How can HR leaders design company cultures that are intentional, adaptive, and aligned with business goals? 

To answer this question, in this episode of the Digital HR Leaders podcast, David Green sits down with Melissa Daimler, Chief Learning Officer at Udemy and author of ReCulturing: Design Your Company Culture to Connect with Strategy and Purpose for Lasting Success.  

With years of hands-on experience at Adobe, Twitter, WeWork, and now Udemy, Melissa brings a wealth of practical insights on how to build cultures that stand the test of change. 

Here’s what you can expect from this conversation: 

• How trends like skills-based strategies, AI, and flexible working are reshaping workplace culture. 

• What a healthy culture really looks like—and how to build it intentionally. 

• How Udemy is aligning its culture with skills-focused goals and preparing for AI’s growing impact. 

• Tips for staying clear and aligned as priorities shift rapidly. 

• Common missteps organisations make when trying to design culture—and how to avoid them.  

This episode, sponsored by TechWolf, is packed with real-world advice and insights that HR and learning leaders can start applying right away.  

TechWolf is an AI-powered solution focused on one mission: delivering reliable skills data for every role and every employee in your organisation. 

With TechWolf, companies like HSBC, GSK, IQVIA, Workday, and United Airlines have accelerated time-to-hire by 32%, boosted internal mobility by 42%, and saved around $1,000 per employee annually on talent management. 

Visit techwolf.com for more information.  

 Links to Resources:  

• MyHRFuture Academy: MyHRFuture 

• Insight222: Insight222 

[0:00:00] David Green: Despite the rapid pace of change in the workplace, driven by topics such as new ways of working and advances in technology, one thing remains constant, the critical role of organisational culture, which has again been highlighted by Gartner as a top five priority for Chief People Officers in 2025.  Culture is the connective tissue that aligns strategy, purpose, and people.  And as my guest in this week's episode highlights, culture should be designed with intention.   

I'm David Green, and today on the Digital HR Leaders Podcast, I'm joined by Melissa Daimler, Chief Learning Officer at Udemy, and author of the book, Reculturing: Design Your Company Culture to Connect with Strategy and Purpose for Lasting Success.  Drawing from Melissa's research and own extensive experience as a practitioner at companies including Adobe, Twitter, WeWork and now Udemy, Melissa and I will explore the ingredients of a healthy culture, how leaders can approach culture with intention, and the practical steps organisations can take to align their culture with business goals.  Melissa will also share practical insights into Udemy's approach to embracing these shifts and offering valuable advice for HR and learning leaders navigating these changes.  For anyone interested in building and sustaining a thriving workplace culture, this episode is packed with insightful takeaways.  So without further ado, let's dive in. 

To start off, could you share a little bit with our listeners about your career journey that has ultimately led you to where you are today? 

[0:01:52] Melissa Daimler: Sure, that's always a big question, especially when you've been doing this as long as I have.  So, I've been in tech for over 25 years.  I've been really lucky and grateful to have had the opportunities that I've had.  I say that I learned a lot and really cut my teeth in HR at Adobe.  So, I was in the People Partner area and really built out organisational development at Adobe, was there for an unbelievable 11 years, which seems crazy when I say this to any of the millennials.  They just look at me like they have no idea what that even means, given the tenure in a lot of companies now.  But had the opportunity, as a lot of us do in bigger companies, to take on different roles, and I think we're gonna talk a little bit about skills.  And then, hopped over to Twitter, which was what I would call in its glory days, and was really able to build the learning and OD team from scratch there, building that company from less than 1,000 employees to 4,000, became a public company, so that was that was a lot of good learning there.  Had a journey at WeWork, learned everything that you should not do in a company and building company culture.   

Then, the opportunity here at Udemy was huge.  I've been here three years and really came in to -- it was after I wrote my book, Reculturing, and had my own consulting gig for a few years.  And so, they wanted to reculture themselves.  They were evolving as a learning organisation and really thinking differently about culture and learning and how that connects.  So, it was a huge opportunity for me to not only build internally, but to also have a say in the product and how we're thinking about our solutions, and then work directly with customers like me, so getting to really understand what the needs are.   

