The Transform Dialogues Featuring Tom Whitty

Original Event Date:
February 2, 2026
5
minute read
The Transform Dialogues Featuring Tom Whitty

The Transform Dialogues Featuring Tom Whitty

In this edition of The Transform Dialogues, Tom Whitty joins the conversation to explore leadership, transformation, and what it truly takes to drive meaningful change in today’s organizations. Grounded in real-world experience rather than theory, the dialogue focuses on how leaders can navigate uncertainty, balance performance with humanity, and build cultures that sustain growth over time. The session invites leaders to slow down, reflect, and rethink how they show up—for their teams, their organizations, and themselves.

Session Recap

The conversation opens with a candid reflection on how leadership expectations have shifted in recent years. Tom emphasizes that transformation is rarely driven by grand strategies alone—it happens through everyday decisions, behaviors, and moments of trust. He discusses how leaders often underestimate the emotional and relational dimensions of change, focusing too heavily on execution while overlooking the human experience.

As the dialogue unfolds, Tom shares insights on navigating complexity, leading through ambiguity, and resisting the pressure to have all the answers. He highlights the importance of curiosity, listening, and humility, noting that strong leaders create space for others to contribute rather than positioning themselves as the sole problem-solvers. The discussion also touches on burnout, pace, and the tension between urgency and sustainability.

The session closes with a forward-looking perspective on leadership transformation—encouraging leaders to move beyond performative change and instead commit to consistent, values-driven actions that build credibility, resilience, and long-term impact.

Key Takeaways

  • Transformation happens through behaviors, not just strategies.
  • Leaders don’t need all the answers—but they do need curiosity and humility.
  • Trust is the foundation of sustainable change.
  • Listening is a leadership skill, not a passive act.
  • Culture shifts when leaders model the behaviors they expect from others.
  • Pace matters—burnout undermines long-term performance.
  • Authentic leadership builds credibility over time.
  • Change feels personal to employees, even when decisions feel strategic.
  • Psychological safety enables innovation and honest dialogue.
  • Consistency is more powerful than one-time initiatives.

Final Thoughts

This Transform Dialogue reinforces a simple but powerful truth: real change starts with how leaders show up every day. Transformation isn’t about moving faster or doing more—it’s about leading with intention, empathy, and clarity. When leaders invest in trust, listening, and human connection, they create organizations that are not only more resilient, but more capable of meaningful, lasting impact.

Program FAQs

1. What is the focus of the Transform Dialogues series?
Honest, human conversations about leadership, culture, and organizational change.

