How should teams review deals in order to learn from losses?

Steve Goldberg · Dec 13, 2023

Deal reviews should change by stage of the quarter — early on the goal is discovering what you don't know (power, problem, value prop, MEDDPIC gaps), and by mid-quarter you must have agreed mutual action plans that are tracked continuously

Running this process every quarter produces more consistent closing throughout the quarter rather than everything landing at the end

12:47 20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft

Ben Fiechtner · Aug 2, 2024

Week one of the quarter should start with slip deal reviews because slipped deals are the easiest path to commit

Those are deals that were supposed to happen already, so reviewing them is homework on where the number can be shored up rather than beating people up

16:21 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Ben Fiechtner · Aug 2, 2024

In week one a leader should be realistic and only require the forecast number to tie out to commit deals, rather than pushing hard for upside

It's still early, QBRs haven't happened, and in most organizations he's worked in reps don't even have the commit deals to back into the penciled number

Scope: you still ideally want a reverse waterfall where deal walk-up exceeds commit and pipeline exceeds best case; applies to week one specifically

17:36 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Ben Fiechtner · Aug 2, 2024

Even though renewal risk review is only about 5% of the forecast call, spotting an at-risk top-10 renewal in week one and swarming it immediately is far better than dealing with it ninety days later

A new quarter gives you time to launch a sprint call or deal review while the outcome can still be changed

19:27 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Jeanne DeWitt Grosser · Mar 9, 2022

Teams should run deal pre-mortems mid-cycle — deliberately tearing a live deal down to surface all the ways it could be lost — not just loss reviews after the fact

An intellectually honest teardown before the loss lets you proactively shore up weaknesses and rebuild the deal stronger

26:03 20 Sales: The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go Wrong | How To Identify 10x Sales Hires and How To Structure the Hiring Process in Sales with Jeanne DeWitt Grosser, Head of Americas Revenue & Growth @ St

Mark Goldberger · Apr 19, 2023

The way to see around corners in a deal is to run toward the danger — deliberately enumerate every way you could lose the deal.

Listing the loss scenarios gives you a map of what to overcome; worst case you prepare for objections that never come, best case you're ready when they do.

15:03 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp

Kevin Egan · Jul 12, 2023

The best sales leaders run deal reviews focused on why the deal won't happen rather than why it will, using a framework like MEDDIC or MEDDPICC

The manager's job is to see around the corner and find weaknesses in the deal plan so the team can cover the gaps

29:59 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Lori Jimenez · Aug 2, 2023

A deal review should not be story time — its whole point is identifying where the gaps are and what resources and support are needed to accelerate the deal.

Narrating who you met and what they said doesn't answer who is making the decision or where you are in the process.

42:51 20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

Carles Reina · Feb 14, 2026

Every pipeline review should end with 'what are your blockers and how can I help', and those blockers should be aggregated by region and published across the whole organization

It shows the company how much more revenue could be made if blockers were solved and gives everyone visibility into where each region stands

27:53 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Julian Teixeira · Mar 7, 2025

Small teams should have everyone in the pipeline review, but as you scale you should run a tiered cadence where AEs self-inspect, report to frontline leaders, and summaries roll up to the exec team

Involving the whole team drives accountability at small scale; at larger scale the cadence with frontline inspection and probing questions preserves hygiene

Scope: varies with company size

34:20 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Carles Reina · Feb 14, 2026

A sales team never becomes too large for pipeline/best-practice forums — you subdivide by region and keep running them

You simply run multiple meetings (UKI, Nordics, Southern Europe, Western Europe) rather than dropping the ritual

40:15 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Matt Plank · Dec 20, 2024

Deal reviews are only useful if the manager pokes holes in the rep's account of the deal; simply accepting the rep's next steps and moving on is worthless

Salespeople are optimistic by nature, hear what they want to be true, and often don't ask the second- and third-layer questions to verify it

Scope: requires a relationship where the rep doesn't feel friction from being challenged

34:25 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank

Julian Teixeira · Mar 7, 2025

The layered roll-up is necessary rather than bureaucratic: at scale direct AE-by-AE reviews would take eight hours, and you cannot simply trust AEs to self-report their pipeline

There are too many moving parts and too much emotion in selling — a rep can convince themselves a deal will close on a feeling, so having someone keep them honest is mission critical

35:28 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Steve Goldberg · Dec 13, 2023

A deal review is bad when people aren't being honest

14:37 20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft

Steve Goldberg · Dec 13, 2023

The first line manager is the most important part of any sales process, and leaders should run deal reviews separately with sellers and with first line managers and triangulate the two accounts