So, I would say the main themes of my career, David, were really about two things: one, systems thinking, I know that's one of the things that you talk about and enjoy talking about.  And so, how do we think about organisations as a system?  How do things connect?  How do we make sure that the strategy connects with the culture, connects with the purpose?  And then, I think the other piece is, really about scale or building, how do we take what we have today from the processes, the practices, the values, the behaviours, the strategic way of working, and make sure that we keep those foundational components, but we also figure out ways to be agile and scale and build?  So, I'm a builder.  I love building teams and thinking about ways to scale both people and processes.  So, that's how I would sum up my career. 

[0:05:17] David Green: That's really helpful.  So, we're going to dig in a little bit about reculturing and some of that systems thinking that you talked about, then we're certainly going to talk about skills.  But before we do that, I guess one of the interesting things that you have at Udemy is you are essentially customer zero for the organisation.  So, your issues, as you refer to, you're helping your company develop the product that they ultimately will then deliver to other customers, which must be quite an interesting thing.  I mean it's not many people -- I've spoken recently to Nickle LaMoureaux, the CHRO at IBM, who's similar, and I've spoken with Microsoft and Workday in the past, but there aren't many organisations where you work in an HR or a Chief Learning Officer role and you're effectively a customer zero.   

[0:06:06] Melissa Daimler: Yeah.  It's hard.  I mean, I talk a lot about polarities and I would say it's both exciting and challenging every single day.  When I first joined, I remember talking to our CEO at the time, and I told him after the first week, I said, "This is just overwhelming because I just feel like there's so many decisions and meetings and opportunities for me to be part of that I am. And then there's things that I feel like I should have been in that I just couldn't".  And he said, "I think you really have to radically prioritise and figure out where we can best leverage you and your team in some of the strategic opportunities that we have".  So, yeah, I mean it's super-exciting and I do think we think of ourselves as customer zero, as you said, and I think it's really important when we're talking to customers that we're also thought leaders.  So, we don't just talk about what we're doing internally.  We have such a huge advantage to have 16,000 other customers that are also thinking through some of the things we're challenged by with regard to AI and skills, and I know we're gonna talk all about that.   

But we obviously use our product and think differently about how to embed it into total holistic learning experiences.  And so, we give all that away to our customers, especially if it works.  We also share what doesn't work, where we've failed or where it hasn't quite turned out how we wanted.  But it's just, to me, all about idea exchange.  And we learn a lot from customers as well and bring some of those ideas, not only into our learning team, but as you said, into our actual product. 

[0:08:14] David Green: So, at Insight222, we recently published some research around the people analytics operating model, which we actually saw as an ecosystem interest, and it all links together.  And we found that there's five key trends elevating people analytics, and I think these are elevating HR functions, frankly, globally, so: new ways of working, particularly thinking about hybrid work; actually trying to empower societal change, so thinking particularly around DEI; building a skills-based organisation, we're going to talk about that; delivering digital transformation; and embracing Gen AI.  And I want to ask you, given obviously you authored a book, Reculturing: Design Your Company Culture to Connect with Strategy and Purpose for Lasting Success, how would you say these trends affect organisational cultures?  And then just to set you up nicely, given the title of the book, would you say that they call for reculturing? 

[0:10:28] Melissa Daimler: The title of the book was intentional, that I do see culture as a verb, not a noun.  It is not a thing, it is not a happy hour, it is not a game of ping pong, it is an ongoing way of working, and it's a system.  And so, I talk about the idea that really culture is not just values, but it's the behaviours, it's the processes, it's the practices that we do every day.  And so, all of those things that you listed, I think are key areas of focus that we need to be looking at as HR leaders.  And the theme of today, and really even the past three years is, how do we continue to be agile?  How do we continue to, again, build on some of the great things that we already have, but how do we think a little differently now with additional tools, AI, different skills that we didn't even know we needed a year ago?  So, I think of culture as really being an active part of the system.  And I think every individual has an opportunity to change culture.   

