972 Lena McDearmid:

Wings of Inspired Business Podcast EP972 – Host Melinda Wittstock Interviews Wryver CEO and Founder Lena McDearmid

Melinda Wittstock:

Coming up on Wings of Inspired Business:

Lena McDearmid:

You have to have two things that are highly recursive that must exist in order for people to truly innovate, and that’s psychological safety and playfulness. And what psychological safety and playfulness bring forward into a company that allows innovation is trust. Am I allowed to fail without being basically reprimanded or shunned? Can I bring bold ideas and take big risks, and it be explored and celebrated, or am I going to be held accountable and finger pointed? So, when you can put your values on the wall and say, you know, we do the hard things or we’re always kind or whatever your logos or mottos are, but it truly comes down to under pressure, how people are allowed to on their worst day be supported and coached and managed and listened to.

Melinda Wittstock:

So many companies make bold claims about their company culture, but how many truly live up to their hype? It’s one thing to get clarity on company values; it’s a whole order of magnitude different to actually operationalize those values successfully. If you’re an employee, you know what makes the difference; if you’re an entrepreneur building a business you may not realize the multiplier it is to focus early on creating a culture not of perks but purpose. Lena McDearmid is an expert in all things company culture. A serial entrepreneur, she founded Wryver to help businesses small and large improve their performance by creating truly inclusive and inspirational company cultures.

Melinda Wittstock:

Hi, I’m your host Melinda Wittstock and before we get going with this episode of Wings of Inspired Business, wishing you a happy belated International Women’s Day. It’s a day to honor ourselves, and each other, and everything that makes you and your contribution to this planet unique and beautiful just by being you. Now, and every day and every moment, is the time to know and stand in our true value. Ok now to the show, and if you’re new here, this is the place where we share the inspiring entrepreneurial journeys, epiphanies, and practical advice from successful female founders … so you have everything you need at your fingertips to build the business and life of your dreams. I’m all about paying it forward. I’m a five-time serial entrepreneur, and I started this podcast to catalyze an ecosystem where women entrepreneurs mentor, promote, buy from, and invest in each other. Because together we’re stronger, and we all soar higher when we fly together and lift as we climb. If you’ve been listening to any of the past 971 episodes, please help us get the word out about the show. Please subscribe so you never miss an episode. Tell your friends and colleagues, share the episode and leave a quick 5-star rating and review on Apple, Spotify or wherever you get your podcasts. We really appreciate it. Thank you! 

Melinda Wittstock:

Melinda Wittstock:

Today we meet an inspiring serial entrepreneur who built a successful fintech business before embracing a new mission to help companies transform their cultures from the inside out. Drawing on more than 20 years in the business world, Lena McDearmid shares why company culture isn’t just a “nice to have,” but an absolute necessity for sustainable success. Today we debunk common myths about company perks versus true culture, explore how to create the psychological safety and trust that drive innovation, and why culture is the ultimate differentiator—even more important than product, funding, or market. 

Melinda Wittstock:

Lena shares how to invest in your culture from Day 1 of your business, and why it supercharges your growth. You’ll also learn the pitfalls founders face as they scale, how women leaders are uniquely wired to build collaborative teams, and why a great people-first team culture is vital especially now as AI and new technologies reshape the workplace.

Melinda Wittstock:

Let’s put on our wings with the inspiring Lena McDearmid.

[INTERVIEW]

Melinda Wittstock:

Lena, welcome to Wings.

Lena McDearmid:

Hi. Thanks, Melinda. It’s so great to be here.

Melinda Wittstock:

Well, I like talking to other serial entrepreneurs. You built a couple fintech companies and now you’re helping other companies get their culture right. What was the impetus that made you want to go do that?

Lena McDearmid:

Great question. I think what I discovered along my 20 plus years in the career field that I’m in is I started to notice patterns in different corporations, whether it’s large companies or small startups or my own company, that started to emerge that made culture become more of a nice to have and more of a absolute strategy that underpins the difference between successful outcomes in businesses and unsuccessful. And so, I wanted to start my career and my next company, river, with, with a very significant portion of our focus on culture. Rebuilding inside of corporations and helping them with the tools and structure and what that means.

Melinda Wittstock:

Yeah, so you say culture is not a nice to have and it’s actually mandatory. I mean, you can see it anecdotally, certainly with companies that those that have this really great culture, and we’ll define culture in a moment, tend to outperform those that don’t.

Melinda Wittstock:

So, let’s start at the basics. What makes a great culture?

Lena McDearmid:

Yep, absolutely. So, most people confuse culture from perks and so they think culture is benefits and PTO and off sites and even swag. And those are great, but those are not culture, those are perks. What is culture? It really lives in the nuances that makes up how a company makes decisions, how they disagree, who gets listened to when things are moving really quickly and stakes are high and it starts to be the environment of what it feels like to work within your organization and to kind of like ground this a bit more. There’s a significant amount of research done on business failures and startups that, gosh, over the last five or 10 years, where what they’re finding is the reason, most common reason for business failures, both startups or mature businesses, 65% failure rate is due to culture, either through founder misalignment, leadership being unable to work together, or team structure is, you know, resistant to collaboration. So, it’s not the product necessarily, it’s not the market, it’s not even your funding. It all kind of comes down to what it is to work within the organization and how the members and the people in the leadership team take together.

