Signs Your Sales Cycle Needs Improvement

I met a sales team that tracks 27 different metrics. But none of them matter. They measure: - Calls made - Emails sent - Meetings booked - Demos delivered - Talk-to-listen ratio - Response time - Pipeline coverage But they all miss the most important number: How often prospects share your content with others. This hit me yesterday. We analyzed our last 200 deals: Won deals: Champion shared content with 5+ stakeholders Lost deals: Champion shared with fewer than 2 people It wasn't about our: - Product demos - Discovery questions - Pricing strategy - Negotiation skills It was about whether our champion could effectively sell for us. Think about your current pipeline: Do you know how many people have seen your proposal? Do you know which slides your champion shared internally? Do you know who viewed your pricing? Most sales leaders have no idea. They're optimizing metrics that don't drive decisions. Look at your CRM right now. I bet it tracks: ✅ When YOU last emailed a prospect ❌ When THEY last shared your content ✅ How many calls YOU made ❌ How many stakeholders viewed your materials ✅ When YOU sent a proposal ❌ How much time they spent reviewing it We've built dashboards to measure everything except what actually matters. The real sales metric that predicts closed deals: Internal Sharing Velocity (ISV) How quickly and widely your champion distributes your content to other stakeholders. High ISV = Deals close Low ISV = Deals stall We completely rebuilt our sales process around this insight: - Redesigned all content to be shareable, not just readable - Created spaces where champions could easily distribute information - Built analytics to measure exactly who engaged with what - Trained reps to optimize for sharing, not for responses Result? Win rates up 35%. Sales cycles shortened by 42%. Forecasting accuracy improved by 60%. Stop obsessing over your activity metrics. Start measuring how effectively your champions sell for you. If your CRM can't tell you how often your content is shared internally, you're operating in the dark. And that's why your forecasts are always wrong. Your move.

Every sales leader obsesses over the same metric: "How do we shorten our sales cycle?" 90-day cycles become 60-day cycles. 60-day cycles become 30-day cycles. Everyone celebrates the "velocity improvement." 6 months later, average deal size has dropped 40% and customer churn is through the roof. 🕺 Folks, sales velocity ain't about speed as much as its about removing friction from the buying process. Speed-obsessed teams end up creating ARTIFICIAL (read: bullshit) urgency: - Discount deadlines that train customers to wait for sales. - Pressure tactics that make buyers uncomfortable. - Rushed discovery that misses critical requirements. - Demo-heavy processes that skip proper qualification. The result is often faster cycles filled with smaller, lower-quality deals that churn faster than you can replace them. It might make sense to kinda flip this on its head and focus on doing the opposite: - Slow down discovery to understand the real problem. - Involve more stakeholders early to prevent surprises later. - Build business cases that justify larger investments. - Design onboarding that ensures customer success. In general, SMB deals average 60-90 days while ENT deals take 6+ months, but ENT deals are typically 5-50x larger in value. Also, per some fancy research from SBI, a sales approach that focused on "pushing" prospects through faster cycles actually increased sales cycle times, while approaches that "pulled" buyer context shortened cycles. This obsession with velocity creates a bunch of problems. First, you start measuring activity instead of outcomes. Reps optimize for moving deals through stages instead of moving customers toward decisions. Second, you sacrifice deal quality for cycle speed. The fastest deals are often the worst deals. So, what should you optimize for instead? Friction reduction: - How many unnecessary steps can you remove? - Where do deals stall most often, and why? - What information do buyers need to make confident decisions? - Which stakeholders need to be involved from the beginning? Here are the metrics you'd wanna look at: - ACV trends. - Customer satisfaction at 90 days. - Expansion revenue rates by cohort. - Churn rates by sales cycle length. The companies with the best "velocity" often have the longest sales cycles in their category. They build relationships that lead to bigger deals. They involve stakeholders who prevent implementation failures. They create urgency around business outcomes, not arbitrary deadlines. Some deals SHOULD take 6 months. Trying to compress a 6-month decision into 60 days is asking for trouble. Remember: a 180-day cycle that closes a $500K deal with 95% retention is infinitely better than a 60-day cycle that closes a $150K deal with 60% churn, right? Velocity isn't necessarily about how fast you close deals but it SHOULD be about how efficiently you close the right deals.

A VP just called me about a rep who's been working a "hot lead" for 6 months with zero progress. Here's how our diagnostic conversation went: Me: "Do they have confirmed budget?" VP: "Well, the rep says not exactly confirmed..." Me: "What's their timeline for making a decision?" VP: "They said maybe this year, maybe next..." Me: "What's their decision process?" VP: "Uh, I think the VP has to approve it..." Then I asked the question that exposes every fake deal: "What would have to happen for them to say no?" Complete silence. That's when I knew this "opportunity" was a complete waste of time. Here's the hard truth for sales leaders: If your reps can't answer these basic qualification questions, they're not working real opportunities. They're chasing ghosts. The signs your team has a qualification problem: → Sales cycles that drag on for months with no progress → Forecasts full of "thinks," "maybes," and "hopefullys" → Reps who can't explain why a prospect would reject them → Pipeline inflation with terrible conversion rates Real opportunities have: ✓ Identified budget and clear decision authority ✓ Timeline driven by genuine business need ✓ Defined process with known stakeholders ✓ Specific criteria that could disqualify you The best sales teams I work with qualify aggressively and early. They'd rather have a smaller pipeline of real deals than a bloated forecast of fantasies. Your reps' time is your most expensive resource. Stop letting them waste it on deals that were never real in the first place. — Sales Leaders, want to be a world class sales manager and get your team crushing quota? Go here: https://lnkd.in/ghh8VCaf

Stop Predicting Sales Outcomes. Start Identifying Fragility. Nassim Nicholas Taleb's "Antifragile" offers a powerful insight: we're terrible at predictions. Sales leaders often fall into the trap of building huge, fragile pipelines hoping to hit their targets by sheer volume. But this only leads to disappointment. Instead, let's identify fragile deals early on. Fragility is a far better predictor of lost opportunities. Key signs of a fragile deal: 1. Unclear Motivation: Your prospect doesn't HAVE to change. 2. Pricing Mismatch: They're known to be price-sensitive, but you're premium. 3. Weak Buy-In: Limited stakeholders, especially senior ones. 4. Low Client Effort: Actions don't match words. 5. Unmapped Buying Process: You have no idea what they need to decide. 6. Fuzzy Timeline: Only vague end-of-quarter guesses. 7. Multiple Competitors: Your win probability is NOT what your CRM suggests. What to do? Instead of gauging "deal health," count the red flags. The more fragilities, the higher the risk. But, importantly, these weaknesses are often fixable. Early intervention is key! Call to Action: Did I miss any warning signs? Build a better way to forecast and take control of your pipeline. Share your 'fragile deal' indicators in the comments! #sales #forecasting #pipeline #antifragile #salesleadership Follow me for more B2B Sales and Sales Leader startegies