When I was marketing director at a community college, our website was a disaster.
Everyone on my team knew it. We’d been asking for a redesign for years.
But there was always something else that took precedence. Budget allocations happened at the institutional level, and marketing projects had to compete with every other department’s needs. We kept getting pushed down the list.
And the issues kept building (confusing navigation, buried information, out-of-date content, poor user experience), along with the band-aid fixes (another PDF, a new “landing page”, a shadow site created by a division chair). Finally, the website problems became so glaringly obvious that the right people started noticing—the college president, the board of directors, VPs—and suddenly, the website redesign that had been “on the list” for three years got approved in a matter of weeks.
The broken website was always the problem. But it didn’t become a priority until the right people felt the pain and had the authority to do something about it.
Want more content like this? Find all of my thinking at Strategy & Story on Substack.
Now, I see the exact same pattern in B2B.
Businesses will live with generic messaging, content that doesn’t convert, and random marketing tactics for months or years. Not because they don’t know it’s a problem, but because nothing has forced it to become the priority.
Then something changes. A new boss who asks uncomfortable questions. A reorganization that exposes what’s been broken. Competitive pressure that makes the status quo untenable. Changes in margins or revenue that force a reckoning. Some external factor that makes the problem impossible to ignore or deprioritize.
We’re selling to humans — who are messy and flawed — in organizations where decisions compete for budget, attention, and political capital. And understanding what makes those humans bump your problem to the top of their list makes it far easier for you to become the obvious choice
The Triple Threat
I’ve worked with enough founders now to see that three specific things have to converge before someone pulls the trigger:
Messaging — what you tell people you’re about. This isn’t just taglines and elevator pitches. Done well, your messaging proves you understand your buyers’ context and can bridge the gap between their current reality and where they want to be. It should reveal your differentiation without you having to explicitly claim it. Show, don’t tell.
Positioning — what people actually believe about you. Not what you tell them. How they place you in their mind compared to everyone else they could hire. Here’s the uncomfortable truth: you don’t control positioning. You can only influence it through consistent messaging and behavior. You can’t claim a position. You can only earn it by proving you deserve it over and over.
Buyer Context — the specific moment when your buyer decides they need what you’re offering. It’s rooted in a pain point you solve, sure. But it’s sparked by something else that makes “now” the right time.
Most founders focus exclusively on messaging. They obsess over their homepage copy. They rewrite their LinkedIn headline seventeen times. They hire copywriters to “make it sound better.”
But if you don’t understand the actual moment when someone becomes desperate for what you offer, your tactics will always misfire
The Upward Spiral
When you get them right, messaging, positioning, and buying triggers work together to send growth into an upward spiral.
Buyer triggers sharpen your messaging. When you know the exact moment someone becomes desperate for help, you can speak directly to that moment. Your messaging stops being generic and starts feeling like you’re reading their mind.
Strong messaging reinforces positioning. When your messaging consistently speaks to specific triggers and situations, people start to believe you’re the expert for those exact situations. You’re not just “another consultant.” You’re “the person who fixes X when Y happens.”
Clear positioning attracts more people with the right buying triggers. When you’re known for solving a specific problem at a specific moment, the people experiencing that moment find you. They self-select. They show up pre-qualified.
More exposure to buying triggers deepens your understanding of positioning. Every conversation with someone at that trigger moment teaches you more about what they need, what they’ve tried, how they think. This makes your positioning even more precise.
Refined positioning makes your messaging even stronger. The tighter your positioning, the easier it is to craft messaging that resonates. You’re not trying to appeal to everyone. You’re speaking directly to the people who need exactly what you offer, exactly when you offer it.
And the cycle continues.
This is why getting buyer context right matters so much. It’s not just one piece of the puzzle. It’s the piece that makes all the other pieces work together.
But if you skip understanding buyer context and jump straight to “let’s fix the messaging,” you’re just polishing words. You might sound better, but you won’t convert better because the foundation isn’t there.
It Starts With Triggers
When I start working with a new client, one of the first things I ask is: “Tell me about your buying triggers.” The answer reveals where the foundation is cracked.