Melinda Wittstock:

Right. So, for instance, if a company is all about innovation, right, and put that on their website…

Lena McDearmid:

Yep.

Melinda Wittstock:

But it’s different to actually fuse that into your whole operational being. To innovate in invariably means people need to be able to fail. So, what does it look like to fail in your company? Are you punished for failing or are you encouraged to fail? What do you do with the learnings of that? How is that operationalized? So, talk to me a little bit about how you operationalize. 

Lena McDearmid:

That’s right, that’s right. So, in order to innovate, you have to have two things that are highly recursive that must exist in order for people to truly innovate, and that’s psychological safety and playfulness. And what psychological safety and playfulness bring forward into a company that allows innovation is trust. And so, what trust is in psychological safety at its merit is meaning am I allowed to fail? Am I allowed to fail without being basically reprimanded or shunned? Can I bring bold ideas and take big risks, and it be explored and celebrated, or am I going to be held accountable and finger pointed? So, when you can put your values on the wall and say, you know, we do the hard things or we’re always kind or whatever your logos or mottos are, but it truly comes down to under pressure, how people are allowed to on their worst day be supported and coached and managed and listened to. Versus are you going to isolate and reprimand and kind of cut off the relationship? So, I love values. I think they’re great targets to have and I’ve built them myself. But what underpins it is what’s the truth? What happens when, when failure happens, like you said it, right, that’s the greatest test of culture is, is there psychological safety? That’s the bedrock of your organization that allows people to take big steps, big statements, big innovative ideas and try.

Lena McDearmid:

And if the outcome is less favorable, are they still okay to kind of go ahead?

Melinda Wittstock:

Yeah, but inherent in all of that though, it takes time. Like it takes time to listen to somebody or that failure or allow the learning. And so, in startup culture, when you’re like moving fast, breaking things, you know all that in the Valley, right, And you’re a lot of pressure to hit metrics and all of that. That’s perhaps why people end up thinking, oh well, we’ll get to that later.

Lena McDearmid:

Right, right. Always, always get to it later. The thing is with culture and teaching it and leading it and doing it inside of organizations, that culture exists, whether you focus on it or not, it’s going to exist naturally by whoever has the loudest voice, the biggest impact. Right. It’s going to. If you’ve got leadership that is avoidant, when issues come up, people get strongly. There’s no listening, there’s no conversations, no pushback, there’s a fear of safety, that their job’s at risk if they want to disagree with their leadership or if people are in meetings and you’re noticing people are getting minimized or over talked or passive aggressive things are happening and it’s not getting called out in the conversation. What you ignore basically is providing permission.

Lena McDearmid:

So, it’s reteaching leadership what the signals look like that they may not even intentionally be sending or ignoring. It’s providing people with a bit more awareness of what culture actually is and what it feels like to have it successfully working in your favor. There was a study done by Google over two years where they interviewed, I want to say, over 200 different teams from their pods with the intention of trying to understand why are some teams really high performing, and some aren’t. Their expectation that was, that it was some composition of team structure, leadership and like collegiate experience. And so, after doing two years’ worth of research and hundreds of interviews, what they actually found out was the number one causation for successful high performing team was the presence of psychological safety.

Melinda Wittstock:

Right. And what’s right, it makes so much sense. And the problem is not everybody’s self-aware enough to be able to create that like so you, I mean it probably all extends from the, you know, the executive team, the founders. But like the classic founder mistake is, you know, hiring people like them.

Lena McDearmid:

Yes.

Melinda Wittstock:

And then not understanding people who aren’t like them. So then suddenly that person’s not a good, not a cultural fit.

Lena McDearmid:

We call that pattern matching, Melinda. Where people are like, I just want other people that look like me, that feel like me, that see like me. That must mean it’s good. And where I find it to be better is when you’re not looking at pattern matching, when you’re looking at the ones that are not a culture fit, they’re a culture enhance. They’re going to allow you to expand. They’re going to be, they’re going to bring a new way of leadership. They’re going to talk about the environment and what it feels like to make tough decisions. They’re going to lead with vulnerability when they fail in their roundtable conversations.

Lena McDearmid:

I used to have them every Tuesday with my entire team. And where we would be best and show up most often successfully is when we brought where we made shortcomings. And you lead like leaders go first. Be okay with saying like I made a mistake on that decision last week and I regret it. Here’s what I’m going to do about it. And holding yourself accountable and modeling it, you have to teach it. It is not intuitive. And not everybody who’s a leader should be leading people.

Lena McDearmid:

And that’s a real truth. Just because you’re the best at your role in your, your particular skill does not necessarily mean you are great at leading people. And if you don’t love leading people, you should not be leading people. 

Melinda Wittstock:

So, you may be like the visionary founder, and you have this great idea, and you know how to do a lot of things like yeah, your expertise and such, but that does not make you good at people. So having self-awareness, say as the CEO and founder of a company, when do you invest or find the money to bring say a chief of staff on or someone who loves this, who’s really great at that or a role that you’ve had like a chief culture officer.

Lena McDearmid:

Right.

Melinda Wittstock:

And that’s tricky because you’re short of cash.

