Hello everyone, and welcome to The Upstream Leader. My name’s Jeremy Clopton—glad to be with you here today. This is going to be a slightly different episode than normal. Normally we go about 25 to 35 minutes, this is going to be somewhat brief because it’s not exactly the podcast episode that I’d intended to record. It’s really because the idea that keeps moving around in my mind, which has come up through retreats, it’s come up at our HeadWaters Conference recently, is one that I think is so incredibly important that it warrants its own quick conversation with you here today. My original plan was, “Hey, let’s do a recap of HeadWaters, talk about all the great speakers and takeaways and everything”—and don’t get me wrong, that episode is coming—it’s just not going to be today.
Instead, I really want to talk about a lesson that hit me while I was at HeadWaters, subsequent to HeadWaters, and it really made me reflect on something that’s been a theme of a lot of retreats so far this year, and that is the value of connection. The conversations that I had with people in the hallways, at the reception, in the breaks, after HeadWaters, at breakfast, at dinner, all of those conversations tended to revolve around the fact that people love getting to connect with others. For some individuals, they brought their entire leadership team or their entire core firm team, and they were able to connect at a deeper level than they normally do in the office; for others, they were able to connect with leaders across the profession, like-minded managing partners, like-minded partners, and were able to really develop those meaningful relationships. Even for our team here at Upstream, the ability for us to be together for a few days and spend time at dinner, at breakfast, overall during the course of the conference together, was so incredibly valuable.
And that really has me reflecting on the value of connection, and really all the benefits that come from connections. So the things like trust and unity and the ability to work together in high stress environments and understand who it is that we’re working with; the ability to be engaged, to have friendships, to have meaningful relationships and how important connection is to all of that. Which leads me to a significant question that I want to pose, which is: “Are we truly connected, or are we simply connected to things and people with no real connection?” And I’ve been wrestling with this idea quite a bit lately, which is why I thought it might make a good episode here today, because when I think about where we’re at in 2025, middle of the year we’re in, connection—or should I say “connectedness,” let me change my words there—connectedness is arguably at an all time high. With technology the way that it is, video capabilities, texting, slacking, teamsing, emailing, all of the various tools that we have—technology being the tool—we have got, arguably, more tools than ever before to connect us to other people.
But what I feel like I’m seeing, and what I’ve heard from several others is, we are perhaps more connected technologically than ever before, but we have less connection than ever before. And I define “connection” as more of an emotional presence: the ability to really have meaningful conversations with individuals. Yes, we are constantly reachable, but I don’t know that we ever actually reach out in a meaningful way. And this came up at HeadWaters, this has come up in retreats, this has come up in so many interactions with firms. Let’s be honest, it’s come up in interactions outside of business as well. Do we have meaningful connection with individuals in our work lives, in our personal lives, and in the blend of the two?
What I’ve seen at HeadWaters was the value of people making time, making space to share a snack, share a meal, share a drink, share a laugh, where phones weren’t around, laptops weren’t around, instead you had people simply milling about in the common area, in the lobby, in the foyer—for my Canadian listeners, the foyer (“foyée”), as I’ve been instructed to correct it to from time to time—people were simply milling about, slowing down and having conversations. And that included some of the youngest professionals in attendance with more senior professionals, like-minded, across geographic boundaries, folks from some of our Canadian firms, talking with folks from our U.S. firms, large firms, small firms, tax, audit, consulting, advisory, CAS, outside the profession, vendors, all of the various things. And don’t get me wrong—there were business transactions taking place, there were conversations about how we could help one another, but at the same time, there were a significant number of what I would refer to as “unscripted moments” where meaningful relationships were being developed: where they were getting to know one another and talk about where they came from, what they did, what they were passionate about, how they show up in work, how they show up outside of work, and really building connection.
The same thing is happening at retreats. It’s a conversation that I’ve had with several firms over the past year or so. Retreats, though they are great for business, they’re great at helping you work on the business, the real magic—from leadership retreats, partner retreats, all firm retreats—the real magic is the camaraderie building that takes place when people get together and they share stories. They show up in an authentic, unguarded way that shows who they are, what they’re passionate about, where their interests lie. It’s a type of vulnerability that doesn’t require you to consciously think about vulnerability, because we’re not worried about the business context, we’re not worried about, “Am I being efficient? How will I code this time?” The time that’s devoted to creating connection is an investment like no other. And I’m seeing that in partner retreats, leadership retreats, all firm meetings, at our HeadWaters conference.
As I said, at various meals, we had the privilege of getting to have a few folks join our team for lunch that were attending by themselves—or for dinner, excuse me—they were attending by themselves and we were chatting to the lobby and said, “Hey, you want to join us for dinner?” And we got to sit and talk and get to know one another. Don’t get me wrong—yeah, we talked over the course of the conference. It was more of that business sense in a session. But at dinner, where it’s a relaxed environment and the walk there, the walk back, real magic happens because that’s where connection takes place.
