Why Your Discovery Call Isn’t Finding Real Problems | Bite-Sized Tactics

Why Your Discovery Call Isn’t Finding Real Problems | Bite-Sized Tactics

Max Licht (Enterprise AE @ MaestroQA) breaks down his shadow-based discovery process. This technique goes beyond typical discovery calls, allowing you to witness firsthand where inefficiencies and bottlenecks are happening. 1. Identify the Painful Process - Research the customer's current workflow and tools (e.g., Excel, Salesforce) to understand the manual, time-consuming steps involved. - This reveals where inefficiencies exist, giving you a clear picture of the pain your solution can alleviate. It also helps you identify the "drag them through the glass" moments where the pain is most acute, which is critical for building urgency. 2. Set Up the Shadowing Session - Frame the shadow as a collaborative step to fully understand their process. Instead of just making claims, say something like, *“Before I make any promises, I want to fully understand your current reporting process to see where we can add the most value.”* - This approach shifts the focus from selling to problem-solving, making you a trusted partner rather than just a vendor. It also sets the stage for a more meaningful business case. 3. Conduct the Shadow - Watch the prospect use their current tools and processes. Take notes, capture screenshots, and pay attention to friction points, inefficiencies, and workarounds they rely on. - Seeing the workflow in action often reveals unspoken pain points and limitations that even the prospect might not articulate in a standard discovery call. This firsthand observation helps you tailor your pitch to the reality of their day-to-day work. 4. Use Shadows to Build a Business Case - Use the insights gathered to frame your solution as a direct response to the pain points you observed. For example, highlight how your tool eliminates specific inefficiencies, reduces manual steps, or streamlines complex reporting. - This concrete evidence makes your pitch more credible and aligns your solution directly with their business goals, increasing the likelihood of internal buy-in. 5. Follow Up Strategically - After the shadow, summarize your findings in a follow-up email or meeting, highlighting specific pain points you observed and how your solution can address them. Use this to drive urgency and move the deal forward. - This reinforces your credibility as a problem-solver and keeps the conversation anchored in real, observed issues, rather than hypothetical value propositions. 6. Use the Shadow as a Catalyst for Future Conversations - Reference specific pain points in later stages of the sales cycle, using them to frame your solution as a clear, tangible fix for their current frustrations. - This approach keeps the focus on solving their problems, reducing friction in the decision-making process and increasing the likelihood of a successful close. RESOURCES DISCUSSED: ⁠Join our weekly newsletter⁠ ⁠Things you can steal⁠ ⁠Save $50 on any 30MPC course with code “PODCAST”

Episoder(512)

Hall of Fame: Maddy Jackson

Hall of Fame: Maddy Jackson

FOUR ACTIONABLE TAKEAWAYS If you feel like you have leverage in a deal, but haven't gotten in front of the right stakeholders to progress the deal, use that as a non-negotiable to begin negotiations Sit down and write down your own "Gives" and "Gets" that you can trade with your buyer during a sales cycle Someone liking your offering does not make them an effective champion, ask questions like "Is {title} aware of these conversations?" to test them When trying to get access to power use labelling statements like "I often hear {title} likes to weigh in, is that the same for you?" PATH TO PRESIDENT’S CLUB Account Executive @ Webflow Account Executive @ SafeGraph Account Executive @ Procore Technologies RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

16 Sep 202432min

How to Ask For The Meeting and Make Sure They Show Up (Tenbound Podcast)

How to Ask For The Meeting and Make Sure They Show Up (Tenbound Podcast)

This is an except from the Tenbound podcast with David Dulany Check out the GTM podcast here: https://tenbound.com/podcasts/ Join our weekly newsletter Things you can steal

13 Sep 20248min

248 (Lead) Having Immediate Impact When Taking Over a Sales Team (Chris Nethercote, Common Room)

248 (Lead) Having Immediate Impact When Taking Over a Sales Team (Chris Nethercote, Common Room)

ACTIONABLE TAKEAWAYS Empower your reps with a clear discount menu, outlining what’s approved for negotiations. Include things like signing during the trial, committing to case studies, or G2 reviews to speed up late-stage deals. Before taking over a team or segment, review call recordings and data like sales cycle length and ACV to identify where you can have the biggest impact. Assess the spacing between sales calls and find opportunities to consolidate steps or reduce gaps to shorten the sales cycle. Introduce a structured proof of concept (POC) with three defined calls over 14 days, dictating trial activities and clear exit criteria for smoother decision-making. CHRIS' PATH TO PRESIDENTS CLUB Head of Commercial @ Common Room Vice President of Sales @ Metadata Head of Sales @ Metadata Sr. Account Executive @ Metadata RESOURCES DISCUSSED Things you can steal Join our weekly newsletter