Lena McDearmid:

Yeah, always. Right. Yeah. I mean it’s normally where I find it to be the most influential. And it’s not even when you’re bringing in people because normally you’re not bringing in individuals until you’ve raised capital or you’ve hit revenue and you’re expanding for growth. But like when you’re early stage, when you’re just in your idea, proofing out your concept, getting your product to market, trying to get your first customer onboarding, it’s not the person you need to bring in yet. It is self-awareness. It is conversations where you’re needing to look around at yourself in your own kind of self-audit and maybe you have a mentor or a board member or an investor at this point who could help you be a mirror to yourself.

Lena McDearmid:

But recognizing if you don’t like something, if you know that you’re not in this lane of people management, that’s going to make it very difficult for you to execute your vision. If you’re the visionary founder, that’s fantastic. It’s not enough. It’s not enough to carry the, the idea into the real world. And if you’re going to be collaborating, building teams, and that’s part of your go to market is expansion, then you absolutely need to be looking at your second hire or your first hire, I guess you should say. And if that first hire, it can’t necessarily be just an expert who knows how to build the thing really well. It’s got to have a multi-layer. And that’s the difference that I’m seeing in kind of this next generation of leaders that are coming forward where they’re recognizing that you have to have more levels of leadership than just expertise in one skill set.

[PROMO CREDIT]

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Melinda Wittstock:

And we’re back with Lena McDearmid, serial entrepreneur and the founder and CEO of Wryver, a consultancy that helps leaders create organizations where people and performance thrive together.

[INTERVIEW CONTINUES]

Lena McDearmid:

They’ve got to be more well-rounded in having conversations and communicating and confronting hard truths and accountability. And that’s what I see in the future of work. And what is being asked for by the employees that are coming is they want a more rounded leadership structure and model. Because the old models are running out of time and it’s time for us to rethink the way that we lead and the way that we communicate. And so if you’re in an early stage in your building and the ideas are coming, I would say your first hire needs to definitely be more focused on the growth of the humans that are going to be doing the work and how we create a culture, an environment or a system, an ecosystem where people can be most successful and able to really kind of show up as their full selves and innovate and collaborate and take big risks and have large conversations safely. Yeah.

Melinda Wittstock:

Just giving that this idea of psychological safety is so important.

Lena McDearmid:

Important.

Melinda Wittstock:

I mean, because people are often afraid to just ask a question because they think the question is gonna, I don’t know, out them somehow as being or something.

Lena McDearmid:

Right? Absolutely.

Melinda Wittstock:

Want to create a culture where people are able to ask questions because then it reveals like what they don’t know or where they need help. Just going slower at that beginning stage is gonna make everything go faster.

Lena McDearmid:

Right.

Melinda Wittstock:

There’s much more clarity because a lot of founders think everyone’s going to be able to read their mind and like they, like they, they can’t.

Lena McDearmid:

Yeah. I think a lot of founders and even just a lot of leaders that have been doing the game for a while have a couple of pressures that they place upon themselves. I did it myself. You think you have to look like the leader, right, you have to be the big bravado. You have to have the loudest voice in the room. You need to have all of the answers to all the various questions.

Lena McDearmid:

And candidly, that’s just not true. In fact, it’s the anti-culture where you show up best in. The leaders that I find that are doing such great work and that I’m really optimistic about are the ones that kind of meet you, where they are, where they’re like, listen, these are my shortcomings. This is, you know, I used to tell people these are my leadership shortfalls. I have a tendency when I’m stressed out to cancel a meeting because I go in hermit mode and I start to give away my vulnerabilities. I start to tell people, this is how you can hold me accountable. These are areas that I’m not strong in. This is how I really like to collaborate.

Lena McDearmid:

It’s vulnerable for sure. But what happens when you open up and are vulnerable with someone else? It gives them permission to do it themselves. And then you just start to build these trust foundations where people feel like they can say just a little bit more about themselves. And then you begin to get to know each other, how you work together, how each person thinks and motivates and teams and partners. And in the teams that have been the strongest in the organizations that I’ve been a part of, it is because they have figured each other out and they can hold accountability and in space for people to really explore, like how to partner together.

Melinda Wittstock:

Exactly. Just even like getting ideas from the team. Something that in my companies that we’ve experimented with very well actually, you know, for the most part, is being able to give people the opportunity to come up with like, crazy ideas.

Lena McDearmid:

Yeah. Like go nuts. No bad idea.

Melinda Wittstock:

And like without judgment. Right. Someone says, oh, that can’t be done because of that. No, no, no, that’s not what this meeting is exactly.

Lena McDearmid:

Like you almost. And sometimes, you know, back to your kind of question a few minutes backwards, like, how do you start? Sometimes it’s in different exercises. Right. It’s not necessarily a trust fall, but it may be. Bring the team in locally where we can all see each other. Eye contact is key. And we walk into the room with the expectation that we’re going to come up with ideas and nothing’s off the table. No’s not an option.

Lena McDearmid:

We’re going to try to figure it out what would have to be true to make this work. What’s the wildest. And you give people permission to feel safe, to be bold, safe to speak out loud, to laugh and have a little bit of fun as you get creative. And then it just starts to flex that muscle. Muscle of trust. And then psychological safety. And then the shoulders start to drop, and people start to show up and maybe quit being the guarded employee. Because we all walk into our career with a role.

