Leadership Breakthroughs
Leadership Breakthroughs are designed to Awaken Awareness of what’s getting in your way and to discover new ways to develop your Leadership potential.
Leadership Breakthroughs
The Power of Connection
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Tom Lemanski is an executive coach and leadership advisor at Chicago Executive Coaching. If this conversation sparked something for you, visit https://chicagoexecutivecoaching.com to learn more or get in touch.
Welcome to Leadership Breakthroughs, where executive coaches and leaders explore the mindsets and strategies that drive real growth. I'm your host, Alex, and today we're talking about something that sounds simple but isn't connection. Real connection. And why the tools we use to stay in touch might actually be getting in the way. I'm joined by Tom Lemanski, founder of Chicago Executive Coaching. Tom, welcome.
Speaker 1Good to be here, Alex.
SpeakerTom, you wrote a piece recently that opens with a question I don't think most leaders stop to ask themselves. When you send a text, are you trying to connect or are you trying to be heard? What's the difference and why does it matter?
Speaker 1Those two things sound like they should be the same, but they're not. When you're trying to connect, you're actually interested in the other person, what they're thinking, how they're doing, what they need. When you're trying to be heard, you're managing your own output. You're sending a message and moving on. The problem is texting is almost perfectly designed for the second one, and we've convinced ourselves it serves the first.
SpeakerSo you're not saying texting is bad. You're saying we're using it in a way that doesn't do what we think it does.
Speaker 1Right. It's not that the tool is evil, it's that we've drifted toward using it for everything, including things it can't actually handle. You can schedule a meeting in a text. You probably can't repair a relationship in one. But if we're being honest, people try to do both in the same thread and wonder why things feel off.
SpeakerThere's a researcher you reference in the piece, Sherry Turkle, who described this as being connected but alone. That phrase has stuck with me since I read it. What does that actually look like in a leadership context?
Speaker 1What it looks like is a leader who is technically reachable at all times, but genuinely unreachable when it matters. Their team can text them, email them, ping them on whatever platform the company uses this year. But when someone needs a real conversation, when there's something uncomfortable or uncertain or emotionally loaded, they get a reply that covers the surface and closes the loop fast. The leader feels responsive. The team member walks away feeling managed, not heard.
SpeakerAnd I imagine the leader doesn't even know that's happening.
Speaker 1Almost never, because the metrics look fine. Emails return, messages answered, response time fast. What doesn't show up in any of that is whether people feel seen, and that gap compounds over time. High touch is the opposite. It's the face-to-face conversation, the phone call, the meeting where you're actually in the room with someone. It's messier, slower, and you can't control it the same way. But that messiness is where real communication actually happens. The pause, the eye contact, the things someone says when they weren't planning to say anything.
SpeakerThat word control keeps coming up. Is that what this is really about? Leaders choosing communication that they can control?
Speaker 1A lot of it, yes, and I understand it. When you're running a team or an organization, your words carry weight. You're aware of that. So the ability to draft, revise, and send feels like good judgment. But there's a cost. What you're editing out is vulnerability. And vulnerability is what creates trust. If your team never sees you unedited, they don't really know you. And if they don't know you, they're not going to take the risks that growth requires.
SpeakerThat's a real tension for leaders, though, right? Because there's also a version of unfiltered that's just undisciplined.
Speaker 1Completely fair. This isn't an argument for leaders to just say whatever comes to mind and call it authentic. That's not courage, that's noise. The point is more targeted than that. There are specific interactions that matter where the other person needs presence, not polish. A tough performance conversation, a moment where someone on your team is struggling, a decision that's going to ask something significant of people. Those moments deserve more than a well-crafted message.
SpeakerYou reference a TED talk in the piece from a coach named Jeremy Boone who works with athletes. He draws a distinction between empathy and compassion. How does that land in a leadership context? Those two words get used almost interchangeably.
Speaker 1They do, and they're not the same thing. The way Boone frames it, empathy is feeling what someone else feels. You're absorbing their experience. Compassion is different. Compassion is being moved by what someone is going through and then doing something about it. For leaders, that distinction matters. Empathy can actually leave you stuck. You feel what your team feels, you get pulled into it, and you don't move. Compassion is the thing that gets you off the sideline. You understand and then you act.
SpeakerSo compassion has more utility for a leader.
Speaker 1Both matter, but yes, compassion is what drives behavior. Boone offers two questions to build it. Before an important interaction, ask yourself, what does this person need right now and what can I give? Not what can I get from this conversation, not how do I handle this efficiently? What can I give? That shift is deceptively simple and genuinely hard to do if you're not in the habit of it.
SpeakerI want to push on that because there's a version of that that can sound a little soft for someone running a hard-charging organization. What can I give? Does that translate when you're running a quarterly business review or dealing with underperformance?
Speaker 1It translates everywhere, but it doesn't mean the same thing in every situation. What can I give in a performance conversation might mean I'm gonna give you clarity. I'm gonna give you honesty that most people won't give you because they'd rather avoid this. That's not soft. That's actually one of the more demanding things a leader can do. The leaders who can't have that conversation aren't being tough, they're taking the easy path by staying vague.
SpeakerThat's a reframe worth sitting with.
Speaker 1Not because they enjoy conflict, but because they understand what happens when you don't. You lose time, you lose trust, and eventually you lose people.
SpeakerSo what's the practical ask here? You close the piece with a challenge to the reader. Notice when you reach for a screen instead of a face. That's the starting point.
Speaker 1That's it, just notice. Before you type something, ask yourself if this is one of those moments that deserves more. Most techs are fine as texts, but some of them are reaching for a shortcut in a place where there isn't one. When you start to notice the pattern, you start to make different choices. And those choices accumulate into a very different kind of leader over time.
SpeakerIf someone's listening to this on their commute and wants to try one thing this week, what would you tell them?
Speaker 1Pick one conversation you've been handling by text or email that probably deserves to be a real conversation and go have it. Not because it's easier, it won't be. But because the person on the other end will feel the difference, and so will you. Before you walk in, ask yourself one question. What can I give here? Not what do I need to say, not how do I get through this? What can I give this person in the next 20 minutes? That question alone will change how you show up. And showing up is where connection actually starts.
SpeakerThat's leadership breakthroughs. Thanks to Tom Lemanski for a conversation that cuts through the noise and makes you think twice before you reach for your phone. You can find Tom's Leadership Breakthroughs blog and coaching programs at ChicagoExecutive Coaching.com. We'll see you next week.