Simon Says be an Optimist

Simon Sinek, best selling author of “Start with Why” (and 3rd most popular TED speaker of all time), sits down with Christy Lake, Chief People Officer at Twilio, to discuss the Great Resignation.

“More than 24 million people quit their jobs between April and September of 2021” says Christy. The figure is astounding. It’s made up of people from every industry and every geography.

Simon got his start in ethnography. Christy studies people and culture at Twilio everyday. They both recognize nothing can be better and more real than human connection.

If you have a distributed work force, you actually have to do more to create relationships, you can’t just allow it to be organic like it is in the office.

Simon’s team has a Monday morning huddle for 45 minutes to an hour, and says “there’s no discussion of work, it’s strictly human connection.”

Funky Time by Hurca

He says this is how we find out some people have kids, somebody’s parent is in the hospital, or someone loves to cook.

It’s important to work together, even though you’re not actually together.

The only difference is, now, we need to do these things prescriptively, when they used to happen organically.

Suddenly off-sights have more importance now. They become about people needing to spend time with each other.

Underrepresented populations have not had some of the experiences that they would typically have, like micro-aggressions. Christy asks Simon, “how do you think that looks in the future, when populations are able to opt-out of being in-person, choose to be home more often?"

“Empathy runs through it all,” Simon says. “It’s about the importance of listening. Find where people stand, and how they feel.”

We’re emotional animals. We react and make decisions based on our feelings, which include ego, fear, anxiety, and all the things!

It feels like the past few years have been “holding up a mirror, revealing a lot of things that we didn’t see, and it became starkly clear to see the difference and recognize that I get this here, and not there” Simon says. Someone who disagrees with company decisions needs to be seen and heard. This is vital.

“We have a huge advantage being able to point these things out, and talk about them, rather than just feel uncomfortable and don’t know what it is."

This puts pressure on all of us as employers to think about creating equitable experiences for all employees. 

Intertwined by Nahuel Brad

“Whether it’s remote first, or some kind of hybrid combination, how do we ensure that folks who may choose different paths, still have access to career development opportunities?"

At the end of the day, we’re here to do good work, and hopefully continue to learn and grow. 

"The pressure is on" she says.

Simon used to tell people, “let go of work and have personal time, don’t work on nights or weekends.” Since the pandemic he had to pull back on that, explaining that now he doesn’t know when people want to work. “Maybe they want to go to the gym in the morning, start work at 10-11pm, and stop around 7-8, because they’re happy to do that."

This makes communication even more essential. “I have to bring my kids to school, would it be okay if I start work at 11am, which means I can’t attend any meetings prior? Can we push meetings past 11am?”

"The answer is probably yeah” but what strikes employees (and discourages them) is the demand or announcement.

Groups by Kasia Bojanowska


Christy smiles and says “expectation management makes the world go round."