Lena McDearmid:

Right. We all feel like we put on our suit. This is who we are. In my work environment, when I go home, I’m a little bit different, but I’m trying to work to a place where can we integrate ourselves more in work? And what would it feel like to be able to be yourself as wild and unique and, you know, all the things as you can be and how much more beneficial would that be for your career and your role? And then the company that you’re working inside of, and the company has to meet you there. Like you can’t just show up vulnerable and nobody else is there. That’s, that’s dangerous. But it starts in little moments like you just said, like in the rooms that are safe.

Melinda Wittstock:

Right. So, there’s this very masculine driven culture of command control, the art of war, all that stuff frankly infects, you know, most of American business. Right. And, and, and it’s just the way it’s done. And there is a very ego driven and in it, like you said, like just moments ago, it’s not really working anymore. Certainly Gen Z, and it started with millennials, just aren’t having it.

Lena McDearmid:

Right.

Melinda Wittstock:

We tend to lead naturally quite differently. Like we’re more inherently collaborative, right?

Lena McDearmid:

Yes. Yeah.

Melinda Wittstock:

Do you see the differences? I know this is all a spectrum. Like when we talk about gender, right. Do you see, like when you’re consulting with these different companies, the differences between female leadership and male leadership? And where can women really excel? Because I think we’re wired a little bit differently. We’re more likely to be able to do this with more ease. 

Lena McDearmid:

Yeah, yeah, no, you’re, you’re spot on. I often tell people when they ask me, they’re like, what type of companies are reaching out to you? Is it mostly people from HR? Is it mostly? I’m like, nope, it’s women CEOs. And they get it. They get it innately. As soon as I start talking about it, something vibrationally clocks in. But what women are better? I’ll say, better. We create community just naturally.

Lena McDearmid:

That feminine energy is communal. We enjoy the community building. We enjoy sharing and exchanging conversation and vulnerability. We get into the, the deep of it if we allow ourselves to. The masculine energy and the management style and methodology has been around since, you know, the manufacturing days when we needed to have that kind of build and build a thing and produce a product and it’s very linear. And it worked, right?

Melinda Wittstock:

Men are much more linear than women.

Lena McDearmid:

Yes, yes. And that, and it worked. We needed to build systems and organizations and empires and people. But now that time is ending. In fact, emotionally it has ended for me, but it is waning. And this new crop of conversations around the future of work and that, that community type of leadership where it is more network, it is more women that are taking charge and leading because it comes intuitively to us, we are able to walk into a room and fill the room and read the room and respond in kind, while also guiding in a different type of energy. And what is exciting to me is that right now at this moment in history, more women in their midlife and beyond are starting new companies because they’re picking up the, basically they’re picking up the charge, and they are building companies with clarity and integrity and all of this emotional intelligence which is necessary in this coming AI world. We are going to need more people who can be creative and lead with emotions and conversation and redefining what success looks like and what leadership looks like and choosing to build in that way.

Lena McDearmid:

So, there is a movement that is happening and that will continue to come. And it’s, it’s not just rebellion, it’s a reconstruction of how we’re going to do it because we’ve got many women coming behind us and men too, that are looking for something different. The Gen Z’s and even the Gen Alphas, their expectation is this isn’t good enough. We got to figure it. Y’ all got to help us figure all this out. And so that’s part of the generational shift that I am deeply, deeply energized and I’m happy to start shaping what comes next.

Melinda Wittstock:

I think that’s very interesting. And I mean just even if I put on my hat as a venture partner and the women that come and present their cultures like almost 100% of the time are just a whole other level. They have great collaborative skills. We actually evaluate teams based on that or of course, because we can see, and you can see it in the data, like you can even see it in the financial performance of companies are returning on average between 62 and 72 cents more on every dollar invested.

Lena McDearmid:

And it’s like Melinda, it’s almost like if you’re just looking at it from pure numbers, it never makes sense. While women aren’t always bet on more because of the output and the performance. That’s why I’m always gobsmacked that we’re still at 2% of interest or capital going to women.

Melinda Wittstock:

Exactly. Me too. I really want to invest in those companies. They’re just, they’re just better.

Lena McDearmid:

They’re just better. I. I don’t know. And I think it’s because women, for so many generations have had to learn to navigate how to be, how to show how to perform in environments that are not set up for us to be successful. They are literally anti women. And we are still coming in and knocking down all the metrics.

Lena McDearmid:

And at some point you have to look around and be like, she’s an athlete, because she’s been navigating through this torrential kind of landscape for decades. And so why would you not. They figured it out. We know how to be successful even when we shouldn’t be in some of these situations. And so, I’m happy to see more venture funds going towards women. I see more about small. I have a lot of women in my network now that are also female investors. That’s what we need.

Lena McDearmid:

So, thank you for what you’re doing. We need much more. We need the other portfolios to start recognizing. And let’s get this caught fire. Like, I can’t imagine what the world would look like if we just took the number from 2% to 5%.

Melinda Wittstock:

Exactly. Exactly. Right. So, I want to get into how you work at Wryver. First of all, the types of companies you mentioned that more likely that women CEOs are coming to you. What, what stage are they at? What are their biggest hurdles that they’re trying to work on?

