The $250K enterprise deal with DataCorp sat in my forecast for six weeks. Champion was enthusiastic, technical evaluation going well, close date pushed twice but still felt solid. Sarah, the rep, presented it in every weekly deal review with the same story: "Great conversations, moving forward, legal reviewing the contract."
Our deal reviews followed a rhythm: Sarah talked for 12 minutes updating everyone on where things stood. Her manager, Tom, asked two surface-level questions. "When do you think it'll close?" and "Anything you need from us?" Sarah said two weeks, maybe three. Tom nodded. "Sounds good. Keep me posted."
I watched this play out four times—same deal, same update pattern, same vague timeline. Something felt off, but nobody pushed deeper. The review ended. We moved to the next deal.
Two weeks later, Sarah pinged Slack at 4pm on a Friday: "DataCorp went with the competitor. They said we were too complex for their team."
I pulled the Gong recording of their final call. The decision-maker mentioned they'd tried to get budget approval three weeks ago but finance questioned the ROI. Their champion couldn't articulate the value clearly enough. The economic buyer was never actually bought in—he was just humoring the champion.
All of this was visible. We just never asked the questions that would have surfaced it.
We'd spent four hours across multiple reviews talking about a deal we never actually understood. We missed that the champion had no executive sponsorship. We missed that budget wasn't secured. We missed that the competitor was positioning on simplicity while we kept adding complexity to the pitch.
The deal review process failed because it was theater, not diagnosis. We treated reviews as status reports instead of strategic problem-solving sessions that uncover risks before they kill deals.
That loss changed how I think about deal reviews. They're not progress updates. They're collaborative investigations that test assumptions, identify blind spots, and develop winning strategies through structured inquiry.
Here's what I learned about running deal reviews that actually improve win rates instead of documenting future losses.
The Redesigned Review: TechFlow Deal Walkthrough
Three months after the DataCorp loss, I sat in on a deal review that worked completely differently.
Mike, a mid-level rep, was reviewing a $180K deal with TechFlow, a mid-market logistics company. But this time, we'd required pre-work. Mike had submitted a one-page brief 24 hours before the review: deal snapshot, MEDDIC scores, specific risks he'd identified, and one clear question: "How do I get the VP of Finance engaged when my champion says 'don't worry, I'll handle it'?"
The Zoom opened with Mike's brief already on screen in a shared Google Doc. Tom, the manager, started annotations immediately. No recap needed.
Tom: "Mike, you scored 'Economic Buyer' as yellow in your MEDDIC. Walk me through how you know the VP of Operations has budget authority for $180K."
Mike hesitated. "My champion—the Director of Operations—said his VP has discretionary budget up to $200K."
Tom typed in the doc margin: "Verify with finance direct?" Then: "What does discretionary mean in their approval process? Who signs the contract?"
Mike: "I... don't actually know."
That pause was the first crack. In the old reviews, Mike would've said "the VP has budget" and we'd have moved on. Now Tom was probing the assumption.
Sarah, a senior rep sitting in, jumped in: "Mike, I had a similar deal last quarter. 'Discretionary budget' turned out to mean 'can spend without board approval' but still needed CFO sign-off for vendor contracts. Took an extra three weeks."
Tom: "Mike, your close date is in four weeks. If there's a CFO approval step you don't know about, that's your timeline risk. Can you ask your champion directly: 'Who signs the contract and what's their approval process?'"
Mike nodded, typing the action into the doc: "Ask champion about contract signature process and approval chain."
Tom moved to the next risk: "You marked Champion Risk as green, but I'm worried. If your champion is telling you not to involve his boss, that's either overconfidence or he knows his VP won't support this. Which is it?"
Mike thought. "He's been at the company eight months. Still proving himself. Maybe he wants to own the win?"
"Or," Sarah added, "he's not sure his VP sees the problem as urgent."
The energy in the room shifted. This wasn't a status update—it was a diagnostic investigation. Tom pulled up a competitive loss from two months ago, same pattern: champion blocked executive access, deal died in procurement when economic buyer questioned need.
Tom: "Mike, what's your hypothesis test? How do you figure out if the VP actually supports this?"
