I spend a lot of time talking about how the most important thing in a sale is to define “success” in your customer’s terms, but it occurs to me that I’ve never gone into much detail on exactly how to do that. We’re going to fix that today.
This is one of the most important steps in selling – and it’s also one that’s skipped often. Before you can solve a customer’s problem, the customer has to know what solving it actually looks like – and much of the time, they don’t. They might not even know what’s possible. They have a vague sense that something is wrong, or that something could be better, but they haven’t defined what “better” means in any concrete way. If you help them define it, you’ve done something most of your competitors never will, and you’ve done it during the part of the Buyer’s Journey where the sale is actually won or lost.
Why Customers Show Up Without a Definition of Success
When a customer enters the Investigation phase of their Buyer’s Journey, they’re trying to figure out what they need, but they usually haven’t thought it through as clearly as you’d assume. They know they’re dissatisfied and they want a change, but they often haven’t considered what a successful outcome would actually look and feel like once they have it. You can help them envision it.
I see this constantly. A customer says they want to “improve efficiency” or “reduce costs” or “get better service,” but those are headlines, not definitions. If you ask three different people inside the same company what “better service” means, you’ll get three different answers, and none of them will be specific enough to act on. If you take that headline at face value and run straight to a solution, you’ll find out at the worst possible moment that you solved the wrong problem.
That’s why helping a customer define success isn’t preparation for the sale – it’s the most important part of the sale. Remember that 80% of your chance to win or lose is determined by the time you ask your last question, and a huge chunk of that 80% lives right here.
The Five Things You Need to Know
Helping a customer define success means getting concrete answers to five questions, and the deeper you go, the more powerful your position becomes.
First, what do they absolutely want to avoid? What should never happen? Customers are often clearer about their fears than their hopes, and knowing what would constitute a disaster for them tells you where the landmines are buried. If you trip one of these later, the deal is dead no matter how good the rest of your solution is.
Second, what do they absolutely want to have happen? These are the non-negotiables, the outcomes that have to be there for the customer to consider the purchase a success. Don’t accept headlines here – drill down until you know exactly what the outcome looks like on a specific day, in specific terms the customer describes themselves.
Third, what are the nice-to-haves? These are the bonuses, the things that would be great but aren’t dealbreakers, and knowing the difference between a must-have and a nice-to-have keeps you from over-engineering a solution around something the customer doesn’t actually care that much about.
Fourth – and this is the one almost nobody asks – if you’re talking to anyone other than the top person, how are they rewarded personally if your solution succeeds? The president or CEO cares about the company’s outcome, but the manager or director you’re often dealing with has a personal stake too. Maybe success here gets them a promotion, or a bonus, or simply the relief of not getting chewed out anymore. It takes a lot of trust for a customer to share this with you, and you won’t get it early in the relationship, but if you earn it, it’s the most powerful motivator of all. People buy for company reasons, but they decide for personal ones.
Fifth, if there are multiple stakeholders in the decision, you’d better know every one of their definitions. The CFO’s definition of success isn’t the operations manager’s definition, which isn’t the end user’s definition, and a solution that nails one while ignoring the others will get killed by the person you didn’t bother to understand. Map the stakeholders, and then map what success means to each of them individually.
While you’re doing this, you need to set the timeframe correctly. Even when salespeople do define success in the customers’ terms, they often think only of immediate success; i.e. how the customer evaluates the solution immediately after delivery or implementation. Often, it’s more useful to ask the customer how they’ll evaluate the success a year or more down the road, after the ‘glow’ of the startup has long since passed.
This Isn’t Manipulation
I want to be clear about something, because helping shape a customer’s definition of success can sound like you’re steering them toward what you sell. You’re not tricking them into wanting your solution – you’re helping them think through dimensions of the problem they hadn’t considered, and some of those dimensions happen to be ones where you’re strong.
The customer comes out of the conversation with a clearer, more complete picture of what they need, and you come out of it positioned as the person who helped them see it. That’s not a trick, that’s value, and it’s the kind of value that customers remember when it’s time to decide. You’re also highlighting urgency that already exists, rather than trying to ‘create urgency’ after you have proposed and you’re desperate for a deal.
Remember – sales isn’t something we do to the customer, it’s something we do with the customer.
This Beats the “Solution Barf”
A customer who hasn’t defined success can’t properly evaluate any solution, including yours, because they have no standard to measure it against. You can have the best offering in the market, but if the customer doesn’t have a clear definition of what they’re trying to achieve, your superiority is invisible to them.
When you help the customer define success first, you give them the measuring stick they’ll use to evaluate every option – including your competitors. If you’ve done the work of helping them think through what really matters, that measuring stick will tend to favor the things you do well, because you helped build it. The salesperson who races to the solution is asking the customer to judge a contest where nobody agreed on the rules.
This is also why so many deals stall in the Evaluation phase. The customer can’t decide because they were never clear on what they wanted, so every option looks like a coin flip – and a coin flip is a decision most people would rather postpone. If you helped them define success up front, the Evaluation phase gets dramatically easier, because they already know what they’re looking for.
Navigating the Definition of Success
The next time a customer tells you what they want, resist the urge to start solving it. Slow down and help them define what success actually looks like first, because that definition is worth more to them – and to you – than any solution you could lead with.
Work through the five questions. Find out what they need to avoid, what they need to achieve, what would be a nice bonus, how the people in the room are rewarded personally, and what success means to every stakeholder in the decision. Be genuinely curious about their world, because that curiosity is what separates you from everyone else who just wants to pitch. Do that, and you won’t just sell them something – you’ll help them understand their own situation more clearly than they did before you showed up.
For greater understanding of your buyers:
Make sure you attend my June 25, 2026 Webinar, “It’s Not Your Pipeline: Where Buyers Live and How They Actually Buy,” at 11 AM Central. See the description and register here.