Lena McDearmid:

Yeah, I love startups. I’ve been in five or six, and that’s just a great environment. I will always love a startup. And I’m normally between A and B round, right?

Lena McDearmid:

They’ve gotten some funding; they’ve got their product in market. They’re right before their ramp, right. Right before the growth. The fun part where they’re trying to figure out, like, how do I expand from my team? You know, what gets you there may not. You know, what got you there may not get you to the next level. And so, they’re bringing me in often to kind of do an assessment of their go to market and their operational execution.

Lena McDearmid:

And I love that stuff too. How I enter those inner those conversations is always like, but I’m a culture first. Like none of this will stick. This will all be like building a house on sand if we don’t recognize what the culture currently is. And I’ve got some, some CEOs and founders that are also men. And so, they’re early A to B stage. And I enjoy that when we’re really building and really setting the structure and starting to have conversations about leadership methodology and vulnerability and all of that.

Lena McDearmid:

And we walk them through kind of an assessment and so they’ll bring me in either to do an oversee, you know, I’ll do a quick analysis, I’ll interview their different leaderships, I’ll look at their team structure, we’ll look at even their roadmap and kind of what their vision, plan and goals are for the next 18 or 24 months. I’ve also got other companies that are a little bit older, maybe 10 years, and they’re going through a transformation where they’re not pivoting necessarily, but they’re recognizing that their current structure stated and they need help in how do I bite off this transformation. You know, one bite at a time. Especially in AI. That’s, that’s one we’re getting a lot where people are recognizing that they’re current technology is going to need to be updated and how do they go about this change management and also keep the people intact.

Melinda Wittstock:

And that point on that point, it’s very interesting too because levels of adoption of AI are pretty uneven, all this discussion of the AI bubble because people don’t know how to implement it. And what people are learning is that AI works best in like a human AI kind of partnership. But how do you train for that? How do you make people feel comfortable with it? There’s all this mistrust. It’s a huge area.

Lena McDearmid:

It’s huge. And that’s the one that I’m getting the most. And you know, I’ve got some male CEOs, so it’s not male versus female. It’s just easier. I find adoption much easier with female leadership structure. But where people are coming to me now, they think they’re coming to me with a problem on transformation or expansion and that’s what they’re trying to solve because they’re revenue focused. I understand they’re trying to like they hit their numbers and give back to their investors. And those are critical goals.

Lena McDearmid:

But when you’re coming into me, I’m going to start talking about where’s the tension, where’s the frustration happening, where’s the area of the organization that everybody’s exhausted and burned out and there’s a little bit of resentment and high attrition. I’m going to go there first and then I’m going to, with permission and of course, transparency. If it’s a larger project, some people bring me in for a day or two just to have an individual kind of stuff, skills, conversations. Some will work with me on a very fixed based project where it’s like, hey, we’re doing a transformation of this department, can you come in for a couple of weeks and you know, help us through that? And some are doing a much larger transformation and so they’ll bring us in for kind of a mentor, advisor, potentially board member, where we’re sitting on the executive team, you know, as an adjunct basically and kind of being a voice of leadership. And those are my favorite. Like I can come in and do any portion of the execution and help guide you through it. But mine is always going to be tilted toward. We’ve got to talk about what it feels like for this transformation for your employees.

Lena McDearmid:

We have to talk about how AI is intimidating to some people within your organization that are not Gen Z, right, that are in a different age gap that we’re going to have to talk about upskilling and calming some of those nerves. And that AI isn’t just this new transformation coming, it’s, it’s a tool if, if leveraged correctly. And in a couple of years, we won’t even call things AI. It’s just going to be what it is that we’re using to run. Exactly. I tell people all the time this is our next, you know, dot com and the way we handle it matters. And so, companies right now are just throwing, they’re buying all the tools, right? They’re buying all the AI and they’re handing it out to their employees. But they’re not teaching the psychology of what it feels like to kind of start learning this and what it looks like.

Lena McDearmid:

And just like you said, it is going to be a human in the middle of this AI transformation. The AI is the tool. The humans are now going to have to have discretion and creativity and leadership. It’s going to actually put the onus more on people, management and leadership than anything else that AI is going to bring. It may bring speed; it may bring ability to collapse time as you’re developing and AI and data scientists and all of those specialty groups. But what it actually is going to require is that the leadership team knows how to manage people. More creativity with more creativity and more communication and setting strategy. And you’re not measuring output and hours worked because that’s not really going to match anymore.

Lena McDearmid:

We’re not looking at things under the same structure that we once did.

Melinda Wittstock:

So, the metrics themselves.

Lena McDearmid:

Yeah. They will change.

Melinda Wittstock:

Give me an example of that. Of where, say, what’s on a metric of like, I don’t know, they’re a performance marketing person, right, and they’re charged with increasing your monthly actives and your daily actives and your LTV. And you know, they’re looking at all these different things or your return on ad spend or whatever.

Lena McDearmid:

Right.

Melinda Wittstock:

And they’re tied to those goals. But like how would their role. Yeah. Like when you’re thinking of company culture.

Lena McDearmid:

Yeah, it depends. So, you’re still going to want metrics? Like I’m still going to want to know what my ROI is. I’m. Even if I’m running a call center, I’m still want to know what my average handle time is and how long it’s taking to service that client. The metrics matter. What’s different is if you’re using a tool inside of I’ll use a call center because I’m more familiar with it. Recently in a recent project we did where the hours that were currently being spent listening to calls and quality monitoring and then giving scoring and then giving that information back to the team and saying this is where we’re drowning. This is what we’re not doing it at.