Mike: "I could ask my champion to do a 15-minute business case alignment call with his VP. Frame it as 'ensuring we're positioned for quick procurement once technical validation finishes.' If champion pushes back hard, that's a signal."
Tom added to the action list: "Propose VP alignment call by EOW. If champion resists, escalate to discuss."
They spent eight more minutes on competitive positioning—TechFlow was evaluating a simpler but less powerful competitor—and technical validation risks. Every risk got a specific test or action.
The review ended after 22 minutes with a shared doc showing:
- 6 specific action items with owners and deadlines
- 3 hypotheses to test (champion strength, budget process, VP urgency)
- 2 potential derailers flagged (approval chain, competitive simplicity message)
- Next review scheduled in one week to assess progress
Mike closed with: "This was helpful. I thought I understood the deal but now I see the gaps."
Two weeks later, Mike's hypothesis test worked. The champion did push back on the VP call—signal confirmed. Mike escalated to Tom, they got creative with a "customer success preview" that included the VP, uncovered the VP's real concerns, addressed them, and closed the deal in five weeks instead of losing it in procurement.
That's the difference: preparation that eliminates status updates, structured questions that surface hidden risks, collaborative problem-solving that develops strategy, and specific actions that test assumptions before they become losses.
The Deal Review Framework
Pre-meeting prep (rep completes before review):
Deal snapshot:
- Customer name, industry, size
- Opportunity value and stage
- Timeline to close
- Competitive landscape
- Decision-makers and champions
Qualification:
- BANT/MEDDIC scores
- Pain points identified
- Economic buyer confirmed
- Decision criteria known
Current status:
- Last interaction and outcome
- Next scheduled activities
- Outstanding questions or concerns
- Confidence level (1-10) and why
What rep needs help with:
- Specific question or challenge
- Where they're stuck
- What they're unsure about
This prep ensures reviews focus on problem-solving, not information gathering.
The 30-Minute Deal Review Structure
Phase 1: Context (5 minutes)
Rep provides quick overview:
"This is [Company], $150K ACV, competitive against [Competitor X]. We're in technical evaluation stage. Champion is strong but economic buyer hasn't fully bought in. I need help with a strategy to engage the CFO who's skeptical about ROI."
Not a full recounting—just enough context for productive conversation.
Phase 2: Qualification assessment (5 minutes)
Manager asks probing questions to test deal quality:
"Walk me through how you know the economic buyer has budget." "What happens if they don't solve this problem this quarter?" "Who in the organization wants this deal to NOT happen? Why?" "What's their plan B if we don't work out?"
These questions surface risks rep might have missed.
Phase 3: Competitive positioning (5 minutes)
If competitive:
"How did [Competitor X] come into the deal?" "What are they emphasizing in their pitch?" "Where do they think they're stronger than us?" "What trap questions have you asked to expose their weaknesses?"
This ensures rep has competitive strategy, not just hope they'll win.
Phase 4: Strategy development (10 minutes)
Collaboratively solve the specific challenge rep raised.
Example:
Rep: "I need to engage the CFO but can't get on their calendar."
Manager: "Who introduced you to the champion? Can they facilitate intro to CFO?"
Rep: "Champion reports to VP of Ops, who reports to CFO."
Manager: "What if we propose a business case workshop with VP of Ops and CFO together? Frame it as 'ensuring leadership alignment on expected ROI' before moving to contract. That gives CFO reason to attend."
Rep: "That could work. I'll propose it to champion today."
Outcome: Specific action with timeline, not vague "try to get CFO involved."
Phase 5: Next steps and accountability (5 minutes)
Document commitments:
Rep commits:
- Propose business case workshop to champion by Friday
- Send ROI one-pager to VP of Ops for review
- Schedule technical validation call with IT lead
Manager commits:
- Reach out to warm contact at customer's company for intel
- Review proposal draft before rep sends
- Join CFO call if scheduled
Follow-up: Review these commitments in next check-in.
The Risk Assessment Framework
Part of deal review is identifying what could go wrong.
Risk categories to probe:
Champion risk:
"If your champion leaves the company tomorrow, does this deal die?"
If yes: Champion isn't strong enough. Need broader stakeholder support.
