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The Pivotal Stories Every Startup Leader Should Be Able to Tell

Stashed in: Founders, Leadership!, Startup Lessons, Awesome, Stories, @sherylsandberg, startup, Startup, @firstround, Theranos, Cognitive Bias

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Stories are about demonstrating real emotion.

This means really inhabiting and feeling the frustrations, fears, stress and disappointment that your team encounters along the way. These aren’t positive emotions. They’re hard to weather and relive. As a manager, it’s easy to want to be teflon, to have all the answers, to seem effortlessly successful (and therefore credible). But real credibility comes from accepting how hard things really are and providing a roadmap for others to survive and grow stronger from similar challenges.

“At Facebook, I worked for a guy named Dan Rose who was really, really good at this,” says Faul. “In 2012, we faced a number of tricky situations and Dan would tell us stories about his time at Amazon and similar struggles he faced there. He was open about having the same anxiety we were all feeling at the time. Because he shared that so freely, we trusted him when he explained how he’d navigated through those tough times. It gave people a level of comfort that we’d find a way to work through it.”

By empathizing and making himself vulnerable to criticism, Rose built trust and confidence. It feels counterintuitive to let down your guard. You think it will have the opposite effect, but you have to lean into that tension and discomfort. As much as you can, you have to put yourself in the place of the people on your team so you can authentically relate.


“Being vulnerable is one of the most powerful things you can do as a leader because it shows you’re genuine. Being genuine builds trust. Trust is the key to getting anything done,” says Faul. “If you’re willing to tell everyone on your team about your mistakes, your shortcomings, what you’re currently working on to get better, you seem more human. It’s easier for people to connect with you. They have an easier time believing what you say, and that you’re taking their wellbeing into account.”

It also gives people permission to take bigger risks in their own work. If your team knows about times you tried to do something and failed, they will also see that you recovered and went on to succeed. They won’t feel hard-pressed to be perfect or place small bets so they always win. When you’re at a startup, you can’t afford to play it this safe.

“At Facebook, Sheryl [Sandberg] used to talk very publicly and encourage other leaders at the company to talk very publicly about things they tried that didn’t work and what they learned from it,” says Faul. “She would tell specific stories about the smartest people she knew, how they had stumbled, and how they had worked through failure. The way she told these stories, the people were very real to us. The feelings they experienced when they failed were very real. But the idea that the company was learning and moving forward was also very real. She made it clear these experiences were the foundation of Facebook’s culture and something to take pride in.”


One of the key failure stories Faul shares draws his time at Pinterest. Early on, he worked on major projects related to the company’s culture. “I know there were many pieces of this I approached the wrong way. I made some bad decisions, including one that didn’t get the response we wanted at all inside the company — it just didn’t land,” he says. “It was my first big, visible failure as an executive, and I knew it reflected poorly on me. I had to work through that, acknowledge the failure, apologize for it, discuss it over and over again. It was incredibly hard for me to do.”

Instead of sweeping the episode under the rug, he now tells this story again and again. Whenever his team confronts a similar situation or makes a mistake, he recalls it. Because the truth is, he did get through it. His team at Pinterest not only survived but went on to other successes. Knowing that recovery is possible on this level generates productive psychological safety for everyone involved.

There’s another story in this genre Faul tells, that almost everyone working at a startup will relate to at some point. After he was at Facebook for a while, Sandberg — his manager at the time — hired someone new to take over a large part of his job. “This was honestly one of the hardest moments in my career — one of those big moments where I felt like a failure, like I wasn’t moving forward,” he says. “When we talked, she told me that it was because the company was scaling and this is a normal function of scale. Now I can see it was 100% the right decision, but at the time it felt awful.”

Fault’s told this story 100 times, he says, to make it clear to people on his team that this is something even the best employees will go through at fast-growing companies. It’s important that he admits the depth of the emotion he felt, and even that he questioned what was happening and doubted himself. Because this is what he knows people he manages will experience.