Lena McDearmid:

You need to spend less time on the call. Those are great metrics. Right. They’re fine. It’s measuring output, hours logged impact. What’s different now is now AI is embedded into that telephony system. Right. And it’s listening to calls and it’s queuing and it’s serving up feedback in real time on the data points of what was missed, what was made.

Lena McDearmid:

And so, when you’re sitting down with that same quality scorecard, with that same CSR that’s on your front line, you’re spending much more time hopefully walking through the numbers. But you’re able to more, more realistically because as pulled the tone forward, as pulled the repetitive statements forward, as made that conversation effort from the supervisor who’s having to listen to those calls every week collapsed. So now that supervisor has more time to develop the skills with that with that CSR who’s struggling, able to more quickly recognize, well, what’s. Where are you struggling at? Are you struggling because you’re not understanding the problem? Are you struggling because of the multiple systems that we have you working through? There’s a collapse in effort over what I call the administrative work that normally would take a lot of time from leaders and managers having to manage their workforce that’s collapsed, AI’s collapsed that now we’ve gotten the time back where it’s actually the people, development people awareness of what it feels like in the environment, how are we training, how are we leading. And so, it gives, if taken advantage of space where leaders can actually go back to leading and looking through why things are not working or why things are working. And it’s not always just the numbers. Like somebody takes too long on a call or somebody keeps messing up. It gives more hours and minutes back in the day that if leveraged correctly, people can take in for leadership, true development.

Lena McDearmid:

Because the number one thing that I’m seeing on teams of the past kind of world and strategy is that we weren’t really spending a whole lot of time developing and leading people and training people. We were giving them numbers; we were telling them what to hit. When they didn’t hit it, we were holding accountability for it and having them read a book or go through a workshop. And I’m finding that the problems were never in the training or the process sometimes, but it was more the awareness of where things were sticky. And we didn’t talk about it, and we just accepted that the system was slow and that it was difficult for the, the employees to work. We weren’t looking at. Well, if you make it difficult for them to work, if the environment that they’re in is not set up for success, if they don’t have a leader that they feel like they can be honest about where they’re struggling, then they’re never going to get better. It’s not going to improve, it’s just going to get ignored and then they’re going to quit complaining and they’re going to get quiet.

Melinda Wittstock:

Right. So, this is a really important point about AI and the efficacy of it. If you can have it take away a lot of that administrative time, it gives you the time to be more aware of building your culture and of leadership development and developing your team and really listening and all those different things. Right. I think that’s a really important way, you know, to, to, to look at that, you know, for sure.

Lena McDearmid:

And, and I think also with AI, what’s it where we’re going to really need AI to be held accountable too is it comes back to the quality of the querent, right, the individual building the AI models and what information the data that’s going in, whether it’s bias or not, like data is AI, is data created, it is what we are telling it to do. There is still a human that is creating the start point and the prompts and so there’s going to be more expectation is what were the assumption sets that you used? How did you validate your findings? What’s the quality of the information that you’re putting in? Like there’s going to be an expectation on the doer, the user, the builder, that just because you can go fast does not mean it’s quality. Like getting something done and then I have to fix it over and over again because we don’t have quality inputs, we’re not validating our assumption sets. There’s going to be a higher expectation that fast is no longer the measure of good quality, the output of that. So, we’re going to have to get off that linear old school manufacturing timeline of go it fast, do it fast. No, that, that’s never successful fast and speed or knob strategy, they create anxiety, they create rush, they create lack of critical thinking. We’ve got to get to a place where quality long term and understanding the why. What are we building? What are the risks around it, what are the assumptions that we’re doing? Who are the people that we’re leveraging and impacting by building this? It’s going to be and I call it a full stack leader, the type of leadership where you understand the front line, the middle layer and the back.

Lena McDearmid:

Like everything that it takes to build and lead and do. You’ve got to have the full spectrum, not just your portion of the pie. Metrics are great and timelines are going to collapse, and things are going to go faster, but we still have to be accountable. We still have to make sure that the quality and effort of what we’re doing and then how we’re leading and guiding and paying attention to the signals from our team, those are the true indicators of what’s working and what’s not working.

Melinda Wittstock:

There’s such a correlation too between internal companies, company culture and customer success. Like if you’ve ever walked into like a hotel or a restaurant or wherever, where there’s a happy culture, I mean the service level is going to be so much better. Just the energy of the place, just literally its energy is going to be positive and like you’re gonna feel comfortable there. And I’m reminded of Tony Hsieh’s book, Delivering Happiness. So Tony, of course, was the founder of Zappos.

Lena McDearmid:

Absolutely, absolutely.

Melinda Wittstock:

…Bought by Amazon years ago for a billion dollars, ostensibly not doing anything different than Amazon was doing. It was like a, you know, selling shoes.

Melinda Wittstock:

But it was different because its culture was different. It was counterintuitive because he actually rewarded people for talking to customers longer. Like, yes, I was reminded of this because you were talking about call centers. Yeah, yeah. So instead of trying to get people off the phone and like, churn as many as possible, they were being rewarded for keeping people on the phone. They’d be talking, ordering pizzas for people, I don’t know, like, doing whatever. And yes, it was a totally different.

