How to Stop Losing Winnable Deals in 2026 (Execution Framework)
- Carla Macciocu
- 2 days ago
- 15 min read
Most pipeline reviews focus on what reps say will close. Few focus on why winnable deals are dying.
The deals that hurt most are not the ones you never had a chance at. They are the ones where the buyer had budget, had pain, had urgency, and still chose a competitor or no decision.
These losses are not random. They follow patterns that show up in call recordings, follow-up emails, and CRM data. The problem is that most teams are not inspecting for them.
This article gives you a framework to identify the exact behaviors that kill winnable deals—and how to coach against them using observable evidence.
TABLE OF CONTENTS
2. Why teams keep losing deals they should close
3. The 11 execution failures that kill winnable deals
4. How leaders should review this in practice
5. Frequently asked questions
6. Decision point
WHAT A WINNABLE DEAL ACTUALLY IS (AND IS NOT)
A winnable deal is not a deal where the prospect seemed friendly. It is not a deal where they said they liked the demo. It is not a deal that has been in pipeline for four months because "they're still interested."
A winnable deal meets three criteria, all of which must be observable:
1. The problem is quantified
The buyer has stated the business impact of the problem—in time, money, or risk. If you cannot find this in your call notes or CRM, the deal was never winnable. It was a conversation.
2. The buying process is mapped
You know who else is involved, what their role is, and what happens after your champion says yes. If you only know one name, you do not have a winnable deal. You have a single point of failure.
3. The next step is mutual
The buyer agreed to a specific action with a specific date. Not "let's reconnect soon." Not "I'll check internally." A calendar invite they accepted.
If any of these three are missing, the deal is not winnable yet. It is a hypothesis.
What a winnable deal is not:
• A deal where the buyer asked for a proposal (proposals are not commitments)
• A deal where the buyer said "this looks great" (politeness is not intent)
• A deal that has been forecast three quarters in a row (that is a zombie, addressed below)
WHY TEAMS KEEP LOSING DEALS THEY SHOULD CLOSE
The standard advice for improving win rates is to "improve discovery" or "handle objections better." This advice is too vague to act on and too broad to inspect.
Here is why it fails in practice:
Teams confuse activity with qualification.
A rep books a meeting. The prospect shows up. The rep runs a demo. The deal enters pipeline. None of this proves the deal is winnable. It only proves that a meeting happened.
Managers inspect pipeline size, not pipeline quality.
Most deal reviews ask: "When will this close?" Few ask: "What did the buyer say when you asked what would happen if they did nothing?" If the rep cannot answer that question, the deal is not qualified. It is a placeholder.
Playbooks describe stages, not behaviors.
A typical playbook says: "Stage 3: Discovery complete." It does not say what discovery complete actually means. So every rep defines it differently. Some reps move deals to Stage 3 after one call. Others never move deals at all because they are unsure what qualifies.
Coaching happens after the deal is lost.
Most deal reviews are post-mortems. The rep explains what happened. The manager nods. Nothing changes. Coaching that happens after a loss is too late to save the deal and rarely specific enough to prevent the next one.
Objection handling is taught as scripted response.
Standard playbooks list objections with scripted answers: "Too expensive? Justify ROI." This teaches reps to respond instead of understand. When a buyer says "it's too expensive," that could mean five different things. A scripted response addresses none of them.
The result: teams lose deals that were winnable because no one inspected the specific behavior that killed them.
If any of this sounds familiar, you have two options:
You can audit your pipeline yourself using the framework below. Or you can get help identifying exactly where your deals are breaking.
THE 11 EXECUTION FAILURES THAT KILL WINNABLE DEALS
Each failure below includes: what the behavior looks like, what signal proves it is happening, how to fix it, and a template or example you can use immediately.
1. Discovery stays on the surface
The goal:
Uncover a problem the buyer needs to solve, not just a situation they are in.
What goes wrong:
Reps hear a fact and treat it as pain. Example: "We can't track X data point." That is a situation. If there is no stated consequence—revenue lost, time wasted, risk created—it is not a problem. It is a detail.