I hear so often, even from our own employees, and I have these thoughts too, and have had them in my career, I do think that we all have agency in building culture.  And I know that a big component of a strong culture is the leadership team.  They definitely have to be aligned with the values and the behaviours and what we're reinforcing.  And I do think we all play and are responsible for playing a key part in building that culture and reculturing every day. 

[0:12:26] David Green: And I actually, I've seen your TEDx video, where you talk about the reculturing and the whole systems thinking behind it, which I think I could really relate to.  So, for those listeners that haven't seen that that TEDx video, which I would recommend that you look at by the way, listeners, and maybe haven't read your book yet, could you share a short synopsis of what reculturing is about and why people should read it? 

[0:12:54] Melissa Daimler: Having been in this industry for so long, I have read a lot of books on culture, I've listened to a lot of lectures on culture and for a while, I had just been craving more articles and commentary from operators, you know, from leaders inside the system.  And so much of this was theoretical.  You have consultants who've never set foot into leading an organisation talking about, how do you build healthy cultures, and it just fell flat for me.  And having been in some pretty powerful and healthy cultures with Adobe and Twitter and then having had that contrast at WeWork, it became even more important to me to write something from an operational perspective, from the front lines as a leader, to say, "Here's my perspective, here are my stories of where I have seen culture work really well in terms of how I've defined it.  And then, here's where I think it's gone wrong".  And so, that was the compelling reason that I wanted to write a book. 

I think most books that I've read, I mean, a lot of books can be an article.  Mine started with an article.  I wrote an article for HBR after I left WeWork, after a lot of reflection, and just that was really the impetus for the book.  It went viral and a lot of people had asked, "Hey, how do you do this?  Tell me more, share more stories with me about where this goes wrong".  So that's really, I would say, if you ask my husband or other people how long it took to write the book, I mean, they'll tell you 20 years because I've been kind of writing it for that long.  But yeah, ultimately it was after WeWork, I really just wanted to put a stake in the ground and say, "This is what I think good culture is and this is what it isn't". 

[0:15:07] David Green: And I think you actually talk about it, as I said, as a system, don't you, where it starts with values-based behaviours, I think? 

[0:15:15] Melissa Daimler: Yeah, I mean I would say it is more behavioural from my standpoint.  I think I gave this example in the TED Talk.  You can have two very different companies both talking about the value of innovation, but have very different outcomes that they want from that value.  One may want to speed up their innovation process, one may want to slow it down to have more quality ideas.  And we did this at Adobe.  We didn't just talk about teamwork, we actually talked about what would that look like?  You know, if we were teaming together effectively, what are some of the behaviours that we would be doing?  And frankly, what would we not be doing?  I think it's good to have those conversations as well.   

I would say, if I were to write that book again today, and we're talking about this more at Udemy and with other customers, I would go further and talk about skills.  And so, as we think about even our value of always learning, we have a behaviour of engaging in constructive debate, and we debated that one a lot, because there are so many companies out there that have learning as a value, but the actual behaviours are likely different.  We thought at Udemy that in order to learn most effectively, we had to debate more, we had to really make sure that we were getting different points of view.  And we also realised that we weren't good at that.  And so, what are the skills that you need to make sure everybody has across the organisation to exemplify that behaviour of constructive debate and that value of always learning?  So, I think skills and behaviours tie really nicely together when you're thinking about building a more intentional culture.   

[0:17:27] David Green: And I think again in the video, I like the way you connect those behaviours and the skills, how you connect that into processes and practices.  And I think that's something that I think will resonate with our listeners.  I don't know if you could describe that a little bit. 

[0:17:43] Melissa Daimler: Yeah, I mean the whole employee life cycle, for as long as you and I have been around, hasn't changed.  I think you still need to hire great people, you need to onboard them, you need to develop them, you need to reward them, you need to give feedback.  And so, how do you take that kind of baseline of foundational processes, leverage that, to really integrate and infuse some of these core behaviours?  We've been on a journey at Udemy, and I've done this before at Twitter and Adobe, and a lot of companies do this.  So, when you're hiring somebody, how do you make sure that, taking the always learning and constructive debate, tell me about a time when you have constructively debated someone, and how did that go?  What worked about that?  What didn't work about that?  So, making sure that your values, behaviours are embedded into your core talent processes like  hiring, like development.  I know we're going to talk a little bit more about skills-based orgs, but I've always been, from my entire career, looking at ways to be more intentional in connecting all of those parts of the system, and especially when it comes to learning.   

