Pain Points Don’t Close Deals
Tony Wiedenski converts 80% of his discovery calls into clients. It starts with knowing the difference between a pain point and a business problem.
Last week, Tony Wiedenski of RevUp Sales ran a workshop for the 10x Solo community on how he converts 80% of discovery calls into paying clients.
For context: the traditional win rate for most B2B sales teams is ~20%. When Tony starts with a client, that’s usually his baseline, and his goal is to get them to at least 40% within a year. His own close rate is 80%.
He compressed about five hours of material into 45 minutes, so this recap only scratches the surface. But everything hangs on one idea:
Buyers will tolerate pain points for years, but they spend money to solve business problems. So why are most of us still pitching the pain?
Let’s build up to why that matters.
You sell advice. So the only currency that matters is trust.
Tony opened by asking everyone what they sell. Product marketing. Customer-led messaging. “Time for money,” Spencer joked.
Tony’s answer: strip away the deliverables, and every one of us sells the same thing. Advice.
I pushed back on this in the session, because I knew someone would: don’t clients also pay for the deliverables? The content, the app, the website, the actual stuff they get?
Tony’s take: the deliverable is how the advice gets delivered. It’s the product of the advice, not the thing being bought.
That reframe is important because of what it implies. A prospect who realizes they need advice can get it anywhere: their investors, their board, a friend, ChatGPT. The only way they buy yours is if they trust you as the best source (or expert).
Which raises the question: what builds that trust on a sales call?
The expert always wins
Tony’s first theme: in every sales conversation, the expert wins. 100% of the time.
Sometimes the expert is you. You’ve taken the time to understand their situation, they’ve confirmed your read on it, and your recommendation lands as the obvious next step. It’s very hard to say no to someone who understands your business better than the alternatives do.
Sometimes the expert is the buyer. They walked in with their own theory of what they needed; you never displaced it, and they made their decision based on it (for better or worse). Tony told the story of losing a deal to a consultant recommended by a board member. The buyer believed “someone the board vouches for” was part of the answer, and Tony never surfaced that criterion, so he never got the chance to address it. The buyer stayed the expert, and Tony lost the deal.
His second theme is the flip side: assumptions block deals. You look at a prospect’s website, see the messaging is a mess, and assume they need what you sell. You pitch a great call (process, experience, and deliverables) and still lose. You skipped the part where you confirm what’s actually going on: their motivation to change, their goals, what the mess is costing them. Anything you’re assuming needs to get confirmed.
Both themes point at the same job: spend the majority of your sales call understanding their world, not presenting yours.
The four questions every deal must answer
What does “understanding their world” need to produce? Tony frames it as the four questions running through every buyer’s head: the ones a CFO who’s never met you would ask when your contract hits their desk for approval.
Why do we have to change at all?
Why can’t we fix this with what we already have?
Why do we have to do it now?
Why this person instead of another option?
Answer those objectively in your proposal, and you’ve done the buyer’s internal selling for them. It becomes very hard to say no.
Notice that only question 4 involves competitors. That matches where deals actually die. By Tony’s numbers, about half of lost deals go to indecision and the status quo (”let’s revisit next quarter”). Another 35% go to competing priorities: you were real, but something else mattered more. Only 15% are lost to an actual competitor.
In most deals, you’re competing with “do nothing,” not with another provider.
Pain points vs. business problems
Beating “do nothing” comes down to the distinction Tony spent the most time on.
A pain point is an annoyance or inefficiency. It lives at the task level. It’s usually felt by the people doing the work, not the person signing the contract. It’s measured in hours, manual steps, missing pieces: we don’t have anyone to do this, our messaging is inconsistent, this takes too long.
Pain has one property that kills deals: it can be tolerated. Tony’s own website went live in September, and he knew it wasn’t good. He’s lived with it since. Businesses tolerate pain every day, which means a pitch aimed at pain is competing against “we can keep living with it,” and losing half the time.
A business problem is different. It’s a serious issue that:
shows up as a KPI or leading indicator that leadership regularly monitors
gets fixed indirectly. You can’t force a win rate up by decree; you take a bet on something that moves it
connects in a straight line to money: cost, revenue, or future investment
Win rate is Tony’s example. He doesn’t do the selling and can’t force customers to buy, so he fixes win rates indirectly. But a 20% win rate means the company literally can’t grow: can’t spend profitably at the top of funnel, can’t hit the revenue goal, can’t raise the next round. That’s why people buy.
One warning from the discussion: don’t confuse business problems and impacts. Saving money is an impact, not a problem. The chain runs pain points → business problem → impact. You sell the specific problem in the middle: “Your win rate is 20% because your reps push features and skip discovery. Here’s what fixes that.” Specific enough that no tool comparison matches up against it.
I also asked Tony how many business problems you can credibly claim to solve. His answer surprised me: no more than 4. Total. He recently ran this exercise with a $100M company with roughly 30 services. They solve only three business problems. If your list is longer, most of the entries are pains wearing a problem costume.
How to uncover this without an interrogation
You don’t need a long list of questions. You need the prospect talking, and a way to catch what Tony calls cues: the moments in their answers that should trigger your next question.
The vague cue. Anything undefined or unmeasured. “I had a lot of issues with my last fractional CMO.” A lot of issues can’t just float by. Write it down, come back, define it, quantify it. Listen for “a lot,” “not enough,” “too long,” “inefficient.” Once you train yourself to do this, Tony warns, you can never unhear it, even in your personal life.
The curiosity cue. The out-of-the-blue question. “Wait, do you also do X?” We tend to answer these fast to sound credible. Wrong move. That question means they’re trying to connect your offer to something in their world you haven’t heard about yet. Say “tell me more. Why do you ask?” and let them talk. That’s often where the real issue is hiding.
A prospect might talk for 15 minutes straight off your opening question. Track every cue as they go; otherwise, you’ll only remember the last thing they said. Then chase the one that gets you to a business problem fastest.
Even if you never get to a crisp business problem on the first call, quantifying and defining the pain is already a head start most sellers never take.
D.E.A.L.: the four things that have to be true
Everything above is the first and most important piece of Tony’s deal-management framework, the D.E.A.L. Progress System™:
Develop the business case for change. Can you objectively answer the buyer’s why questions with quantified pain and an agreed-upon problem? That’s the whole first half of this post.
Engage the buying committee. Even a founder-led deal has one: a business partner, a head of sales, a spouse. If you can’t reach them directly, enable your champion. “How will they decide? Here’s what to share with them.”
Align your solution to the business case. Line by line: here’s what I heard, here’s what addresses it in my offer.
Lock in the timeline. Skip “when will you decide” and ask when they want the results. Then work backward. Buyers don’t know how long procurement, reviews, and vacations take. Working backward from the outcome date is what turns “let’s meet in three weeks” into “we need the proposal next week to get the result by Q4.”
With this framework, even the deals you win can be audited for what you never actually confirmed. And the deals you lose stop being mysteries.
Your next discovery call
One exercise before your next sales call:
Write down the 1 or 2 business problems your offer actually solves (KPI-level, leadership-monitored, tied to money).
Test each one: is this a true business problem, or just a pain in disguise? (”They’re spending hours on X” is a pain. What happens because of those hours is the problem.)
Then run the call with one goal: get one pain defined and quantified, and connect it out loud to one of those business problems your offer solves.
That’s the expert position, and the expert always wins.
Keep building,
Garrett
P.S. When you’re ready, here are two ways I can help you:
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