Observable signal:
Listen to any discovery call. If the rep does not ask a follow-up question after the buyer states a challenge, discovery is surface-level. If the CRM notes say "Prospect has problem with X" but no quantified impact, discovery failed.
How to fix it:
Require reps to document the consequence of every problem in the CRM. Not "they struggle with reporting." Instead: "Manual reporting costs 10 hours/week and delayed Q2 board deck." If consequence is blank, the deal cannot advance.
What this sounds like in a call:
Surface-level:
Buyer: "We don't have visibility into rep activity."
Rep: "Got it. Let me show you how we solve that."
Depth:
Buyer: "We don't have visibility into rep activity."
Rep: "What do you mean by visibility exactly?"
Buyer: "I have no idea if reps are actually running discovery the way we trained them, or if they're just demoing and hoping for the best. I only find out when the deal stalls and I ask what happened."
Rep: "What happens when you don't have that visibility?"
Buyer: "We miss forecast. Last quarter we were off by 40% and the board asked questions we couldn't answer."
Rep: "What did that cost you internally?"
The first question clarifies what the buyer actually means, and now you know the real issue is execution consistency, not just reporting. The second uncovers the consequence. The third quantifies the impact.
Without the clarifying question, you risk solving the wrong problem, or quantifying something the buyer never said.
2. Pain is not quantified
The goal:
Attach a number to the problem so the buyer can justify the purchase internally.
What goes wrong:
Reps accept "this is a priority" without asking what it costs. Without a number, the buyer cannot build a business case. Without a business case, deals stall or lose to "no decision."
Observable signal:
Review any deal in Stage 3 or later. Search the notes for a dollar amount, a time cost, or a risk metric. If none exist, pain is not quantified.
How to fix it:
Add a required field in the CRM: "Cost of inaction." Reps must enter a number before moving past discovery. In coaching, ask: "What did they say this problem is costing them?" If the rep guesses, the deal is not qualified.
CRM field example:
Bad Entry: "They said it's a priority"
Good Entry: "10 hrs/week manual reporting = ~$25K/year in analyst time; delayed board deck triggered audit inquiry"
If your CRM does not have this field, add it. If reps leave it blank, the deal does not advance.
3. The demo is a product tour
The goal:
Show the buyer how your product solves their specific problem.
What goes wrong:
Reps show every feature. They click through settings, configurations, dashboards the buyer did not ask about. The buyer cannot project themselves using the product because the demo is generic.
Observable signal:
Watch any recorded demo. Count how many features are shown before the rep connects a feature to a stated pain. If more than two features go by without referencing the buyer's problem, the demo is a tour.
How to fix it:
Demos must follow this structure: state the pain, show the feature that solves it, confirm it matches their need. No feature gets shown unless it ties to something the buyer said in discovery. Put this in the playbook as a checklist.
Demo structure (playbook-ready):
For each feature you plan to show:
1. Restate the pain: "You mentioned [specific problem from discovery]."
2. Show the feature: "Here's how that gets solved." (60 seconds max)
3. Confirm fit: "Does this match how you'd want to handle it?"
If you cannot complete step 1, do not show the feature. A demo is not a tour. It is proof that you listened.
4. No clear next step
The goal:
End every interaction with a specific, mutual commitment.
What goes wrong:
Reps end calls with "I'll send over some info" or "Let's reconnect next week." These are not next steps. They are open loops that give the buyer permission to disappear.
Observable signal:
Check the CRM. If the next step field says "follow up" or "check in," there is no next step. Listen to the last 30 seconds of any call. If the rep does not propose a specific date and action, the pattern is broken.
How to fix it:
Every call must end with a calendar invite sent before the call ends. Train reps to say: "I'll send a 15-minute invite for Thursday at 2pm to review the proposal with your CFO. Does that work?" If the buyer declines, that is data. If the rep does not ask, that is a gap.
