Three Conversations Pretending to Be One

A friend tells you something hard. They’ve just lost something — a job, a relationship, a parent, an animal — and they’ve come to you. Within thirty seconds, you’re telling them about a time something similar happened to you, and how you got through it. You feel helpful. You feel close to them. You feel like you’re being a good friend.

They are not having the same experience.

“What mentoring does is, it tells stories about solutions. Which is way different from coaching, which is asking questions to get to solutions. Which is different from counseling, which is you’re asking questions to get to problems.”

Jayne Heggen offers this distinction from the world of professional practice — three named, trained, intentional roles. But strip away the professional context and the same three stances are running through every difficult conversation we have. We just don’t name them. We don’t even notice we’re choosing between them. And most of the painful mismatches in our most important conversations come from choosing the wrong one without knowing we chose anything at all.

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Look at what each stance actually does. Mentoring tells stories about solutions — “here’s what worked for me when I went through something like this.” Coaching asks questions that lead toward solutions — “what do you think might help here?” Counseling asks questions that lead toward problems — “what’s actually going on for you right now?” Each is genuinely useful. None is universally appropriate. And the gap between what someone needs and what we reflexively offer is where conversations curdle.

The default, for most of us, is mentoring. Someone shares a struggle and we reach for our own experience because that’s the most generous-feeling thing we can offer — proof that we understand, evidence that they’re not alone, a path through that we’ve already walked. The intention is good. But mentoring assumes the speaker has identified the problem and is ready for solutions. If they’re somewhere earlier in the process — if they don’t yet know what the actual problem is, or if they need to feel heard before they can think — then the story we offer doesn’t reach them. It just covers the silence they needed.

The person speaking almost never knows which mode the listener is in. They show up with a thing to talk about and trust the conversation to figure itself out. Meanwhile the listener, often without realizing it, has already chosen a stance — usually whichever stance feels easiest to them in the moment, not whichever one would actually serve. The conversation proceeds with both people thinking they’re in the same room while standing in different ones.

You can sometimes hear the misalignment in real time. The speaker keeps trying to return to the texture of their experience; the listener keeps redirecting toward what should be done. Or the speaker is asking — implicitly or directly — for help thinking through something, and the listener stays in counseling mode, asking ever-deeper questions about feeling, when what would actually help is a question that opens forward rather than down. Neither person is wrong. They’re just having different conversations with each other.

We almost never ask for conversational consent. We don’t say “do you want me to help you think through this, or do you want to talk about what’s underneath it, or do you want to hear what worked for me?” We just pick. The question feels awkward, maybe even clinical, when applied to friendship. But its absence is the exact thing that lets us perform the wrong kind of helpfulness with great sincerity for years.

There’s a humbler version of the same move that doesn’t require any vocabulary at all. It’s just a pause before responding — long enough to notice that you have a choice. Long enough to ask whether what’s about to come out of your mouth is the thing this person actually needs, or just the thing that’s easiest for you to offer. Sometimes the answer is yes, story me. Sometimes it’s no, ask me a question. Sometimes it’s no, just sit here.

We treat “having a conversation about something hard” as one act. It’s three. The moments where someone walked away from us feeling unheard, when we were certain we’d shown up — those aren’t failures of caring. They’re failures of mode.

Which raises a strange question to leave open. How many of the conversations in your life that felt almost-but-not-quite right were actually two people doing different things in the same room, both trying very hard, both getting it wrong in a way neither could quite see?


This field note references the Podtalk episode “Joy with Jayne Heggen,” published November 3, 2021.

This work was produced using AI language models directed through an editorial system designed by Craig Constantine. The author selected all source material, designed the creative framework, directed the editorial process, and made all acceptance and revision decisions. The prose was generated by AI under sustained human editorial direction.

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