2. Is this session tactical or reflective?
Reflective, with practical leadership insights drawn from real experience.

3. Who should attend conversations like this?
Leaders, managers, HR professionals, and anyone driving change.

4. Does the session focus on culture or strategy?
Both—but with an emphasis on the human side of execution.

5. What leadership skill is emphasized most?
Listening, trust-building, and self-awareness.

6. How does this apply during times of uncertainty?
It encourages leaders to lead with clarity, empathy, and steadiness.

7. Is transformation presented as a one-time effort?
No—it's framed as an ongoing practice.

8. What role does authenticity play in leadership?
It builds trust and credibility over time.

9. How can leaders avoid burnout while driving change?
By balancing urgency with sustainability and care for people.

10. What’s one action leaders can take immediately?
Pause, listen deeply, and lead with intention rather than reaction.

Click here to read the full program transcript

All right. We are here for the Transform Dialogues live at Transform part of the People Strategy Leaders podcast. My name is Zach. I'm Amy, and we're joined with Tom Witty. Tom Witty, thanks for joining us. Really excited to kind of be on the floor here talking about the transformation of work, the new ways that organizations are doing things. So thanks for joining. I'm curious, as we are on that topic, what are certain movements or, or challenges or decisions that you're seeing out in the world of work today that are top of mind for you? Sure. Well, first off, thanks so much for having me. It's great to meet you both and to be here. I think some of the biggest things that we're seeing here at my, especially within my company up Flex, which started out originally as a platform to provide on-demand workspace to remote workers, obviously saw a boom during the pandemic when largely folks were pushed into remote situations and companies reorganized. Now, the biggest thing to answer your question that we're seeing is the pendulum's starting to sw swing back a little bit. And so there's obviously been a lot of mandates coming from the top down of how can we bring our people back to the office? But employees, once they prove that they could do their work from home and, and enjoy a level of flexibility for the first time that they'd never had before, I was sort of reluctant to give that up. And so some of the biggest challenges we've seen are really people, leaders being caught in the middle of that tug of war and then trying to figure out the right balance of that. And so increasingly we're seeing companies really trying to figure out how do they optimize that in-office experience? How are they trying to get people to want to come back in voluntarily by giving a, an experience that really gives back, um, something of value makes it worth their time and effort to do that, um, so that they can appease both sides, but it's not an easy task. It sounds like a pretty tough dilemma for a lot of organizations, right? Because, uh, yeah, as a, from a people officer standpoint, you see like the engagement scores and some of the feedback about the remote or hybrid flexible work environments. And then on the other side, you see certain organizations making pretty aggressive moves with their return to office policy, right? That's like, Nope, starting next month, five days a week, no exceptions on location. We're back in the office because that's who we are. Right? Yeah. And, and I don't have enough, uh, you know, behind the scenes look into where those decisions are coming from, but yeah. Where, where do you feel like those pressures are coming from? Like why, uh, are some of those mandates being rolled out and, um, is there a more effective way that you see organizations approaching that decision? Yeah, great question. I, I, listen, I think these mandates can come from a variety of places. My personal opinion is a lot of it's rooted in just legacy thinking, and this is the way we've done things. This is the way we've known that people are working. This is the way that we can ensure that those organic serendipitous moments do actually occur. Um, but sort of the more modern thinking that we're trying to, you know, bring to the table at Aflex is really the concept that these moments can actually be engineered intentionally, and those moments don't necessarily need to occur in a owned or released office building. Now that solutions like ours and many others exist, where you can have on demand space that when used in an intentional manner, you can bring people together for those reasons, um, and create space for those interactions to happen while still maintaining flexibility. The other benefits to that, of course, is that when you don't necessarily root yourself in having to have a dedicated office for these things to occur, there's cost savings involved, right? When you're only paying for the space you need when you need it to get people together for those reasons, that allows people to rightsize their portfolios. And funny enough, that's sort of what happened organically during the pandemic. A lot of companies did scale back their office footprint. Now all of a sudden they're trying to bring back all these people into a lot less space. Yeah. We've seen some of these headlines lately, of course, where people can't find a desk on peak days. There's not the meeting room that you need can't even find a parking spot, right? All this stuff is sort of in the news. And so that's actually been a great forcing mechanism for our business to try and invent some new solutions, some of which we've recently rolled out that leverage modern technology and, and AI to really help optimize the in-office experience for our