Coach Customers: How to Dig Deeper

Most salespeople talk too much about their solution. Customers expect it. You expect it. Everyone's waiting for the pitch.

But here's what happens when you use coaching skills instead. Customers discover outcomes they didn't know they needed. They say what success looks like in their own words. They volunteer stakeholders you'd never have found. And they thank you for the conversation.

The core skill that makes this possible: exploring implications. Take the most significant element from their response and dig deeper with your next question. By the third or fourth question, you're in territory neither of you has explored. That's where breakthrough clarity emerges.

This isn't about being a coach. It's about using coaching techniques as tools to help customers understand what success means to them.

Conventional Selling: You ask your prepared discovery questions. What challenges? What budget? When decide? You gather information to pitch your solution. You show your expertise. Success means they agree to your proposal.

Sales Reset Selling: You ask about the outcomes they’re seeking to achieve. Clarify their most important themes and explore them in greater depth. Dig through three or four levels until you're exploring new territory together. You help them discover what they need. Success means they can describe their outcomes clearly, captured by your AI note-taker in their own words.

The shift: from gathering facts to creating clarity. From showing expertise to helping with discovery.

Step 1: Ask About Outcomes, Not Problems

Start with: "What would success look like for you?" Not challenges. Not pain points. Success.

Listen to their entire response. Don't interrupt. Don't jump to solutions.

Step 2: Pick the Most Significant Element

Choose the one word or phrase that matters most in what they said. Often, it's the outcome they mentioned. Sometimes it's a constraint. Sometimes it's who they mentioned.

Trust your instinct. What felt most important?

Step 3: Dig Deeper

Make that element your next question. "Tell me more about [that element]." Or "What would [that element] enable?"

Listen to their complete response again.

Step 4: Dig Deeper Again

Take the most significant element from their second response. Make it your third question.

By now, you're deeper than normal discovery ever goes.

Step 5: Dig Deeper Once More

The fourth question is often where magic happens. You're often in territory neither of you expected. New insights emerge. Hidden stakeholders surface. Outcomes get clearer.

Example:

Four questions. Explored implications. Discovered what mattered.

The Opening Question Set:

The Exploring Implications Phrases:

The AI Note-Taker: Use Teams, Zoom, Gong, Fathom, or another AI tool to record conversations. AI captures everything in their words. You can be fully present, not taking notes.

Review transcripts after calls. See where you explored well. Spot where you jumped to solutions too fast.

The Practice Framework: Daily 10-minute AI role-play. Ask AI to play a customer. Practice exploring implications. Get AI feedback on your questioning quality.

Minimum Standard: Three levels of digging deeper per conversation. You ask about outcomes. Customer responds. You explore once. Explore twice. Explore three times.

Good Standard: Four levels consistently. You're in new territory. Customer is discovering insights. You're capturing stakeholder names and outcome details.

Excellence: Exploring implications becomes natural. You sense which element matters most. Customers say, "I hadn't thought about it that way." New stakeholders emerge. Outcomes get specific and measurable.

Progressive Development:

Like learning to see gaps on a football, rugby or hockey pitch. At first, you think about it. Eventually, you just see them.

Your Manager Will See: Call recordings that show the depth of questions. Transcript analysis showing exploration patterns. More stakeholders per deal. Proposals with customer-defined outcomes. AI scores showing outcome clarity improvement.

Customer Feedback Signals: "You asked questions we hadn't considered." "This conversation helped us think." "Can you help us discuss this with our other stakeholders?" "You're different from other salespeople we've met."

Measurable Indicators: Number of stakeholders engaged (should grow from 2-3 to 4-6+). Proposals containing specific success criteria. Win rates on qualified deals. Depth of exploration (average 4+ levels).

Documentation Requirements: AI transcript of every customer conversation. Key outcomes captured. Stakeholder names noted. Success criteria documented in customer's words.

Pick one customer conversation this week. Use the exploring implications approach.

Ask: "What would success look like?" Listen completely. Take their most significant element. Ask: "Tell me more about that."

