Chapter 3:
First, Find North

Jamie’s enthusiasm about booking a quick demo sparks a deeper conversation about what truly drives every successful sales interaction: the rep’s intention. This chapter unpacks why your intention matters most — and how aligning that intention around the buyer’s real problem, real fit, and a real win changes everything.

Morning Huddle: The Quick Demo Dilemma

The Wednesday morning huddle buzzed with slightly more energy than Monday’s cautious start. The daily rhythm was beginning to feel less foreign, the structure less imposed and more like guardrails. Updates flew around the room with increasing efficiency. When it was Jamie’s turn, his enthusiasm was palpable.

“Good news!” he announced brightly, leaning forward slightly. “Locked in a big demo with Quantum Solutions for this Friday! Got the VP of Product, Michael, super interested after just one discovery call yesterday.”

Nods and quiet “nice one” comments went around the room. Gavin offered a faint smile. “Fast progress, Jamie. Impressive momentum.” He paused deliberately. “Tell me, what specific problem did Michael say he was hoping this demo would help him solve?”

Jamie blinked, the bright energy dimming slightly. “Well… he mentioned roadmap chaos… slipping schedules, team misalignment. Sounded pretty textbook for our planning module, honestly. He seemed really frustrated by it.” Jamie’s energy returned as he focused on the action taken. “So I jumped on the chance to show him how we fix exactly that, booked the demo for Friday. Seemed like the logical next step.”

Gavin nodded slowly, acknowledging the sequence. Good intent, heard pain, moved fast. Standard playbook. But was the focus on the symptom (‘chaos’) or the underlying problem? Was the solution prescribed before the diagnosis was complete? Gavin made a mental note. “Okay, good energy. Keep the momentum. Let’s focus on solid prep for that demo,” he said, keeping his feedback neutral for now, saving the deeper dive for the upcoming Friday session.

Transition: Shifting from Selling Features to Ensuring Fit

As the team scattered after the huddle, Gavin contemplated Jamie’s update. The quick demo booking wasn’t wrong, necessarily, but it highlighted the next core mindset the team needed to internalize. Too often, their primary focus felt tactical: book the meeting, hit the activity target, match keywords mentioned by the prospect to features listed on a spec sheet.

The real goal, the intention that builds trust and leads to sustainable partnerships, needed to be deeper. It had to shift from ‘What can I get?’ (a meeting, a demo, a PO) to ‘Is there a genuine, solvable problem here where we are the right fit, and pursuing it makes sense for everyone involved?’ That deeper intention changes everything – the questions asked, the pace of the deal, the willingness to walk away. It would be Friday’s focus.

Friday Training: Real Problem, Real Fit, Real Win

Friday, 3:00 PM. The team settled into the war room chairs, perhaps slightly more curious after the week’s focus on process and the structure Gavin was steadily implementing. Gavin stood by the whiteboard, displaying the core four-quadrant diagram and the DAILY HUDDLE node they’d added previously.

“Alright team,” he began, his tone focused but conversational. “Listening to calls this week, reviewing deal notes, thinking about Jamie’s Quantum demo prep – I see a pattern emerging, both in our wins and our stalls… and it all ties back to one thing: Setting your True North. That’s what today’s session is about.”

He continued, “The best conversations, the ones that build real trust and lead to successful, long-term partnerships, aren’t just about pitching our solution well. They’re grounded in a very clear intention from the start.”

He posed the question he’d been mulling since Wednesday’s huddle, opening it to the group. “When you first connect with a prospect, what’s your absolute True North? What guides your interaction above all else?”

The team offered familiar, tactical answers, similar to their initial reactions in Chapter 1: “Book the next meeting.” “Qualify them.” “Understand their needs.” “Guide them to our solution.”

“Okay,” Gavin acknowledged, validating their responses. “Those are all actions, necessary steps in the process. But what’s the underlying goal? What’s the intent behind those actions?” He leaned forward slightly. “Think about being a buyer for a moment. We’ve all been there. You can feel the difference instantly between someone pushing their own agenda – hitting their number, moving you to the next stage – and someone genuinely trying to understand if they can actually solve your problem in a meaningful way.” Nods around the room affirmed the shared experience.

“Exactly,” Gavin continued. “Our underlying intention leaks through in our questions, our tone, our focus. To build deep trust, that intention needs to be unambiguous, aligned with actually helping them succeed.” He turned to the whiteboard, picked up a marker, and drew a line branching from the coffee mug icon in the Mindset quadrant.

TRUE NORTH

“This is our framework for that intention,” Gavin stated, underlining the three core components he wrote below the header. “Before we get caught up in features or demos, we need to validate alignment across these three critical dimensions:”

→ FIND THE REAL PROBLEM

♦ What Hurts — and Why?

“First: Find the REAL PROBLEM. We have to go beyond the surface symptom, the buzzword like ‘roadmap chaos’ that Jamie heard. What truly hurts the business or the team, and why is it hurting? We need to diagnose the root cause, understand the real pain and its impact, not just react to the initial statement.”

