Which lost deals should be treated as acceptable rather than as failures?

Doug Adamic · Sep 8, 2023

The only inexcusable reason to lose a deal is being surprised — a properly run campaign should surface every stakeholder and competing initiative in advance

If you're good at your profession the reason for the loss should be evident before the end; surprises mean the campaign wasn't run as required

Scope: accepts you don't win them all

38:01 20Sales: Why Everyone is Responsible for Demand Generation, How to do Great Sales Discovery, How to Reduce Sales Cycles and Create Urgency and Deal Reviews; Good and Bad Reasons to Lose a Deal with Doug Adamic, CRO @ Brex

Doug Adamic · Sep 8, 2023

Not knowing the financial position and funding pattern of the organization you're selling to is inexcusable, and if a funding wobble kills the deal it means the value proposition was too weak or the coverage too narrow

You should anticipate the probability of such events and weigh them against the depth of the value proposition and the impact you'd have on the organization

Scope: some events are genuinely uncontrollable

39:15 20Sales: Why Everyone is Responsible for Demand Generation, How to do Great Sales Discovery, How to Reduce Sales Cycles and Create Urgency and Deal Reviews; Good and Bad Reasons to Lose a Deal with Doug Adamic, CRO @ Brex

Brendon Cassidy · Mar 8, 2024

When a committed deal is lost, the rep has to feel it — it should be a serious weekly one-on-one discussion, though not a firing offense

Otherwise there's no point in having reps commit deals at all

Scope: applies to committed deals, not best-case ones; not grounds for firing; the manager may share blame for missing the warning signs

30:33 20Sales: Outbound Sales is Dead Today, Why Demand Generation Will Move Back Under Marketing, "Wisdom" that Everyone Needs to Unlearn About Sales & Why You Should Never Hire Someone You Do Not Know in Your First Five Hires with Brendon Cassidy

Matt Plank · Dec 20, 2024

'Legal didn't finish the red lines' is the worst reason for a committed deal to push, and it is the rep's failure rather than an external event

A pushed deal means the rep forecasted it to land and it didn't; at the end of an evaluation reps should ask how contract processing, signing authority and legal review work, and parallel-track those steps rather than starting them only after getting a yes

Scope: applies to deals the rep committed to the forecast

36:10 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

Lauren Schwartz · Oct 19, 2022

Losing a deal because you don't actually solve the customer's problem is a qualification failure — painful and wasteful of resources, but coachable

It means the team invested cycles on a problem the company never intended to solve, which is a miss in qualifying them out of pipeline, and qualification can be taught

31:45 Qualification failure losses are coachable not catastrophic

Lori Jimenez · Aug 2, 2023

Losing a deal because of a genuine product/use-case mismatch with the customer is an acceptable loss

Winning a deal you can't serve creates churn, and building one-off resources for a non-ICP customer isn't repeatable; better to move on to real ICP customers

44:10 Icp mismatch losses are acceptable

Lori Jimenez · Aug 2, 2023

A bad reason to lose is failing to anticipate competitive positioning, which traces back to weak discovery

If you didn't ask deeper questions about the customer's top priorities and core goals, a competitor can out-position you on what the customer actually cares about

44:57 Losses to competitive positioning reveal weak discovery