One of my clients runs a creative agency. Talented team. Fifteen years in business. Great portfolio. But they were losing deals to competitors who frankly weren’t as good.
They explained that new clients come to them “when they need to rebrand”, which is technically true but completely useless for strategic positioning.
So we walked through his last few closed deals to understand what was happening that specific week when those clients reached out.
Client 1: A massive influx of new investment allowed them to expand their services, and they realized their current brand did not accurately reflect who they had become.
Client 2: A major industry conference presented an opportunity for massive exposure, but their current website didn’t reflect how the company had evolved, putting their reputation at risk.
Client 3: After dominating the local market for decades, a new competitor came to town, and they needed to elevate their digital presence to compete more effectively.
“When they need to rebrand” is a pain point, but it’s one that companies can (and do) ignore for as long as they can. But, “they’ve lost a deal to the same competitor for the third time that quarter” is a trigger. That’s a specific moment when doing nothing stops being an option.
Once we could articulate those triggers, the positioning became clear. Instead of “creative agency” they are “the agency for established brands whose evolution has outpaced their identity”, and the messaging sharpened dramatically. We anchored it in a point of view that only they could own. We spoke directly to their ideal buyers, creating assets and content that immediately resonated with what they were thinking and feeling.
Questions To Ask Your Customers
Every founder should ask their buyers these questions.
“What made you decide to take action right now on this issue?”
This reveals the moment the pain point became unignorable. They might say “we’ve been thinking about this for a while”, but something happened that week that made them pick up the phone.
“What were some of the alternatives you considered or tried before talking to me?”
This reveals what they’ve already done to “figure it out” and why those solutions didn’t work. It’s why they are exasperated, frustrated, and feeling like they can’t do this alone anymore.
“Why do you think the solution I’m offering is going to work?”
This reveals how they’re already thinking about you. What they believe about you versus everyone else they considered.
When you aggregate these responses across multiple customers, patterns emerge. You start to see:
- Exactly when people decide they need help (and what creates that urgency)
- What mistakes they make trying to solve it themselves (and what you’re being compared to)
- How they perceive you differently from alternatives (and whether that matches how you want to be positioned)
That becomes the foundation for everything else.
We can then work on positioning, by defining how you want to be perceived and identifying where that’s not coming through in your messaging or customer experience. We know what needs to be fixed, or what should be amplified.
By that point, the messaging basically writes itself, and we just need to make sure it is accurate and consistent across every channel, from the homepage, to LinkedIn, sales conversations, referral partner materials, content strategy, and so forth.
The sequence matters. You cannot define positioning and messaging until you understand buyer context — the combination of pain points, alternatives, and triggers.
Buyer Context as the Throughline
Knowing your buyers’ context becomes a touchstone by which you can measure the strength of every other aspect of your marketing strategy.
Ideal customers – not just demographics, but situations
One of my clients runs an HR consulting group. He describes his ICP as: “Growing companies that need HR support.” That’s literally every company between 10 and 500 employees. Also every HR consultant’s ICP. Also completely useless for positioning.
When we dug into his actual customers and their buying triggers, we found something much more specific:
“Companies where the office manager who holds all of the company knowledge in their head has just decided to retire.”
That’s not a demographic. That’s a situation. And if you’re in that situation, you recognize yourself immediately.
“We serve B2B professional services firms with 11-500 employees” helps you find names in a database.
“We make your institutional knowledge transferable, so you aren’t stuck without a password when your office manager is sick” helps the right people recognize themselves in your message and know instantly whether you’re for them.
Differentiation — not just claims, but proof
Every cybersecurity firm says they “understand the unique needs of their customers.”
Those are claims. Claims are cheap.
Differentiation comes from describing the exact situation where your approach matters.
A cybersecurity firm was trying to differentiate by saying “We understand manufacturing.” Okay, but why does that matter?
When we mapped it to triggers, it clicked: “Standard IT security rules don’t work on the production floor because operators are focused on safety and speed, not password policies. Our engineers understand that tension, and know how to keep your OT systems secure without slowing production.”