→ FIND A REAL FIT

♦ Can We Help — In a Way That Matters?

“Second: Find a REAL FIT. Okay, let’s say we’ve accurately diagnosed the real problem. Now, can we genuinely help solve that specific problem? And critically,” he tapped the highlighted phrase he added, “can we solve it in a way that truly matters to them? Will they see and value our unique contribution? Is the fit clear, demonstrable, and differentiated in their eyes?”

→ FIND A REAL WIN

♦ Should We Do This — Together? Now?

“Third: Find a REAL WIN. Assuming there’s a real problem and we’re a real fit, should we pursue this opportunity? Is it ethical? Is it strategically sound for both of us? Is the timing right for them, given their other priorities and resources? Is this deal set up to be a genuine win for the customer and for us?”

He tapped the third question again. “If the answer to any of these isn’t a confident yes after diligent discovery, our True North framework should guide us. Sometimes the most valuable, trust-building action is acknowledging, ‘Based on what we’ve learned, it doesn’t seem like this is the right fit, or the right time, for us to work together on this specific issue.’”

He drew an arrow and added the final guiding principle, the mantra for this concept:

IF THEY DON’T HAVE A REAL PROBLEM,

YOU DON’T HAVE A REAL PROSPECT.

“Internalize this,” Gavin urged, his voice firm but encouraging. “It focuses our energy ruthlessly. If they don’t have a real problem that we are a real fit for, creating a real win for both sides… then they’re not a real prospect for us right now. Pushing forward might serve our activity metrics or fill our pipeline temporarily, but it doesn’t serve their success, and ultimately, it wastes our most valuable resource – time.”

Jamie looked thoughtful, processing the framework against his own recent experience. “So… with Quantum’s ‘roadmap chaos,’ I should have focused first on ‘What hurts and why?’ to understand the real problem driving that chaos before assuming our planning module was the obvious answer and jumping straight to the demo?”

“Exactly,” Gavin affirmed. “Your intention shifts from ‘Pitch the feature!’ to ‘Understand the pain.’ Ask questions like: ‘When you say chaotic, what does that look like day-to-day for your team?’ or ‘What’s the tangible impact of those slipping schedules you mentioned?’ Diagnose first. Earn the right to talk about solutions.”

Chris, ever practical, jumped in. “But what if they ask for the demo early? Some prospects just want to see the product.”

“Fair question,” Gavin replied. “You meet them where they are, but gently guide back to intention. Frame your response around ensuring value for them. You could say, ‘Absolutely, Michael. Happy to schedule that demo. And to make sure the 30 minutes we spend together is incredibly valuable and directly addresses what really hurts regarding that roadmap chaos, could we spend maybe 10 minutes digging into the ‘why’ behind it first? That way, I can tailor the demo precisely to your most critical issues.’ You gently guide back to diagnosis – ensuring Real Problem and Real Fit – before prescribing the solution.”

Real-World Application: Chris’s Diagnostic Shift

Gavin later reinforced this during his next one-on-one with Chris, reviewing a call recording from the Apex Industrial opportunity. On the recording, the prospect, Mark, mentioned struggling with “inefficient reporting” and immediately asked about pricing.

“Okay Chris, watching this back, what was your first instinct when Mark asked for pricing right after mentioning ‘inefficient reporting’?” Gavin asked.

Chris reviewed his notes. “Honestly? My reflex was to give him a ballpark price range and start talking about our reporting features, maybe offer a quick demo of the dashboard.”

“Standard response,” Gavin acknowledged. “Now, apply the Primary Intention framework. What needs to happen before talking price or features?”

Chris thought for a moment, mentally overlaying the framework. “Focus on Real Problem first. Ask something like… ‘Mark, appreciate you asking about price. Before we get there, help me understand – when you say inefficient reporting, what really hurts day-to-day because of that? What’s the specific impact on decisions or workload when the reporting isn’t delivering what you need?’ Dig deeper on the problem first?”

“Exactly,” Gavin confirmed. “Diagnose what hurts and why. Then assess if we have a Real Fit that addresses that specific pain in a way he’ll value. Only then, once the problem and fit are validated, does it make sense to discuss pricing or schedule a feature-focused demo. You earn the right to prescribe the solution by proving you understand the actual disease, not just the initial symptom.” Chris nodded slowly, the practical application clicking into place.

Coaching Session Reflection

The alignment exercise felt promising. Gavin logged the early wins, gaps in understanding, and action steps to reinforce direction: 

What Went Well:

• Framework structure landed well – Real Problem, Real Fit, Real Win seemed clear and logical to the team. Provided a needed layer on top of just ‘finding pain’.
• Connecting to Jamie’s situation worked – Using the Quantum demo scenario as a lead-in made the concept immediately relevant and less abstract. Saw the lightbulb go on for him.
• Buyer empathy point resonated – Contrasting being ‘sold to’ versus ‘helped’ seemed to connect universally based on nods.
• Practical application in 1:1 – Chris was able to apply the ‘Real Problem first’ thinking directly to his Apex Industrial call recording, showing the concept translates to action.
• Mantra felt sticky – “If they don’t have a real problem…” seemed to capture the essence effectively.

