Leadership Levers
This podcast spotlights leaders' actions so they may enhance their organization’s performance and culture.
We feature CEOs and industry-recognized Subject Matter Experts (SMEs) who share their experiences and insights on three key challenges: people, performance, and profit.
If you are a leader who wants to learn from your peers about improving performance and financial returns, please join us.
Leadership Levers
Walking the Digital Floor - Leading Culture & Performance in a Hybrid World with Charles Windsor
The relationship between organizational culture and business success has never been more critical - or more complex. How can today’s leaders strengthen culture in ways that drive performance and connection, especially across remote and hybrid teams?
In this Leadership Levers episode, we sit down with Charles Windsor, CEO of Oakwood Systems Group and TalentPort Inc, to unpack the connection between culture, performance, and leadership in professional services.
Drawing on 40 years of consulting experience, Charles shares practical lessons on how culture evolves - and why it must be intentionally cultivated, especially in a hybrid world.
He explains why culture isn’t just atmosphere - it’s the framework that gives people purpose, fuels innovation, and drives profit.
The conversation takes an interesting turn as Charles details his approach to remote hiring, emphasizing that distributed employees must “put two feet into the business.” He shares the criteria his team uses to evaluate remote fit and how those cultural cues can make or break employee engagement.
Charles shares his philosophy of hiring for attitude over aptitude, why he interviews every candidate, and how his company’s values - risk-taking, community, mindset, and humor - shape performance from the inside out.
His message to leaders is clear - culture is a leadership responsibility, and communication is its most powerful tool.
“How do you walk the floor digitally?” he asks. The answer, he argues, determines whether your team is simply working - or truly thriving.
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Welcome to the Leadership Levers Podcast. I'm your host, Will Gladheart, CMO at the Culture Think Tank. At the Culture Think Tank, we empower leaders with metrics that strengthen culture, drive performance and return. We're here today to learn about the actions leaders have taken to address organizational change. Today, our guest is Charles Windsor, CEO of Oakwood Systems Group & TalentPort Inc. Thanks so much for taking the time to join us.
Charles Windsor:Thanks for having me, Will I appreciate it?
William Gladhart:Excellent. Well, let's begin by having you share with our audience a bit about yourself, your background and the organizations that you run.
Charles Windsor:A couple things. First, I guess I'm a father and a husband of two girls that are early 30s. I'm even a grandparent. I've got two grandchildren now Surprisingly how that happens when I'm so darn young. I've also been married for 37 years.
Charles Windsor:I've been in, I guess, in the world of consulting oh, my goodness, probably close to 40 years, believe it or not. Coming out of a background of kind of psychology and then an MBA in finance, I got into sales and eventually landed at what has become Accenture and spent a dozen years there in Ernst Young, before jumping into the entrepreneurial pool, as it were, and starting a business in 1999, which it was a consulting business that I built and sold over a period of three years and bought Oakwood in 2003. And then, as a part of that opportunity to start Talentport occurred, probably three or four years later. It's almost a compliment we can dig in, if it's of merit, the difference between Oakwood, which is more of what we characterize as a consulting managed services business, versus Talent Port, which is a staffing company. Anyway, high level about those two companies.
William Gladhart:Thank you for sharing that. I think it's interesting that you started another company out of need that grew out of your own business. That was a complimentary service. Why not go double all in on the entrepreneurial bent? And thanks for sharing that about your journey In our conversations. Would you share why you believe a healthy culture is critical?
Charles Windsor:I think that culture is certainly important in anything we do, whether it be in a big company, small company. The term culture itself, I think, has probably been used quite a bit. It certainly is the glue that I believe in companies tends to give people a sense of being a part of something other than just a job and a paycheck. I think it's this notion of culture, ultimately within the work life has also been kind of a challenge with culture in your home life. So there's some things that are kind of interesting there. I versus as you could look back through the decades and say you know, what's the culture of a company in the 50s versus the culture of a company in 2025? Quite different, I think you might agree Absolutely. So I would say kind of just in terms of our world, a healthy culture and the importance of it.
Charles Windsor:Companies really that are, I believe, successful tend to have open communication, right Collaboration and teamwork. There's a sense of continuous learning and development. There's a sense of work-life balance. There's a feeling that your views are important you could use I don't know the DEI is even a term we can use anymore. It seems to now have different connotations, but it's certainly critical. Diversity, inclusion and understanding of people's views is incredibly important. Recognition and reward right, some level of ethical and companies need to have folks that are ethically and honest and show a sense of integrity and I would say just maybe even this notion of the ability to have a company that can innovate and adapt, I mean, to the world today. Look at what's going on in the world today. My goodness, I bet you almost every company out there is trying to say, okay, what do we do now? Right, you can't just stay as a task. I think culture, without kind of glamorizing it anymore, is incredibly important to many businesses and certainly ours.
William Gladhart:Yeah, Well, I love that you touch on culture, tying to not only the bottom line of the organization but also the purpose of employees and staff, and then how it ties to innovation, because those are three key areas that we often find that there are lags or there are gaps in how the organization is operating or how the leader is communicating. So with that in mind, let's begin with our first question. It's been our experience that leaders tend to struggle in three key areas people, process or profit. In your role as a leader and a CEO, could you identify an area that represented a cultural challenge or just a challenge in general within your organizations?