Script for the last 60 seconds of any call:
"Before we wrap, I'll send a 15-minute calendar invite for [specific day and time] to [specific action: review proposal with your CFO, walk through security requirements with IT, etc.]. Does that work for you?"
If declined: "What day works better?"
If vague ("I'll check my calendar"): "I want to make sure we don't lose momentum. What's the next step on your side, and when will that happen?"
If the buyer will not commit to any next step, that is a signal. Note it in the CRM. Adjust your forecast. Do not pretend "let's talk soon" is progress.
5. Follow-ups add no value
The goal:
Re-engage the buyer with something useful, not just a reminder that you exist.
What goes wrong:
Reps send "just checking in" or "wanted to bump this to the top of your inbox." These emails get archived. They signal that the rep has nothing new to offer.
Observable signal:
Pull the last five follow-up emails a rep sent. If any of them could be described as "checking in," the pattern is present. If none of them include a new insight, relevant content, or reference to the buyer's stated pain, follow-ups are noise.
How to fix it:
Every follow-up must include one of three things: a recap of their pain (not your features), one insight they can act on, or a specific next step. Add a follow-up template to the playbook that requires these elements. Review follow-ups in coaching.
Follow-up email template (playbook-ready):
Subject: [Their pain] + next step
Quick recap from our call:
• You mentioned [specific problem] is costing [quantified impact].
• We discussed [specific solution feature] as a way to address this.
• Next step: [specific action] on [specific date].
One thing that might help as you evaluate this internally: [one relevant insight, case study link, or data point].
If the rep cannot fill in the brackets, they do not have enough information from discovery. That is a separate problem.
6. Zombie deals stay in forecast
The goal:
Remove deals that will not close so pipeline reflects reality.
What goes wrong:
Reps keep deals alive "just in case." Deals get pushed week after week with no movement. Forecast accuracy drops. Managers plan against revenue that will never arrive.
Observable signal:
Run a report: deals that have been in the same stage for more than 30 days with no logged activity. These are zombies. If more than 20% of pipeline qualifies, forecasting is fiction.
How to fix it:
Define exit criteria for every stage. Example: "If no contact in 14 days, deal moves to nurture." Enforce this automatically or in weekly reviews. Celebrate when reps kill zombies. A clean pipeline is healthier than a bloated one.
7. Objections get scripted responses
The goal:
Understand what the buyer actually means before responding.
What goes wrong:
Playbooks list objections with canned answers. "Too expensive? Justify ROI." But "too expensive" can mean five things: not budgeted, budgeted but over, competitor is cheaper, fishing for a discount, or other concerns hiding behind price. A scripted response addresses none of these.
Observable signal:
Listen to any call where the buyer raises an objection. If the rep responds immediately without asking a clarifying question, the pattern is present. If the rep says "I understand, let me explain why it's worth it," they are scripting.
How to fix it:
Replace scripted responses in the playbook with diagnostic questions. For "too expensive," train reps to ask: "Help me understand, is this outside the budget entirely, or is it a matter of the price exceeding what was allocated?" Add a column to the objection list: "Questions to ask before responding."
Objection diagnostic: "It's too expensive"
Do not respond. Ask:
• "Was this budgeted at all, or is this a new expense?"
• "Is the price higher than what was allocated, or is budget the wrong category entirely?"
• "Are you comparing this to another solution, or to the cost of doing nothing?"
• "If price weren't an issue, would you move forward—or are there other concerns?"
Only respond once you know what "too expensive" actually means. A discount offered to someone who was fishing for one costs you margin. A discount offered to someone who has a cheaper competitor might not even win the deal. Diagnosis first.
At this point, you have seen seven execution failures that kill deals.
If you are reading this and recognizing patterns in your own team, you have a choice: keep auditing on your own, or get a structured process to fix this in 9 weeks, with a live playbook your team will actually use.
8. Single-threading
The goal:
Build relationships with multiple stakeholders so the deal survives personnel changes.