One of the best stories to encourage great work, behavior, actions, etc. is a story exalting an individual has exemplified these traits.

“Stories are incredible tools for reinforcing the quality of work you want to do or the type of behavior you want people to exhibit,” says Faul. “Especially when you’re trying to help your team live the company’s cultural values, giving them lots of rich examples of people doing it already makes a huge difference.”

For instance, Faul has continually noticed how hard it is for people to offer feedback to managers, particularly those a couple tiers higher in the organization. As a result, leaders often get the least amount of constructive advice for improvement, when they should probably receive the most. People are afraid. They’re intimidated. They don’t want to offend or burn bridges. Telling people it’s important to offer this feedback isn’t enough. The only thing he’s seen work is telling stories that champion this behavior.

“At Facebook, there was a well known story about an intern who, when given the chance to ask a question of a top executive, offered constructive feedback about a television interview the person had recently given,” says Faul. “That story has been told now dozens of times to show how important it is to speak your mind if you think leaders can get better. To show that that type of courage — to say something difficult to help boost performance — will be rewarded.”

You want good example stories to become part of company lore. This is how values truly become the fabric of your startup — not by posting them on the walls or repeating them during an all hands. “There are now thousands of Facebook employees who can probably tell you some version of the intern story,” says Faul.

Repetition is your key to success here. Even if people memorize your mission, vision, value statements — they probably won’t internalize them. Stories about other people living these words are the best way to make them meaningful.

“At Pinterest, CEO Ben Silbermann did this extremely well,” he says. “He would start every all hands meeting with a customer story — a different customer every time — and how different people within the org had made success happen for the company and that customer. He’s always deliberate and crystal clear. Everyone got to see our mission and the way we want to work in action through these stories every other week.”


Inspiration requires even more rehearsal than the other types of stories. Whenever Sandberg needed to rally people behind a project or cause, they would dedicate hours to refining their language, practicing and infusing their words with the emotion they wanted people to feel.

“Trying to be inspiring and missing the mark is painful and damaging,” says Faul. “I know because I tried to do it a many times before I was ready. Now I take the time to think through every inch of these stories. I feel that I owe it to my team. It’s one of my biggest responsibilities.”

Knowing what you want to say is a good start, but you really need to have the right structure. You want to sit down and outline. What information should come first? Who are the protagonists people can relate to in your story? What is the arc of the narrative that makes the story new, interesting, different, counterintuitive, resonant? When you practice in front of people, what grabs them? When do you see the emotion on their faces? How can you double down on those remarks? Sometimes, Faul’s team members will see him apparently talking to himself in his car in the parking lot. But he’s not. He’s practicing stories.

“You have to figure out what works for you. I personally don’t like memorization because it doesn’t feel organic, and my delivery can be a bit stilted. Some people love memorization,” he says. “Some people want note cards with the four bullet points they have to hit. The real advice here is to do whatever makes you feel and act comfortable. That’s all that matters. And know that it will definitely feel uncomfortable the first few times you do it. That doesn’t mean you’re doing it wrong.”

Remember, an inspiring story is a service you're providing for people you care about.

There are several components most inspiring stories share.

First, they’re aspirational. They touch on what the future could look like. Actions your team could take. Quality you have the ability to deliver. Stretch goals are motivating. People want to tackle new things so they can learn and grow. The suspense adds drama that moves people to be their best. There’s positivity in accomplishing a leap, of course. But don’t discount the positivity that comes out of trying, failing and learning too. Don’t be afraid to set the bar high.

Competition inspires. People instinctively want to be the best. But you don’t have to be talking about competition with another company or a common enemy. You an talk about competing with last year’s numbers, last month’s customer pipeline, etc. People want to compete with themselves. But if you don’t frame things in this way, you’re missing out on that source of motivation.

Express the confidence you want people to have in themselves and the organization. Act as if it’s already been earned. You know something they don’t. You see the successful outcome already. According to Faul, this was another strength of General Mattis.

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