Best Practices for Client Pain Point Discovery

Here's a lil secret about “check in" or cadence calls with your customers. Many of us were taught that these touchpoints are to understand how the customer is using our product, address any issues, and identify expansion opportunities. Here's the fatal flaw in that theory. Your customer hasn't woken up thinking about your product today. They're not sitting around wondering how to use more of your features. And they certainly haven't assembled a list of needs for you to solve. They have a job, with a job description and priorities they need to execute. So, at best they think of your product maybe 40% of their. At worst its 0%. So, how could we approach customer discovery in a constant fashion? 1 - Build a hypothesis on what business objectives this account is trying to achieve this quarter/year, and seek to understand what you're missing as an outsider. Find this in their latest earnings call, leadership announcements, press releases about new initiatives. Bring it to the call, and frame it as, "This is what I can observe from my research - what did I miss?" 2 - Be curious about HOW your champion currently believes they will accomplish those goals, and seek to understand HOW they formed that opinion. Example: Company's goal is to reduce customer acquisition costs by 30%. Your champion believes they need better lead scoring. They believe this because Marketing keeps sending "bad leads" to Sales. 3 - Introduce evidence that contradicts those beliefs/assumptions. Our goal isn't to tell them they're wrong. It's to introduce an insight that reveals a crack in their thinking. "We analyzed 200 companies in your industry and found the ones with the lowest CAC actually focus first on conversion rate optimization, not lead scoring." 4 - Give them a formula to calculate the implications of continuing with their current approach. This is NOT about your ROI. This is about the cost of continuing down their current path. Always tie this back to a P&L impact: increased costs, decreased revenue, or missed growth opportunities that affect the bottom line. Make it concrete, not conceptual. 5 - If you've piqued their curiosity, suggest that they collect the inputs needed to calculate the size of the problem, and bring those to the next call. Don't jump to how your solution helps yet. Just agree that you'll explore the size of the opportunity together. Customer success calls shouldn't feel like a product usage review or a veiled sales pitch. They should feel like two colleagues looking at the business landscape together, with you bringing outside perspective they can't see from within. The most valuable CS teams don't just ensure adoption—they impact their customer's P&L. When your discovery connects directly to revenue growth, cost reduction, or margin improvement, you transform from a vendor contact to a strategic advisor. What would happen if your CS team approached discovery this way?

I’ve developed a repeatable framework that consistently gets prospects to open up about pain points and acknowledge the impact. 1. “Menu of Pain” Questions: Instead of asking generic things like “What keeps you up at night?”, I list the three most common problems I solve and let the prospect choose. I’ll say: “Typically, when I speak with others in your role, they’re facing challenges like A, B, or C. Which one is most relevant for you?” By giving them a menu, I keep the conversation focused, demonstrate expertise, and make it easier for them to open up. 2. The “Magic Moment” Question: Once a problem surfaces, I’ll ask: “When was the moment you realized that was a problem?” That question always gets a story. And stories give me context, emotion, and insight into what actually triggered the pain. It’s one of the best ways I’ve found to connect tactical issues to their larger business implications. 3. Humbling Disclaimers: I’m not afraid of bold questions, but I always preface them with humility. I might say: “I know this may be a direct question, but would it be ridiculous to assume this issue needs to be fixed to hit your goals this quarter?” That disclaimer softens the delivery, makes the question palatable, and gets me honest, candid answers. I’ve found that you don’t need 20 impact questions - one or two, framed the right way, can uncover massive problems that drive urgency. 4. Transparency on Next Steps: At the end of discovery, I want transparency, not ambiguity. I’ll often say: “People usually take these calls for one of a few reasons - just researching, needing to solve something immediately, or somewhere in between. Which bucket are you in?” That way, I either secure real next steps with someone serious or I gracefully qualify out. For me, it’s better to know the truth than chase a deal that isn’t real. Stay curious.