So, I think really looking at all of those processes in the talent and employee life cycle, and using those when you're thinking about embedding behaviours and even skills, is just a much more intentional way to drive change effectively. 

[0:19:24] David Green: What do you believe are the key elements of a healthy culture?   

[0:20:18] Melissa Daimler: I think culture is active.  I think if you think about culture as just a thing that you have to check off, you know, "We have to talk about our values, let's just do that exercise and throw them on the wall or throw them on the website", you might as well just not do it.  It's kind of like engagement surveys.  Like, if you're not gonna do anything with this information, don't bother to ask, because it's all about the action plan and it's all about what happens after you've declared that, so I think looking at culture as an active system, as really connected to your strategy and figuring out ways to embed in your processes, and then telling stories around it.   

I think good companies, at every kind of all-company meeting, have examples of, "Hey, let's talk about a team that was able to get out a minimal viable product this last quarter, because they were courageously experimental", that's one of our values as well.  And the behaviour in that is, we reward version one or iteration versus perfection.  And so, I think the more you share stories of what this looks like when we are living our values and behaviours and when we're developing our skills around that, I as an employee can understand it more.  We all understand and connect more with storytelling.  I think good companies not only define values and behaviours, they also are actively embedded into processes.  They're ongoingly telling stories about it and they're reviewing their culture.  Not every year necessarily, but we do strategy planning ideally, I mean I think we're doing a lot more, a whole other conversation, but at least once a year.  I'm not saying you have to look at your culture once a year, but I would say, and I talk about this in the book, there are key inflection moments of an organisation where it might be a good time to take a step back and say, "Hey, let's take a look at our values and behaviours again and if this is really what we need going forward".   

So as an example, at Adobe, change of CEO, that was a moment for us to look and take a minute and look at our values and behaviours.  Changed our business model, bought one of the biggest companies that we had ever bought in the history of our company, with Macromedia.  Those were two major things that happened in the business where we, again, took a beat and said, "Okay, what do we need going forward?"  Because I also think that is important when you're looking at your culture.  It's not just the values and behaviours that you have today, it's what are those aspirational kind of values, behaviours, skills, that you know you're going to need to scale to that next phase of your company's growth. 

[0:23:35] David Green: How are you shaping your culture to support your skills-based organisation goals? 

[0:23:41] Melissa Daimler: Yeah, it's a big question.  I think at the beginning of this year, one of the things that we were trying to figure out is just, what is a skills-based organisation?  A lot of our customers were talking about that too.  It's good to first define what it is you're looking at before you tackle it.  And again, we went back to that life cycle again.  I think ideally, a skills-based organisation is embedding skills throughout how it's working, through the hiring, through the development, through the rewarding.  And so with that context, what are the initial steps that we should be doing to become a skills-based organisation?  There's a number of things that we've done just without the use of technology that I think any company can do.   

I think one of the big ones was around hiring, was to kind of question ourselves and hiring managers when they had, "Education", on the job description.  Frankly, when they even had things like, "15 to 20 years' experience", really?  Is that really necessary?  Because when we dug in and really talked about the skills needed for this scope of work, they didn't need 15 years' experience and they didn't need a college education.  I think there are a couple of examples I can think of where actually, it was five years of experience and when we opened it up to not have the education component, obviously this is in a lot of the research, you get a much larger pool of candidates and more diverse ideally.  So, I think from a hiring perspective there's a lot you can do to think differently about skills.   