Do it three times. Reach the fourth level if possible.

After the call, review the AI transcript. Where did you explore well? Where did you jump to solutions? What did you learn about digging deeper?

You as Seller:

Your conversations become more interesting. Customers open up in ways they don't with other salespeople. You discover deals you'd never have found. Your pipeline gets stronger through better qualification.

You learn faster than competitors still pitching. Exploring implications reveals patterns across customers. You spot opportunities they miss. This advantage builds over time.

You stand out. Customers remember you. They bring you in earlier. They volunteer information. Your personal brand becomes "the person who helps us think."

Your Customers:

They discover clarity they didn't have before. Exploring implications helps them say what outcomes they'd struggled to define. They see connections between stakeholders they'd missed.

Multiple stakeholders get heard. Digging deeper naturally surfaces more people who care about outcomes. Everyone's priorities are explored, not just those of the first person you meet.

They make better decisions. When outcomes are clear, they choose solutions that actually fit their unique needs. Implementation succeeds because expectations were properly set. They achieve what they hoped for.

Your Sales Manager:

Pipeline quality improves dramatically. Deals have clearer outcomes. Forecasts become more accurate. Win rates increase on qualified opportunities.

CRM captures meaningful information. Instead of generic notes, there are specific details about outcomes. Instead of vague next steps, there are stakeholder engagement plans.

Team learns faster. When managers review explored conversations, they spot coaching opportunities. Call recordings reveal exactly where sellers require improvement. Improvement becomes systematic, not guesswork.

Senior Leaders:

Revenue becomes more predictable. Exploring implications improves qualification. Bad-fit deals get identified early. Resources focus on winnable opportunities.

Customer success rates improve. When Sales uses coaching skills to define clear outcomes before the contract, Operations knows what to deliver. Finance can measure value. Legal has enforceable success criteria.

Competitive advantage grows. While competitors pitch faster, you learn more. Customer insight builds up. Market position strengthens. This isn't small gains, it's exponential over time.

Your Colleagues:

Operations get precise deliverability requirements. Exploring implications surfaces implementation details early. No more overpromising. Cross-functional teams can plan properly.

Customer Success knows the exact success criteria. Handoffs become smooth. Everyone works from the same outcome definition. Internal conflict disappears.

Finance and Legal get measurable criteria. Digging deeper defines specific outcomes. Contracts become clearer. Risk allocation improves. Renewal decisions have an evidence base.

Most salespeople ask discovery questions, then pitch solutions. Sales Reset teaches exploring implications: take the most significant element from a customer's response and dig deeper with your next question. By the fourth question, you're in territory neither of you expected.

This isn't about gathering information for your own use. It's about helping customers discover clarity they didn't know they needed. "What would success look like?" leads to efficiency needs, which in turn lead to capacity constraints, ultimately driving board-level transformation initiatives worth 10 times your original deal.

The breakthrough enabler: AI note-takers capture everything in customers' words. For decades, the barrier was documentation. Salespeople had great conversations but couldn't capture them properly. AI solves this completely. You can be fully present, digging deeper, while AI records it all.

Exploring implications accelerates sales cycles through better qualification. It improves pipelines through clearer outcomes. It creates a competitive learning advantage as you spot patterns competitors miss. And customers thank you for conversations that helped them think, not just gave them quotes.

This is a 12-18-month capability journey. Like learning to see gaps on a rugby pitch, exploring implications becomes instinctive through deliberate practice.

Are you curious whether your organisation is ready for outcome-accountable selling?

Our 90-minute Vision Workshop explores what's possible when coaching skills replace normal pitching. Valuable whether you proceed or not. Five acts, genuinely interesting, might be uncomfortable.

Choose Values & Mindsets - Exploring implications requires the right mindset shift first. Read this before practising the questioning approach.

Engage Stakeholders - Digging deeper naturally surfaces more stakeholders. Learn how to work with multiple voices effectively.

Co-Create Proposals - Exploring implications captures outcomes in customer words. Learn how AI turns those transcripts into strong proposals.