3 Out of 4 Projects Fail Due to Misdiagnosis... here’s how to change that. The Doctor Framework: In a consulting world crowded with “solutions,” what if the secret to true client impact was a shift to diagnosis first? The Doctor Framework is designed to help senior executives-turned-consultants leverage their expertise in a solutions-based sales approach. Here’s why this method is a game-changer for creating long-term client relationships and real outcomes: 1. Diagnose the Pain 🩺 Much like a doctor would with a patient, this phase is about identifying core issues... not just symptoms. Research shows that 80% of s uccessful client interactions hinge on active listening (HubSpot, 2021). For consultants, that means asking pointed questions and focusing on what the client’s really saying... often between the lines. This phase sets the tone for trust and accurate problem-solving. 2. Verify & Prioritize 📋 Too often, consultants jump to solutions without fully verifying the core problem. In fact, 75% of misaligned projects stem from a misunderstanding in the initial discovery phase (PMI, 2022). Encourage clients to prioritize their biggest hurdles and validate the diagnosis before prescribing. This ensures they’re bought into the process, which paves the way for collaborative solutions. 3. Co-Create the Solution 🤝 People support what they help create. Rather than prescribing a one-size-fits-all answer... work with clients to co-create their roadmap, personalizing it to their needs. This consultative approach builds trust and client ownership, leading to better buy-in and outcomes. According to LinkedIn, solutions tailored with client collaboration improve client retention by 42%. 4. Start with Small Wins 🏆 Quick wins build momentum. In fact, research from McKinsey shows that starting with small but impactful projects leads to a 30% higher likelihood of client re-engagement. The goal is to: - secure initial buy-in - build credibility - set the stage for longer-term partnerships. Propose a quick-hit project to deliver immediate results, reinforcing the client’s confidence in both the process and the partnership. 5. Become the Trusted Advisor 🔗 Once the foundation is laid, follow-up and deepen the relationship. Check-in regularly, provide added value, and actively look for new opportunities to expand your impact. By positioning yourself as a long-term ally, not just a vendor, you’ll move from “consultant” to “advisor.” Statistics reveal that 90% of clients who see consistent value are more likely to refer additional business. Ready to level up your consulting approach? Implement the Doctor Framework and start creating meaningful, lasting relationships. Anything you'd add?

Assumptions can lead to costly mistakes. My first SaaS company didn't go anywhere. I thought I was so smart, but going after the wrong people + building for wrong people cost me everything. Lots of hours put in, very little output. Most marketers think they know who their ideal customer is, and they think they know them. But until you validate your assumptions, you’re operating on guesswork—and guesswork is expensive. When I launched the first version of Wynter, I targeted copywriters... after all, who cares more about copy than them? Turns out most of them did not want any messaging validation work ("I don't like people judging my work" lol) + they didn't have any money. There was no pain they felt on their end regarding messaging validation. The pain was all in-house, felt by people hiring the copywriters: will this work? What does my ICP really care about? How can we make this copy stronger? My ICP research work had been lackluster, and I paid the stupid tax (six months of wasted efforts). A strong ICP (ideal customer profile) is built on real insights—validated, actionable, and directly tied to your audience’s needs. Avoid my mistakes and continuously refine your ICP: 1. Interview your customers: Talk to recent buyers or lost deals. Learn why they chose—or didn’t choose—your solution. Focus on the specific triggers that drove their decision and the language they use to describe their needs. 2. Survey your target market: Use target market surveys to dig into pain points, priorities, and decision-making processes. If you're in B2B, Wynter will deliver responses in 48 hrs. 3. Analyze sales conversations: Dive into sales call transcripts using tools like Gong or Chorus. Spot patterns in objections, common themes, and recurring questions your prospects raise. 4. Test your messaging: Use tools like Wynter to test key website pages with a vetted audience that matches your ICP. 5. Study competitor positioning: Analyze competitors’ messaging to uncover what they emphasize and where you can stand out. For example, if their messaging focuses on efficiency, can you carve a niche around customer experience and support? 6. Audit internal data: Review internal resources—support tickets, chat logs, and retention data. Who uses you the most, who gets the most value out of you? 7. Create iterative feedback loops: Insights aren’t static. Use tools like Wynter and Gong regularly get a pulse on your ICPs changing needs and perceptions. Building a strong ICP isn’t about guessing; it’s about listening—through tools, conversations, and data. The payoff? Better targeting, clearer messaging, and avoid paying the stupid tax.