Your sellers don’t have a closing problem. They have a knowing problem.
When conversion rates stall, most CEOs look at activity metrics. The real gap is usually what sellers were never taught about the buyer’s world.
What would you think if your doctor walked in, skipped every question, and immediately recommended surgery?
You would leave. You would tell your friends. And you would never go back.
Yet this is roughly what happens on most sales calls. A seller shows up, talks about the product, asks a few surface-level questions, and then tries to map features to whatever the buyer just said. The buyer, meanwhile, is sitting there thinking: I already researched this online. Why am I on this call?
Here is what I am seeing consistently across the companies I work with. The sellers who struggle are rarely lazy. They are almost always under-equipped. They were trained on the product, handed a list, and told to go. Nobody taught them how their buyer thinks, what metrics keep that buyer up at night, or what problems exist in the buyer’s world that the buyer hasn’t even identified yet.
The fix is not a new script. The fix is a strategic decision that starts with the CEO.
Watch below or on our YouTube channel
The outsider who saw what everyone else accepted
Becc Holland spent years selling enterprise heating, lighting, and cooling projects to governmental buildings and school districts in Texas. The floor on those deals was $2 million. The sales cycles stretched a year and a half. In that world, you did not batch-blast 2,000 emails and hope for a reply. You drove to the buyer’s door. You knew their world before you walked in.
She built this company not because founding looked appealing, but because the broken practices she kept seeing compelled her to act. That is a particular kind of founder story: not the one where someone sees a market opportunity and races toward it, but the one where someone absorbs enough frustration, enough evidence that things could be better, and finally decides the personal cost of building is lower than the cost of staying silent.
Why buyers freeze (and what that means for your team)
Here is a number that should reframe how you think about your pipeline: 80% of deals are lost to indecision.
Not to a competitor. Not to budget cuts. To indecision. The buyer sees the problem. They even acknowledge it is big enough to matter. And they still do not move.
Holland’s explanation for this is worth sitting with. Buyers are scared of outcome uncertainty. They worry about picking the wrong product. They worry about what happens if they swipe the card and the solution does not work. Nobody gets fired for not buying software when a discount was available. People do get fired for purchasing something that fails to solve the problem.
So the buyer’s default, two to three times stronger than the impulse to act, is to stay still.
This is where most sales approaches fall apart. If a seller’s only play is to surface a pain the buyer already knows about, the buyer will nod along and then do nothing. They already knew about that pain before the call. Knowing about it is not what was keeping them from acting.
What moves a frozen buyer is discovering something they did not know. A problem underneath the problem. A risk they had not calculated. A metric that is trending toward trouble before it becomes visible. That is where the diagnostic model comes in.
Selling as a diagnostic profession
Holland frames selling the way medicine works. A doctor does not walk into the room and say, “You have stage four cancer” before asking a single question. A doctor asks targeted questions based on deep knowledge of how the body works, looks for indicators the patient may not have noticed, and arrives at a diagnosis the patient could not have reached alone.
The same logic applies to selling. If your sellers are asking, “What’s keeping you up at night?” or “What’s the impact of not solving this?” they are asking the buyer to do the diagnostic work. And if the buyer already knew the full scope of the problem, they would already be solving it.
Holland’s approach flips this. She teaches sellers to learn the top 20 leading indicators that their buyer persona is measured on, the industry averages for those metrics, and at what point those metrics start causing problems. When a seller knows, for example, that network latency above a certain threshold typically causes server downtime, and that the average backup success rate for companies of a certain size falls below a critical benchmark, that seller can ask precise diagnostic questions. Not “Do you have a problem?” but “Are you over 40 employees in your IT department? Is your average server uptime below 99.5%? If so, you may be running into an issue you haven’t flagged yet.”
That is the difference between attracting demand and creating it.
Attracting demand means reaching out to the slim portion of the market that already knows they have a problem and is already shopping. Holland points out that outbound conversion to that slice averages about 6%. Inbound, where the buyer has self-selected, runs around 35%.
Creating demand means finding problems the buyer did not know they had. When a seller surfaces one of those, the buyer leans in. They pull in decision makers. They find budget. Because now they have new information that makes staying still feel riskier than acting.
The onboarding problem most CEOs do not see
Here is where it gets practical, and where most companies are unknowingly undermining their own teams.
Holland describes a pattern she encounters over and over. A company has a four-week onboarding program for new sellers. The first weeks are filled with meeting the founders, meeting the marketing team, learning the internal tech stack, getting certified on the product, maybe going to lunch with an AE or a CSM. At the very end, there is a small deck about the buyer.
Holland’s position is that the buyer manual should occupy three and a half weeks of that four-week onboarding. Not a small deck at the end. The dominant focus.
This resonates with a pattern I see across the CEOs I work with. The CEO became a CEO because they knew the problem deeply. They lived in the buyer’s world. They had conversations with buyers that were rich with context, knowledge, and the ability to spot things the buyer had missed. Then they hired sellers and said, “Sell my product.” And all of that buyer knowledge stayed locked inside the CEO’s head.
The strategic move is to transfer that knowledge. Not just product knowledge. Buyer knowledge. What does a CTO worry about? What metrics define their performance review? What does their day actually look like? What are the common failure points in their world, and at what thresholds do they become urgent?
If you are a CEO and you have never asked your clients to sit on a panel so your sellers can learn how buyers in that role actually think, this is one of the highest-leverage things you can do this quarter.
What to examine this week
If I could sit down with every CEO reading this, here is where I would start.
Go look at what your sellers are actually sending. Not what they are supposed to send. What they are actually sending. Pull up the email logs. Look at the subject lines. Read the first lines. Holland notes that 90% of the time, sales leaders know what the emails are supposed to look like but have not checked what is actually going out. One CEO I know received a forwarded email from a prospect who was so appalled by the outreach that she sent it directly to the CEO as a courtesy. That CEO had no idea those emails were representing the company.
Then look at how much of your onboarding is about the buyer versus about the product and the internal org chart. Count the hours. The ratio will tell you a lot.
Finally, ask yourself: do my sellers know enough about the buyer’s world to find a problem the buyer has not yet identified? If the answer is no, the gap is not effort or talent. The gap is knowledge you have not yet passed down.
Selling should feel like helping because, done well, it is helping. Your buyers want an expert in front of them. They want someone who can find what they missed, who can make their world better than it was before the conversation started. Holland’s conviction, the one strong enough to push past the 90% of her that never wanted to be a founder, is that sellers and buyers actually share the same goal. The CEO’s job is to make that possible by equipping sellers with the knowledge to diagnose, not just pitch.
Fifteen minutes a day learning about your buyer’s world. That is Holland’s challenge to every seller and every CEO leading a sales team. It sounds small. The compounding effect is not.
0 Comments