First line managers hold the weekly and daily one-on-ones, so they're the ones positioned to detect dishonesty; running parallel reviews surfaces the gaps

14:40 20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft

John McMahon · Nov 28, 2025

Win/loss reports are close to worthless because reps don't really know why they won and certainly don't know why they lost

There's nothing to learn from documentation authored by people who misdiagnose their own outcomes

36:33 Win loss reports are worthless reps misdiagnose

John McMahon · Nov 28, 2025

The fastest way to diagnose a sales organisation is to sit in a forecast QBR, and most such reviews are performances of authority rather than genuine coaching

CROs and first- or second-line managers are often more impressed with their position of power than with coaching; they rush through questions for the audience, when in fact one rep's mistake is shared by a hundred others in the room

55:36 Reviews are coaching moments not authority displays

Lauren Schwartz · Oct 19, 2022

Storytelling rituals — deal reviews, fireside chats, postmortems — should be treated as a data collection mechanism and a way to move the product roadmap, not just internal comms.

They spread the customer experience both to other departments and to other sellers, on top of programmatic capture in the CRM.

9:22 Storytelling rituals function as data collection and roadmap drivers not just comms

Lauren Schwartz · Oct 19, 2022

Specific deal reviews should be run weekly, led by the AE rather than the manager, with the full cross-functional selling team present

Frequency keeps constant progress in slow enterprise cycles, and bringing all perspectives uncovers gaps the team can close together

30:30 Ae led weekly deal reviews with full cross functional team

Doug Adamic · Sep 8, 2023

Deal reviews should be aggregated by frontline managers per segment and interrogate the customer's challenges, constituent coverage, data received and the path to a decision — including a fast no

Nobody wants to be in perpetual processes; the review's job is to find where information is missing so both parties can decide to partner or cut bait

36:11 Reviews drive to a decision including a fast no

Frank Fillmann · Mar 22, 2023

Deal reviews should require a 'why' slide that reasons from the customer executive's long-range priorities and the quantified value of solving them, with the technology appearing only at the end

It forces the rep to think through the client's problem through the customer's lens rather than the product's lens, and for public companies the material is available in the 10-K

36:54 Deal reviews must open with a why slide reasoning from customer priorities not technology

Matt Plank · Dec 20, 2024

Pipeline reviews should be run manager-to-rep in a one-on-one setting rather than across a whole segment

You can't sit around a 40-person segment and do deal reviews — it isn't time effective

35:39 One on one reviews not group segment reviews

Carlos Delatorre · Jan 24, 2025

When a deal slips, the leader's job is to extract the learning; the answer to why must be something the team failed to do or did that they shouldn't have, and failing to analyze it squanders the pain.

Pain is a great teacher, so not extracting the lesson wastes the opportunity to improve.

51:17 Root cause must be something the team controlled

Kevin Egan · Jul 12, 2023

When a deal 'slips to next quarter', the key question is whether it was formally committed or merely being pursued — these are very different situations, and a committed deal that misses warrants a full deal review to determine whether the problem is pricing/product or sales execution

You need to distinguish forecasting failure from opportunistic pull-forward to diagnose the real problem

30:58 Distinguish committed slips from opportunistic pursuit

Kyle Norton · May 30, 2025

Pipeline reviews and deal reviews are unnecessary in SMB sales

The business is programmatic — top-of-funnel from marketing, BDR projections, butts in seats, ramp and average attainment let you compute the landing number from dashboards, so bottoms-up per-deal confidence checks make no sense

39:42 Smb programmatic forecasting makes deal level pipeline reviews unnecessary

Jeanne DeWitt Grosser · Mar 9, 2022

Loss reviews should include product and customer success as well as sales, because losses resolve into three buckets — go-to-market/messaging problems, operational deal-velocity roadblocks, and product gaps

The findings need to influence both the product roadmap and go-to-market changes, so those owners must be in the room

27:17 Cross functional loss reviews

Mark Goldberger · Apr 19, 2023

You should run a deal review for any deal material to hitting your quarterly or annual goal, which means far more deal reviews than most teams anticipate

Without digging into deal dynamics, stakeholders and org mapping, a committed deal can slip or close lost, which is painful for everyone

41:04 Review every deal material to the number

Rich Liu · Jun 7, 2023

Deal reviews create the most value on mid-stage deals that need to move from 10–25% to 51–90%, not on the deals already slated to close this quarter

Late-stage deals just need close plan, EB access and validation checks, whereas the mid-stage cohort is where the review actually changes the outcome

37:47 Focus reviews on mid stage deals

Rich Liu · Jun 7, 2023

A deal review should include the rep, the frontline manager and an executive (VP Sales, SVP Sales or the CRO)

39:01 Rep manager and executive in the room