I spent 9+ hours creating a 75-page analysis of 10 strategy sessions I conducted last year. Overkill? Maybe. Insanely valuable? Absolutely

But before I tell you why, let me ask you something.

Have you ever reread your own website and thought, “This technically makes sense but it doesn’t quite sound like me anymore”? Or had someone say, “I love what you do,” followed by a question that made it clear they didn’t actually get it?

That’s the pattern this analysis uncovered: why smart, capable, successful people still struggle to explain what they do, and why throwing more tactics at it doesn’t help.

I had a hunch the same blindspot would show up again and again. (I was right. It did in all but one session.)

It’s the same blindspot I see in most copy audits and discovery calls, which means there’s a very good chance you’re not immune either. 🤷🏻‍♀️

Today I’m breaking down:

• which sessions I decided to deep dive into and why
• the exact process I used
• the specific insights and patterns I uncovered
• the psychology behind them
• where I went wrong (this one hurt)
• how I’ll use the data to help you

Before we get there, here’s how this started.

What kicked this whole thing off

This didn’t start as a noble attempt to publish insights. It started because within the time span of one month, 3 people asked me the same question: “What’s the difference between your strategy session and a copy audit?”

They'd all read my website. One told me, kindly, that it made things more confusing.

Yeah, not ideal since clarity is literally my job. 😭

That's when I knew I had to look deeper. Not just at my own messaging, but at why this pattern keeps showing up—for me, and for the smart, capable people I work with. If the messaging strategist's website is creating confusion, this blindspot is bigger than any of us realize.

Why this kept slipping past smart people

If you don’t know what you’re looking for, you’ll almost always confirm what you already believe. And if you’re too close to the work, which most experienced operators are, that’s a real problem.

Especially when things mostly look like they’re working.

You’re getting referrals and some people are saying yes. Nothing’s blown up, but you feel like you’re waiting for the other shoe to drop.

That’s not an accident. This is the kind of misalignment that tends to show up once the business has outgrown the way you used to explain it. Your brand’s evolved but your message hasn’t.

That kind of tension doesn’t get fixed with more tactics.

This usually shows up as small but persistent friction. You find yourself re-explaining your work more than you want to or fixing confusion on sales calls.

The problem isn’t effort or execution; it’s that you can’t see the pattern clearly from inside your own head. Which is exactly why I wanted to step back and look at this across multiple sessions instead of treating each one like a one-off.

What they were actually trying to solve

Across all the sessions, a few clear patterns emerged, the real jobs to be done (JTBD). Not just what people said on the intake form, but what became obvious once we started working.

Functional
​(what they were trying to do in real life)

• Put words to what they do without oversimplifying or sounding generic
• Stop rewriting their story every time they wrote a page, post, or pitch
• Say yes to visibility opportunities without scrambling to “get their messaging together” first
• Make strategic decisions from a place of clarity instead of second-guessing everything.

Emotional
​(how they wanted to feel underneath all of it)

• Feel seen without being boxed into a niche, title, or watered-down version of their work
• Trust themselves again instead of editing their voice into something stiff or overly polished
• Get out of their own head and stop circling the same questions on repeat.

Social
​(what they needed others to see)

• Let the message do the trust-building so they weren’t fixing confusion on sales calls.

Most of these businesses had grown through referrals. That part was working, but referrals only get you so far.

When someone lands on your website, hears you speak, or encounters your work without context, the message has to make sense without you in the room.

That’s where things were breaking down. Even though the issue showed up in the same way for many of them, the reasons why were all different.

If your message only works when you’re in the room to explain it, it’s not doing its job of getting people to understand what you do and why you’re chooseworthy. That’s a trust gap.

If you leave this unaddressed, it’s frustrating yes, but the real cost is the conversions you should be getting: people who are a good fit but hesitate, ask for clarification, or drop off entirely.

The worst part is it’s not because they didn’t want or need what you offer, but because your message didn’t help them decide and make it an easy yes.

The thing that kept showing up (like your MIL’s “helpful” advice)

Most people came in with problems that made sense on the surface. These were smart people doing good work.

Several came thinking they needed something tactical like copy tweaks or a second set of eyes, while others thought messaging was the issue.

What they actually needed was clarity because the real problem was always at least one layer below what they initially thought.

“Stacy pinpointed my messaging blind spots in ten minutes, which humbled me real quick. She helped me identify the real problem and clearly laid out the steps toward a solution.” - Susan Lee

There was only one client who got surprisingly close right out of the gate. But even they were caught off guard by what came up during the session: The real tension wasn’t strategic; it was emotional.

They realized their biggest pain point wasn’t about messaging at all. It was about confidence. They weren’t just struggling to communicate clearly. They didn’t fully trust themselves to say what they really wanted to say, and that wasn’t unique to them.

