This website uses cookies

Read our Privacy policy and Terms of use for more information.

Something happened this week that I've been turning over in my mind since it landed in my inbox.

I want to share it — partly because I think you'll recognize something in it, and partly because I need to be honest about the part I played in setting it up.

Earlier this year, we tested an offer that I was skeptical about from the very beginning.

The Collective — for those of you who aren't members — is my flagship community for consultants building independent businesses. The full membership includes live coaching calls, community, content, and direct access to me. It's built around the belief that a huge part of what makes it valuable is, frankly, me. My coaching, my feedback, my ability to get on a call and help someone see something they couldn't see on their own.

We started hearing from people who wanted to join but couldn't swing the full price. So we did what seemed reasonable: we tested a downsell.

A lower-tier option where members got access to the community and the content, and I'd give asynchronous written feedback — but no calls. No live coaching. Just me responding to their posts in the community.

From the jump, something felt off. Not about the people — they were great. About the offer itself. It wasn't aligned with the kind of experience I want to create.

My competitive advantage isn't the content. It isn't the community, although I love it and it’s rapidly becoming a competitive advantage.

It's the coaching. And you while you can deliver that asynchronously, it’s not the same. We didn't sell many of them, and the ones we did felt increasingly like a mismatch — not because the members weren't capable, but because the container wasn't right.

I mentioned this casually to one of those members this week. Said we were thinking about discontinuing it, that it wasn't working the way I'd hoped.

I don't fault myself for sharing it. That's just who I am with my community. Transparency isn't a strategy for me — it's how I operate.

But I did forget something I occasionally need to remind myself of. Once something is out of my hands, I can't control what people do with it.

And sometimes they run with it in directions I didn't expect and didn't ask for.

The messages started arriving shortly after.

The Messages I Didn't Ask For

Four. Five. I honestly lost count.

Long, detailed, thoroughly researched messages.

  • A complete rethinking of my offer stack.

  • New positioning language.

  • Advice on surveys I should run and interviews I should hold.

  • Suggestions for how to restructure the Collective, what I should be selling instead, how I should be talking about what I do.

Each one building on the last, each one more confident than the one before it.

He'd spoken to five members. Out of ninety.

I want to be clear. I don't think he had bad intentions. He was trying to help. He thought he was being generous with his time and thinking. He thought — I could feel it in every message — that he was demonstrating his value.

Look at how carefully I've thought about this. Look at how much I care. Look at what I've put together for you.

What he didn't see is what I saw almost immediately.

He had maybe 3% of the information you'd actually need to advise someone on their business.

  • He hadn't seen the financial picture.

  • He didn't know the offer history — what had been tried, what had failed, what had been deliberately ruled out and why.

  • He hadn't been in the strategy conversations.

  • He'd talked to five people out of a community of ninety and from that sliver he'd constructed a complete diagnosis and a full prescription.

The messages weren't the problem. The confidence was.

There's something else worth naming. I didn't ask for any of it.

I mentioned something in passing — I didn't say "what do you think I should do?" I didn't open a door to a strategic consultation. And that matters, because there is something inherently condescending about telling someone what they should do when they haven't asked for your help. Even when the intentions are good. Even when some of the ideas are solid.

The moment you start prescribing to someone who didn't ask for a prescription, you've made an assumption — that you know better, that your perspective is valuable enough to impose, that they need you to see what they can't. That assumption is condescending whether you mean it to be or not.

This is exactly what I wrote about on Thursday — premature solutioning. The pattern of jumping to answers before you've done enough work to actually understand the question. (If you haven't read that one yet, [start there] — because what I'm about to say makes a lot more sense with that context.) Reading those messages, I was watching it happen in real time, aimed directly at me. And it was — I won't pretend otherwise — deeply clarifying.

Not because it stung. Because I recognized it.

I've Been This Person

When I started my business, I had very little idea what I was actually doing. I had good instincts, genuine enthusiasm, and a deep confidence in my ability to figure things out as I went.

Someone would get introduced to me because they were struggling with a marketing problem. Before I'd fully understood what was actually wrong — before I'd asked enough questions, before I'd sat with the situation long enough — I'd already be running.

We could try this. What if we did that. Here's what I'd do if I were you.

And sometimes it worked. I'd get my foot in the door. I'd close the deal on the energy of it, on the sense that I had ideas and wasn't afraid to share them. But then I'd get inside the engagement and realize I had no actual idea what I'd committed to.

I'd pitch directions that were missing the mark because I hadn't slowed down long enough to understand the real problem. I'd promise things I'd then have to scramble to deliver.

That scramble — that constant feeling that my business was always just about to fall apart — wasn't bad luck. It was the direct consequence of moving faster than my understanding.

I don't fault myself for it. It's genuinely how I learned. But now, I know exactly what it cost me.

