This is a transcript of episode 162 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

We discuss two very different stories about leaders that communicate a cultural message pithily and clearly, and reflect on why these stories were effective and how all of us can communicate culture in this way.

Show links:

Listen to the episode on SoundCloud or Apple Podcasts.


Listen to this section at 00:14

Squirrel: Welcome back to Troubleshooting Agile. Hi there, Jeffrey.

Jeffrey: Hi Squirrel.

Squirrel: So a reminder to listeners that we have all kinds of events coming up next week by the time this goes out. So we have two conferences we’re speaking at. I’m doing a workshop on Decoding Tech Talk. Jeffrey, I think you’re doing dojos like 24/7. I don’t know, have more dojos than I’ve ever seen. And all of that is on If you go to the events page, you’ll find all kinds of exciting things we’re doing. The last week of March is just mental. I don’t know why we signed up for so many things, but listeners can find us if they’re not sick of us at lots of places.

Jeffrey: Yeah.

iPods and Aquariums

Listen to this section at 00:53

Squirrel: And with that, let’s actually get started. What are we talking about this week, Jeffrey? Well, we’re going to be talking about something that we use a lot on the podcast, which is stories and memorable stories that hopefully. Particularly the idea of deliberately using memorable stories as signifiers of your internal company culture. And there’s a story that you’ve been telling, I’ve heard you tell a couple of times recently that’s a good example, can you give us that story?

Squirrel: Absolutely. So this one is about Steve Jobs. It’s about Steve Jobs when he had just come back to Apple, so in the early 2000s and one of the most important things about this story is that I know this story and now all of our listeners will know this story and explain what that’s about when we get done with the story.

Squirrel: So it’s surprising that we know it and it’s good. Well, it’s illustrative that we know. So Steve had had this vision or somebody told him about this vision of a thousand songs in your pocket. It was very exciting. The leading tech was the Sony Walkman or something like that, which was relatively big compared to the iPod, which this would eventually turn into. So somebody in Apple decided to work on this project and Steve told them to, I’m sure. And in secret. They produced the very first iPod prototype and it was a little square and it had wires hanging out of it and it was the only one in existence. And the team walked in to see Steve in his office and they said, “Steve, look at this, it’s a thousand songs and it fits in your pocket!” And he took it and he turned it around and looked at it and threw it back down on the desk and said, “it’s too big.” They said, “Steve, Steve, I’ve got it as small as we possibly can. We can’t shrink it anymore, this is just incredible. Look at what we’ve done. It’s so much smaller.” And he picked it up again. He said “still too big” and put it back down. They said “But Steve, we can’t do any more, it’s impossible.” He shushed them, picked up the only iPod in existence, the prototype with the wires hanging out of it and walked over to the aquarium that he had in his office and into the aquarium. He dropped the only iPod in existence to the shock of the people standing around. Who would now have to recreate the thing. And he pointed to it and he said, “look, there are air bubbles coming out of this prototype. That means you haven’t taken all the space out of it. Don’t come back to me until you’ve taken all the space out of it.” And he threw them out of his office. And the important thing about this story, as I said, is that we know this story because what happened was the people got thrown out, went and told other people because it was so shocking and noticeable and demonstrative and surprising and this had a big effect on Apple. And we’ll put the link to the original story in the show notes. One of the people who worked under Steve said this affected everybody because nobody wanted their iPod thrown in the aquarium, even if they were working on a disk drive. So they wanted to make sure that they paid careful attention to detail and weren’t sloppy, because even though Steve wouldn’t look at the vast majority of decisions people would make, he had communicated through this action that attention to detail was important to Apple. So he had communicated the culture that he wanted in this way.

Jeffrey: I agree it is a completely memorable story. Now, this came up in part because we were talking to someone and we were describing the importance of storytelling inside of your organisation, and also that stories are the unit of idea transmission so that you want to have memorable stories that you can tell internally that will tell people what’s important, you know, who are we? How do we behave? And this story fits several of those ideas, it has the idea of attention to detail matters and it had that impact on the culture. Now, an interesting thing happened here, when we chose to do this, as we were talking about before we got on the air, I had some real ambivalence about using this story, which was I worry about too many people who think that they are Steve Jobs or that the right ways to be kind of abusive and they’ll use this is like, ‘yep, see, Steve Jobs was demanding. And that’s why I can be demanding. And, it’s like one of those rules of the universe, you’re not Steve Jobs.’ But the other thing, too, is that I don’t think Steve Jobs was really, choosing a story. I think you look back and you said yourself ‘he was communicating through this what he wanted.’ And I think he was to those people, but not necessarily everyone else. I think he was being himself. And so I wonder then about kind of are we telling people, you know, if you want to have memorable stories, you should make dramatic, violent acts? I’m worried about the message we might be telling here with that story.

Squirrel: Sure. Why don’t I tell another story that is not quite as dramatic, but is equally memorable and it doesn’t have Steve Jobs in it and see if that one works.

Jeffrey: Let’s try that.

A Memorable Story

Listen to this section at 05:55

Squirrel: OK, so this is a story about someone both Jeffrey and I know, a CEO of a company that I worked for and the Jeffrey now works for. And this CEO had absolutely painstakingly negotiated this gigantic contract with a massive, massive bank. And you can imagine the armies of lawyers who descended on our offices and negotiated with this person, the CEO, late into the night. And they were discussing subparagraph Q and redlining things. And it was hundreds and hundreds of pages. So he called me into his office one day and he showed me the contract. He said “it’s done.” And I thought maybe he would have it bound in gold cloth or something. I wasn’t sure what he was leading up to by telling me. I was celebrating. I was very, very happy that I could see him again because he could stop being on the phone to the lawyers all the time. And what he did was then a very surprising thing, which I found very memorable. And it’s exactly the same as the Steve story, that the noticeable thing about this is that we know the story. He picked up the contract this thing had worked so hard on and he put it in a drawer and he closed the drawer and he said, “Squirrel, we are not going to look at that contract again. What we are going to do is focus on making this gigantic bank really, really happy. And if I ever have to open that drawer again and look at anything that’s in that contract, we have failed.” And then he sent me out of his office.