See how that’s not just a claim? It’s positioned directly against what these companies have already tried (implementing IT security in an operational environment) and explains why that didn’t work. That’s differentiation backed by buyer context.
Positioning — not just identity, but delivery
I worked with an AEO/SEO agency whose decision-makers were mostly marketing leaders and CMOs at mid to large size corporations. Their biggest challenge was convincing CEOs that brand marketing could deliver measurable ROI.
His positioning was: “Our SEO delivers brand growth you can prove.”
Which could be said by any digital marketing agency, ever. It doesn’t tell you when you need him versus someone else.
When we dug into his actual wins and surveyed some of his buyers, we found the pattern: because his results demonstrated measurable traffic increases from AI search engines, it proved that content delivered a clear ROI.
So we updated his messaging to reflect this positioning, “Our proprietary methods get your content cited by AI search engines, which proves your brand marketing is worth the investment”
That’s not just “who we are.” It’s “why we’re the right choice versus everyone else you could hire.”
Offers — not just services, but solutions that feel obvious
This is where most people completely miss the mark. And I’ll admit that I used to be one of them.
When I first started my business, I described my offer as “marketing strategy consulting.” And when people asked me what that meant… I struggled.
My buyers weren’t waking up thinking “I need marketing strategy consulting.” They wake up dreading a networking call when they don’t have a clear elevator pitch, or wondering if they will get enough referrals this month to keep paying their VA.
And before they call me, they’ve already tried stuff. More posting. Better graphics. Running ads. Sending a newsletter. Sales drag, wins are slow and hard fought, and inbound leads are rare or nonexistent.
My offer had to acknowledge that journey. Instead of saying “I’ll help you figure out a marketing strategy”, I say “I help you gain control of your pipeline by sharpening your positioning, messaging, and content so you can attract buyers instead of chasing them”.
The first one is too vague to connect to an acute problem. The second explains why this solves what their previous attempts (more ads, more content, better sales scripts, hiring help) couldn’t. That’s an offer informed by buyer context.
Messaging — not just a tagline, but the whole story
Here’s where it all comes together.
Messaging is not just your website headline, it’s everything your buyer needs to know in order to make an informed, confident decision to buy from you. It needs to speak to their specific situation, acknowledge what they’ve already tried, and explain why your approach works when others haven’t.
Without buyer context, you’re forced to describe yourself in generic terms: your capabilities, your processes, your features. You sound like everyone else because you’re speaking from your own perspective.
With buyer context, you’re describing the exact moment when what you offer becomes the clear solution. You’re speaking to their current reality. You’re proving that you understand their situation and can be trusted to solve it with them.
That’s what makes you the obvious choice instead of just another option.
A Warning: AI Is Not Your Buyer
Please don’t ask ChatGPT for your customers’ buying triggers. At best, it will give you an aggregate summary of plausible situations based on whatever data it was trained on. At worst, it will make up things that sound just reasonable enough to be possibly true, but actually make you sound completely out of touch with a real prospect.
Real buying triggers are specific, visceral, and often surprising. They come from actual conversations with actual buyers where you ask: “What was happening that made you finally decide to do something about this?”
Ask your last 10 customers what was going on right before they decided to work with you. Schedule calls with people in your ideal audience and ask what’s happening now, what they’ve experienced, and why they have or haven’t taken action yet.
AI can help you spot patterns in conversations you’ve already had, but it can’t replace having those conversations.
This is literally the foundation of your entire marketing strategy, so it is worth doing right. Every minute you spend on this work compounds through every marketing action that follows.
The Thread That Binds
Once you understand buyer context, it becomes the thread that connects every aspect of your marketing.
Use it to tighten your ICP. Sharpen your differentiation. Strengthen your positioning. Focus your offers. Make your messaging actually resonate instead of just sounding like everyone else in your category.
Buyer context makes your marketing more efficient. You can focus on the right people, in the right places, at the right time instead of spraying content everywhere hoping something sticks. And in my experience, it makes the work more interesting. You’re not just guessing what might work, you’re speaking directly to the moment when someone realizes the status quo isn’t tenable anymore and they need help.
This makes you an obvious choice instead of just another option.
Leave a Reply