customers. For years, we've helped them solve the on-demand workspace needs for their remote distributed teams. Now they're really coming to us and say, how can you help us now with a lesser footprint of office space, make sure that we get the right people in at the right times with each other? And so how can we use technology to understand those collaboration patterns within and across the enterprise to ensure those cross-functional interactions are done in a dynamic and real time manner, which is just not something that traditional solutions or methodologies really ever were designed for based on how we're now working. Yeah. You talked about some of the experiences that can be created and making sure they're intentional. Can you give us some examples of what you've seen or what you've sure guess have been a part of strategizing? Yeah. We actually developed an entire playbook, um, alongside not just us. We work with some of the best minds and organizational design and culture experts. And some of my favorite examples is so particularly new joiners, right? Like we often hear that, you know, younger generations and Gen Z in particular are the ones that are sometimes most negatively impacted in fully remote environments. They don't get the sponsorship and mentorship, um, that they would get if they were alongside more senior folks in an office environment. Um, so engineering those types of moments and interactions by pairing folks. So even though maybe we're not even on the same team, but we happen to live near each other and there's not a corporate office nearby. So how can we bring us together for those types of interactions? We have another customer of ours, um, PowerSchool tech company, and they're national in nature. They've used our spaces in a very intentional way to, for company all hands events. They sync together what they call power pods, which are just localized clusters of employees at an up flex on demand location. They then sync up all those groups of power pods together for the company wide virtual event. So that's a culture play. Yeah. Right. Um, so there's many others. We have about 30 of these sort of, you know, playbook plays that companies sort of work with us on running, but that's just the on demand side inside the office. They're really, now, again, the, the even more prominent now than the on-demand side is how do we really make sure that, you know, when you ask me to come in, that it's going to be the right people that I need to be with, that I'm not forced to sit there on Zoom meetings or teams meetings all day long, which I could have done from home, right? Yeah. That's what's caused some of the biggest pushback on return to office mandates and saying, why are you forcing me to do this? I could have done this from home. There's nothing special or incremental about me coming in. So that's the biggest thing for Summit. I really like this kind of paradigm shift to like experiences within the design and, and using that to help fuel the strategy that you're trying to achieve, right? Versus, uh, like, uh, the traditional ways, like the legacy thinking on it. And it also aligns a lot with what we're seeing in the l and d side where rather than making people sit through modules or a learning course, right, they're designing micro experiences Yes. To really play in touch with whatever the, the skill is that they're trying to develop and using that to propel behavior change, skill development and outcomes that they're going for. And I I, I was even thinking as you're sharing that, I was like, Ooh, I wonder if like, the playbook can even get as specific as, alright, we're gonna design a decision making experience because as a team, we gotta make a decision here and we should be together to collaborate on this. So we're gonna gather, and it's, that's the experience. Or, and then you can do it around innovation, collaboration, or more culture, team building play. Uh, it just feels more outcome based. That's Exactly right. Those are some other examples. Hackathons, sprints, um, you know, we have to, you know, brainstorm on a particular project or, or, or challenge that we're up against. Um, we've also partnered with other folks. I come from a wellbeing background, so it's still very near and dear to my heart. And so, you know, the concept of scaling, uh, what used to be like very focused, um, in real life, like resilience trainings or, or leadership development experiences, we can now scale much broader. If you, you know, adopt that same model of you bring, you know, localized folks together, um, and then sync them up, um, across these spaces, it's a way of, you know, getting that out to more people, which, which is, which is really exciting. But yeah, there's a lot of variety use cases, but I think, you know, the, the, to come denominator to almost everything that we're doing, whether it's optimizing companies own in office experience or creating an equitable experience for the non-office workers that are distributed and, and using the on demand spaces, is this concept of intentionality, right? Mm-hmm. There being a reason why folks come to a building. And the biggest mindset shift is it doesn't necessarily have to be the particular building. It could be any building, right? It's as long as when I go to some space that there's value in it for me in coming to that, I love that, right? Like, why does it have to be the, the office space? Mm-hmm. It could be this local coffee shop, it could be the park, it could be all these different, I mean, there's so much on your space in within cities too. So you could get really creative with like, all right, let's take the team, have a micro experience type engagement to move whatever our objectives are forward. I cares for, for this to continue to