Why Most Company Cultures Fail and How Great Leaders Fix Them

Melissa Daimler: ReCulturing ​ Jason S. Bradshaw: What if the culture you think you have isn't the culture your people are actually living? Mostly just talk about culture, like it's a plaque on the wall, a thing they have. But today's guest says that culture is something you do, and if you don't design it, it designs you.

​ Jason S. Bradshaw: Melissa Daimler has helped shape the culture behind some of the world's most influential companies, Adobe, during its SaaS revolution. Twitter, during its hyper growth era. WeWork during one of the most turbulent chapters in corporate history and most recently at Udemy, where she has led transformation of learning, talent and culture in the age of AI.

She's the author of ReCulturing, a book that has become the blueprint for leaders who want to build cultures that actually work. Culture is where strategy, behaviors, and systems line up to create real performance, not just pretty posters. So today we are diving into the truth most leaders avoid. Culture isn't an aspiration, it's an operating system.

And every decision either strengthens it or weakens it. This is gonna be a powerful one. I'm Jason S. Bradshaw and this is Chats with Jason.

Melissa, welcome to the show. Melissa Daimler: Thanks, Jason. It's great to hear your overview of culture. Jason S.

Bradshaw: So Melissa, take us back. What moment in your early career made you realize that culture isn't a vibe? It's a system. Melissa Daimler: I first realized that it's part of the system when I was at Adobe, so this takes me back...

I've been in tech for over 20 years now, and at Adobe I learned a lot about the connection between culture and strategy, and even the purpose of the company. We had, the good fortune of having Donna Morris, who's now the SVP and Head of HR at Walmart. She was the head of HR eventually at Adobe. And I think she, with Shantanu, the CEO, understood that, as you said in your introduction and that I emphasize all the time, culture is not the fluffy part of the business.

It's not the happy hours. It's not the slogans as you said, but it really is something to be leveraged much more powerfully than I think companies do. So at Adobe we didn't just realize that as part of the system, we operationalized it. And so when the company did go through a massive transformation to become more of a SaaS company, we had to not just look at our business, we had to look at how we were running our business, and that's culture.

So everything from looking at our organizational design to our leadership skills, to how we made decisions, to how we were gonna operate in many more countries than we were currently operating in. To again, be successful, we had to not just think strategically, we had to think culturally. Ever since then have really looked at culture as a set of practices and processes and behaviors that if leveraged well and connected to the strategy, it can be a huge differentiator for your business.

Jason S. Bradshaw: Makes a lot of sense. I'm wondering whether there's a belief about culture that you held early in your career that now you go... no, that's not right and you've changed your belief.

Melissa Daimler: I think what I was told earlier on, and I am old enough to have lived through the.com .bust era is that, culture is for HR to run. It is the free food.

The happy hours. It's the ping pong tables. It's the games. It's the nice to have.

So that is what I was taught. And what I was lucky enough to experience again early on is, wow, this is much bigger than just happy hour. So I, very early on was able to shift those beliefs. It's unbelievable to me today that people still don't leverage culture, as strategically as I think they should.

Jason S. Bradshaw: I'm sure we'll get into that a little bit deeper. I'm wondering though, you know, you've said before that culture efforts fail because values never become behaviors. What's the biggest mistake leaders make when they're you know, so called fix the culture?

Melissa Daimler: Well, I think first of all, they go into it with an old belief, an old definition of what culture is, and so I think when I'm working with CEOs or founders today, and even when I was inside as an operator, one of the first things we did was just get a level set on. What do you think culture is? And what has been your experience with culture? And so I think all of us getting on the same page on, the definition of what culture is, and isn't, is really important.

I have turned down business. I have declined to work with some people who have said we just need a bunch of values for you to create. And that's just not, I don't think that's going to be value add for them. It's gonna be a waste of money.

It's gonna be a waste of time. And I think it does a disservice to the HR and people industry. If the intent is just to check a box and say, as a founder or as a CEO, we created and posted our values on our website or on our wall, then, I don't think we should do that. So I think that's the mistake that a lot of companies make is they think that we're done once we have that list.

And I think that is just the beginning because a true culture work and what I talk about with reCulturing is that I always give the example of innovation. I'm in Silicon Valley and we talk a lot about innovation, but innovation for one company could mean something very different for another company. And so let's talk about what good looks like in each of those. One company I worked with, at the stage they were in, they actually wanted to slow some ideas down because they were realizing they were spending way too much money on some of of the ideas that weren't fully baked.

And so they created this behavior of asking each other why we need to do that now. And the other company that I worked with was going way too slow and they needed more ideas out there and so they wanted to get a minimal, viable product out as fast as they could. So they made it okay to be 90% good. It didn't have to be a hundred percent or beyond that.