What goes wrong:
Reps sell to one person. That person becomes their "champion." When the champion goes on leave, changes roles, or gets laid off, the deal dies. The rep never met anyone else.
Observable signal:
Check any deal in Stage 3 or later. Count the number of distinct contacts logged. If only one name appears, the deal is single-threaded. Ask the rep: "Who else have you spoken to?" If they cannot name two other people, the deal is at risk.
How to fix it:
Require reps to document at least three stakeholders before a deal enters late-stage pipeline. Train them to ask: "Who else cares if this doesn't move forward?" and "Who might think this isn't the right approach?" Make multi-threading a stage gate, not a suggestion.
Questions to add stakeholders (use in any call):
• "Who else is involved in this decision?"
• "Who would need to sign off before this moves forward?"
• "Who might think this isn't the right way to solve this problem?" (finds detractors)
• "If this doesn't happen, who else feels the impact?"
• "Who handles the contract and procurement process?"
Document every name. Log them in the CRM. If you only have one contact in a deal, you have a single point of failure.
9. CRM stages do not match buyer reality
The goal:
Pipeline stages should reflect where the buyer is, not where the rep hopes they are.
What goes wrong:
Stages are defined by rep activity: "Demo completed," "Proposal sent." These describe what the rep did, not what the buyer decided. A buyer can receive a proposal and still be in early evaluation. The CRM says Stage 4. Reality says Stage 2.
Observable signal:
Ask a rep to explain why a deal is in its current stage. If the answer is "because I sent the proposal," stages are rep-centric. If the answer is "because the buyer confirmed budget and is scheduling a meeting with procurement," stages are buyer-centric.
How to fix it:
Redefine stages based on buyer actions, not rep actions. Example: "Stage 3: Buyer has confirmed problem, quantified impact, and identified other stakeholders." Update the playbook. Audit existing pipeline against the new definitions.
10. Recaps do not help the buyer sell internally
The goal:
Send a short document the buyer can forward to their team.
What goes wrong:
Reps send 21-slide decks or multi-page summaries. The buyer does not read them. They definitely do not forward them. The internal sale never happens.
Observable signal:
Ask a rep to show you the last recap they sent. If it is longer than one page, it is too long. If it does not include the buyer's stated pain, your solution, and the next step, it is missing the point.
How to fix it:
Standardize recaps: one page maximum or one slide per topic. Structure: their problem, the impact, how you solve it, next step. Add a template to the playbook. Review recaps in coaching. If a buyer could not forward the recap to their CFO and have it make sense, rewrite it.
Recap structure (one page max, playbook-ready):
1. The problem (their words, not yours)
"Your team is spending 10+ hours per week on manual reporting, which delayed the Q2 board deck."
2. The impact
"You estimated this at ~$25K/year in analyst time, plus the audit inquiry it triggered."
3. The solution
"[Your product] automates the reporting workflow, reducing that time to under 1 hour/week."
4. Why now
"You mentioned the board is asking for better visibility before the Q3 review."
5. Next step
"We're scheduled to review this with your CFO on Thursday at 2pm."
If the buyer could forward this email to their boss and it would make sense without explanation, you have a good recap.
11. No exit criteria
The goal:
Define what must happen for a deal to stay in pipeline—and what removes it.
What goes wrong:
Deals linger because there are no rules for when they die. Reps keep deals alive based on hope. Managers do not challenge them because there is no shared standard.
Observable signal:
Ask: "What would have to be true for you to remove this deal from pipeline?" If the rep cannot answer, exit criteria do not exist. If the answer is "if they stop responding," that is too late. The deal already died weeks ago.
How to fix it:
Define exit criteria for each stage. Example: "Stage 2 expires after 21 days of no scheduled next step." Document these in the playbook. Review them in pipeline meetings. Make removal a normal part of hygiene, not a failure.