I think from the technology perspective, we use Workday, a lot of companies use Workday.  So, I think the foundational component for any organisation is to first just understand what skills you have in the organisation.  And so, we've started to get all employees into Workday to understand, based on self-attestation, what skills do you have currently?  So, we're figuring out what that looks like over this next year.  We have a lot of assessments on our own platform, mostly on the technical side.  I think the challenge that we're having a lot of conversations around internally, as well as with our customers, is that I don't like the term 'power skills' or 'soft skills', but the 'leadership skills', I'll say.  How do we check on how good you are at communicating effectively or asking good questions, coaching your employees, giving that constructive feedback?  So, a lot of work being done there.   

But I think the exciting thing for me in the skills space is really identifying in a much more intentional way what skills we currently have in an individual and at organisational level, what skills do we know we need for the future?  And then, what's our gap, and how do we address that gap?  Do we hire for that gap, or do we develop for that gap?  And it's probably a little bit of both.  But I think the first thing that I get really excited about is just to be super-clear about the landscape. 

[0:27:35] David Green: So, I'd love to hear what you're doing at Udemy to ensure your culture and people are ready to embrace this transformation, this age of AI.   

[0:27:47] Melissa Daimler: Yeah. that's a big question.  I would say, in terms of AI, like a lot of things, the biggest thing that we're trying to reinforce across our organisation, and again in talking to a lot of -- I mean you talk to a lot of companies as well, is really making it safe to experiment and to make time to have conversations about this.  Right before this call, we had a team meeting and we're now weekly on Fridays making space for talking about a tool with AI.  Today, it was Notebook LM, and we were experimenting with that.  It's crazy.  You can put your LinkedIn profile in it and it creates a podcast.  And so, we were just trying to figure out what are some use cases internally that we could, with the constraints of our legal team, that we could be doing differently?  So, I would say first and foremost, making space to learn about AI.   

We did a huge effort last year, last December, as an entire organisation.  Everybody goes through the same kind of learning path, but we embedded in that learning path our platform discussion questions as a team too, because we all know that's the best way to learn.  So, you just did an asynchronous exercise, you watched a video, but now you practised something, now let's talk about it.  What prompts did you use?  How are you thinking differently about prompt engineering?  What's zero-shot prompting versus one-shot prompting, which I didn't know about.  So, I think that was such a great way to kind of exemplify what you said about being customer zero, like using our own platform, but also making space for talking about AI, the different use cases we could do with AI, and encouraging people to continue to have those conversations.   

So, I would say this year, some of the other things that we're doing, going back to storytelling, we're sharing opportunities in our all-company meetings of how we're using AI and our functions.  We just rolled out this last week, Powered by AI, as a feature in Udemy, where I always say with AI, you never have to start with a blank page again.  The opportunity to not have to create a learning path from scratch, but to just throw in, "I want to create a learning leadership", and then it prompts you with more questions and gives you a much more precise set of skills that you're going to learn in these courses and lectures.  And I would say with our own team, we've done a lot of work around even things like, we had a youth case list last year where we had to build out a manager assessment.  We didn't have a lot of time, we lost our vendor partner that we normally would work with, so we used ChatGPT.  We got it done in a day and instead of paying $30,000, it was nothing.   

So, I think we're also trying to figure out different ways to, I was just talking our CEO about this a couple of weeks ago, what are some ways that we can, even by function, lead the way with AI?  So, open enrolment just started with us.  Could we create a chatbot that answers a lot of the benefits questions that are coming up?  I would say 80% of those questions could be answered by a chatbot.  And so, it would save our benefits team a lot of time that they could then use to be much more strategic elsewhere. 

[0:32:08] David Green: Again, based on your experience, thinking about the listeners and most of the listeners on this podcast are HR professionals such as yourself, how can organisations stay more intentional about their culture?  What are the some of the systems that they can put in place to kind of get that intentionality there? 

[0:32:29] Melissa Daimler: I would look at your values and behaviours and really try to figure out, how do those tie to your purpose and your strategy?  Are you clear on what it would look like if those values were really showing up in your organisation?  And from that, how do you make sure that there's opportunities to kind of reinforce those behaviours and skills?  We talked a lot about processes, but I'm such a big fan of ritual and habits and practices that you can do on a daily, weekly basis within your own team.  So, take a moment maybe with your team every week and talk about one of the behaviours, or how did those show up for you this week.  Or, maybe there's a theme this quarter that you can talk about in your team meetings.  But looking at your practices around meetings and communication and connection, where could there be opportunities for you to infuse or integrate behaviours and skills more intentionally there?  Because those are things we're already doing.   