be outcome based, uh, for the organizations engaging with maybe this type of mindset. What are the typical outcomes that they're most like focused on? Or, or really maybe embracing this on? Is it because this is really a more productive way to run the business and we're trying to reach high performance? Is it more of an engagement play, right? Where we're trying to bring experiences and a sense of connection to our people, and this is gonna retain and engage our people? Like what are the key objectives that you find people more focused on with this philosophy? Yeah. It's, it's a great question. Um, I would say it, it really depends on who our, our owner is. Um, and so we oftentimes will be, you know, owned by a workplace leader, owned by a people leader, even folks in on the real estate side, if it's more of a pure cost savings, optimization play, um, for the folks in, you know, the people side of, of the business or even workspace, um, workplace, which increasingly is rolling up into hr. From what we're hearing, companies are really reorganizing in that fashion quite a bit. It's oftentimes, um, talent acquisition, right? So we're not in a war for talent anymore, but I still would argue that we are still in a war for the best talent, and the talent at the top does still have the position of power and can demand flexibility, can demand certain types of arrangements that they've grown accustomed to and fond of. And so that can be a strategy in saying we've been, we found a way through innovative thinking, through innovative solutioning to give you some degree of flexibility, but also to still give you that in-person interactions that we know are that X factor magic for our business. Yeah. From an outcomes and productivity standpoint. And this is how we go about it. And so that can become a competitive edge from a talent acquisition and retention perspective. Certainly it has productivity outcomes when again, you are bringing teams very focused efforts for those micro experiences that are designed to achieve specific goals or to advance specific initiatives and projects. Um, or it can really just, um, you know, we've seen this offered at some of our customers as a complete flexibility perk, right? So for all of our companies, we now have access to Aflex. You know, I have a two and a half year old daughter at home. I love her to death, but sometimes she's noisy and I've, you know, and when I'm trying to work at home and sometimes it's nice to be able just to go get an up flex desk for the debt, right? So there's some companies that are even just thinking about it from a pure total rewards up flex is a benefit perspective and that's fine. And it can really be everything in between or some combination thereof. Really just depends on, you know, sort of who we're engaged with within the business. That makes sense. How does that resonate with you? I mean, I know you have a, a couple young ones at home too, and like, I'm thinking like, uh, you know, a remote worker, we're a small team, we're fully dispersed. There's no office space to begin with. Yeah. Uh, but I'm also like, I can go insane staying at home too long by myself. Right. I'm like, I just need to be surrounded by people. Yes. So I'm like, okay, cool. This sounds like a great program, but yeah. How does this resonate with you as a parent as well, and like having flexibility but also choice maybe to engage with that? Yeah. I love this idea. I think it's phenomenal. And I think even, you know, some of the things that we've talked about, because we both are in the same city. Like if our companies encourage us to meet with other professionals, you know, so they let us allow, you know, build our professional development and our networking and, you know, we're both in trying to build our businesses too. So there's that opportunity. But I, I think if you look at that idea of having intentional spaces where you can go when you want to go, when you need to go, um, yeah. From a wellbeing perspective, I think that makes a ton of sense. So I really like that. That's a really interesting idea too, that kind of sparked in my head, was how do you maybe enable your employees to engage with their customers Yeah. Within their office. Like, in a way, or like within spaces. The sales, the Sales use cases is a, is a, is a very common one with our customer Base. Right. You know, it's oftentimes a, a point of folks getting started with us is they'll take their outward customer facing teams who are out trying to meet folks, create that opportunity, even just from a travel perspective. Right. You know, we, our perspective, you know, we envision a world not a couple years out where it's gonna be like, you book your flight, you book your hotel, you book your workspace, right? Where, wherever you're gonna be, whether it's a meeting room 'cause you're meeting with a client or prospect mm-hmm. Whether it's, you just need a place to go and be around other humans. Maybe not be in your hotel room all day long. Right. Um, or get outta the house. I love, you know, enjoy. Like I live in a, in a, in a small town in Florida and, but there's a couple of great coworking spaces. They're on our platform and I love going there often, you know, and just to meet folks from other companies. Yeah. And I've developed some great relationships and, and to your point, built my network out in that regard. And, you know, that's been one of the biggest, you know, negative impacts on that side of the equation with remote work is that isolation aspect. Mm-hmm. And so the connections are good whether they're within the company, but I would also also good even externally outside the company as well. Yeah. Yeah. 