Exit criteria checklist (for pipeline reviews):
For each deal, ask:
• Is there a logged next step with a specific date? (If no → flag)
• Has there been any buyer-initiated activity in the last 14 days? (If no → flag)
• Is there more than one stakeholder documented? (If no → flag for single-threading)
• Is the cost of inaction field populated with a real number? (If no → flag for weak discovery)
• Has the deal been in this stage longer than the defined threshold? (If yes → review or remove)
Any deal with two or more flags should be discussed. Any deal with three or more flags is likely a zombie.
HOW LEADERS SHOULD REVIEW THIS IN PRACTICE
This section is a coaching checklist. Use it in deal reviews, call coaching, and pipeline audits.
What to listen for in calls:
• Does the rep ask a follow-up question after the buyer states a problem?
• Does the rep ask about the consequence or cost of the problem?
• Does the rep connect features to stated pains during the demo, or just click through?
• Does the rep end the call with a specific next step and a calendar invite?
• When an objection is raised, does the rep ask a clarifying question or respond immediately?
What to check in deal reviews:
• Is there a quantified cost of inaction in the CRM?
• Are there at least three stakeholders documented?
• Is the next step a specific action with a date, or a vague intention?
• How long has the deal been in the current stage?
• When was the last logged activity?
Red flags that signal risk:
• "They said they'll get back to us." (No mutual next step)
• "The champion is handling it internally." (Single-threaded, no visibility)
• "We're just waiting on budget." (No quantified pain to justify budget)
• "I sent the proposal last week." (No follow-up with value)
• "They loved the demo." (No confirmed problem solved)
What should be updated in the playbook:
• Exit criteria for each stage (with specific timeframes)
• Required fields before stage advancement (cost of inaction, stakeholder count)
• Follow-up templates that include pain recap and next step
• Objection section rewritten as diagnostic questions, not scripted responses
• Demo structure tied to stated pains, not feature list
If you do not have a playbook that includes these elements—or if your playbook exists but no one uses it—that is the problem to solve first.
The Pimp My Playbook program builds this with you in 9 weeks, using your live deals as the foundation. You finish with a documented process your team actually follows.
FREQUENTLY ASKED QUESTIONS
How do I get reps to actually use exit criteria?
Enforce them in the CRM. If a deal hits the exit threshold, it auto-moves to nurture or gets flagged for manager review. Do not rely on reps to self-police. Build the system so compliance is easier than avoidance.
How do I know if discovery is actually deep enough?
Look for consequences, not just problems. If the CRM says "they struggle with reporting," that is surface. If it says "manual reporting delayed their board deck and triggered an audit inquiry," that is depth. Train reps to ask "what happens if you don't solve this?" and document the answer.
What if the buyer refuses to give a next step?
That is information. A buyer who will not commit to a next step is telling you the deal is not a priority. Note it. Adjust your forecast. Do not pretend a vague "let's talk soon" is progress.
Should I coach these behaviors one at a time or all at once?
One at a time. Pick the failure that is most common in your current pipeline. Focus coaching on that for 2-3 weeks. Inspect for it in every deal review. Once it improves, move to the next one. This is exactly how the Pimp My Playbook program is structured—one execution gap per week, applied to live deals.
We have a playbook but no one uses it. What do we do?
A playbook that is not used is not a playbook. It is a document. The problem is usually one of three things: it is too long, it is not tied to real deals, or there is no inspection mechanism. Fix those three and usage follows. If you want help rebuilding it the right way, that is what the program is for.
DECISION POINT
You have three options:
1. Implement this yourself.
Audit your pipeline against the 11 failures. Update your playbook with the templates above. Schedule weekly coaching sessions focused on one behavior at a time.
2. Get a structured program to do it with you.
The Pimp My Playbook program builds your playbook in 9 weeks using your live deals. You finish with a documented process, a trained team, and a manager activation kit to keep it running.
3. Use a tool that enforces this automatically.
The Pimp My Playbook app connects your playbook to real calls and surfaces execution gaps before deals are lost. It turns call recordings into coaching priorities and playbook updates—without waiting for post-mortems.
If you are unsure which option fits, start with a call. We will review your current pipeline and tell you where deals are breaking.
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