you.

Without trust, people aren’t willing to make the short-term sacrifices. They won’t believe that you can help them achieve that future vision. People won’t follow a leader they don’t trust. It simply doesn’t happen.

Whether you want to lead one person or a thousand, it all starts with trust. And we earn trust by consistently demonstrating three things: character, connection, and competence.

“Be more concerned with your character than your reputation, because your character is what you really are, while your reputation is merely what others think you are.” — John Wooden

Weak character is limiting. It overshadows everything else that you do. Regardless of your talent, drive, or intelligence, people won’t trust someone with a questionable character.

Character tells people what to expect. It helps them understand what drives your decisions. It helps them see the logic behind your actions. This consistency builds trust.

One of the biggest signs of character is also one of the simplest: Do you keep your promises?

It’s unfortunate that the simple act of doing what you say you’re going to do is enough to make you stand out in today’s world. But we’re surrounded by people who make commitments with little intent of following through on their word.

When you’re leading a large group, this becomes even more important. While people may be willing to offer second chances in a small team, they’re much less tolerant of a senior leader. The larger the group, the more people who will form a long-term impression after a single occurrence.

It’s important to build this discipline early, when there are limited people pushing for your attention. Recognize that you won’t be able to do everything. And be discerning with your commitment. The best way to keep the promises you make is to only make the promises you’ll keep.

“To lead people, walk beside them.” — Lao-Tsu

After character, people also need to see that you’re looking out for their best interest. In order for them to trust you, they have to believe that you can empathize with their current situation. As the old saying goes, “No one cares how much you know until they know how much you care.”

It’s easy to lose sight of this, especially as your responsibilities grow and you have less time to deal with people individually. As demand grows beyond your supply, it’s natural to minimize the time spent connecting with others and developing this empathy.

But this creates a vicious cycle. Without these connections, everything becomes more difficult. Trust erodes and it takes more time and effort to accomplish things with your team. All of which leads to further frustration, more time commitments, and less opportunities to re-forge this connection.

Nothing happens without connection. Regardless of your intent, if you don’t take the time to understand the people you’re trying to lead, they’ll resist both you and your message. People don’t follow ideas or causes. They follow leaders who convince them of the value in those ideas and causes.

It’s important to build these behaviors early. Prioritize the time to make yourself available to people. Learn their names. Find out how they’re doing. And let them know you appreciate them. Most importantly, listen.

Once you develop the habit of connecting with people individually, it’s something you’ll continue to do regardless of how many people you’re leading.

“I am, as I’ve said, merely competent. But in an age of incompetence, that makes me extraordinary.” — Billy Joel

After character and connection, people want to follow leaders that they believe will win. Before people will trust that you’ll help them realize a future vision, they need to believe that you’re capable of delivering on it.

They need to see that you’re good. They need to see that you have the skills and ability to push through the inevitable obstacles that will come up along this path.

The time to build these skills isn’t when you’re leading 1000 people. It’s not when every mistake will be broadcast for everyone to see. We all know that failures aren’t the end of the world, but some cause a much harder recovery than others.

Push yourself now. Build the habit of attacking that discomfort now. Make learning inherent to your process. And focus on getting a little bit better every day.

Whether 10,000 hours makes you an expert or not is debatable. But we only get good through practice. Whatever you want to do, start doing it. And then do it again. And again. And again.

“That’s exactly why you should do it now.” — Paul Graham

The more that you try to accomplish in life, the more you begin to recognize that it all comes down to leadership. The success of any challenge that involves other people will rise or fall based on the quality of leadership. And the crucial factor in leadership is trust.

All of this occurs at the individual level. The size of the group may increase, but we still need to establish trust with people as individuals. And we do that by consistently demonstrating character, connection, and commitment.

As responsibilities grow, this only becomes more difficult. Start building these practices today. There’s no better time than now.

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