Yesterday, I ran a mock call with a stellar inside seller. He is sharp, driven, and he pushes relentlessly. Still, I had to stop him mid-stride and reset how he thinks about discovery. That moment reminded me how often this step is taken for granted. We think we know what it is. People treat discovery as a quick box-tick before the “real” sales work begins. In reality, discovery is the first real human moment of the sale and it sets the slope of the entire deal.
If you run a non-tech business, you might be thinking, “Discovery is not one of my problems.” Stay with me. Sure, the most sophisticated version of discovery is more relevant in complex B2B technology sales, BUT the same mindset helps any entrepreneur who needs real insight before proposing value. Even in marketing planning, your discovery lens determines whether your campaigns are educated guesses or grounded in customer truth.
What discovery actually is
Discovery is the intentional, structured conversation where you, the seller, uncover the prospect’s current reality, the cost of that reality, and the risks of leaving it as is. You are not there to perform your pitch. You are there to surface pain, context, constraints, stakeholders, and desired outcomes, so any later recommendation is credible.
A helpful rule of thumb: aim for a 80:20 listening ratio. The prospect should do most of the talking. Your job is to guide, not talk for the sake of comfort.
Why it matters more than people admit
It changes who needs whom. Before discovery, it can feel like you are asking the prospect for a favour. Once real pain is on the table, the meeting is no longer a favour to you. It becomes a lifeline to them.
It prevents no-shows and “grudge meetings.” When a meeting is booked without a shared understanding of pain, attendance drops and engagement is low. When pain is clear, people show up and lean in.
It sets the constraints of the deal. Budget, authority, timeline, and scope become visible once you understand the true problem. Otherwise you pitch into fog.
Where the stakes are highest
In complex B2B tech, discovery requires more craft. You are selling into systems, processes, controls, and senior stakeholders who think in risk, cost, and outcomes. Consumer playbooks do not map neatly here. Discovery in this context needs judgment, pattern recognition, and the ability to hear what is not being said.
This is why “let the most junior person do the first call” often backfires. Seniority here means experience and subject-matter grasp, not age. The first human conversation is the moment to recognise patterns, follow weak signals, and turn vague symptoms into concrete business risk.
Discovery for appointment-setters: stop selling calendar time
If your primary job is to book meetings, discovery is still your job. Do not sell a 30-minute slot as a favour. Surface a problem in the short call, then position the meeting as the next step in solving that problem.
A simple micro-flow:
Scout to open the territory.
Probe where you find heat.
Name the pain and link it to impact.
Offer the meeting as a practical step to address what they just confirmed.
Example close:
“Given the payroll risk and the ticket backlog you described, would it help if we spend 20 minutes mapping options with your ops lead on Thursday morning, or later that afternoon?”
That is not a calendar plea. That is a next step that respects their problem.
Scouting vs probing: the practical question set
Use scouting questions to map the terrain. When you find a hotspot, switch to probing questions to uncover cost and risk. Below are sample questions you can pull straight into your next call or customer interview.
Scouting questions
These open the conversation and expose areas worth exploring.
What is breaking in your environment right now?
What is not working so well, even if it is still “working”?
Are you running into anything you are uncomfortable with?
Is management complaining about anything on this front?
Are users complaining about anything in day-to-day work?
Is there anything we could do to make things a bit easier this month?
Is there a particular bottleneck you are running into regularly?
Is there one task that creates the most rework or delays?
What is causing you personal stress in this area?
Probing questions
Use these once you sense a live issue.
Where do we bleed money because of this, even indirectly?
If this continues, what could an auditor or regulator flag?
Could this create reputational risk for the company or any directors?
If we fixed one thing this quarter, which change would move the needle most?
Who else is affected, and how do they feel it day to day?
What has already been tried, and what happened?
If nothing changes by month-end, what is the practical consequence?
Diagnosis before prescription
If a prospect opens with “We want solution X,” resist the urge to celebrate. A good doctor does not write a script because the patient asked for it. Stay in discovery until the underlying condition is clear. Then recommend with confidence.
The power dynamic you must reset
If you catch yourself thinking, “Please just give me 30 minutes,” pause. That thought is a signal that shared pain is not yet visible. Keep working the questions until both of you can name the problem and its cost. Once that is true, the meeting is not charity. It is the rational next step.
Common anti-patterns
Pitching during discovery. You feel productive, but you are closing the learning window and pushing the prospect back into avoidance.
Template-only question lists. Scripts are a starting point. Real discovery demands you adapt to the answers you hear.
Junior-only first calls by default. If the first human moment sets the slope, staff it with enough experience to recognise and pursue weak signals.
Selling the meeting instead of surfacing pain. “It is only 30 minutes” devalues the conversation. Clarify pain, then propose a next step.
A quick practice plan for teams
Set the ratio. Track talk-time for discovery calls. Aim for 80:20 in favour of the prospect.
Role-play weekly. Use the scouting and probing lists. Practice switching from surface symptoms to business risk.
Summarise and test. After five minutes, summarise what you have heard and ask, “Did I get that right?” Adjust based on their correction.
Log pain, cost, risk. After each call, capture the specific pain, the operational or financial cost, and any compliance or reputational exposure. Patterns will emerge.
Debrief no-shows. When a meeting falls through, inspect the prior discovery. Was the pain shared and specific, or was it assumed?
For entrepreneurs and marketers
Even if you are not running enterprise sales, discovery is your friend. Use these same questions in customer interviews, focus groups, and post-purchase calls. Ask less about opinions and more about lived friction. Your positioning, offers, and creative will improve because they will be grounded in real constraints and real goals.
A short dialogue to model the feel
You: “What is breaking in your environment right now?”
Prospect: “Nothing is breaking, it is just a bit slow.”
You: “Where do you feel the slowness most in a normal week?”
Prospect: “Month-end reconciliation.”
You: “If it stays this way through the quarter, what is the practical impact?”
Prospect: “Finance will keep working weekends. Also, we keep missing internal reporting deadlines.”
You: “So the cost is overtime and delayed reporting. Any compliance risk if deadlines slip again?”
Prospect: “Yes, our external auditors flagged it last year.”
Now you have pain, cost, and risk. The next step sells itself.
Final thought
Discovery is not a polite preamble to your pitch. It is the work that earns the right to recommend anything at all. Do it well and the rest of the sale gets lighter. Treat it casually and you load the deal with drag you do not need.
Make it rAIn, KG