Sales discovery
There’s a version of a sales discovery call that feels less like a business conversation and more like being processed at a government office.
“How many employees do you have?”
“Where are you headquartered?”
“How long have you been in business?”
“What are your goals this year?”
Eventually you expect the rep to ask whether you’ve lived at your current address for more than six months and tell you to take a number.
The strange part is that a lot of these calls are technically following the training.
The rep has a discovery sheet. Management has decided these are the 17 things we need to know. Salesforce has empty fields that MUST be filled. So everyone politely participates in this little administrative ceremony while the actual reason the customer took the meeting sits untouched somewhere in the background.
I think discovery is probably the most important part of most B2B sales conversations.
I also think it’s one of the easiest parts to overcomplicate.
The best discovery conversations I’ve been part of have structure underneath them, but they still feel like conversations. They have direction. They move relatively quickly. And they get to the actual problem without making the buyer feel like they’re completing an intake form.
There is a category of sales questions that should probably be retired.
“Where are you guys located?”
“What does your company do?”
“How large are you?”
“How many employees do you have?”
If the answer is sitting six inches away from you on a laptop with internet access, asking the customer to recite it personally seems unnecessary.
Do a little research.
Look at their website. Look at LinkedIn. Check the CRM. See whether your company has spoken with them before.
That last one should be obvious, yet I’ve watched it happen plenty of times at larger organizations.
An SDR books the meeting. The AE is busy. Nobody looks at the account history. Then the customer gets on the call and is asked the same questions they answered for another rep 18 months ago.
The customer remembers the previous conversation.
Your company apparently suffered a traumatic brain injury.
Preparation matters because it affects credibility.
I want to join a call with at least a basic understanding of the company, the person’s role, what businesses like theirs tend to struggle with and which customer stories might actually be relevant.
I’m not trying to pretend I already understand their entire business.
I’m trying to avoid making them start at kindergarten.
Good preparation should also give you a hypothesis.
Maybe companies like theirs tend to run into a certain operational problem. Maybe someone in that role usually cares about a particular metric. Maybe you’ve solved a similar issue for another customer.
You can bring those observations into the conversation and let the buyer correct or expand on them.
That immediately feels different from showing up completely blank and asking them to educate you.
Situational questions still matter.
You need context.
The problem is when context becomes the destination.
A simple rule I like is this:
A situational question should help you ask a better question next.
“How are you handling that process today?”
Fine.
Then:
“Where does that tend to break down?”
Much better.
“How many opportunities are typically moving through that stage?”
Useful.
Then:
“When those get stuck, what does that do to your forecast?”
Now we’re getting somewhere.
Questions around budget, decision process, metrics, stakeholders and authority matter too. Frameworks like MEDDICC exist for a reason. At some point I need to understand how an organization would actually make a decision.
But timing matters.
If I’m five minutes into the conversation asking about procurement, budget approval and who signs the contract before we’ve established whether there is a meaningful problem to solve, I’m basically asking the customer to qualify themselves for my pipeline.
Nobody enjoys that.
Discovery really has two jobs.
First, understand whether there is a problem worth solving.
Second, understand how the organization could realistically make a decision to solve it.
You need both. I just don’t think they always need to happen in the opposite order.
One of the biggest lessons I’ve learned selling across different industries is that the first problem you see isn’t always the problem worth solving.
One of the clearest examples came from an enterprise furniture company we worked with at Epigraph.
We had originally talked to them years earlier about a visual product configurator.
The obvious pitch was straightforward.
Better visualization.
Better digital experience.
Potentially better online conversion.
Great.
Except a large portion of their business happened through dealerships and their sales organization.
We were talking with the national sales leader.
Online conversion wasn’t exactly keeping him awake at 3:00 in the morning.
As we got deeper into the conversation, we started understanding what happened after customers configured and purchased furniture.
Their products could involve a large number of individual component SKUs. When customers made changes to an order, tracking those components and processing the change could become extremely cumbersome. In some cases, it could take days.
Now we had something.
We weren’t talking about making the website prettier anymore.
We were talking about fixing a broken operational process.
We could build a configurator connected into Shopify that handled much of that complexity automatically.
What originally looked like roughly a $15,000 opportunity became a $172,000 deal.
That experience reinforced something I’ve seen repeatedly:
Sometimes good discovery reveals that the thing you walked into the meeting planning to sell is the least interesting thing you could sell them.
You only find that out if you’re actually listening.
The industries I’ve sold into have been very different.
The shape of the problems tends to be surprisingly consistent.
Something is costing money.
Something is wasting time.
Something is introducing risk.
Something is creating friction.
At HomeAdvisor, I worked with contractors who frequently had unused capacity.
“How far out are you booked?”
That’s useful context.
If the answer is only a few days:
“What happens when you’ve got two guys available Friday and nothing for them to work on?”
Now we’re talking about the actual problem.
At ZoomInfo, a sales team might be making a huge number of outbound calls but connecting with only a small percentage of the people they’re trying to reach.
You can talk about data quality for 20 minutes.
Or you can understand what happens when ten salespeople spend a meaningful percentage of every day calling numbers that don’t work.