So I was just asking not only what that value is, but what does good look like if you were to see people being innovative in this company. So I think it's just really important to what I call codify culture into those behaviors, and then you can actually do something with them. You can then bake those into some of the core processes that you're already doing. So interviewing and hiring, onboarding, developing people, rewarding having some consistent approaches to giving coaching and feedback around the dreaded performance review process.

To me, the question that I always ask to, when people want to kind of codify their culture is, are you looking at this as one more thing to do? Or is this ultimately something that you think is going to help your business and your strategy be more effective? And so if it's the latter, then yes, we will work together and I think it'll be much more successful. Jason S.

Bradshaw: Makes a lot of sense and I can't agree more that the work doesn't end when you've done the posters or created the list. That's step one of many steps to shaping a culture. I'm wondering, how do you define culture? Melissa Daimler: So I define culture as...

first of all, it's a verb. It's something we do. It's not something we have, and it's a system of what I call behaviors, processes, and practices that are connected to the larger organizational system. It's not a one and done thing.

Like I've been in companies, I think at Adobe, we didn't call it reculturing at the time, but we recultured three times because there were major inflection points, turning points. We bought two major companies. We had two acquisitions. We had a CEO change.

The SaaS transformation. There were a lot of places where we had to reset on. Was this still the culture that we want to drive and design? And mostly, a lot of the values didn't change, but how those values showed up behaviorally did.

So I define it as a system of behaviors, processes, and practices that are ongoingly exemplified in the company and reviewed. Jason S. Bradshaw: So let's just say I'm a senior leader, new to a business, and I'm wanting to understand what its real culture is not what's on the posters. Where should I look first and why is it never as simple as just reading that so-called company values?

Melissa Daimler: I do think, culture shows up in, the everyday behaviors that we do. You can see culture in how decisions are made and how people are communicating with each other. How you run meetings. How open and supportive is learning and development in an organization.

And so I think the first actionable step that I always tell leaders and even employees is when you look around day to day, and when you're in meetings what are those great employees, those high performing employees doing? How are they communicating? How are they making decisions? How are they being collaborative?

And then what are they not doing even? You can learn a lot with observing what they're not doing. Are they pausing before they're saying anything in a meeting because they want other people to get their voice heard? Are they asking more questions?

Are they taking time to do an after action review after some major launches and really getting everybody's point of view? I think you can really learn a lot by looking at your high performers and even your low performers on what good looks like. So I always start if it's a company that already has values I might start with saying, let's look at those values. How do those show up for you?

What does that mean to you? And mostly it has a very different meaning to senior leaders. And I talked to a number of employees and in these cultural audits too, and that's always fascinating and surprising to the CEO and the senior leadership team because they thought they were super what those values were. Jason S.

Bradshaw: Yeah, and often super clear isn't actually replicated in their behaviors. They feel they've communicated something, but then they haven't walked the the talk, so to speak. You've worked with some phenomenal brands. You were with Twitter during its hyper growth stage, and obviously that organization has transformed a little bit, in recent years.

In that hyper growth phase, how did you build systems that could keep up with that growth without breaking people? Melissa Daimler: Yeah, I do say that I was at Twitter in what we call the glory days - 2000 to 2016. And to your point, it was a lot of growth. I think there were a few things there.

I think we had Dick Costolo was the CEO at that time. He was very supportive and motivated to make sure that we codified our culture at the time. We had 10 different values, and we were developing a management and leadership learning experience for the first time. He was actually leading a manager session himself that reinforced a lot of those values.

And then we built on some of the teaching that he did as a CEO to further and, leverage that experience. So I think we had some really good leaders who wanted to make sure that this is the challenge in any fast growing company. How do you make sure that you're keeping the essence of what is so great about that culture when it was 20 people who sat in a sofa every Friday to review what just happened for the week? To...

when I left that company it was 4,000 employees globally. We grew very fast. So I think we were able to keep the core values but the behaviors shifted over time. And so we made sure to codify those.

And even at the end, the last year, we were able to create even feedback loops and feedback mechanisms based on those core behaviors and the skills that employees needed to develop. I think there are moments, very simple moments in any company that you can reinforce the culture. Like I said we had a lot of all team meetings and we, at every meeting, we had a value that was represented and we made sure to reinforce that in the different presentations that people did. Examples of what teams, really exemplified each of the values.

So, there's pretty simple but powerful ways to reinforce culture, again, not as an add-on, but is just part work . Jason S. Bradshaw: Yeah, I love that it's about the way we work, what we do as opposed to making it an individual's responsibility for the whole company. Talk about about diversity, you've gone from Adobe transforming into a SaaS company and doing acquisitions.

