Fancy Discovery Questions Don’t Work (Ask These Qs Instead) | Keenan | Ep. 291 (Sell)

Join the 30MPC Discovery Course waitlist TODAY and get first dibs + $25 off your first TWO months of Club Pass: https://clubpass.30mpc.com/discovery-course. ACTIONABLE TAKEAWAYS: Use Humbling Disclaimers: Preface tough questions with softening statements like, “I’m not quite sure how to ask this,” or “This might feel direct.” It lowers defensiveness and makes hard questions land better. Dig Into Prospect Rumblings: Prospects often hint at problems rather than state them outright. Listen for vague concerns and use a humbling disclaimer to drill deeper into the real issue. Refine Bucket Questions: Instead of stating, “Every CRO faces these three problems,” add nuance: “Many CROs I speak with mention challenges like…” This avoids defensiveness and keeps the conversation open. Follow a Clear Flow: Get permission to ask questions, surface problems without assumptions, prompt for real examples, then use humbling disclaimers to quantify impact without making prospects uncomfortable. CHARLES' PATH TO PRESIDENTS CLUB Founder @ DiscoveryCoach.io Sales Enablement Manager @ AlphaSense Lead Revenue Enablement Manager @ CB Insights Senior Sales Training Manager @ CB Insights RESOURCES DISCUSSED Discovery Course Join our weekly newsletter Things you can steal

There is an extreme over-rotation in sales on setting next steps. Setting next steps is NOT always a good thing. 🛑 Bad: Never setting next steps 🟡 Okay: Setting steps on every deal 🟢 Good: Setting steps on REAL deals Instead, first determine if the deal is worth setting next steps with at all. Then, you should recommend the appropriate next step, but only if your prospects have proven that it's worth keeping them in your pipeline. That's where the Five Minute Drill comes in: Three questions you can ask at the end of every single call to determine if and how you set a next step. 𝐐𝐮𝐞𝐬𝐭𝐢𝐨𝐧 1: 𝐃𝐨 𝐘𝐨𝐮 𝐖𝐚𝐧𝐧𝐚 𝐁𝐮𝐲? If you can practice ONE THING, it's this. Any time you offer a demo, a pilot, a proposal, you are giving your time away to a prospect. And that's fine. But only if you get something in return. If you're investing more time with them, you should expect that they won't waste it and affirm that this is actually leading somewhere. 𝐐𝐮𝐞𝐬𝐭𝐢𝐨𝐧 2: 𝐖𝐡𝐞𝐧 𝐝𝐨 𝐲𝐨𝐮 𝐰𝐚𝐧𝐧𝐚 𝐛𝐮𝐲? You can't properly suggest a next step until you understand their timeline to solve the problem we just agreed upon. If they want to solve this problem in 3 weeks, we'll use their answer to drive far more urgency than if this weren't a problem to solve for 6 months. 𝐐𝐮𝐞𝐬𝐭𝐢𝐨𝐧 3: 𝐇𝐨𝐰 𝐝𝐨 𝐲𝐨𝐮 𝐰𝐚𝐧𝐧𝐚 𝐛𝐮𝐲. Guess what, the last question isn't a question. You should always suggest and confirm next steps because you've sold your software far more times than they've bought it. Frame your ask in terms of their best interest, not yours. Based on what you learned in the first two questions: what is the next step you need to take to solve their problem by the time they want it solved? And don't just suggest one next step, suggest next-next steps so they explicitly buy into a sales process, not a free 60 minute demo. Full breakdown of the 5 minute drill: https://www.30mpc.com/newsletter/how-to-set-next-steps-in-sales-with-the-5-minute-drill Join our weekly newsletter: https://hubs.li/Q02NJQ8p0 Things you can steal: https://linktr.ee/30mpc_youtube #30Minutestopresidentsclub #30mpc

ACTIONABLE TAKEAWAYS: No Last-Minute Coaching: Avoid changing a rep’s game plan in the 30 minutes before a call. It signals distrust and forces them to scramble, leading to a worse outcome. Stick to One Coaching Theme: Don’t introduce a new area of improvement after every call. Focus feedback on a consistent theme to drive real progress. Align on Call Emotion: Before a discovery call, ask your rep how they want the prospect to feel. This sets the right tone and helps shape their delivery. Know Your Role in Calls: As a manager, decide if you’re leading, coaching, or just reading the room. Adapt based on the rep’s experience level and the call type. ALEX'S PATH TO PRESIDENT'S CLUB: Founder & CEO @ Alluviance Director of Sales Commercial @ Outreach Director of Sales Corporate @ Outreach Territory Account Executive @ Microsoft RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

