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Hosted by Tom Henschel

How to Deepen Relationships at Work
May 2025

255

Knowing she’s never been good with people, a leader seeks coaching to help her deepen relationships in ways she can tolerate.

May 2025

255

How to Deepen Relationships at Work

Tom Henschel

Learning Likeability

Grace’s performance reviews showed high marks for projects and processes. Her skills with people, however, scored quite low.

During our first coaching conversation, talking about what she wanted from the coaching, she said, “I’d like to learn how to be likeable. I’ve always been the smart one, the good one, but I’ve never been that good with people. And in this company, I see it, relationships are currency. My balance is pretty low.”

I asked, “When you say you were always the smart one, how far back are you talking?”

“Oh, forever,” she said. “My folks were scientists. They made me feel smart, ever since I was little. Which was great for problem solving and thinking things out, but not so great for making friends. I was the school nerd.”

I didn’t speak.

“It’s been bothering me with my one-on-ones,” she said. “I always schedule at least thirty minutes on my calendar, but we rarely use it all. They sit down, we go through our lists, they get up, they leave. We talk about work, but after that, I don’t have much to say. I know that’s why I get those low scores. I just don’t know what to do differently.”

I asked, “If you wanted to talk about something that wasn’t about work, what would you talk about?”

“I don’t know. Ask about their family maybe? I’m embarrassed to admit this, but I’m not even sure I know who’s married and who isn’t. I always feel that’s intrusive and personal.”

I asked, “Did it feel intrusive and personal when I asked you how far back you’ve been the smart one?”

“No, but that’s different,” she said.

“Different how?”

“Well, isn’t that why you’re here? You’re supposed to ask that stuff.”

I laughed. “The intrusive, personal stuff?”

She laughed too. “No, I didn’t mean that! I mean, don’t you need to get to know me as part of your job?”

“It helps, for sure,” I said. “And I think you’re saying the same thing – deepening relationships with people is an important part of your job, too. You say that’s what you want for yourself.”

She shook her head. “I just feel so bad at it. But yes, I want to learn. So, let me ask you what you asked me: when you want to deepen a relationship, what do you do?”

Matching Purpose

I thought a second, then said, “Two things come to mind. I match. That’s first. Then, I’m curious. I ask a lot of questions. That’s second.”

“You match?” she asked. “What are you matching?”

“Any number of things. For a start, I want to know if our purposes match. Are we defining success the same way? If so, if our purposes match, that’s one way to deepen our relationship.”

She said, “I hope my direct reports have the same purpose for doing their work as I do. Ew! Hearing myself say that, it’s probably ridiculous. Why would they? Huh. Match purpose. Okay. What else do you match?”

“The other person,” I said. “For a long time now, I find myself matching all sorts of things with people. Breathing. Rate of speech. Their whole energy level. Matching is pretty automatic for me these days.”

“Do you do it with me?” she asked with interest.

I nodded. “Like I say, it’s pretty automatic, so, yes, I do.”

“I can’t tell,” she said. Then, quizzically, she asked, “Does that mean you’re different with different people?”

“To some extent, I suppose. But don’t you find that? Don’t you find yourself drawn to people who have your same basic energy level, because it’s really comfortable? But you can shift it if you have to.”

She said, “I don’t want to sound like a cliché, but that’s why I don’t like the sales meetings. Their amps are always dialed up to eleven. I can do it for a little, but not long.”

Matching Energy

“Because it’s hard to match their energy,” I said, agreeing. Then, “I’m curious. Think about your one-on-ones for a second. If you overlay the whole idea of matching onto your one-on-ones, what does that do to the picture?”

“I don’t know. I guess I’m willing to try it. It’s weird to think about. Isn’t it kind of manipulative?”

“I don’t know. I’m doing it with you. Do you feel manipulated?”

She laughed. “No, I like you!”

“I’m glad. And I’d like to suggest that one part of the reason you like me is because I’m calibrated to match you. The reason I don’t think it’s manipulative is because I’m not trying to gain advantage. I’m not tilting the field in my favor. I’m deepening the relationship. To me, that’s not manipulative.”

