The best way to share and embed cultural DNA is person to person. When you’re growing fast, the new people you just hired most likely have some responsibility to hire as well, so a week of orientation isn’t going to cut it.

If you have fifty people who understand your culture and add a hundred who don’t, you will lose that culture. It’s just math.

So when bringing in new employees—especially execs—you shouldn’t just throw them in the deep end, hand them a branded company notebook, and think you’re done. The first month or two are crucial and should be a period of positive micromanagement. Don’t worry about getting too in the weeds or not giving them enough freedom. Not at first. A brand-new person needs all the help they can get to become really well integrated. Explain how you do things in detail so they don’t make mistakes and alienate the rest of the team right off the bat. Talk to them about what’s working and what isn’t, what you would do in their position, what’s encouraged and what’s verboten, who to ask for help and who to treat with kid gloves.

That’s the best way to immerse someone in the culture, style, and processes of a team. Give them the push they need to start running with the pack rather than leaving them standing on the starting line, reading some docs, hoping they’ll catch up.

Always remember that it’s scary joining a new team. Not knowing anyone. Not knowing if you’ll fit in. Not knowing if you’ll succeed.

That’s why I started doing brown-bag lunches with the CEO. Matt did them too. Every two to four weeks, we’d gather a crew of 15–25 new hires and existing employees and have an informal lunch. We tried to cross-pollinate different people from different groups, a good mix from around the company. No managers, no executives, no keynote presentations. Just an

opportunity for them to get to know the bogeyman at the top and for me to get to know them. They asked me about our products, our policies, about me and Matt and our history at Apple. About why we didn’t allow massages, about why we had so many code names. [See also: Chapter 6.4: Fuck Massages.] And I asked about what they were excited about, what they were working on, why they joined.

It was my chance to highlight why their role was important, to talk about how their team’s goals powered our company goals, about our culture and our products and new projects and what was going right and what wasn’t. New employees had the chance to come directly to me with their questions as well as meet existing employees who were already steeped in our culture, who could help them and lead by example.

Any employee could come to five lunches a year. And each lunch was a cultural inoculation, a vaccine against indifference and apathy, against thinking that what you do doesn’t matter and that nobody at the top knows who you are.

He affirmed that we all have a story to share and something to learn from one another. That if we take time to connect, we can learn anywhere and from anyone.

When Eric Schmidt was CEO of Google, he said, “We run the company by questions, not by answers.” Their Friday afternoon company wide meetings were famous for the wise questions that were posed from line-level employees to leadership.

So often I’m called in to help lead conversations about mission, value, and purpose. When, really, the only questions that matter are those that tell us who we are and wish to be.

• How would our organization respond were we to hear all the things that are being said, regardless if they are being said with words or deeds? 

• What does it mean to be a leader at our organization? 

• What does it mean to be grown, a fully actualized adult? 

• How would we feel if our children were to work for the company we’ve created or the team we lead? 

• How has the unsorted baggage of what has happened to us shaped who we are as leaders? 

• When our employees and colleagues leave our sides and our company, what do we want them to say about our time together? 

• What do we believe to be true about the world? 

• What do we, as a community of people working toward a common goal, believe the world needs?

One way to keep meetings short and avoid the signalling that comes from repeating information that everyone knows is simply asking everyone, “What do you know about this problem that other people in the room don’t know?