What Didn’t Go Well / Opportunities:

• Initial answers still tactical – The first responses to “What’s your True North?” were still very action-oriented (book meeting, qualify). Need to keep reinforcing the underlying mindset.
• Risk of “Real Win” being overlooked – This is the hardest part. Need to actively coach on assessing mutual fit, timing, ethics, and having the courage to disqualify based on this, not just problem/solution fit.
• Framing the ‘guide back’ needs practice – The script for handling early demo requests is good, but reps need to practice delivering it confidently and collaboratively, not confrontationally.
• Ensuring follow-through – Seeing Jamie change his calendar entry is positive, but need to confirm this translates into different questions being asked in the actual Quantum call.

Action Items:

• Review top deals using RP/RF/RW lens – In next week’s 1:1s, specifically ask reps to assess their top 1-2 deals against all three criteria. Probe the ‘Real Win’ factors.
• Role-play the ‘guide back to diagnosis’ scenario – Use part of the next Friday session or 1:1s to practice handling prospects who push for demos early.
• Ask about disqualifications – In huddles/pipeline reviews, specifically ask if any deals were disqualified recently based on poor fit or timing (reinforcing the Mantra).
• Check Jamie’s Quantum discovery notes – Follow up after his rescheduled call to see if the diagnostic questions changed based on the session.

Debrief: The Power of Genuine Intention

Later that week, Gavin overheard Jamie rescheduling his meeting with Quantum Solutions. The new calendar entry read: ‘Quantum – Deeper Discovery Call (Focus: Root Cause of Roadmap Chaos & Business Impact)’. Jamie murmured to himself as he typed the agenda, “Okay, need to diagnose what really hurts about that chaos first… understand the why before showing the what…”

Gavin made a quiet note. The shift was subtle but significant. Focusing on Real Problem, Real Fit, and Real Win changes the conversation. It builds trust faster. It qualifies deals more accurately. And as he’d reinforce with Chris, remembering the Mantra – If They Don’t Have a Real Problem, You Don’t Have a Real Prospect – means that integrity sometimes requires walking away if you can’t create a Real Win. That integrity builds more long-term credibility than forcing a bad fit ever could.

“Master the intention,” Gavin had coached Chris. “It’s the foundation for everything else we build.” The foundation was being laid.

✦ ✦ ✦

Gavin’s COACHING Plan: True North

Session Focus

• Introduce Primary Intention Framework: Real Problem, Real Fit, Real Win.
• Shift mindset from tactical selling (booking meetings, pitching features) to strategic alignment.
• Emphasize diagnosing the “Why” before prescribing the “What.”
• Establish the Mantra: “If They Don’t Have a Real Problem, You Don’t Have a Real Prospect.”

Talking Points

• Your underlying intention always leaks through; ensure it’s focused on their success.
• Being a buyer vs. being sold to – leverage that universal feeling.
• Real Problem: Go beyond symptoms/buzzwords. What really hurts? Why? Quantify if possible.
• Real Fit: Can we truly solve that problem in a way they value? Differentiate.
• Real Win: Is this mutually beneficial? Ethical? Right timing/resources?
• Sometimes “No” is the right answer – builds more trust than forcing a bad fit.
• Connect this directly to Discovery – Intention drives the questions you ask.

Questions to Ask the Team

• “Think about a deal you lost recently where you thought you were aligned. Which of these three elements – Real Problem, Real Fit, or Real Win – might have been weaker than you realized?”
• “How comfortable are you asking the ‘Should we do this?’ type questions to gauge mutual commitment and timing?”
• “How can focusing on ‘Real Problem’ first change how you prepare for or open your next discovery call?”
• “When might it be right to walk away, even if the prospect seems interested initially, based on this framework?”

During the Meeting

• Initial reactions to the framework – does it resonate, confuse, or feel confrontational?
• Are reps connecting this to specific deals (like Jamie did)? Encourage application.
• Note pushback or questions about handling prospects who want to skip diagnosis (like Chris’s demo question). Ensure the framing guidance is clear.
• Listen for language shift – moving from feature-talk to problem/impact focus during discussion.

Where I Might Need to Step In

• Reinforce that this isn’t about slowing down, but about increasing effectiveness and reducing wasted effort on misaligned deals.
• Provide clear examples/role-play for how to gently guide prospects back to diagnosis if they jump to solutions/demos early.
• Connect the “Real Win” element explicitly to long-term reputation and the cost of failed implementations (subtly referencing potential future topics like Advisor Integrity).
• Ensure the Mantra lands as a focusing tool, not a reason to avoid challenging discovery.

Related Chapters

• Chapter 4: Questions First. Glove Later.
• Chapter 17: Trust Over Quota
• Chapter 8: Diagnose the Pushback
• Chapter 1: The Mandate