At ChannelAdvisor, the issue might involve an e-commerce company managing products and inventory across multiple marketplaces.
“How many marketplaces do you sell on?” gives me context.
“What happens when inventory changes and all of those marketplaces need to stay synchronized?” gets me closer to the business problem.
You don’t need a library of magic discovery questions.
You need to understand what you’re trying to uncover.
This is usually the hardest part.
The customer finally acknowledges a problem.
And somewhere inside the salesperson’s brain:
THEY SAID PAIN. OPEN THE DEMO.
Everyone relaxes. We survived discovery. The PowerPoint can come out.
I think that’s usually too early.
If someone tells me a process is inefficient, I want to understand what “inefficient” actually means.
“How much time is the team spending on it?”
“Who else gets pulled into that?”
“What happens when it goes wrong?”
“How often does that happen?”
“Do you have a sense of what that costs?”
“If the business keeps growing and nothing changes, what happens?”
Sometimes those questions should be quantitative.
Sometimes they should simply follow the consequence.
The best ones usually feel like a logical continuation of something the buyer just said.
And this is uncomfortable for a lot of reps because you have to resist the urge to rescue the conversation with your solution.
The existence of a problem alone doesn’t necessarily create urgency.
Companies can survive inefficient processes for an astonishing amount of time.
There are probably billion-dollar organizations right now moving mission-critical information around in a spreadsheet called FINAL_v7_USE_THIS_ONE.xlsx.
The customer needs to understand why solving the problem deserves attention compared with everything else happening inside the business.
Good implication questions help them do that.
They don’t manufacture pain.
They help the buyer understand the consequences of pain they already told you exists.
There is another extreme.
The rep does great discovery.
They understand the current situation.
They uncover the problem.
They know why it matters.
They understand what the customer wants instead.
They understand what happens if nothing changes.
And then they ask twelve more questions.
Why?
Because twelve questions remain.
At some point, stop.
You do not receive bonus points because the customer talked for 70 percent of the meeting.
You don’t get a plaque because discovery lasted 42 minutes.
A strong rep can sometimes uncover more relevant information in ten focused minutes than someone else gets in thirty.
Discovery isn’t graded by duration.
You have enough when you understand the problem well enough that the solution has context.
One of my favorite sales contradictions is what happens next.
A rep spends half an hour carefully uncovering exactly what the customer cares about.
Then they share their screen and say:
“Great. Let me tell you a little bit about who we are.”
No.
We just did all of this work.
Use it.
If the buyer gave you three specific problems, show them the parts of your solution that address those three problems.
The rest can wait.
Discovery should tell you what to show.
More importantly, discovery should tell you what NOT to show.
A feature that has nothing to do with the buyer’s problem doesn’t become more relevant because your product team worked really hard on it.
Tie the presentation directly back to what they said.
“You mentioned that your team spends days reconciling those changes. This is the part I wanted to show you because it changes that process.”
Now the presentation feels like the conclusion of discovery instead of the beginning of a canned sales pitch.
I also try not to end a meaningful sales conversation with:
“I’ll send some information over and we can reconnect.”
This is where opportunities go to die.
Whenever possible, I want another meeting on the calendar before we hang up, even if the date is tentative.
Momentum is much easier to maintain than it is to recreate.
Ideally, there is also some mutual work between meetings.
Maybe I need to prepare pricing, build something, get an answer, create a business case or bring in another resource.
Maybe they need to confirm a number, speak with someone internally, find something or bring another stakeholder into the next conversation.
It doesn’t need to be a major assignment.
This isn’t homework detention.
The point is that both sides are investing in moving the process forward.
And if there’s a longer gap between meetings, I try to make every touchpoint useful.
I avoid “just checking in” whenever possible.
If my entire reason for contacting someone is to remind them that I continue to exist, I probably haven’t given them a compelling reason to respond.
Bring something.
Answer something.
Share something relevant.
Advance the conversation.
The best discovery calls I’ve been part of rarely feel like a sales methodology being performed.
There is still structure underneath them.
I’ve learned a lot from SPIN Selling, Challenger, MEDDICC and other frameworks throughout my career. Those methodologies help you understand what you need to accomplish.
But the customer shouldn’t feel the framework.
They should feel like they’re talking to someone who understands their business, asks relevant questions, listens carefully and knows when to follow an interesting thread.
By the end of the conversation, something should be clearer than it was at the beginning.
Maybe the customer understands the size of the problem better.
Maybe they see a downstream consequence they hadn’t connected before.
Maybe you realize the opportunity is much bigger than you originally thought.
Or maybe you both discover there really isn’t a compelling reason to move forward.
All of those are useful outcomes.
If all you accomplished was filling out every field in Salesforce, congratulations.
Salesforce is thrilled.
But the buyer probably isn’t.
After more than a decade selling across everything from transactional sales to complex enterprise deals, the biggest lesson I’ve taken from discovery is pretty simple:
Know what you’re trying to understand, prepare enough that you don’t waste the buyer’s time, and then listen closely enough to let the conversation take you somewhere you didn’t expect.
The framework should guide the conversation.
The customer should never feel it.