Harmful Assumptions in Sales Pipelines

Assuming trust is like assuming you locked your front door. You don’t realize your mistake until something’s missing. In sales, that “something” usually includes: – Pipeline – Expansion – Retention – Referrals – Forecast accuracy – And eventually…credibility Not because you lost a deal. But because you lost visibility. It’s not dramatic churn that kills the quarter. It’s the quiet overconfidence that goes unchallenged. The illustrious Erica Phelps broke this down in a Sales Assembly session this week. Her point was that most reps confuse friendly with committed. - Quick email replies - Enthusiastic check-ins - “Excited to renew!” energy All of it feels like progress...until procurement ghosts you, your champion leaves, or your multi-year customer signs elsewhere without a word. Overestimating trust doesn’t just sting. It costs you. According to a Walton College study, a single-unit increase in overestimated trust = - $7M in lost revenue - $1M in missed referral pipeline This isn’t about bad selling. It’s about deal delusion. Reps operating on assumptions instead of proof. Erica shared a story about a rep who managed a six-year customer. High engagement Frequent communication No red flags Then they finally got the CPO on the phone: “Oh - no one told you? We signed with someone else six months ago.” No renewal. No expansion. No recovery. Here’s how leaders can operationalize trust inspection: 1. Make validation a forecast requirement. Ask: “When’s the last time we explicitly confirmed intent with the economic buyer?” A friendly check-in doesn’t count. 2. Require multithreading on every must-win deal. Champions don’t close deals. Committees do. And if your forecast is tied to a single contact, it’s fiction. 3. Pressure-test the ‘surprise list.’ Ask your team: “If we lost this deal tomorrow, what would shock us?” If the list is long, you’re not forecasting...you’re hoping. 4. Build trust into deal inspection, not just MEDDPICC checkboxes. Train managers to probe for political risk, internal noise, competing priorities - not just surface-level qualification. Politeness is not a pipeline stage. It’s a liability if you mistake it for progress. Great reps don’t assume trust. They test it. They validate it. They stress it BEFORE the quarter does. Because the biggest threat to your number isn’t the objection you hear. It’s the silence you misread. Validate the trust. Or write off the revenue.

The Pipeline Problem: A First-Principles Look at Real GTM Solutions “We don’t have enough pipeline” remains the top GTM challenge in my conversations. My question - What are we going to do about it? Previously, I used First Principles thinking to highlight flawed pipeline assumptions. Today, I would like to share how a First Principles mindset can provide a solution to those problems. Spoiler alert - the content here represents the building blocks of a First Principles Pipeline Generation framework that I’ll be sharing soon. First Principles means stripping away inherited beliefs - “that’s the way it has always been done” - and focusing on the core truths about buyers, their pain points, and how they want to buy. Instead of more low-quality MQLs, think about creating a GTM machine that consistently produces revenue‐ready mid-stage pipeline. I would love to hear your thoughts on the five First Principles solutions below to common pipeline problems: 1) Discard Volume‐Only Thinking -Fundamental Truth: Not all leads are created equal. -Solution: Shift from raw lead volume to conversion efficiency and revenue impact. Track pipeline velocity, win rates, and ICP fit, rather than fixating on MQL count. 2) Identify True Buying Signals -Fundamental Truth: Buyers who feel urgent pain will actively seek solutions. -Solution: Replace MQL‐centric scoring with Problem‐Qualified Leads (PQLs)—prospects who exhibit strong intent signals. 3) Design Around the Buyer -Fundamental Truth: Buyers move nonlinearly, self‐educate, and engage on their schedule. -Solution: Map your pipeline stages to actual buyer actions, not just internal sales steps. Track signals like demo requests, consultation requests, or event triggers. 4) Make Pipeline a Team Sport -Fundamental Truth: Silos lead to “pipeline leakage.” -Solution: Align marketing, sales, and Revenue Operations on the same ICP, the same metrics (pipeline velocity, CAC, conversion rates, and unit economics), and continuous feedback loops. 5) Adopt a Buyer‐First Mindset -Fundamental Truth: A genuinely customer‐centric approach drives better conversion and loyalty. -Solution: Prioritize trust‐building, value‐focused content, and ongoing engagement with your ICP over quick‐hit lead generation. Thanks for reading! My question to you. Are these five First Principles “mom and apple pie” or do they form the foundation for a future GTM machine that can manufacture qualified, revenue‐ready opportunities? I’ve also included an updated version of Winning by Design’s Data Model, which helps visualize where to optimize and invest for improved pipeline performance #firstprinciples #GTMexecution #WinningbyDesign

A VP of Sales told me they had 40 qualified opportunities worth $20 million. They were lying to themselves. This wasn't intentional deception. This VP genuinely believed his pipeline was strong.  His CRM showed 40 opportunities in various stages, totaling significant revenue potential. But when we dug into what "qualified" actually meant, the picture changed dramatically. I asked him to walk me through his top 10 deals. Here's what we found: Deal 1: "Great relationship with the buyer."  Me: "Who makes the final decision?"  Him: "The buyer has to present it to their board." Deal 2: "They've asked for references."  Me: "What's their compelling reason to change?"  Him: "They want to modernize their systems." Deal 3: "We're the preferred vendor."  Me: "When did your rep last speak to someone with budget authority?"  Him: "I'd have to check." By the tenth deal, it was clear this VP had no idea what was really in his pipeline. He was tracking activities, not information. What they thought they had: 40 qualified opportunities worth $20 million. What was really there: 8 deals that could actually close that quarter, representing about $5 million. And 3 of those deals represented 70% of their target. This is the pipeline lie most companies tell themselves. They count opportunities based on stage progression rather than qualification depth. Just because someone moved from "prospect" to "qualified" in your CRM doesn't mean they're actually qualified. It might just mean your salesperson had a second conversation with them. Real qualification means you can answer specific questions: What's their compelling reason to change? Who makes the decision? What's their process? What could prevent them from moving forward? If your salespeople can't answer these questions, you don't have qualified opportunities. You have conversations. The fix isn't better pipeline management software. It's better qualification standards and the discipline to enforce them. Stop measuring how many opportunities you have. Start measuring how much you really know about each one.

6 assumptions that marketing and sales teams make that kill your pipeline (and what to do instead): In marketing, never assume: ❌ That your messaging is on point because your founder worked in the industry 10 years ago ❌ That your content consumption preferences equate to your prospect’s preferences ❌ That your prospect is ready to make a purchase Instead, do this: ✅ Complete regular interviews with both internal and external stakeholders. Bonus if you can talk to a recent lost opp. ✅ Provide multiple ways to consume the same content (video, text, social, blogs, podcasts, etc.!) ✅ Give your prospect enough information to self-educate at least 70%+ (more is better) of the way through the buying process. Read They Ask, You Answer by Marcus Sheridan. In sales, never assume: ❌ That your prospect cares about you or your company (harsh but true) ❌ That who you have on the call is the decision maker or has authority ❌ That your prospect remembers any of the info or data they gave you on previous calls Instead, do this: ✅ Give them a reason to care by earning trust. Read Pre-Suasion by Dr. Robert Cialdini. ✅ ASK who ultimately signs the deal and who you need to get bought in from the start. Make sure you understand their buying process front to back. ✅ Remind them using this structure: “you told me last meeting about XYZ pain point (bonus if you remember specific anecdotes, names of people involved, etc.), and here is how we would address that / make your life easier” What would you add to these lists? #b2bmarketing #digitalmarketing #b2bsales