Lena McDearmid:

Metric because they were going at it with truly delighting the customer because the customer actually was important and the experience that the customer was having was part of the service that Zappos off. I. I studied them in my master’s class. I fascinated. I think that’s where my culture foundation started that in Southwest Airlines. And I often tell people, the culture inside of your business will leak out. It will leak out into your product; it will leak out into your customers. It doesn’t stay inside the building.

Lena McDearmid:

And it matters. The care with which you give your employees and the way they feel when they’re coming into work and what they’re creating and what they’re building and how they’re voice is heard shows up in every step of what they do. And so just like you said, you don’t wrap up the phone call quickly because you’ve got to hit an average handle time of under two and a half minutes. You take care of the call until it’s done, and then that customer will reward you through either continued service. A feedback, whatever it is, it amplifies culture, good or bad, is an amplifier.

Melinda Wittstock:

Oh, totally. I mean, I mean, one of the things that was a book years ago called Giftology, right.

Melinda Wittstock:

Just awarding a customer with a random gift or whatever invariably. I know Gary Vaynerchuk was a big part of this when he was building Wine Library. People would go on social media and talk about what a great experience they had, which would bring so many more customers than hiring a whole sales force, for instance.

Lena McDearmid:

Right.

Melinda Wittstock:

That all started with the culture. Richard Branson’s the same thing. Virgin, you know, airlines.  Like just knowing, like, okay, if people are on a flight, they don’t want a hot towel if it’s hot outside, like cold towel, you know, like just ideas like that.

Lena McDearmid:

Right. It seems so simplistic when we say it out loud. Right. It’s like, well, yeah, of course. But then it’s not done. It’s still, there’s so many systems that are still kind of old fashioned and buttoned up and closed off and it’s just, I find it restricting. And I think if we were to recognize that we’re all humans, both customers and employees and CEOs and founders and all of that, and the way that it feels to experience something, you know, what it feels like to do the thing and build the thing, becomes the truth of what it is. And so, working in organizations where the culture has been fantastic.

Lena McDearmid:

I remember those days. I know why we were successful. I know exactly what led to it. It wasn’t because we were the smartest or we had the best idea or we hit the market at the right time. It had everything to do that people felt like they could make impact and they liked to be able to show up and be in a culture and a system that allowed them to thrive and then that paid itself forward and it amplified the mission and that’s why it was successful.

Melinda Wittstock:

Right. So, in, in your roles in your previous startups.

Lena McDearmid:

Yep.

Melinda Wittstock:

I imagine there were a lot of lessons learned of like what was working but what was going wrong. So, tell me about, give me some anecdotes or some of your experiences where things went wrong that really informed what you’re doing right now.

Lena McDearmid:

Absolutely. I mean, that’s how wisdom happens, right. I have a lot more wrongs than rights in my early, you know, journey. So, some of the, the things that would go wrong, I’ll talk about micro steps and then I’ll talk big obvious ones. The first thing I often say now is not everybody is a people leader like I’ve had. So, the number of managers that have told me they hate leading people and they have teams of people, right. I’m like, well then, then get out of the seat, you’re taking up space and no wonder your team struggle. No wonder you’re not hitting your numbers.

Lena McDearmid:

No wonder you have high attrition rates. So that’s the first thing. If you hate leading people, don’t lead people. The second missteps that I have made or been a part of making is allowing somebody’s, what will we say? Confidence to lead when their competence doesn’t match. And so, you’ve got people blue chips that you would bring into the team that are supposed to really beef up your executive team because you’re now in your growth and you bring in all of these, you know, big deals, come from big schools, have a nice pedigree. But their culture, their leadership style, the way that they team, the way they collaborate and create, trust, you don’t check, you don’t interview for that. You miss all of the people part of that leader, and you take for granted the accolades only, and that’s the decision maker. And then you let somebody into your organization and the way that they lead and guide and team.

Lena McDearmid:

If it’s a good apple, great. If it’s a bad apple, it can take down the entire system.

Melinda Wittstock:

Right?

Lena McDearmid:

Because then you’re allowing it to happen. And bad leadership, bad strategy, bad culture spreads. So, hiring with the awareness of how people lead, truly especially through failure and through mistakes, is important in the interview process. Insert an interview process where you were doing culture checks to understand the truth of how people are and call their previous employees, like, add that to the list. I would say the third thing are the microaggressions that happen, happen in conversation and meetings that go unchecked, where people are talking over or interrupting someone or someone’s always getting silenced and it’s just accepted, it’s not called out. And so, people will ask me, they’re like, what do I do in those moments we’re in a meeting and someone’s rude to someone else, what do I do? I’m like, well, if they do it in front of the room, it needs to be addressed in the room. You need to call it out immediately because you’re letting it happen, you know, and sometimes people aren’t aware that they maybe interrupted someone or were rude or constantly only look at the women to take notes in a meeting, even though they’re your peer. Call that out, don’t allow for that.