12 Sep 202436min

247 (Sell) Ask Tough Sales Questions Without Making it Awkward (Charles Muhlbauer, AlphaSense)

247 (Sell) Ask Tough Sales Questions Without Making it Awkward (Charles Muhlbauer, AlphaSense)

ACTIONABLE TAKEAWAYS Instead of focusing on quantifying pain, ask deeper questions about the problem’s origins and previous solutions, this will naturally reveal the impact Find out if the problem is known and cared about across the company or just by one person Ask easy, non-pushy questions like “Why is that a problem?” to get the prospect to share the impact without feeling pressured Position involving decision-makers as beneficial for them, making it easier to get in front of power PATH TO PRESIDENT’S CLUB Founder @ DiscoveryCoach.io Sales Enablement Manager @ AlphaSense Lead Revenue Enablement Manager @ CB Insights Senior Sales Training Manager @ CB Insights RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

10 Sep 202440min

Hall of Fame: Miles Kane

Hall of Fame: Miles Kane

FOUR ACTIONABLE LEADERSHIP TAKEAWAYS When you are trying to clone that first rep, make sure that you don’t confuse personality with skill set. Your customers have the answers. Talk to your customers. Do not do the things that you're horrible at. Hire for the things that are not your strengths. Invest your time in enablement. You and your reps should track how you win each deal for ongoing development. PATH TO PRESIDENT’S CLUB VP, Sales @ Tenderly Founding Member, First Hires Program @ First Round Capital Director, Enterprise Sales @ Drift VP, Sales @ AltoCloud RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

9 Sep 202439min

The Future of Outbound Sales (Topline Podcast)

The Future of Outbound Sales (Topline Podcast)

This is an except from the Topline podcast with Sam, AJ, and Asad Check out their GTM podcast here: https://www.joinpavilion.com/blog/tag/topline-podcast Join our weekly newsletter Things you can steal

6 Sep 202415min

246 (Lead) Challenging Your Reps on Their Deal Risks (Chris Surdi, Ascend)

246 (Lead) Challenging Your Reps on Their Deal Risks (Chris Surdi, Ascend)

FOUR ACTIONABLE TAKEAWAYS Instead of lecturing a rep who hasn't followed expectations, ask what's preventing them from doing the task. This helps identify roadblocks or allows the rep to own up to the issue. When discussing reasons for making a change, focus on three questions: Why do anything? Why with us? Why now? The "why now" should have a specific date tied to an event. Link the urgency of change to concrete events, such as a software switch, new hire, market trends, or growth initiatives like entering a new market. Ask your reps key questions like when the economic buyer last bought something similar and who typically pays for software in their industry to ensure they understand the buyer’s decision-making process. PATH TO PRESIDENT’S CLUB Head of Sales, Retail @ Ascend Strategic Account Manager @ Ascend Strategic Accounts @ Sourcegraph Head of Enterprise Sales @ Segment Enterprise Sales Executive @ Braintree (a PayPal company) RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

5 Sep 202436min

245 (Sell) How to Outplay Competitors and Win High-Stakes Rip & Replace Deals (Jason Bay, Outbound Squad)

245 (Sell) How to Outplay Competitors and Win High-Stakes Rip & Replace Deals (Jason Bay, Outbound Squad)

FOUR ACTIONABLE LEADERSHIP TAKEAWAYS In rip-and-replace deals, start by asking why the existing solution was chosen to understand the problems and motivations behind it. Late in the deal, confirm with your champion if you’re their top choice. Use their guidance to strengthen your position against competitors. When prospects compare you to competitors, suggest specific aspects to evaluate that highlight your strengths and expose competitors' weaknesses. In rip-and-replace deals, emphasize key product gaps that significantly impact the business, and ensure decision-makers are committed to addressing them. PATH TO PRESIDENT’S CLUB Founder & CEO @ Outbound Squad Owner @ Jason Bay Consulting Director of Marketing @ Chamber DS, Inc. Marketing Director & Corporate Sales Trainer @ National Services Group, Inc. RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

3 Sep 202440min

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