Budget risk:
"Do they have budget allocated, or are they planning to request it?"
If requesting budget: Deal timing is uncertain. Factor that into forecast.
Competition risk:
"What would make them choose [Competitor] over us?"
If rep doesn't know: Competitive understanding is weak. Need better discovery.
Technical risk:
"What could come up in technical evaluation that would kill the deal?"
If there's a blocker: Address it proactively now, not during procurement.
Decision-making risk:
"Who can say no to this deal? What would make them say no?"
If rep hasn't mapped all stakeholders: Blind spot exists.
Uncovering these risks early allows time to mitigate. Discovering them during procurement is too late.
Deal Review Cadence
Weekly deal reviews:
Focus on deals in active sales cycles that need strategic input.
Criteria for weekly review:
- Opportunity value >$X threshold
- Stage: Demo scheduled through negotiation
- Rep requested review or manager flagged risk
Monthly pipeline reviews:
Broader look at full pipeline health:
- Stage distribution (too much early stage? Not enough late stage?)
- Aging analysis (deals stuck too long in stages?)
- Win rate trends (improving or declining?)
- Forecast accuracy (are forecasts reliable?)
Weekly reviews are tactical (help win this deal). Monthly reviews are strategic (is our overall pipeline healthy?).
The Forecast vs. Deal Review Distinction
Deal reviews and forecast calls serve different purposes.
Forecast call:
- Goal: Predict what will close this quarter
- Focus: Commit, best case, pipeline
- Output: Revenue prediction
Deal review:
- Goal: Increase probability of winning specific deals
- Focus: Strategy, risks, next steps
- Output: Action plan
Don't conflate them. Forecast pressure makes reps sandbag in deal reviews.
Separate the calls. Deal reviews should be safe space to acknowledge risks and ask for help.
Manager's Role in Deal Reviews
Managers should coach, not interrogate.
Good manager behaviors:
Ask questions that uncover insights:
"What surprised you in the last conversation?" "If you were the prospect, what would concern you about us?" "What's the one thing that would make this deal easy to close?"
Share pattern recognition:
"I've seen deals like this before. The CFO skepticism usually means [X]. Have you considered [approach]?"
Offer tactical help:
"Want me to join your next call with the economic buyer? I can address the ROI questions directly."
Bad manager behaviors:
Interrogation instead of collaboration:
"Why haven't you closed this yet?" "Why didn't you ask about budget?"
Pressure instead of support:
"This has to close this quarter. Make it happen."
Passive observation:
"Keep me updated."
Managers who coach improve win rates. Managers who pressure create forecast gaming.
Deal Review for Different Deal Stages
Early stage (discovery/qualification):
Focus questions:
- Is this real, or tire-kicking?
- Do they have pain worth solving?
- Can we win this?
Output: Qualify in or disqualify out.
Mid-stage (evaluation/technical validation):
Focus questions:
- Who are we competing against?
- What's their decision criteria?
- Are we positioned to win?
Output: Competitive strategy and differentiation plan.
Late stage (negotiation/procurement):
Focus questions:
- What could derail this in legal/procurement?
- Are there any last-minute blockers?
- How do we accelerate close?
Output: Closing plan with clear timeline.
Different stages need different strategic conversations.
Peer Deal Reviews
Don't limit reviews to manager-rep. Peer reviews are valuable too.
Peer review format:
Rep presents deal to 2-3 peers. Peers ask:
- "How did you handle [objection]?"
- "Why did you position it that way?"
- "What would you do differently if you could start over?"
Benefits:
- Reps learn from each other's tactics
- Less pressure than manager reviews
- Builds team collaboration
- Surfaces creative strategies
Schedule monthly peer deal review sessions where reps rotate presenting and reviewing.
Documenting Deal Review Insights
Reviews only matter if insights get captured and acted on.
After each review, document:
In CRM (on opportunity record):
- Key risks identified
- Action items for rep
- Action items for manager/team
- Next review date
In team knowledge base:
If review surfaced reusable insight:
- New competitive tactic that worked
- Effective approach to common objection
- Successful stakeholder engagement strategy
This builds institutional knowledge beyond individual deals.