Twitter through, its growth and glory day, shall we say. And WeWork, which, there's even a movie about some of those turbulence times at WeWork. What does culture look like in a crisis? can you have a culture in a crisis?

Melissa Daimler: Yeah, I've yet to watch that movie because I lived it. But I talk about it a little bit in my book ReCulturing. I can now say that I really appreciate having worked at WeWork for a year because it amplified how important culture really is. And if you don't consider culture as you're growing and you just look at your revenue and your strategy then, things don't always turn out and we all know of course what happened with WeWork.

I think when I was there, we weren't quite in crisis mode. We were still in the preventative mode. We saw what was coming but we were able to do an exercise around the values. We started to codify them.

We built some of the first management development programs around the world. But, I was just there a year, so it was definitely harder to shift the meaning of culture from... you saw the movie, I don't know if you read the book, but there were tequila shots happening on Monday evenings and summer camps with thousands of employees coming together over three days. And I think the thing I learned there and try to emphasize is, one of the pieces of culture is practices.

Practices And Practices change over time. They're dependent on how big you're getting. When WeWork first started, they had these beautiful gatherings every year with employees in the backyard I think of one of the founder's homes and volleyball, barbecue, everything you can think of at a summer camp. But as you evolve, when you're 5,000 people like having a summer camp we may wanna think differently about what that practice should look like and how to make that safe for every employee.

And I think one of the challenges was the need to keep the practices the exact same way at 5,000 versus 50 or So I think what leads to crisis is the inability to reflect and talk through how we need to change as we're scaling and growing as a company. Jason S. Bradshaw: a lot of sense and a great reminder that what worked yesterday, or five years ago, it may not work today. And that's not necessarily a bad thing.

It's only a bad thing if we fail to recognize and to evolve. You like a challenge and, AI is certainly throwing up challenges for almost everyone these days. I know your work at Udemy, led you to ReCulturing during that AI shift for them as a company. And I'm wondering.

what did AI force you to rethink about culture, and learning and leadership at large? Melissa Daimler: I think one of the big mistakes that a lot of companies are still dealing with in 2025 is looking at AI as just a technology change and We're realizing more and more that it is more of a culture change. And it needs real change leadership in order to have some of these AI initiatives be effective. So I think one of the things, we did at Udemy in the beginning, was just what a lot of companies are doing now, is just let's do a level set and make sure everybody understands and has AI fluency.

Do you know what a good prompt looks like? But beyond that, we made sure that we created discussion in the teams. We had a team dialogue and questions for teams to discuss around. Hey, I just took this online course, but here are some of the things I learned.

Here are some of the prompts I used. What are some ways that we can think differently about how we're working in our function or our team that AI might be able to augment or automate. And over the last year I know my team, I left earlier this year, but did a lot of work in partnership with the technology teams. So I think the companies that are getting this right are partnering, have a true partnership between the people team and the technology team, because they know that it's not one or the other.

It's not just a change leadership rollout and a culture rollout. It's not just a tech rollout, but it's integrated strategy that we have to do together. I still I lot of companies are getting it wrong. I think it's such a missed opportunity.

Even with the recent announcements. Amazon just laid off 14,000 employees and the communication was that initially it was an efficiency problem and then it's all culture fit problem. It just leaves people feeling fearful. And not really trusting what's next.

And you contrast that with a, Doug McMillon at Walmart who was very transparent, has been transparent since the beginning by saying, we're definitely going to have jobs that are gonna go away and our intention is that we create an equal number of jobs for you that are different. We don't even know what those look but in any case, we will work together to make sure you have the skills you need continue to be successful here. Very different messages with ultimately similar outcomes.

I think there is such a huge opportunity that, we saw this in the pandemic too. You saw CEOs and leaders handle the messaging really well and sharing. I don't have all the answers. Nobody has the answer.

But what I can tell you is this. What we can control is, X, Y, and Z. I think it is a cultural moment in how leaders are managing, leading, and communicating this change. Jason S.

Bradshaw: Makes a lot of sense and I agree that it's the tool itself is just that, it's a tool, but if we don't lead with authenticity and and just show up around what our intentions are, it makes it difficult for people to actually know how they should act, let alone anything else. Don't wanna be all doomsday on AI, where do you see culture and learning evolving next as AI becomes embedded into everyday workflow? Melissa Daimler: Yeah, I'm actually really excited about AI. I think there's huge opportunities and I think a lot of companies are getting it right.

I was just talking to somebody at Visa this week. And they're, they've been doing this for three years - the right way. And looking at, what do we wanna measure? How do we wanna increase?