'cause that's even been a huge topic within our community at chief engagement is like on one end, employees are looking for more connection and relationships with their peers, but they don't want a but they don't want to be forced into the office. They wanna be provided choice and flexibility in how, when and where they work. Yes. Right. So it seems like this really delicate tension and message that organizations have to balance and, and fulfilling those needs, um, because that's what's gonna lead to kind of the performance and engagement they're looking for, for, But what we see is they won't mind coming in if when they come in, that's amazing, right? That they, they do get that 'cause they do crave those connections. Mm-hmm. People do want to be with each other. Right. They do get value that's not lost on folks. It's just that some of the early efforts at return to office have just not delivered on that. Right? Yeah. And so that's what we're trying to get folks to think differently about, You made a great point earlier, why would I come in the office and then have all my meetings on Zoom? Like, and that still happens, right? Because if you don't time it out and make sure that one department is all coming in, if it's a hybrid schedule, they should all be in on the same days then. Right? Exactly. Like make that, that very intentional time together. But that, but nowadays because of hybrid, the way the companies used to go about planning, those things have all become barely obsolete, right. Because we're in such a dynamic, real time changing environment and who I need to work with and collaborate with on any given day is not something that any group of humans could properly manage or maintain on spreadsheets in any possible realistic way. So that's where AI has been such a huge opportunity for us. And so we have a technology, it's actually been around for 10 years, but it's recently made tremendous strides and just autonomously looking in the organization and understanding those collaboration connections to then tell folks when and where to come in with whom so that they get that value. And it's just something that tech can do that teams of people can't really do. I love that. And so that's how we're trying to solve for that. But I agree, it's, it's, you know, no one wants to come in and be on zooms. I also use the analogy sometimes it's like, you ever go to a wedding and have like a great table, right? Mm-hmm. And then go to a different wedding and then like not be at the best table. Like think about how different like that wedding experience is and it's like no different than like coming into the office. Like if you are at that great table at, at the office with all the right people, right? It's, you would love to go to weddings all the time, right? And it's us. It's no different. Yep. See, I don't know if I've ever had that problem. No. But, uh, uh, well this is really exciting. I like the idea of being prompted these like nudges or plays of like, Hey, we noticed that yeah, you two have been having these type of conversations, we already booked you. That's right. This meeting space to have this decision collaboration experience and here's the guide and we're gonna facilitate that for you. Right. And I mean, that sounds so like whole new competitive edge next level. And which kind of translate to kind of our, our closing thoughts here. Uh, we always like to kind of wrap up with these bold predictions, these bold thoughts about like what organizations should be thinking about to stay ahead of the curve. Whether that's a challenge they should be anticipating or a action they should consider taking here, you know, uh, uh, to kind of step into the future. And you've started already kind of talk about that, but yeah. What, what's some of your bold predictions or thoughts? Alright. Um, my biggest bold prediction will be that within three to five years, um, even for folks that do come into an office, right? Or at least some point right now, typically you have to book a space at your own office, right? Nobody likes to do that. I think that's gonna be made obsolete very, very quickly. And that's through the techno types of technologies that I'm talking about that will quickly take away that burden from being at the employee to have to say, I'm coming in on such and such date. I want, I need a desk, or I need a meeting room. Or This is what I, you know, let me choose the thing and have to do that. Technology is gonna quickly take that burden off of them. And just to your point, autonomously, organize folks in the right way. Make sure that the right folks are coming together at the right times, um, tracking the outcomes of, of those interactions and experiences. And that's gonna be, you know, I think that's gonna get us to a world where folks will enjoy it, right? It'll really, that's where I think we can solve for return to office. Yeah. Is in, is in really leaning into that. But it's, you know, we have to recognize that that's, you know, the 180 degrees different from what's been happening for decades, right? So it take a little bit of, of of, you know, coming over, getting over that inertia of that change. Um, but that, that's my prediction. Well this was wonderful. Thank you for joining these transform dialogues live on the floor and I really appreciate that perspective, uh, of yeah. Experiences, right? Let's do the return to ERTE or something, Return To experiences it love it. Instead of the return to the office brand and, uh, yeah, exactly. Let's cut, let's trademark that on, on the brand. Um, I think that's like a, that's gonna be a huge competitive edge for those companies that embrace that. So excited to see you. You spearhead the way on that. Well, thank you. See you both. That's been great. Success. Yeah. Thank you. Thank you.

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