Side note: calling these “strategy sessions” might be part of the problem. Strategy is what I do. Clarity is what people are paying for.

Where the real shifts happened

Every session had an ‘aha’ moment, a shift where things finally started to make sense because we uncovered the root of the problem. (This is always my favorite part.)

Here’s what that looked like.

From thinking it was a website or copy issue to realizing the message wasn’t working for people who didn’t already know them.

→ “I just figured a website tune-up would help… but now I’m seeing the message is off for people who don’t know me.”

From trying to sound “credible” to noticing how much they’d watered themselves down.

→ “We were trying to sound like a business, but I don’t want to lose how I actually talk.”

“The biggest takeaway from our session was to lean into our brand voice. When we try to present as corporate and jargony, it feels inauthentic to the tone of our brand. It was helpful to know that we could celebrate our boldness in copy to both be true to who we are and make a lasting impact.” -Maggie Gremminger

From asking for messaging help to realizing they were standing at a business inflection point.

→ “How do I bring all of this together without it sounding like three different people?”

→ “I feel like I’m still operating in a business that doesn’t quite exist anymore.”

From assuming they had a sales or conversion problem to recognizing a clarity and audience filter problem.

→ “They already want it… they just don’t get it.”
→ “I’m fixing messaging on the sales call.”

From thinking they needed launch messaging to realizing the structure and language had to reflect what people actually want and need.

→“They’re craving systems but resisting structure.”
→ “How do I make this feel easeful and still sell?”
→ “I don’t want it to sound like another bro-y program.”

None of these were surface-level problems and none of them were about copy, messaging, or positioning alone. They were about alignment.

And it wasn’t just them.

Where I went wrong

The irony here isn’t lost on me. This issue exists because the positioning and messaging strategist didn’t clearly position her own offer. Unfortunately, that wasn’t even the most painful part.

Here's what I missed: I had no follow-up process.

These were strong calls with people who already said yes. They gained clear insights, had next steps mapped out in real time, and then… nothing.

I assumed:

• they'd come back when ready
• the urgency was obvious
• they might want to DIY it

That wasn’t always the case. I lost opportunities, for them and for me, because I didn't build the system to support what I was selling.

I thought I had a strategy problem. Turns out it was a process problem.

How I pulled this together (and why the results actually worked)

At this point, you might be wondering how I pulled these patterns out so clearly.

Here’s the short version. After taking a pass at it with my very own human eyes, I enlisted the help of AI.

I started with the intake forms to understand:

• why they booked in the first place
• what problems they thought they were trying to solve
• what they believed they needed going in

Then I analyzed those individually and as a set, looking for overlaps, red flags, and trends.

After that, I layered in the call transcripts to capture what actually happened in real time:

• how they talked about their business
• what shifted once we started digging
• what they needed versus what they came in asking for

From there, I pulled a ridiculous amount of additional data from those transcripts:

• specific voice-of-customer language
• the questions they kept asking
• emotional and strategic turning points
• Jobs to Be Done, both stated and uncovered

I added my post-call notes next. The summaries, feedback, and action steps I sent after each session.

And finally, I looked at what happened after the fact like testimonials and follow up emails.

So yes, you could absolutely try this yourself.

Just know this: the prompts only worked because I had real context, clear goals, and the experience to know what to pay attention to and what to ignore.

What’s next

This analysis gave me clarity and a reminder to take my own advice. Here’s what I’m doing with it, both behind the scenes and in what’s coming next.

For me:

• Updating how I talk about my strategy sessions (because “strategy” is what we do, but clarity is what they’re buying)
• Refining my own positioning and messaging around this offer to clearly articulate the value and why it’s an easy yes
• Reworking copy to better reflect what people actually need to hear to move forward
• Using jobs-to-be-done to make sure I’m mapping to how people actually move through a buying decision
• Looking hard at my systems (especially around follow-up) and building the structure I should’ve had in place already

I’m not stopping with this analysis. I’m going to repeat this same process with my copy audits too. There’s one thing I do already know: what we think we need is actually rarely what we really do.

For you:

This work won't just live in a Google Doc. It's shaping future newsletter content and offers too.

The first thing I'm planning is a workshop on helping you get clarity on what your actual problem is before you try to solve it with tactics.

If you want details when it's ready, click here. (You’re not signing up for anything. No pressure or firstborn required.)

Or if you're reading this and thinking, "Wait, this is exactly what I'm dealing with", book a strategy session.

We'll uncover what's actually blocking your message, why people aren't getting it even when they want what you do, and map out the next steps to fix it. You can book here.

Until next time,

Stacy

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P.S. I’m curious. Where are you spinning your wheels? Is it explaining what you do in a way that makes you the obvious choice?

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