Squirrel: And that was so memorable that I then went and told everybody else about how we were going to approach this bank. And in fact, we never opened the drawer again. We made the bank very happy and all ended well. So in a similar way, that was not necessarily so violent or vigorous, he wasn’t telling me I’d done a terrible job, as Steve was. But it was equally memorable and equally authentic.

Communicate Culture with Stories

Listen to this section at 07:52

Jeffrey: And the thing that links these two stories for me is for one thing, is that you’re telling them. Not just that, but it was, in the case of this company, you went and told the story what you had seen and similarly in Apple, people went and told the story of what they’ve seen.

Jeffrey: And it’s the story that people were were telling we’re sending a signal, a message. We came that sort of idea of, what is it like to be here? And in this case, you know, the second story you have the message of or our goal is to make our client very happy. And you could tell people that and pass it along. And I think that was the kind of Aha moment for me as we were talking about this, I was worried about, well what’s actionable about this? For our listeners, are we telling them, you know, do memorable actions? That seems really hard.

Squirrel: And I think in either cases, as you were pointing out in the Steve case, I don’t think in either case the person who was performing the action, the cultural transmitter, the CEO or Steve Jobs, was thinking to himself, ‘how can I transmit this best? I will come up with it, I will come up with a script and a set of actions, and I will rehearse it at home. And then I will do the thing. I need to turn my wrist this way when I drop it in the aquarium. So that’s most visible.

Squirrel: Wasn’t doing anything like that, but the person was being authentic. The person was acting in a way that was very, very adherence-full. I don’t think that’s a word, but was adhering very closely to the values that he wanted to communicate and that came through in the action. And then I imagine there were many actions, but the ones that were memorable got the message through.

Jeffrey: Yeah, and so then, as you said, they were just being authentic, so which I suppose that is maybe a type of message for people is, be your authentic self. You enact the values that you care about and people will be telling stories about you and maybe that’s another thing, another lesson. People are going to tell stories about you as a leader. If you want them to be telling the stories that are in line with the culture you want, you need to be behaving consistently with that culture. The other thing that came up to me is it seemed to me like one of the challenges that leaders have and one of the duties they have actually is to make their organisation legible to the people within it to help people understand what’s going on. And this becomes more true the larger the company is. I’m currently in a very large organisation, and there’s often times where people are unclear about exactly what’s going on. And that uncertainty is very painful. It can be very helpful that as a leader, when you find people and they’re unsure about what to do, if we can orient them about what’s desirable by using stories. I think this is a case where, as the observer and as the leader, you can you can say, ‘well, what are those events that I have found personally to be memorable to me? What were the things that struck me and to tell those stories? And I can help reinforce my vision of what this place wants to be by the stories that I choose to tell other people. And so now we can say, OK, look, “here’s something you can do. You can you can curate your own memories.”

Squirrel: And your teams and encourage them to carry on and to transmit onward the memories of yourself or other people that match the culture.

Jeffrey: Yeah, and that idea was then the final piece that fell into place for me was the idea that it’s not just my own memories, but I can actually survey my team and ask them and say, “what have been important moments for you here? What’s happened? Maybe what are things I have done that helped you understand our culture?” And now this is even more actionable. “If there’s elements of our culture that you like, what are they and what are the things that let you know that that’s the culture we have?” That’s something that you can do as a as a leader. I’m intentionally using the word leader here and not manager. If anyone could do this. And by doing it, you will be a leader if you start collecting the stories that are about the culture you want to have and say, “here’s examples of how we’ve behaved” and share them and that they can become, by being repeated to each other as reminders, they act as attractors of the kind of behaviour you’d like to have, and people will be more likely to behave in a way that’s consistent with those stories.

Squirrel: And that could be out of fear, as in the Steve Jobs case, where you don’t want to have your phone dropped in the aquarium. I don’t think we’d recommend that one quite as strongly. Or it could be through the power of the example as in the contractor in the drawer story where that’s just a powerful image and it’s hard to get out of your mind and people can latch onto it and use it for a long time as a message about how to treat your customers. Both are powerful. I think I prefer the contract and draw with less fear. I think that’s likely to be more successful.

Jeffrey: And this seems like a great opportunity to to tap into our audience here. Do you have memorable stories that were important about the culture you were part of? And I must say this, they can be good or bad stories because these things are just as true when there’s a negative story. But I’d especially like to curate some of the positive ones. I would love to hear from our listeners about examples, stories that you would tell amongst your teams or amongst your departments or your companies that you thought helped capture the culture of what you wanted to be, the aspirational stories. And I’d love to have some examples from our audience and add to our repertoire so we have people to call on other than Steve Jobs.

Squirrel: Yes, that would be helpful. Excellent. So if you’d like to share some stories, you can find us on You’ll find Twitter and email and I don’t know whatever else we’re on, LinkedIn, you can find us in lots of ways. You’ll find free material there. As I mentioned at the top, we have lots of activities going on next week and into April. So check out the events page for ways to get in contact with us, participate with us in conferences and workshops and other exciting things. And we’ll be here again next Wednesday. And maybe we’ll have some of your stories to talk about. I’ll see you then, Jeffrey. Thanks.

Jeffrey: Thanks Squirrel.