Charles Windsor:And I thought about this question. That's an interesting one, and I would say interesting specifically because we drive our business with our people. This isn't a company that sells a product. We didn't come up with a product. I believe are directly impacted by the culture of the organization that you're trying to generate, or build, as it were. The notion of happy people and happy customers yields a happy company right and happy profit. I would say, of all of those I don't know that your culture, I think, is a byproduct of the business you have, but you can be very intentional about trying to build your culture.
Charles Windsor:In my mind and, by the way, I'm not such a historian that I could frame out examples where companies have had to pivot their culture, but I certainly think that in our world, in the world of technology, which is the core of what we do, we build and implement technology software for primarily Microsoft-centric solutions, but certainly we touch on a lot of other technologies that industry is changing incredibly quickly. If you were talking to a CEO of a manufacturing business or a CEO of a retailer, those businesses are changing as well, but in different ways. I think that the challenge that we have tried to address in terms of our team and the culture of those people. People in our business recognize that we need to produce a profit and, by the way, they have a real direct link because in our business people bill by the hour or they bill by a project or they bill under some guise, and they know that if they do certain things, that produces revenues for the business and ideally it will run a profit. So they have an understanding of the notion of profit. They also understand that our business processes need to be followed.
Charles Windsor:There's a variety of reasons why I want to unpack those for you. In terms of that, we really sell a process for delivering a result. If you think about it, in some sense the challenge that we have culturally is to make sure that the people that we hire fit our culture and the culture that we have fits our people, and so, in that context, part of what I've tried to do is we simply say, well, what is our culture? And again, you could argue that companies put posters up on the walls and of sunsets and whatnot. We try to refine and define our culture in kind of the values that we espouse as an organization and again, we try to embrace those on a somewhat consistent basis. But I'll share what those values are with you, literally just for your audience. That would be fantastic.
Charles Windsor:We encourage responsible risk-taking to find bold solutions and foster personal and professional growth. Hard work is our foundation and humor is our mortar. We actively seek opportunities to help our clients, our team and ourselves through knowledge sharing, volunteering and community events. We believe helping others is a participatory sport. We are inspired to be pushed outside of our comfort zone and are eager to thank those for inspiring us to take a risk, and we encourage everyone to lead through their attitude and approach.
Charles Windsor:An attitude for me personally is I think oftentimes I tend to be the last interview. I interview everybody that we bring on board and some that we don't. That may not be a fit, but I'm tending to interview more for their attitude than their aptitude. I have a lot of folks that evaluate their aptitude under a number of different components, that evaluate their aptitude under a number of different components, and while our business is incredibly rigorous in many things that we look for whether they're analytical skills or certain technical skills or problem solving or critical thinking, whatever I think if you bring somebody with the right attitude and they have some elemental level of foundation, you're going to hire good people. So that's really when we are kind of evaluating those folks. We're trying to evaluate them around an attitude and aptitude, but then, more importantly, fit. Do they fit within the culture of what we're trying to build here?
William Gladhart:Great. Now I think that's a really interesting point that you've brought up in terms of you kind of covered our other questions in your thoughts about the discussion about what the challenge was, especially around people, and then the thing that you identified was really the values that you've laid out for the organization. That the person fit has to be tied to the values and to the other people in the organization. I love hearing about that connectivity, because we've shown statistically that the more connected employees are in an organization, the more they understand their role, the better they feel. The higher they perform, the better revenue gets generated. You know up to 15 to 20, 30 plus percent gains over 12 to 14 months. There is some secret sauce to it's not a secret sauce, but there is something to what exactly you were putting in place and what you have kind of steered your company towards. As we kind of wrap up our conversation today, is there anything else you'd like to share with fellow leaders?
Charles Windsor:I'll unpack it a little bit more for you, because I think the interesting dichotomy of culture today with culture of yesterday and the culture challenge in our world is that we hire people who don't work in two of our physical geographies. So we have quite a few people that are remote workers and I would dare to be so bold as to say I think the challenge that we're seeing with the remote worker movement that occurred during the pandemic and as now companies are pulling workers back into the office we've always had this in the services business, certainly when I worked in the bigger companies, and even when I've been on my own and we were just chatting about earlier is that when you have a remote worker, it's more challenging than ever to make sure that you're hiring those folks for the kinds of things that they're going to bring to the table, other than whether you're going to bill for them. Remote workers we have a set of criteria and evaluation criteria and questions that we use, because remote workers, while they have many of the things you might look for in the job description to be successful, there's certain characteristics you have to evaluate about who can be a successful remote worker, because, as anybody that's worked remotely, there's complications there. There's no separation with work-life balance, right, there's oftentimes distractions. So you've got situations where if you're sitting in a cubicle or sitting in an office, you don't have those, and so the dilemma that we have is not only the ability to be productive in that remote setting, but from a cultural contribution. You have to be much more intentional with remote workers of engaging them to be a part of your culture, to engage them, to put, as I like to call it, two feet into the business versus one foot.
