Compounding Effects of Trust 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.

Most salespeople think bigger commissions = bigger deals. But after managing $1B+ in sales, I discovered a counterintuitive truth: The best salespeople rarely "sell" at all. Instead, they do trust math. The typical sales playbook says: → Handle objections → Push for closure → Follow up aggressively But I've found something different: Every interaction either builds or destroys trust. • Miss a deadline? -20 trust • Don't listen well? -15 trust • Add unexpected value? +20 trust • Do what you promise? +15 trust When trust hits zero, you lose the deal forever. When trust peaks, deals close themselves. This isn't soft stuff. It's math. Track trust like you track revenue. Build it like you build product. Protect it like you protect IP. Trust is the ultimate compounding asset.

Been thinking a lot lately about higher order thinking & the notion of trust Most people in business think in first-order consequences too much …. the immediate cause and effect. Raise prices? More revenue. Cut costs? Higher margins. Make a deal? Get paid. But business (and life) doesn’t operate in a vacuum of simple transactions. To truly build something great, I think you need to think beyond the immediate result and understand higher-order effects. First-order thinking: A short-term transactional mindset. “If I win this deal, I make money.” Second-order thinking: Looking beyond the immediate. “If we push too hard on costs, we fail to invest in our future.” Third-order thinking: Understanding compounding effects. “If we build a reputation for integrity, we attract better long-term partners.” Fourth-order thinking: Designing systems of trust. “If we operate with integrity and deliver beyond expectations, our brand becomes a magnet for the best opportunities.” The Hidden Currency: Trust The highest-order thinkers don’t optimize for a single transaction, rather I wonder if they actually optimize for trust? In my experience trust is the invisible and underrated force multiplier: Reduces friction. Increase speed. Builds resilience. Attracts the best best talent and opportunity. Most businesses undervalue trust because it doesn’t show up immediately on a P&L. But trust compounds in ways that money never can. Short-term thinkers chase deals. Long-term builders invest in trust. The choice is yours.

The Broken Windows Theory, a concept in criminology, suggests that visible signs of disorder (such as broken windows left unrepaired) encourage further vandalism and crime, ultimately leading to urban decay. The idea is that small neglects can create an environment where larger problems thrive.  Parallel in Sales & Marketing: The "Broken Pipeline" Syndrome In sales and marketing, a similar dynamic can occur when small failures or neglects compound into larger performance breakdowns. Here’s how it manifests:  1. Neglected Lead Follow-Up → Lost Opportunities     - Broken Window: Unanswered emails, ignored inquiries, or slow response times.     - Effect: Prospects lose interest, trust erodes, and competitors step in.     - Prevention: Automate follow-ups, enforce SLAs, and track response rates.   2. Poor Data Hygiene → Degraded Campaign Performance     - Broken Window: Outdated CRM entries, duplicate leads, or incorrect segmentation.     - Effect: Wasted ad spend, irrelevant messaging, and declining engagement.     - Prevention: Regular data audits and validation processes.   3. Inconsistent Branding → Erosion of Trust     - Broken Window: Mixed messaging, outdated collateral, or unprofessional visuals.     - Effect: Confusion, reduced credibility, and weaker customer loyalty.     - Prevention: Enforce brand guidelines and centralize asset management.   4. Ignoring Small Customer Complaints → Churn & Reputation Damage     - Broken Window: Unresolved support tickets or negative reviews left unaddressed.     - Effect: Public dissatisfaction spreads, leading to lost referrals and retention drops.     - Prevention: Proactive customer success outreach and rapid issue resolution.   5. Sales Team Cutting Corners → Culture of Mediocrity     - Broken Window: Skipping discovery calls, lazy prospecting, or fake pipeline entries.     - Effect: Short-term gains lead to long-term revenue leaks and team dysfunction.     - Prevention: Coach accountability and enforce process discipline.   Key Takeaway   Small failures in sales and marketing, if ignored, normalize poor performance and amplify systemic breakdowns. The fix? "Fix the broken windows early"—address minor inefficiencies, enforce standards, and maintain a culture of continuous improvement to prevent larger collapses.   

I said screw it an I broke the cold DM rule. Used to run the classic outbound playbook. That old mechanical flow. Step 1: DM. Step 2: Wait. Step 3: Pray for a “yes” or chase a “no.” It worked-kinda. But it felt cold. Robotic. Like I was running a factory, not building a business. Here’s where it broke down: - DMs were the first move. No context, no trust. - Content? Missing. Zero signals, zero warmth. - Replies = binary. Yes or no, nothing in between. - No real connection. No network effects. No trust graph. Dude... you know that feeling when your message lands with a thud? Ya... that. The real shift? Stopped leading with DMs. Started building a Trust System. Now, my flow looks like this: → Dial in positioning. Profile clear as day. Category locked. → Post weekly: CONNECT, CLARIFY, ACTIVATE. Not to “go viral”-to be remembered. → Show up in high-trust rooms. Comment. Engage. Become a name, not a pitch. → Wait for the signal: a comment, a profile view, a like. → DM only after trust exists. Contextual, human, relevant. → Suggest a call if there’s pain. Or riff if there’s a skill gap. → Book calls where trust is already loaded. → Share proof. Case studies, testimonials, screenshots. Feed the loop. The result? Conversations are warm. Calls are easy. Pipeline builds itself. Trust is built through signal consistency, not performance spikes. People don’t convert off your best post. They convert off the pattern of trust you’ve earned. You’re not building a funnel. You’re building a trust ecosystem. Are you in?