The Room That Changed How I Listen

A few years ago, when I was figuring out what came after running an agency, I looked seriously at coaching. I ended up in an accelerated ICF certification program — the kind that crams months of training into a single week. Nine hours a day. Intense doesn't begin to cover it.

The program used a Socratic approach: ask questions, help the client find their own answers, don't give advice. That's not ultimately my style — I coach, but I also consult and mentor and give direct input, and I've made peace with the fact that I'm never going to be a purely Socratic practitioner the way ICF teaches. But that week cracked something open in me about what listening actually makes possible.

At one point we were coaching each other — role-playing sessions with the other trainees. I was coaching a woman in the program. She sat down and said she needed help with time management.

My old instinct would have fired immediately. Time management. Okay. Here's what I know about time management. Here's what tends to work. Here's what I'd suggest.

Instead, I asked a question. Then another. Then a few more.

Five or six questions in, the real situation came into focus. She had a full-time job she actually loved. She and a friend had an idea for a coaching business. She wasn't finding the time to work on it and felt guilty about that — which she'd translated into "I have a time management problem."

A few more questions and she told me something she'd clearly never said out loud before: she didn't actually want to start her own business. She didn't want to leave her job. But her father was an entrepreneur and had told her her whole life that she wouldn't be truly successful until she built something of her own.

So she was trying to want something she didn't want, and blaming herself for not having the time to pursue it.

If I had answered the question she walked in with, I would have given her a productivity system for a goal she didn't actually have. The problem she named — time management — had nothing to do with what was actually going on.

This is something I say so often that if you've been on this newsletter for a while you've heard me say it at least a dozen times: our buyers are not problem-aware. They're symptom-aware.

They come to us with the symptom. And if we immediately start solving for the symptom, our solution is worthless — because the underlying problem is still there, untouched, doing exactly what it was doing before we showed up.

Five or six questions. That's all it took to find the real thing.

Why We Skip the Questions Anyway

The most basic version of this mistake, the one that underlies everything else is that we give advice that nobody asked for.

  • We jump to answers because silence feels like lost ground.

  • We prescribe before we diagnose because we're afraid that asking questions signals uncertainty, and uncertainty signals weakness.

  • We think the fastest path to demonstrating our value is to show that we already have the answer — that we can see the solution before most people even understand the problem.

What we don't realize is that this instinct, while completely understandable, is working directly against us.

  • The person who has four quick answers is not more impressive than the person who has one devastating question.

  • The consultant who walks in with a complete recommendation on day one is not more trustworthy than the one who says "I need to understand this more deeply before I can tell you what I think."

  • The member who sends five messages after half a picture is not more helpful than the one who asks, “Can you tell me more about what's driving that decision?”

Rushing to demonstrate expertise is almost always the thing that undermines it. And the attuned people in the room — your best prospects, your most senior clients — can feel the difference even when they can't name it.

What Slowing Down Actually Does

I know this can feel uncomfortable. Especially if you've built a career on being the person with answers. Especially if your confidence is something your clients actually hire you for.

But I've learned over and over that slowing down makes you infinitely more effective.

The actions you take from a place of real understanding are categorically different from the ones you take from speed and instinct alone. They're more accurate. They're more trusted. They land differently. And they compound in a way that the fast answers never do.

Here's the other thing worth sitting with.

Most of the people reading this are going to have their business for at least a few more years. Probably longer — a decade, maybe more. And I know it doesn't always feel that way. When you're in a hard month, it feels urgent. Like you need to figure it out now, this week, before something tips.

But you don't.

You don't have to have all the answers in the next six weeks. And when you operate like you do — when urgency replaces intention — you are far more likely to end up exactly where you don't want to be.

  • Making promises you can't keep.

  • Taking on work that isn't the right fit.

  • Building something that looks solid from the outside and feels precarious from the inside.

The goal isn't speed. It's precision. And precision requires slowing down enough to actually understand what you're looking at before you decide what to do about it.

That's uncomfortable work, especially at first. Sitting with a question longer than feels comfortable. Asking one more thing before you offer your take. Choosing real understanding over the performance of it.

But that's also exactly where the compounding begins. Not in the fast answers. In the right ones.

(Thursday's newsletter gets into this from the other side — specifically what premature solutioning looks like inside a sales conversation, and why the consultants who close consistently aren't the ones with the best answers. They're the ones with the best questions.)

In love, growth, and asking before answering,

Kasey

When you’re ready, here’s how I can help you become an Essentialist CEO":

  1. Building a business that feels out of your control? I’ll reopen the doors to the Essentialist CEO Collective soon, where I give you surgical precision on exactly what YOU need to build predictable revenue. Apply for the Collective here.

  2. Help me grow the Essentialist CEO newsletter and get a prize. Your support is the best way to help me grow, so I want to give you a reward in return. Leave a testimonial here.

Reply

Avatar

or to participate