Charles Windsor:And when you think about the notion of remote workers and you think about the portability of jobs today and I mean there's nothing more portable than IT, skilled folks, right, there's a tremendous demand for them. And there's this industry, not only on the staffing side that I mentioned about another business, but in general, where companies, via LinkedIn, can be recruiting people, and those employees whose images are out on, say, linkedin can be recruited. And so the ability to find folks that fit your culture, that you can bring into the business, that aren't working in your physical offices, you can make sure they're engaged appropriately, you can make sure they're feeling that sense of recognition, reward, a challenge in a business where maybe you're not walking down the hall and you can give them an attaboy or an inaugural kind of thing right. It's complications like that that undermine a leader's ability to foster culture, much less the portability problem. I think I saw a statistic and this was maybe for the, not the millennials, maybe it was the millennials, it could even be Gen Z. There was a statistic that said the average millennial is going to have 15 jobs in their career and if you think about the average career mid-60s 40, some odd years that's a job every two to three years.
Charles Windsor:When you think about a leader, how do I build a culture? Culture comes through consistency, engaged employees, the ability, maybe to be in touch with them. Thank goodness for video right, it certainly helps bridge the gap. And then you combine that with this notion of skills, portability and the gig work environment and folks being able to move jobs easily. I think it creates a tremendous challenge and you've got to find a way.
Charles Windsor:And, by the way, it's one of the biggest things we found in that kind of evaluation of do you put two feet in versus one is those remote workers that are really good at remote work. They put two feet in because they believe that it's their I wouldn't say responsibility. They enjoy reaching out as much as you enjoy engaging them. Whether you're the manager or you're a member of the team, they make a point of engaging with the rest of the organization on a proactive basis. And it's that combination of making sure you got the right folks on the bus, as Jim Collins liked to say, and in the right seats, and make sure those seats fit your business model. It's a complicated stew.
William Gladhart:Yeah Well, I appreciate you bring up that you approach two different pathways for hiring individuals, both in-person and remote work, and there's a different set of criteria. I think you're one of our first guests and leaders that has actually brought that up. Many have remote workers or they have a partial remote workforce, but no one's really addressed those key points and I think it's absolutely imperative that leaders understand that. I mean, it is a difference and it is a different type person that are in different roles. So, again, going back to the communication values, finding the right fit at the organization. So thank you so much for sharing that. Anything else you'd like to add before we wrap up today?
Charles Windsor:You touched on the last thing I was going to mention, and truly, when you said what has been one thing that impacted your culture positively Communication, communication, communication. Yep, right, if you look at the importance of that level of communication, right, whether it's downwards, sideways, upwards, the ability to be able to hear and see from folks, and again, it's a never-ending improvement story. Right, I think, if we were to do surveys every year. More communication, and again, it's got to be the right stuff. Employees don't want exhaustive communication, that you know. Oh my gosh, another email, another CEO missive, charles, you know, pontificating from on high. They want stuff that's going to be relevant to them and they don't necessarily always want to hear it from me.
Charles Windsor:And, by the way, as a leader, I think that gosh, who is that I read about, jensen Wang at NVIDIA has such a flat organization that he has, I think, something like 30,000 people that can email him about anything, everything and anything. Now, granted, that can produce a little lack of focus, but the fact of the matter is you, as a leader, have got to be willing to take the pulse of the organization, not just through HR or just through your direct reports. But how do you talk to the folks, maybe that are two, three levels down or more. How do you find a way to ensure that you're listening to that drumbeat of the organization so that, when it comes to the culture, either you're able to get ahead of it more importantly many leaders can't be all things to all people but that your people and the folks that are in touch with that part of the organization can make sure they surface those things and address them on a productive basis? So that would be my final thought.
William Gladhart:It's the communication stupid. No, I love that because a very wise mentor said to me many years ago he goes, you know, when I was in operations, manufacturing, warehouse, logistics, et cetera, he said don't sit in the office, go walk the floor, know your people, know what they can do, know what their capabilities are, and when you do that and you can do every job that they do, your things will run very smoothly and you will have buy-in from your staff and they will make you look great.
Charles Windsor:Hence beautiful advice. In the world of today, how can you walk the floor digitally? Yeah, how can you walk the floor if they're not there? How can you go down the hall have?
William Gladhart:a cup of coffee, or grab a bite to eat with somebody.
Charles Windsor:Again, that's the dilemma of big companies and small companies.
William Gladhart:Yeah Well, Charles, I've enjoyed having you on our Leadership Levers podcast. Thank you for your thoughts and your time.
Charles Windsor:You bet Will Take care. Thanks so much.
William Gladhart:Thank you for joining us on the Leadership Levers podcast. Find all our Leadership Lovers episodes on the Culture Think Tank website at www. theculturethinktank. com or listen on your favorite streaming platform. We'd love to hear from you about the challenges you have faced as a leader platform. We'd love to hear from you about the challenges you have faced as a leader Tune in weekly as we invite leaders to share their experiences in strengthening culture and performance, one action at a time.