Join the 30MPC Discovery Course waitlist TODAY and get first dibs + $25 off your first TWO months of Club Pass: https://clubpass.30mpc.com/discovery-course. ACTIONABLE TAKEAWAYS: Deflect Product Questions Early: When a prospect asks about your product upfront, redirect by asking what’s happening in their business that made them look in the first place. Avoid the trap of leading with features. Reduce Technical Objections: If a prospect fixates on a small technical blocker, refocus on the bigger business problem. Aligning on major pain points can make minor technical concerns less of a deal-breaker. Dig Beyond Surface Problems: Low win rates aren’t the real problem. The true impact is missing revenue targets, losing reps, or struggling to hit quota. Always tie issues to business consequences. Identify the Root Cause Before Solving: Before proposing solutions, confirm the real problem, its impact, and the root cause. Then present your solution in a way that connects all three. KEENAN'S PATH TO PRESIDENTS CLUB: CEO @ A Sales Growth Company Author of Gap Selling VP of Sales @ 2Wire VP of Sales @ Avaya RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Provide Hypotheses, Not Generic Questions: Instead of broad questions, offer informed hypotheses to invite deeper discussion. Ask Questions to Guide Next Steps: Use questions to guide the process without being pushy, keeping the prospect engaged. Teach Process Over Just Problems: Beyond identifying issues, recommend processes (like a custom demo over a POC) to build trust. Uncover Intent Behind Extra Steps: When extra steps are requested, ask what they aim to learn to suggest simpler options. DAN'S PATH TO PRESIDENTS CLUB: Senior Vice President of Global Sales @ Challenger VP of Sales, Account Management @ Challenger VP of Sales, Major Accounts @ Challenger Managing Vice President, Sales & Community @ Evanta RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

PLAYBOOK TAKEAWAYS: Aim for 70% attainment and 70% participation to create a winning culture. Avoid feast-or-famine environments where only a few reps succeed. Use historical data to set quotas based on pipeline, win rates, and deal size. Every quota increase must be backed by an investment in pipeline, win rates, or deal size. Revisit quotas once per year, unless there’s a massive skew in attainment. Communicate quota changes with transparency and clear justification. Avoid high attainment with low participation, which creates resentment and turnover. Quota planning should be a business decision, not just a sales decision. Keep top reps busy before adding more headcount to avoid diluting pipeline. Simple, fair comp plans drive engagement and motivation. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS Create a Not-To-Do List: Identify low-value tasks to eliminate instead of just adding more effort. Free up time for strategic activities like prospecting and closing. Prioritize RGAs: Focus only on activities that create new pipeline or advance existing deals. Everything else is a distraction. Enterprise Deal Timeline: Q1 is for building a POV and landing initial meetings. Q2 is for discovery and securing an executive sponsor. Q3 is for proposal, negotiation, and procurement. Q4 is for closing. Rule of 100 for Enterprise Outreach: Target the top 20% of accounts with high potential. Reach out to 10 executives with at least 10 touches each—totaling 100 strategic touchpoints per account. PATH TO PRESIDENT’S CLUB Founder of Ian Koniak sales training/consulting Strategic Account Director @ Salesforce.com Director of Sales @ Ricoh RESOURCES DISCUSSED Join our weekly newsletter Things you can steal Ian’s free training

ACTIONABLE TAKEAWAYS: Segmented Team Structure: Down-market teams focus on landing new logos, passing them to expand teams, while up-market AEs handle both acquisition and expansion with retention-based comp. Enterprise Sales Strategies: Use top-down (sell wall-to-wall) or land-and-expand approaches, with the latter yielding higher LTV by scaling through business units first. Deal Inspection Triggers: Monitor $50K deals at stage 3 for POCs and access to power, and stage 5 for mutual action plans and the paper process. Consistent Review Rhythm: Reps update pipelines Monday, managers review Tuesday, deal reviews happen Wednesday, and Eleanor finalizes calls Thursday. ELEANOR'S PATH TO PRESIDENTS CLUB: Head of Sales @ Retool Global Head of Commercial Retention & Regional Director of Commercial Sales @ Segment Global Head of Commercial Renewals and Retention @ Segment Head of Customer Success and Solutions engineering @ Clever Inc RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal 

ACTIONABLE TAKEAWAYS: Understand Rep Motivation: Identify what drives each rep—money, career growth, or exploration—then get their permission to push them toward that goal, laying the foundation for future coaching. Call Out the Situation First: Before changing a rep’s behavior, acknowledge the dynamic at play so both parties are aligned. This prevents resistance and confusion. Leverage Top Performers: Coach high performers by challenging them to reach the next level and putting them in the spotlight to lead trainings, reinforcing best practices for the team. Coach in Buckets: Break down calls into sections and ensure reps get the fundamentals right before refining their style, making feedback more structured and actionable. ALEX'S PATH TO PRESIDENT'S CLUB: Founder & CEO @ Alluviance Director of Sales Commercial @ Outreach Director of Sales Corporate @ Outreach Territory Account Executive @ Microsoft RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS Understand the VEX Scale: Classify prospects as Vetted (using a competitor), Educated (familiar but undecided), Cold (new to the space), or Self-Service. Tailor your approach accordingly. Ask About Their Journey: Send an email upfront asking where they are in their learning process. This helps you position the conversation at the right level. Skip Basic Discovery for Vetted Prospects: If they already use a competitor, focus on their current solution’s gaps and ideal outcomes instead of re-explaining the category. Avoid Restarting Discovery: When new stakeholders join later calls, recap prior findings first, then ask how those problems impact their specific role. JAKE'S PATH TO PRESIDENT’S CLUB CEO @ Skaled Consulting VP Sales @ Nowait, Inc. (acquired by Yelp) Head of Sales & Customer Success @ Chartbeat Vice President of Sales, Success, and Sales Operations @ Glassdoor RESOURCES DISCUSSED Join our weekly newsletter Things you can steal