What I’ve recognized, and I want you to recognize, this level of connection creates a strategic advantage, because no longer do people just care about what they’re doing, no longer do they just care about how efficiently they’re doing it—did they get their to do list accomplished?—instead, they care about building trust. They care about building meaningful connection and relationships that strengthen and allow for collaboration. When people are connected, it strengthens engagement and retention, because we’re no longer just “doing a thing,” we’re working with someone on a common shared purpose.
And I know that for some they’re thinking, alright, well, that’s great. We can build connection, but who’s going to take care of the clients? The people that care are going to take care of the clients. And when someone feels that others care about them and they feel as though there are some in the office that they care about as well, and they’ve got this connection, they’ve got these meaningful relationships, now, all of a sudden they care about the clients and they show up for the clients in a different way because it’s no longer, “I’ve got to care about the client because it’s my job,” but instead it’s, “I care about a client because we have a culture of meaningful relationships and connection.” And yes, there are sessions at HeadWaters that I could tie this to—that’s not the reason for it. The reason that I think about this is such an important topic for leaders, and the reason that I wanted to talk about it on the show, is the fact that connection is something that requires us to essentially disrupt how we’re showing up in business and show up in a completely different way.
If you think about what it takes to deepen connection, I want to give you three actionable practices that can help you deepen connection in your team, in your office, within your firm, within your community at large. The very first thing is we have got to learn to value being present over being efficient. And I know that somebody is going to hear that and think, “Well, we’ve got a business to run and I’ve got to get the work done, and there are times that we actually need to be efficient.” Completely agree with that statement. We are running businesses. We do have work that we have to get done. We have deadlines that have to be met. All of those things are true. Yet it’s also true that if we don’t take the time to be present, rather than trying to be more efficient, we will lose connection.
So what does that mean? It means that when you get to the office—and I know there are some partners that do this, and perhaps they get a little bit of a ribbing by their other partners for doing it—it means that you don’t immediately go to your desk, shut your door, put in your headphones, whatever it may be to get into flow and go, go, go, go, go, go, go, and then at the end of the day, you go home. What it means is when you get to the office, assuming this fits your rhythm, If it doesn’t, maybe it’s after a morning break, it’s for coffee, it’s for lunch, at some point in the day when you get to the office, you take the time to walk around and check in on people: “How was your weekend? How was your evening? How’s the family? How are your friends?” Whatever it may be. It means that you walk up to them at their cubicle, you notice what’s in their cubicle. Everybody puts things, artifacts that talk about who they are, and you ask a meaningful question. Anybody that’s been on a video call with me knows that I almost always have books in my background, then I cycle through the books that are on my shelf. I have a couple other things that would indicate what my interests are. They generate conversation. What that does is it creates meaningful connection over perhaps a shared interest or at least an interest in caring about the other.
So we focus on being present over being efficient. Yes, there are times to get things done, but we have to remember that our people are not machines, they are not robots, they are not an assembly line, and that nearly all of the professional skills that we want them to develop: communication, being advisors, caring, listening, all of the things, are made stronger through connection, are made stronger through learning to be present rather than simply to go faster. I would argue that’s one of our biggest challenges right now in the profession is we are so fixated on going faster and getting more done because we don’t have capacity, and perhaps we’re over-exerted on clients in some firms. We have too much work and not enough people, and instead of realizing that we may need to “right size,” we focus on efficiency, and therefore we lose connection. I’m going to encourage you, find time to be present.
One of the things that we used to do, when I started my career, that I talked to a lot of firms, they’ve stopped doing, is they go to lunch. I would encourage you, when’s the last time that you went to lunch? You took a group, whether it was other partners, other leaders, other peers, you just went around the office and said, “Hey, there’s this great Mexican restaurant down the street. It’s Taco Tuesday. Let’s all go have some lunch,” and actually went, and took the time to do it without worrying about, were you back in 37 and a half minutes so that you could really get into that next task and just go, go, go, go, go.
Second practice that I want to encourage you to do: Prioritize unstructured moments. And this is going to look a little bit different, whether you’re in the office or if you’ve got a virtual team—same thing on being present, I want a point on that real quick. If you have a virtual team, I realize you may not be able to go to lunch with them physically. Create an intentional coffee time, an intentional afternoon snack time, whatever it is, tea time, create those moments of presence.
When I say prioritize unstructured moments, these are the old water cooler conversations that we used to have, when we’d be walking down the hallway, we’d run into somebody and we’d strike up a conversation. Those are unstructured. Make sure that you build those into the day, or at least make time for those to happen. If your calendar—and look, I’m as guilty of this as anybody—if your calendar is completely booked from 8 to 5, or maybe 7 to 6, depending on what your calendar looks like, you don’t have time for unstructured moments, which means you don’t have time for those water cooler moments, but it also means that in the midst of a meeting, you don’t have time to prioritize an unstructured moment: “Hey, how’s everybody doing?” “Well, we’re doing well. This happened. I’d love to talk about in now if we can explore that.” “We don’t have time for that. We don’t have the buffer space for an unstructured moment.” Instead, everything runs exactly according to the agenda and the next task list. Build in time and prioritize time for unstructured moments, the conversations that take you somewhere else.
