Why Founders Skip the Hard Part

Here's something I see when I work with B2B tech companies that have made it past the $1M milestone but can't seem to break through to the next level.

They've built something real. Customers are paying. But they've plateaued. The website sounds like everyone else's. The founder (or sales team if there is one) struggles to explain how they're different. Prospects take forever to close.

So what do they do? They hire a content marketer. Launch some LinkedIn ads. Redesign the homepage. Maybe bring in an agency to "fix the messaging."

Lots of activity. Little traction.

The pattern repeats. More tactics. More rewrites. More campaigns that sort of work but never quite hit their stride.

And here's the thing: most of these founders know, somewhere in the back of their minds, what they're avoiding.

It's Not Ignorance. It's Avoidance.

When I first talk with companies, the conversation usually starts with "our tactics aren't working." Wrong channels. Weak creative. Inconsistent execution.

Dig deeper, and often there's no clear plan—just scattered efforts with no focus.

Dig deeper still, and it's usually a positioning problem. No clarity on what you're positioned against in the market. No articulated differentiation. And no understanding of which customers actually care about that differentiation.

They're not skipping the foundational work because they don't know it matters. They're skipping it because it requires making decisions they'd rather not make.

Part of the avoidance is that founders are often trying to keep the story broad enough for investors while being specific enough for customers. Positioning for customers is about right now—why pick us versus the alternatives available today. (They're not going to open their wallets for something you might deliver in the future.) Positioning for investors is about the future vision. Trying to do both at once is how you end up with vague messaging that serves neither.

Why Positioning Work Feels So Uncomfortable

The difficulty isn't complexity. It’s commitment. Making a few critical choices and sticking to them.

But those choices are hard. And not in the way founders expect.

Saying "we're for these people" means accepting you're not for those people. Saying "we won't do this" means giving up on that revenue (for now, more on that later). Picking a lane means leaving other lanes behind.

And there's another decision founders avoid: defining what they're positioned against.

Usually, companies only think of direct competitors. But that's the wrong answer—or only part of the answer. The real competitive alternative is often the status quo: the way companies are managing to address the problem with manual processes or software tools they already have.

If you don't get clear on what you're replacing in your customer's world, your marketing ends up fighting the wrong battle. You're explaining how you're better than Competitor X when your prospect isn't even considering Competitor X. They're considering doing nothing—continuing with "the way we've always done it."

All of this feels risky. So founders default to vague positioning. "We help companies improve efficiency." "We're a platform for teams." "We enable digital transformation."

Statements that could describe a thousand other companies. Statements that land with a thud because they don't actually say anything, full of flavour-of-the-year jargon and buzzwords. (AI-powered workflow synergy platform, anyone?)

What Staying Vague Actually Costs

Here's the irony: the "safe" choice is actually the risky one.

When your positioning is unclear, prospects invent their own context for understanding you. And they usually get it wrong—comparing you to the wrong alternatives, expecting the wrong outcomes, wondering why you're not cheaper than the thing you're not actually competing with.

Your customers don't understand what you do or who you do it for. Your team gives three different answers to the same question. (Go ahead—ask your sales team, your marketing team, and your product team what you are, who you’re for, and how you’re different. If you get three different answers, you have a positioning problem.) Your marketing creates confusion instead of clarity. Your sales cycles stretch because prospects can't figure out how you're different from the other alternatives they're evaluating.

The result? Reactive strategies. Diluted messaging. Product decisions that lack coherence. Growth that never quite hits its stride.

Most B2B companies plateau at some point—not because of product problems, but because they never got clear on who they're for and how they’re different in a way that really matters to customers.

The Differentiation Problem

Without clear positioning, you end up sounding like everyone else.

Your website could swap logos with three competitors and nobody would notice. Statements like "We help companies grow through AI-driven insights and seamless integration" provide exactly zero differentiation—because every other company is saying something similar.

When I ask founders to show me their competitors' websites, I'm often surprised by how hard it is to tell them apart. Similar images. Same vague promises. Same reluctance to be specific about anything.

This is a positioning problem. And no amount of clever copywriting will fix unclear positioning. You can't message your way out of a clarity gap.

A firm I worked with put it perfectly: "I've been asking people and they're like, 'Well, I think I know what you do, but I'm not sure.'" That phrase—"I think I know what you do"—kept coming up. Prospects, referral sources, even people who'd worked with them before couldn't quite articulate what they did or what made them different.

They are not alone.

What Happens When You Finally Make the Calls

Defining your ideal customers—the ones who love what you do, get the most value, provide feedback, pay on time, stay and grow, and refer you to others—means saying no to some opportunities (that's hard, really hard!). Picking your lane means walking away from adjacent markets (at least for now). Being specific about your value means you won't appeal to everyone.

But something shifts when you do it.

Your team stops disagreeing about tone because they've finally agreed on meaning. Your sales conversations get clearer. Your marketing actually resonates with the people it's supposed to reach. Prospects self-qualify—which means fewer wasted calls and faster closes.

Specificity isn't limiting. It's clarifying. And clarity is what makes everything else work: marketing, sales, product decisions become easier.

You're Not Locked In Forever

Here's something that might make this more palatable: your positioning will evolve.

The work isn't about finding the perfect, permanent answer. It's about getting clear enough to move forward, learn from the market, and refine as you go.

Your positioning should change when your customers teach you something new about how they think about your product or service. It should change when the market shifts, when a competitor repositions, or when your offering evolves.

The goal isn't to nail your positioning for the next decade. It's to get clear enough to reach your next growth milestone—to build traction, generate revenue, and learn from real customers.

And here’s something to keep in mind if you're pre-revenue or just entering a new market: what you're building is really a positioning hypothesis—an educated guess to test. That's fine. The goal isn't perfection; it's clarity enough to learn.

Then you refine. Then you get clearer. Then you do it again.

The founders and CEOs who get stuck aren't the ones who got their positioning "wrong" the first time. They're the ones who never made the decisions at all.

The Sequence That Actually Works

Clarity → Strategy → Tactics.

Always in that order.

You can't build an effective strategy without clarity on what you're positioned against, what makes you different, and who you're for (and not for). And you can't execute tactics that work without a strategy to guide them.

Most founders try to start with tactics because tactics feel productive. Ads running. Content publishing. Activity happening.

But tactics without clarity and strategy? That's just lighting a bag of money on fire. You'll get a little warmth, but not for long.

A Few Questions Worth Sitting With

If you're wondering whether you've skipped the hard part, try these:

Can your team articulate—in one sentence—who you're for and how you're different? Do they all say the same thing?

When prospects land on your website, can they figure out within 10 seconds whether your product or service is for them?

Do you know what you're positioned against—not just direct competitors, but the current behaviour or status quo your customers are using today?

Have you explicitly decided who you're not for?

If any of these give you pause, you might have some foundational work to do.

The Hard Part Is Worth It

I get why founders avoid this. The decisions feel risky. And there's always something more urgent demanding attention.

But here's what I've seen, over and over: the companies that get clear early scale faster and with less friction than those that keep putting it off.

The hard part isn't hard because it's complex or time-consuming. It's hard because it forces you to make choices you'd rather avoid.

Make them anyway. You can always refine later. But you can't refine what you never defined in the first place.

If you're a marketing leader reading this and nodding—you've probably had this conversation with your CEO or founder. Maybe more than once. The foundational work doesn't get easier to sell internally, but it does get more urgent the longer it's avoided.

Know a founder or CEO who keeps tweaking tactics without seeing results? Share this with them. Sometimes the nudge to do the foundational work has to come from someone else.