for the organization that they lead.

We all have heard the stories of the larger-than-life CEO

whose own name and brand transcends the company

that he or she is representing.

This is exciting because you see their names on headlines.

You see them with a big following.

People are interested in leaning in, wanting

to know what this big personality is going to say next,

and what their organization is going to do next.

But there's a big question here of the role that

that CEO plays within our culture, in establishing how

that product, that service that they represent, will service

the nation will service other nations and the world

at large. I think about larger-than-life CEOs

like Steve Jobs, like Jack Dorsey, like Elon Musk,

they have a platform and I would argue then a responsibility

to stand upon it and look at how their products,

how their personalities, how their contributions are

affecting the world and the discourse about the future

of tech, the future of work and the future of how

we interact at large.

Steve Jobs in particular fascinates me.

He could be direct, he could be mean,

but he could be very focused and specific

about what he wanted and the excellence that he demanded

of his people, and in doing so, he created something

that was unlike anything anybody had ever experienced.

He really thought that the beauty was in the simplicity.

The iPhone is just a simple little black rectangle

that has changed how we communicate, how we talk.

STEVE JOBS: Our goal and we think

what serves the customer best

is to constantly be working on making things better.

ANNA BUTRICO: Though a complicated character,

he elevated these questions

of how the form of the things that we consume

influences how we live and work with them.

A CEO has great opportunity to elevate the brand

of a company, to really put it

in the public eye and make people really trust

in the brand that they're buying.

But they also have the opportunity to do the exact opposite.

The risk you run is when that personality,

that brand of the person is bigger than the brand

of what the organization of a whole aims to achieve.

Leadership is important, don't get me wrong

but when leadership steps on the company,

when leadership contradicts what the company wants

to do, then you have a bigger problem.

I'll start with Patrick Byrne

who was the CEO of Overstock.com.

He was a very impressive leader.

He had three degrees. He had long history at Overstock.com.

He had helped them go online.

It was really in the most exciting part

of the business that it had ever been historically.

He ended up having a private blog

where he would talk about the earnings,

where he would foreshadow new developments

within the company but he would also start

to talk about some conspiracy theories that he had

about himself about his role as Overstock.com CEO

and how that interacted with the government.

He believed that he was tied up into a political scandal

that would be a hundred times bigger

than Watergate as he said.

He said that a Russian spy

was intimately involved in his life.

The stock of Overstock.com crashed

because people said who in the world is the CEO

and what is he saying?

And what does that say about the Overstock brand?

The other one we think

about is Elizabeth Holmes from Theranos.

They created this new blood testing technology

that was really fascinating.

What we found though,

is that Elizabeth Holmes was a bit deceptive

in the science, that Theranos technology didn't work.

They had a very easy, accessible result

of a test that they would use

with investors that they would use publicly to say, look

our technology works when behind the scenes, it didn't.

She very intentionally took her board of directors

and made sure that none of them were scientists.

Some of them were former MDs.

A lot of them were policy officials.

None of them really knew much about the specific

blood testing technology that she aimed to create.

So she went completely unhinged

in how she was advocating for the technology,

she'd fire anybody who stood up to protest it.

When selecting a CEO, what should you think about?

Is it best to just think about what values

the organization has and if that person

will fit inside those values?

I think it's a bit tricky

because values just like people constantly change.

Each value is a narrative about who the organization is.

And the leader themself introduces their own narrative

about where they are taking the company.

I think having a really diverse board

of directors is absolutely critical.

You need to have people who hold that CEO accountable

but who have very different views of what the CEO is doing

what industry the organization sits in,

what the objectives are, et cetera, et cetera.

Diversity of thought is

of course important; capability, crucial.

But that thought piece

to really challenge that CEO is critical.