She laughed, as if a riddle had revealed itself. Then she asked, “So, you’re matching what in me? My rate of speech? You mentioned that.”

“Partly, yes. More your whole energy.”

She considered that. Then, “Match purpose. Match the person. Are there more ways to match?”

Matching Conversations

I said, “The conversation. Are you both actually having the same conversation? An example of a conversation that isn’t matched would be, at the end of a long day, two partners talking. One wants to talk about their day and all the twists and turns, and the other partner wants to fix everything they hear. Those two conversations don’t match. And it does not deepen the relationship.”

She laughed. “In my husband’s family we have a joke about ‘The Goodbye Conversation.’ One of his sisters will say that thing, she’ll say, “Okay…” Like, ‘I’m ready to say goodbye now.’ And we all say goodbye and we go back to what we’re doing. And she stays there talking, having her own little goodbye conversation, but we’re all talking about something completely different. We laugh about the fact that her goodbye conversations are their own part of the get together.”

I said, “So you get this concept. People might be talking at the same time but having different conversations. Matching the other person’s conversation deepens the relationship.”

“Not in my one-on-ones,” she said. “From what you say, our conversations match. We’re both having conversations about their work. But our matching is not making the relationship deeper.”

“That’s a good point,” I said. “What might?”

As if remembering something she should have known, she said, “Oh. Okay. Here we are again. Okay, I don’t need to be just having a work conversation, I need to have a – what would you call it? – a people conversation? Is that what’s missing?”

I nodded, saying, “There’s a book called Supercommunicators. The author, Charles Duhigg, talks about this idea of matching conversations. He calls the work conversations Practical, and the people conversations Emotional.”

The Emotional Conversation

She had a flash of horror. “That doesn’t sound attractive at all.”

“Why? What are you picturing?” I asked.

“Emotions. Emotions can make me uncomfortable.”

“Even talking about them? The way Duhigg explains it, the Emotional Conversation may be about emotions, but it’s not emotional.”

She gave a little huff of despair. “Which, I think we’ve established, is not an arrow in my quiver.”

I said, “I wonder if it would be easier if, instead of thinking about feelings, if you thought about being curious.”

“That was your second thing, after matching, right?” she asked.

“Wow, yes, good listening. Two things I do to deepen a relationship is match, and another is to be curious. I wonder if being curious will get you to the same place by a different route.”

“And where exactly am I trying to get to?” she asked.

“The Emotional Conversation. A conversation where people talk about, not just what happened, but how they feel about what happened. They talk about their experience. That’s where we’re trying to get to. Because that conversation deepens relationships.”

She said, “I don’t know. Listen, I see why it would deepen the relationship. But, well, I don’t want to sound stupid, but I’m not certain how I would even start that conversation without sounding like I’m interrogating someone.”

“Really? If you were just being curious about something?” I asked.

“What would that sound like?” she asked.

Deep Questions

I said, “Invite someone to say more about something. I did it with you. We were talking about your low scores and needing to be better at relationships. And I asked you what would you do differently. I invited you to say more.”

She looked at me. “That was coaching, wasn’t it?”

“I suppose. What do you think of it?”

“I liked it. It made me self-conscious, but I didn’t mind it.”

I nodded. “I’m glad. It’s a particular kind of question. It’s a category called Deep Questions, and they’re great for deepening relationships.”

She asked, “Am I right, they’re coaching questions?”

I nodded. “I suppose. But not just coaching questions. Lots of professions use Deep Questions to get people talking about beliefs, values, aspirations. If you can be genuinely curious about how someone is experiencing their life, most likely you’ll ask a Deep Question. And the relationship will deepen.”

She smiled. “I want to be able to do that. I want to learn this.”

Exploring different ways to deepen relationships became Grace’s passion project. Her first attempts at matching felt awkward, but then one day it happened easily. That encouraged her. Even though her progress felt slow, she felt that deepening relationships moved her towards The Look & Sound of Leadership.

Core Concepts:
  • It is not unusual to have higher competence with processes than people
  • People skills can be learned
  • Tune in to the other person’s purpose. Can you align?
  • Tune in to the other person’s energy. Can you match?
  • Tune in to the other person’s conversation. Can you sync up?

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