Measuring Deal Review Effectiveness
Metric 1: Win rate for reviewed deals vs. not reviewed
If reviewed deals don't win at higher rates, reviews aren't adding value.
Metric 2: Stage progression velocity
Do deals move through pipeline faster after reviews? They should.
Metric 3: Forecast accuracy
Are deals forecasted in reviews closing when predicted? If not, qualification is weak.
Metric 4: Rep satisfaction
Do reps find reviews helpful, or do they dread them?
If reps try to avoid reviews, they're not getting value from the process.
Common Deal Review Mistakes
Mistake 1: Reviewing too many deals
Hour-long reviews of 10 deals = 6 minutes per deal = superficial.
Fix: Review 3-5 significant deals deeply rather than 10 shallowly.
Mistake 2: No pre-work
Rep shows up unprepared, spends review recapping basics.
Fix: Require pre-meeting prep submission. No prep = no review.
Mistake 3: Manager dominates conversation
Manager tells rep what to do instead of asking questions to help rep think through strategy.
Fix: 70/30 rule—rep talks 70%, manager 30%. Manager's job is to ask better questions, not provide all answers.
Mistake 4: No follow-through
Action items from review never happen or aren't tracked.
Fix: Document commitments, follow up in next 1:1.
Mistake 5: Reviewing same deals repeatedly with no progress
Deal stuck in same stage for 6 weeks, reviewed 4 times, no advancement.
Fix: If deal hasn't progressed after 2-3 reviews, qualify out or pause.
When Reviews Go Wrong: The CloudStore Deal
Not every team embraced the new review process immediately. I watched one deal review six months into our transformation that showed exactly what happens when teams skip the fundamentals.
Jake, a senior rep, walked into the review with no pre-work submitted. "I've been slammed," he said. "Can I just give you a quick verbal update?"
His manager, Lisa, waved him on. The rest of the team was on their phones.
Jake: "CloudStore, $320K, we're in late-stage evaluation. Champion loves us. Pricing discussions are going well. Competitor is in the mix but we're preferred vendor. Should close by month-end."
Lisa: "Sounds good. Any blockers?"
Jake: "Nope, all green."
Lisa: "Great. Keep us posted."
Six minutes. No questions about qualification. No probing on competitive positioning. No discussion of procurement process. No one asked who the economic buyer was or whether budget was allocated. The shared doc sat blank—nobody took notes.
Three weeks later, Jake reported the deal slipped to next quarter. "Procurement wants more references," he said. Two weeks after that: "They're reviewing the competitor more seriously now." By week six: "Legal raised security concerns we didn't know about."
The deal never closed. Six months later, I ran a loss interview with their champion. The truth came out: their CISO had flagged security concerns in week two of their evaluation, but Jake's champion didn't want to surface it because he thought it would delay the deal. The competitor addressed the CISO's concerns proactively. We only learned about it when procurement sent the rejection email.
A proper deal review would have uncovered this in the first week. One question—"Who in the organization might want to block this deal and why?"—would have surfaced the CISO concern. We could have addressed it with two weeks of technical validation. Instead, the deal died because the review was theater, not investigation.
The difference between a winning review and a wasted meeting isn't tools or templates—it's whether the team has the courage to ask uncomfortable questions and the discipline to test assumptions before they become deal-killers.
What I Learned About Deal Reviews
After watching hundreds of deal reviews—successful ones that saved deals and superficial ones that documented future losses—the pattern is clear: deal reviews aren't about managers checking up on reps. They're strategic enablement sessions that improve win probability through systematic inquiry.
The best reviews uncover what reps can't see on their own because they're too close to the deal. They identify blind spots, test assumptions, and develop strategies that single-threaded thinking misses. They turn vague timelines into testable hypotheses and surface risks while there's still time to mitigate them.
Companies with strong deal review cultures see it in their metrics: higher win rates on reviewed deals, faster stage progression, more accurate forecasts. But more importantly, reps start requesting reviews instead of avoiding them because the process genuinely helps them close business.
For go-to-market teams looking to improve execution consistency, deal reviews become a forcing function for systematic qualification, competitive thinking, and strategic selling. The review structure becomes a competitive advantage—not because it creates more process, but because it surfaces truth before competitors do.