Lena McDearmid:

Right. It’s those small microaggressions and micro steps that they seem so small, but they’re not because it sends a current, it sends an energy. So, in my history, it’s making sure when you’re hiring team members and leadership to come into your organization that you truly understand how they lead through failure and hard times. Because that’s what shows up. Holding accountability to the micro steps and the rudeness and the unkind behavior in meetings and mixed rooms. Don’t allow that conversation to happen. Clear it up immediately.

Lena McDearmid:

And then I think that it just. I mean, we’ll have so many more. I think sometimes keeping people too long is the third One. Right. Loyalty does not mean longevity. And so sometimes you can outgrow people that started the company with you. Sometimes the company can outgrow you as a founder and having those conversations early before it gets there so that you know that that’s on. I was coaching a, a company not too long ago and they’re going through kind of that evolution.

Lena McDearmid:

And when I said that to one of the founders, I was like, at some point, if it’s not now, it’s soon, the company may outgrow you. I think it’s like 92% of all companies change founders or basically the founders step down, and leadership comes in and they were gobsmacked, they’d never heard of it. And I’m like, those are the things where if you stay too long, it becomes hurtful. If you don’t address it, it becomes impactful. And if you bring in the wrong people, it changes your culture. Yeah.

Melinda Wittstock:

It’s so interesting actually. Just even if you look at Microsoft and the difference between Gates to Balmer to Satya Nadella and really focused on culture and that the company was doing really badly, the difference is, is yes. Right. And that’s company needs things at different times.

Lena McDearmid:

It is. And it, and it’s okay to say it like, and say it out loud. Say the things, say the uncomfortable part, say how tough it is in a meeting, say it’s difficult to work here and be successful. Talk about the tension, talk about the fact that one team isn’t getting along with the other team. So, collaboration’s not happening and it’s slowing everything down and bottlenecking. Like have the discomfort up front so that it makes it easier to start having the hard conversations. Like hiding and having conversations in the corner is never going to grow a company.

Melinda Wittstock:

Exactly. There’s so much more we could talk about. Lena, you have to come back on this show. Like we barely scratched the surface of such important work. I want to make sure that people know how to find you and work with you. Tell me a little bit about how you engage with people, like what it costs to work with and what’s the best way to.

Lena McDearmid:

I mean, the best way to really find me is obviously on LinkedIn, Lena McDermott and then Wryver (W R Y V E R) because I like a little rye in my river dot com. And they can always reach out if they’re interested in learning more. If they need us to come in for a day and do an assessment on a certain issue or topic or a larger project and then we base them on if it’s a retainer or ours. So, we can always work with all levels of stage of a company, whether it’s early startup to full mature. And based on the size and effort, you know, we’ll price it and then, you know, reaching out and kind of tell me what your problems are, and I will first have conversations. We’ll do some introduction and discovery work, and we’ll both find if it’s going to be a good match. You know, my requirement always is I want to be invited into your organization. And we all have to agree that we’re going to first talk about culture first before we get into architecting and go to market and expansion.

Melinda Wittstock:

Yeah. I imagine a lot of people come to you thinking that they have a specific problem, but it’s. The problem is actually the culture.

Lena McDearmid:

That’s right. Yeah. The output is. Culture is the problem. The output is revenue loss or, you know, attrition or whatever. Yeah, that’s normally the. It’s kind of like when you have a sickness, but you feel it in your head or whatever. It’s.

Lena McDearmid:

It’s the indicator. Yeah.

Melinda Wittstock:

Right. Okay. Well, this is amazing. Well, thank you so much for putting on your wings and flying with us. And you will definitely have to come back.

Lena McDearmid:

Thank you, Melinda. Thank you so much. It’s been such a great time. I’d be happy to come back.

[INTERVIEW ENDS]

Melinda Wittstock:

Lena McDearmid is a serial entrepreneur and the founder and CEO of Wryver, a consultancy that helps leaders create organizations where people and performance thrive together.

Melinda Wittstock:

If you’re ready to level up your culture, take some of Lena’s advice to heart:

1. Audit your leadership team. Are you hiring for technical chops, or are you considering how well new hires can communicate, collaborate, and handle tough truths?
2. Start a team conversation about culture—ask for stories of what it feels like to succeed (or stumble) in your org, and what helped or hindered those experiences. And Before you invest in more tools or headcount, invest in clarity around “how we work together,” not just what you’re building.

Make sure you find Lena on LinkedIn or at WrYver.com (that’s spelt wry-ver) if you want hands-on help, a quick assessment, or ongoing culture and ops mentorship.

Melinda Wittstock:

And, please take a moment to give us a five-star rating and review the podcast on Apple and Spotify—it helps more entrepreneurs like you find the secret sauce to support and grow their businesses.

Melinda Wittstock:

That’s it for today’s episode. Head on over to WingsPodcast.com – and subscribe to the show. When you subscribe, you’ll instantly get my special gift, the WINGS Success Formula. Women … Innovating … Networking … Growing …Scaling … IS the WINGS of Inspired Business Formula …for daily success in your business and life. Miss a Wings episode? We’ve got hundreds in the vault, all with actionable advice and epiphanies. Check them out at MelindaWittstock.com or wingspodcast.com. You can also catch me on LinkedIn or Instagram @MelindaAnneWittstock. We also love it when you share your feedback with a 5-star rating and review on Apple, Spotify or wherever else you listen, including Podopolo where you can interact with me and share your favorite clips.