Is it speed? Is it efficiency? Is it lowering effort? How do we encourage people to really be innovative and think differently?

How do we give them the skills? I get super excited about the coaching opportunities we have with AI and that is a huge component I think to exemplify culture. There are a number of AI coaching bots out there right now. Some better than others, but even if you have, your core language, large language model, whether you use Gemini or ChatGPT or Claude or whatever, a lot of companies now are leveraging kind of whatever meeting bot you have embedded.

Employees are asking questions on, how could I have shown up better, or what could I have done differently in that meeting? Or, these are the skills that I'm really trying to hone. Did that come through? In the meetings this week.

So when you have that kind of data, when you have somebody kind of sitting next to you in every single meeting to give you feedback, even the best managers are not thank God in every meeting. I think that can bring a whole different flavor to the conversation with your manager around development, because then it's not arguing or debating what do we need to develop. But it's more, here's what the data shows me from my meetings. I think some employees and companies are also leveraging even data interactions from Slack, email, then, talking with your manager about do you see that as well?

What, what are some of the things you think I could do differently to help me build these skill sets even more? So I think, if we use AI and we leverage the tools in some of the ways I'm seeing, I think we could transform some of these core processes that have been like... for 20 plus years, I've been in this industry, we've talked about how awful performance reviews are and how inconsistent coaching and feedback is. And so what if we had real quantitative and qualitative data that we could now leverage and this whole process can be a lot easier and the conversations can be a lot richer.

So I don't know. That's a use case that I see coming up a lot in the companies that are really doing that well are able to kind of even integrate some of those values and behaviors into the bots to make sure that they're reinforcing those behaviors that they want employees to continue to hone. Jason S. Bradshaw: Absolutely.

I also love that it allows someone to take personal accountability for themselves and not have to wait for the manager to give them feedback which, you could argue has always existed, but yeah, sure, people can be personally accountable, but you don't know what you don't know. You've got blind spots, everyone does, and AI definitely can help us see those. I just want to reinforce to listeners that culture, as you say, is what we do. It's how we do it.

And we have cultures in every part of our life. They show up for all of us. If a business leader is listening today, who isn't in HR, perhaps they're in the C-suite or maybe they're just a team leader. How should they think about culturing or reculturing as a growth lever?

Melissa Daimler: Yeah. I do encourage in the book, and I talk about this a lot. I think everybody at every level, in every function across an organization, is accountable for culture. And so if you are an individual contributor listening and you have values, but you're not really clear, you know how they show up, I would ask the questions.

If teamwork is a value to make sure that I'm not surprised at my performance review. What does good teamwork look like to you? If we were having a review at the end of the year and you were acknowledging me for being a good team player, what would some of those behaviors be? And so I think giving people agency to ask those questions and get clarity if they're not already clear, I think is really important.

I also encourage people, if they haven't done this organizationally I put a section in my book around, really strong companies not only have good cultural systems, they have good leadership and personal culture systems. And a lot of the leaders I work with, we work on their personal culture or their leadership operating system. So what are your own values and behaviors and practices, and then how do those kind of compliment or feed into the organizational values and behaviors?

And just having a conversation with your team on this is what I value. This is how I work. This is how I want us to make decisions. This is how I communicate best.

Even starting that within your own team I think is very powerful. Jason S. Bradshaw: Yeah, makes a lot of sense. Well, Melissa, it's been great having you on the show.

Your book Reculturing. We're going to make sure there's a link in the show notes for people to be able to grab a copy of the book and also to follow your work. I absolutely believe in your book and that it's more relevant today than ever for organizations and leaders to understand culture and this notion of reculturing. I'm wondering before I let you go, what's the one chapter leaders should read first and why?

Melissa Daimler: Oh man. I think it's the last chapter actually. It's the chapter on on personal culture. I think I've actually gotten feedback and questions about why didn't you that first, but, I think it's a really nice entry into what organizational culture is because if I understand it as a leader and how it can make such a difference for me and leading a team, I have more access and understanding to how impactful that could be at an organizational level.

Jason S. Bradshaw: Makes a lot of sense. So you've heard it here, the author herself is saying, you can read the last chapter first, only if you promise to go back to the very first chapter and, complete book. Melissa, it's been a delight having you on the show.

It's been fun, went fast. Thank you. So whether your strategy is changing, your team is growing, or your world feels like it's shifting faster than you can lead. Remember this.

Culture isn't what you have. Culture is what you do. And when you design it with intention, everything else aligns. I'm Jason S.

Bradshaw reminding you to transform the experience to transform your business and the world around you.