And they could be in a business context. Maybe you’re talking about somebody’s passions. Maybe it’s actually that you’re going through your errands on the weekend, and you run into somebody at the store. And we’re like, “Oh, I gotta get back, I’ve got this, and I’ve got this, and I’ve got this, and I’ve got this, the kids have this,” whatever it might be. It’s easy to just go, go, go. Connection requires saying, “I’m willing to stop and talk, that I don’t have everything so regimented that I can’t have that conversation.” That’s prioritizing unstructured moments. Look for those. Create those, if you need to. And I realize you may be thinking, how do you create unstructured moments? It means create the moment and then don’t have any structure to it. It’s just an open check in time.
Third thing to deepen connection: If you’re slowing down, you’re being present, you’re finding these unstructured moments, lead with curiosity. Ask meaningful questions. We ask questions that could be meaningful all the time: “How was your weekend? How was this? How was that?” What often is happening though, is it’s transactional, not curious, and we’re not actually listening for the answer. It’s more of a, “Okay, great. Now back to what we were going to talk about.” Leading with curiosity means that you not only ask the first question, you might even ask a few follow up questions because you’re genuinely interested in what they have to say. That’s what it means to lead with curiosity.
That’s what I saw at HeadWaters. People that had never met before, having meaningful conversations, learning about one another, learning about their firms, learning about what they do, their interests, their passions. I see it at partner retreats. Genuine conversations, caring about the other and what they’re doing, vacations, the family. We’ve got to make time for this. We don’t often recognize the value of meaningful connection. And it’s a challenge for a lot of firms. It’s a challenge for a lot of leaders. The business case for it, it’s all about retention and engagement, unity, trust—there are so many business cases for this. But what it requires is that you step back from the busy and you don’t worry about, for leaders that are in my profession, the accounting profession, that you don’t worry about where do you code your time? Well, I can’t charge that to the client,, we were talking about Formula One racing. Well, don’t charge it to the client. We’ve got to figure out how do we ensure we don’t lose connection or that we don’t mistake connection for being connected.
Because I get it—you’re all connected on a regular basis. You see people all day, every day. You work with them regularly. You have lots of conversations. I would challenge you with, do you actually have connection or do you just happen to be connected with those individuals? Because I can almost guarantee you that if you can create meaningful connection, you will transform the culture of your firm if it was absent before. And if you’ve already got some connection, but it’s not where you want it to be, meaningful connection will transform and enhance the culture of your firm greater than you ever thought possible.
One really simple example, there was a managing partner at our conference I was chatting with, he said that for every employee in his firm—north of 450 employees—they get a personalized email from him on their birthday. Said that’s the very first thing he does every day is if anybody has a birthday, he sits down before he gets his day started and he writes them a personal email, wishing them happy birthday. That creates connection, because he also makes sure that it includes something that he knows about them, that it’s not just “happy birthday” and send it. A meaningful note. It’s inviting somebody to dinner that maybe wasn’t expecting the invitation. One of the handwritten notes that I got after our conference recently, somebody saying, “Thanks so much for the invitation to dinner. It was great to get to see your team in that context as well.” From my vantage point, it was great to get to know him as well. Such a great connection that happened there.
So here’s my challenge to you. As you go forward, normally I’d give you a book or I’d give you something there. This episode doesn’t have resources. This episode doesn’t have TED Talks and books that you’ve got to go read to figure this out. I want you to strip back all the over-complication that we do with things, and I’m going to challenge you: I want you to create one moment Of meaningful connection this week. It could be in the office, it could be at home, it could be out in the community, it could be taking the time to interact with somebody—maybe you’re at the airport, a meaningful conversation with a flight attendant or a gate agent or a random person in the restaurant, create meaningful connection. It doesn’t mean that you necessarily have to build those into lifelong friendships, but when we feel connected, it completely changes how we show up. It enhances our mood, it enhances what we can do as leaders, and it’s amazing how good you feel when you know that you’ve got those meaningful connections.
With that, I’d love to hear how do you do this. What are some of the meaningful connections that you have made? I’d love for you to share with me your ideas, maybe how you achieved this challenge, where you went and created a meaningful connection in the next week. Share that with me, reach out on LinkedIn, send me an email, JeremyC@UpstreamAcademy.com. I’d love to learn how you show up and create connection in a meaningful way, because I know for me, it has been an absolute game changer, not only professionally, but also personally, when I’ve learned to slow down, lead with some curiosity, and simply have a conversation that drives meaningful connections. Thanks so much for joining me on today’s episode of The Upstream Leader. I look forward to talking with you again soon.
