Sep 1, 2026 · 21 min · 9 segments
"Either you hired the wrong CEO, or you need to take a step back as a board." Irene Shih has sat on both sides of the governance table, as Board Member and CEO, and she's direct about what each one…
Irene ShihGuest
Christina GreenbergHostSo one of the reasons I was most excited to talk to you, Irene, is we've been thinking a lot about founders, both in terms of founder starting and founder transitions.
And you've just done both, right? You were a founder at an organization that you left, then found a new organization.
So starting with the founding part, when there's no playbook and no predecessor, what does the job require of you? And how do you set up those systems for success?

I think if you have a really great mission, one of the embarrassment of riches you get is that you have a lot of people who are excited to contribute and get involved in some way.

And one of the tougher jobs of being in the founding stage of something is really figuring out what good ideas you're going to start with.

What's the sequence of priorities? And then how to kind of get everybody excited, you know, while we might not be able to do 25 or 30 things all at once, getting people really excited, even those who had some different ideas of like the potential of them to contribute to these like top three things that we're going to do this year.

Maybe this year we're focused on three things, but in three years from now, you know, if this builds, there's a potential to grow in these areas and helping people see that there's the today, there's the tomorrow, and then there's the longer term.

So I would say one of the things that I think is a challenge, but it also comes from the fact that there are so many opportunities and embarrassment of riches when you have a great mission is that you attract people who have a lot of good ideas and want to contribute in some way and helping people to really put a container around all of those great ideas and think about the sequence and priorities that you know, that you're going to do things and getting them excited about that.
And having just experienced a founder transition as well, I'm sure it's on your mind, but how do you set up the structures for a new organization such that someday when you're no longer leading it, it still can thrive without the founder?

I've always really believed in systems, infrastructure, making sure that you are documenting things that you are doing so that it lives somewhere where people can see it, read it, all of that.

But the other part of it that I think is even more important in a transition of any leader, whether they are a founder or not, is that the culture they built survives you.

And I think because, you know, there will always be things that are the spirit of your organization that don't live in documents.

It's that, you know, everyone knows what it looks like to live into these core values because you've lived it so much as an organization over and over again.

You have a culture that is going to continue to run on those values and on those ways of doing long after you leave.

And yes, they'll have the documentation and some of the infrastructural pieces that are still there.
So one of the reasons I was most excited to talk to you, Irene, is we've been thinking a lot about founders, both in terms of founder starting and founder transitions.
And you've just done both, right? You were a founder at an organization that you left, then found a new organization.
So starting with the founding part, when there's no playbook and no predecessor, what does the job require of you? And how do you set up those systems for success?

I think if you have a really great mission, one of the embarrassment of riches you get is that you have a lot of people who are excited to contribute and get involved in some way.

And one of the tougher jobs of being in the founding stage of something is really figuring out what good ideas you're going to start with.

What's the sequence of priorities? And then how to kind of get everybody excited, you know, while we might not be able to do 25 or 30 things all at once, getting people really excited, even those who had some different ideas of like the potential of them to contribute to these like top three things that we're going to do this year.

Maybe this year we're focused on three things, but in three years from now, you know, if this builds, there's a potential to grow in these areas and helping people see that there's the today, there's the tomorrow, and then there's the longer term.

So I would say one of the things that I think is a challenge, but it also comes from the fact that there are so many opportunities and embarrassment of riches when you have a great mission is that you attract people who have a lot of good ideas and want to contribute in some way and helping people to really put a container around all of those great ideas and think about the sequence and priorities that you know, that you're going to do things and getting them excited about that.
And having just experienced a founder transition as well, I'm sure it's on your mind, but how do you set up the structures for a new organization such that someday when you're no longer leading it, it still can thrive without the founder?

I've always really believed in systems, infrastructure, making sure that you are documenting things that you are doing so that it lives somewhere where people can see it, read it, all of that.

But the other part of it that I think is even more important in a transition of any leader, whether they are a founder or not, is that the culture they built survives you.

And I think because, you know, there will always be things that are the spirit of your organization that don't live in documents.

It's that, you know, everyone knows what it looks like to live into these core values because you've lived it so much as an organization over and over again.

You have a culture that is going to continue to run on those values and on those ways of doing long after you leave.

And yes, they'll have the documentation and some of the infrastructural pieces that are still there.
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