Buy me a Chai First Mebbe?

Are they “reaching out “ with curiosity or an agenda?

One of life’s great gifts is to have someone be genuinely curious about you. One of its greatest disappointments is realizing they were never curious about you at all. They were curious about what you could do for them.

Every week I get some version of the same message. They might mention something I wrote, ask a thoughtful question, and say they’d love to connect. For a moment, I’m delighted. I love conversations. I love hearing what people are working on and wondering about.

Minutes later, the next message with a calendar link to meet, usually phone or Zoom. Then a reminder message to schedule. Rinse repeat.

Pretty soon I’m no longer looking forward to the conversation. I’m wondering whether there will be a conversation, a pitch, or an ask of some kind.

I don’t think most of the people sending those messages are trying to manipulate anyone. I think they bought a playbook. Why? Because I’ve bought into those shiny promises more than once in my own career.

Marketing was a huge part of my life for a long time. I believed in systems. I believed in efficiency. I probably recommended some of the very ideas I’m questioning now: reach out, stay top of mind, follow up, make it easy to schedule, personalize the message, use technology to help.

None of that is bad advice. Sometimes it’s useful and I still appreciate a good system.

What I can see more clearly now is where the playbook fails us. It can help us make contact, but making contact and building trust are not the same thing.

A message can introduce us. A calendar link can get us into the same room. Neither one of those can make us truly interested in each other.

Think of it like this.

Curiosity is a way to open a door, but it’s not the best pitch strategy. We all want more than that don’t we? So we stop responding to the insistent emails and LinkedIn messages. We walk away because we assume we know better. Maybe it’s not… true, but this dance can be exhausting.

WHY THEN?

Some people are looking for opportunity. Others are looking for community, connection, or someone who actually understands. Most of us are looking for some combination of those things.

There’s nothing wrong with opportunity, and there’s nothing wrong with a sales conversation when that’s what the conversation is. The trouble starts when a transaction dresses itself up as a relationship, or when “empathy “ becomes another step in a sequence to an end.

We can feel the difference, right? We know when we’re being recognized, and we know when we’re being studied. We know when a question opens a conversation and when it is gathering information.

Curiosity should be real, not a strategy we keep just long enough to earn a meeting. Empathy isn’t a strategy.

Maybe this is what bothers me about the language of relationship-building in business. We talk about Know, Like, and Trust as if they are outcomes we can engineer with enough personalization. But those are human needs. When we gamify them, even thoughtfully, something important gets drained from the exchange.

People deserve to be met. They deserve to be heard. They deserve conversations that don’t leave them feeling like they’ve been harvested.

That doesn’t mean every introduction has to become a friendship or every business conversation should walk through our life stories. It means we can be honest about what we’re seeking and curious about the person before we decide how they might fit for us. Or not.

I didn’t always feel this way. There was a time when I admired efficient systems and clever marketing, and yep, I helped sell some of it too.

These days, I’d rather get to know someone before I ask something of them or them of me. I’d rather we talk about what matters to each and see if that resonates. It takes longer, and it’s worth it.

My friend the gardener.
I know someone who connects more people in an authentic way than anyone I’ve ever met. You might consider him the greatest networker alive. He isn’t. He’s a gardener of community.

He listens. He remembers. He notices that someone mentioned a project six months ago, or that someone else is wrestling with exactly that problem. Then he makes an introduction, not because there’s anything in it for him or because he’s following a process, but because he genuinely thinks two people might enjoy knowing each other. Then he steps back out of the picture.

He isn’t cultivating leads. He’s tending relationships. He follows up because he remembers what someone said. He cares. He collaborates, supports, and creates the conditions for people to flourish together. Sometimes an opportunity grows from that. Sometimes it doesn’t. Either way, the relationship was worth having.

That’s important to me. Opportunity can grow from a relationship, but a relationship doesn’t usually grow from treating someone like an opportunity, or a target.

The distinction isn’t whether we see possibilities in other people. Of course we do. It’s whether we can see the person first.

After knowing my gardener through thick and thin and journeying through our respective careers, we’ve got a sense of trust that is rare in this world. I know if I really need something, or he does, we have an organic version of Know, Like, and Trust, and we talk about it. if you know me, I wouldn’t be at all surprised if you know him too.

I still believe in technology of course, and I believe AI can be incredibly useful. I’ve spent much of my career helping people use technology more thoughtfully, and I haven’t stepped away from it.

I’ve just stopped expecting it to do the work that only we can do. Technology can help us find each other. Automation can remind us to reach out. AI can help us write more clearly. None of those develop an actual interest in another human being. Ot Knowing, Liking and Trusting. That’s still our job.

Show interest before you ask someone to “pick your brain” unless you’ve expressed that you actually care about the conversation. I would do the same for you. I really would.