# Leaders have to test internal stories against customers

Markdown copy of https://realalpha.app/s/leaders-have-to-test-internal-stories-against-customers/ on Real Alpha, the best minutes from long interviews with the people building AI. Cite and link the page, not this copy.

- Speaker: [Bret Taylor](https://realalpha.app/builders/bret-taylor/) · Bret Taylor is co-founder of Sierra. · Co-founded and leads Sierra, an enterprise AI agent company; chairs OpenAI's board and co-created Google Maps.
- Host: [Joubin Mirzadegan](https://realalpha.app/people/joubin-mirzadegan/) · Partner, Kleiner Perkins · Took Palo Alto Networks' cloud business from $2M to $50M+ ARR in a year.
- Show: Grit
- Episode: [How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor](https://realalpha.app/v/6v9q6k8aF6E/), Mar 9, 2026
- Moment: 11:55 to 16:33 of the episode (5 min), playing on https://realalpha.app/s/leaders-have-to-test-internal-stories-against-customers/; the episode from there: https://realalpha.app/v/6v9q6k8aF6E/?t=715

## Quote

> “every time someone tells me a story that essentially is a rationale or like rationalizing why something happened **i'm immediately skeptical**”
> — [Bret Taylor](https://realalpha.app/builders/bret-taylor/) at [15:12](https://realalpha.app/v/6v9q6k8aF6E/?t=912) · Grit

## Takeaways

1. Success claims and failure explanations are often self-serving.
2. Internal narratives can obscure what customers actually experience.
3. Test explanations against customers and seek the other side of the argument.

## About this segment

Bret Taylor explains how blame and internal narratives can hide a failing product, drawing on a Windows Phone story. Leaders need to hear directly from customers and challenge the story they’re told.

From “How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor”, Mar 9, 2026. [Watch the full episode](https://realalpha.app/v/6v9q6k8aF6E/)

## Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

[12:00](https://realalpha.app/v/6v9q6k8aF6E/?t=720) can you explain that? So, especially at larger firms, but I think broadly, you know, success has a thousand fathers, failure is an orphan. And basically what that means is anytime there's a successful product at a company, Claude Code at Anthropic or Google Maps at Google, everyone who's remotely adjacent to it takes credit for it. You know, I've had people who describe themselves as creators of google map that i've never met before like not sure you're involved but i might have been overstated a bit and and then similarly when a project fails everyone deflects blame you know it's like well the product manager blames the engineering team the you know we couldn't really get the marketing we needed the classic thing in enterprise sales is if your sales are bad the sales team blames the product, the product people blame the sales team. And it is actually the

[12:58](https://realalpha.app/v/6v9q6k8aF6E/?t=778) ultimate challenge with recruiting. But as an entrepreneur, it's actually the hardest challenge in building a company. I had a really impactful moment when I was working on Quip, where I went up to Microsoft's campus and saw a lot of people on campus using Windows phones. And I had, you know, down here, there was like, I'd never seen one in the wild, you know, like, you know, they exist, but you know, they weren't, it was just not a popular product. And I went and I talked to someone just on campus. Like I was waiting, I was in a waiting area kind of thing. And they had so much optimism that windows phone was going to beat Android or, you know, beat iOS. And this was like well past the battle being done. You know, like if you had talked to anyone in our circle, they'd be like, no, it's a two-horse race, Android and iOS. But somehow in the echo chamber of Redmond,

[13:54](https://realalpha.app/v/6v9q6k8aF6E/?t=834) Washington, there was still a chance. And you ask like, why is that? Because Microsoft tires really, really smart people. And I think it's arrogant to say otherwise. They hired like some of the best of the best. Somehow all these smart people could convince themselves of something that was self-evidently not true from the outside looking in. Well, if you think about a larger company, Clay gave me this metaphor, but it's like a sphere that grows. And the surface area of the sphere is your engagement with your clients. And the middle of the sphere is your company. And the volume grows faster than the surface area. So what ends up happening is the people in the middle of that sphere, all they can see is the sphere. They can't see the surface. And you end up with internal narratives driving decision making. And I think storytelling kills companies. You end up

[14:42](https://realalpha.app/v/6v9q6k8aF6E/?t=882) of these stories of why your product isn't selling. And that story becomes the truth. When in fact, if that story is probably someone covering their ass, you know, that story is the sales team blaming the product or the product team blaming the sales team. And if you actually think about being in the environment we're in now, which is, I would argue, one of the most competitive environments I've ever been in, the most important thing is understanding the truth about your product market fit about understanding your competitive landscape and so when i say failure is an orphan i always think about it because every time someone tells me a story that essentially is a rationale or like rationalizing why something happened i'm immediately skeptical or i immediately think about all the incentives of all the people involved and sort of synthesize

[15:30](https://realalpha.app/v/6v9q6k8aF6E/?t=930) that story through that lens and i'm always almost seeking out the other right other side of that argument and i think it's why like as a entrepreneur you just need to be on the surface of that that sphere at all times you need to be listening to your customers not you know a middle manager telling you why something happened and it is the hardest part and then when you're doing recruiting and someone says you know explaining something on the resume i can promise you every initiative that was successful.

[16:00](https://realalpha.app/v/6v9q6k8aF6E/?t=960) was solely because of them and everything was a failure was because of someone else like it it's like a tale as old as time and and and then you're like your job is to like as a it's like a detective novel like what actually happened and uh that's where references and all that happened but this is the hardest part of building a business is like fighting storytelling it's like a it's like a vc when you know a company is going well like they were you know they were intimately involved from the beginning and they knew it when nobody else knew and then when it's not going well