Again, one of the other themes I hope you're taking away is, let's not add on more stuff to the already overwhelmed leader in a company.  How do we take the practices and things and processes that are already happening and leverage those to be more intentional, and talk about the kinds of behaviours and skills that we want to see more of?   

[0:34:28] David Green: What are some of the key pitfalls to avoid?  Where have you seen organisations going wrong before, where they're designing and building a culture?   

[0:34:39] Melissa Daimler: I think they stop having the conversations or they stop when they've made the list and they're done, or they don't see it tied to strategy.  I do think that a lot of us are in calendar years and we're in the middle of, or the beginning of strategic planning for next year.  This is an opportunity, even if you don't reculture fully, to take a moment and look at, if this is the strategy that we're trying to build for 2025, don't even say the word 'culture'.  What are the behaviours that we need, or the skills we need, to make sure that our leaders are driving that strategy?  Or, what do we make sure we need to reinforce with our teams to make sure that we're continuing to courageously experiment?  So, I think even having those kinds of conversations with your leaders is a huge step forward.  And again, you don't have to say the word even, you don't even have to say the word 'values'.  I mean, just taking the context of strategic planning and really integrating it with what that would look like.   

I always think about the what and the how.  So, if this is what we're doing for next year, are we clear on how that's going to work?  So, I think having those kind of conversations with each other and with your leaders is a good step forward and being more intentional with your culture. 

[0:36:42] David Green: Well, I can't believe we've almost reached the end already, Melissa.  This is the question that we're asking everyone on this series of the podcast, and it hopefully ties nicely a little bit what we spoke about earlier with skills.  How can organisations leverage skills intelligence to make more informed decisions? 

[0:37:01] Melissa Daimler: I do think it's a nice summary of what we talked about.  I think this goes back to being more intentional.  I think the opportunity we have with skills intelligence, again identifying what skills we currently have in the organisation, what skills we need and what that gap is, we can much more intentionally make decisions around who we need to hire, how we need to develop, how we're rewarding folks.  Even, we didn't get into this, but there's just there's a ton of research going on right now around, how do we reward particular skillsets that aren't as common or that we want people to gain quickly?  So, the opportunity is there to be more intentional with our decision-making, the more knowledge we have around the skills in our organisation. 

[0:38:03] David Green: And I guess for you as a Chief Learning Officer, if you've got an understanding of the skills we need, the skills we've got and what the gap is, and part of the solution is to build, to develop skills within the organisation, you can be then making sure that the learning offerings actually help the company fulfil that, I guess.   

[0:38:25] Melissa Daimler: Yeah, and there's so many opportunities to -- how do you figure, like internal mobility?  Again, that's been around forever, but I think within the context of skills intelligence, we have so many more opportunities to build work experiences or gigs for people to both leverage skills from different functions, but also to your point, to develop skills that they may not be able to develop in their current scope of work.  

[0:39:03] David Green: Really interesting.  It would be interesting to sit down in three or four years' time, Melissa, as we get to 2030 and see how things have changed, because things are changing so fast.  It's been a real pleasure speaking with you today and before we wrap up, where can listeners find out more about you and maybe find out about the Reculturing book as well?   

[0:39:22] Melissa Daimler: Sure, thank you.  melissadaimler.com, my website.  I'm trying to be more active on LinkedIn.  You can find me there, Melissa Daimler.  Those are probably the best places.   

[0:39:36] David Green: And if they want to find out more about Udemy, it's udemy.com, is that right? 

[0:39:39] Melissa Daimler: udemy.com, yeah, for sure.   

[0:39:41] David Green: Perfect.  Well, Melissa, thank you very much.  I look forward to maybe seeing you at a conference in 2025, maybe meeting you in person.  So, thank you for sharing your time and knowledge with listeners of the Digital HR Leaders Podcast.  

[0:39:57] Melissa Daimler: Thanks for having me.