Most GTM deals don’t fail because they were reckless.
They fail because they were reasonable.
The strategy made sense.
The numbers were defensible.
The leadership team agreed.
The decision passed every internal test it was subjected to.
And yet — six to twelve months later — the outcome underperforms.
Pipeline confidence erodes.
Delivery explanations start to drift from decision quality to execution difficulty.
In hindsight, the failure is attributed to market conditions, sales cycles, or “unexpected” competitive pressure.
But the damage didn’t occur during execution.
It occurred earlier, when a small number of assumptions were allowed to pass unexamined — not because they were hidden, but because they felt obvious.
What follows are the GTM assumptions that most consistently show up before otherwise sensible deals quietly fail.
1. “The Buyer Will Behave the Way We Expect”
This assumption almost never sounds naïve when it’s made.
It appears as:
- confidence in buyer urgency
- belief that economic value will override politics
- expectation that internal alignment follows rational evaluation
Leadership teams rarely assume buyers are irrational.
They assume buyers are constrained in predictable ways.
What’s usually missed is not whether the buyer values the solution — but how the decision will actually be made inside the organisation.
In many enterprise and mid-market environments:
- buying authority is fragmented
- incentives are misaligned
- delay is safer than commitment
Competitors understand this.
They don’t try to win on value alone.
They reposition the decision itself.
They:
- sell to a different internal sponsor
- reshape the buying committee
- introduce alternative sequencing that slows momentum
From the outside, the deal still “looks alive”.
Internally, forecasts remain intact.
But the original assumption — that the buyer would behave as expected — has already been invalidated.
By the time pipeline data reflects reality, the organisation has already staffed, planned, and committed around an outcome that no longer exists.
2. “We Understand the Competitive Landscape”
Most leadership teams do understand their competitors — at least structurally.
They know:
- who the main players are
- how offerings compare
- where pricing sits
What they underestimate is how competitors reposition around live GTM decisions.
Competitors don’t wait for public announcements.
They infer strategy from weak signals:
- hiring patterns
- pricing adjustments
- partner alignment
- early customer wins
These signals appear before leadership believes a decision has been made.
This creates a dangerous lag.
Internally, the organisation still believes it’s in a planning phase.
Externally, competitors are already reacting.
They adjust positioning, messaging, and deal structures while leadership is still debating execution details.
The result is a GTM bet that was rational when approved — but increasingly fragile by the time it reaches market.
3. “Timing Risk Is Manageable”
Timing risk is almost always acknowledged.
It is rarely modelled.
Leadership teams tend to assume:
- sales cycles may lengthen modestly
- budgets may tighten temporarily
- execution quality can compensate for delay
What’s missed is that timing risk compounds non-linearly.
A small delay doesn’t just push revenue out.
It:
- changes competitive posture
- weakens internal confidence
- increases board scrutiny
- hardens scepticism
Timing becomes political.
Once a decision is perceived as “late”, every metric is interpreted through a different lens.
Deals don’t fail because timing shifted.
They fail because timing shifted after commitment was locked in — when reversal is no longer cheap or reputationally safe.
4. “If It Doesn’t Work, We Can Adjust”
This assumption is comforting.
It implies optionality.
In practice, many GTM decisions create structural momentum:
- headcount commitments
- leadership credibility
- internal narratives
- board expectations
Once these are in place, adjustment becomes performative rather than substantive.
The organisation appears flexible, but the core bet remains intact.
By the time evidence suggests a HOLD or STOP, the cost of acting on that evidence feels higher than continuing — even if continuation increases risk.
The decision has effectively become irreversible, not because it was designed that way, but because momentum was underestimated.
5. “The Data Will Tell Us If We’re Wrong”
Data does speak.
It just doesn’t always speak in time.
Most GTM dashboards are designed to confirm progress:
- pipeline coverage
- activity metrics
- utilisation and output
Early warning signs rarely appear as red flags.
They appear as:
- noise
- edge cases
- “temporary softness”
Competitors, however, act on these weak signals early — because they are not politically or emotionally invested in the original decision.
By the time internal data becomes conclusive, competitors have already repositioned.
The dashboard didn’t fail.
It simply answered a different question than the one leadership needed answered.
6. “This Is a Commercial Decision”
Many GTM bets are treated as commercial decisions.
In reality, they are organisational decisions.
They shape:
- internal power dynamics
- leadership credibility
- future hiring constraints
- board confidence
These second-order effects influence outcomes as much as pricing or product-market fit.
Ignoring them doesn’t make them disappear.
It simply ensures they surface later — when they are harder to diagnose and harder to unwind.
Why These Assumptions Persist
None of these assumptions are irrational.
They persist because:
- they are rarely false in isolation
- they only break in combination
- their impact is delayed
Each assumption feels defensible at the moment it’s made.
By the time the combined effect becomes visible, the organisation has already moved on to execution narratives.
The original decision is no longer examined.
The Competitive Reality
Competitors don’t need perfect information to exploit these assumptions.
They only need:
- partial visibility
- patience
- asymmetric positioning
Which is why many GTM failures feel surprising internally — and obvious externally.
From the outside, the warning signs were visible.
From the inside, they were rationalised away.
What This Means for Leaders
The most dangerous GTM bets are not the aggressive ones.
They are the reasonable ones that were never stress-tested properly.
The question is not:
“Is this strategy sound?”
It is:
“Which assumptions would make this fail — quietly — after commitment?”
Related Analysis
This analysis is expanded in the Competitive Deal Playbook, which maps how competitors reposition around live GTM decisions — often before leadership teams realise the decision has already become externally visible.
Before You Commit Capital, Credibility, or Momentum
Technology CEOs are increasingly using decision-grade GTM due diligence before high-stakes commercial bets — not to outsource judgement, but to ensure the decision stands up before it's made.
When a GTM decision is hard to unwind — a senior hire, a pricing change, a market entry — the cost of being wrong compounds quietly. Two quarters slip away before you know it failed.
Commercial Bet Due Diligence (CBDD) is a short, independent review used before commitment. It evaluates a single GTM bet across product, pricing, positioning, sales, and customer growth — and concludes with a clear verdict:
- Review a sample CBDD board memo — the artefact CEOs and boards use to govern these decisions
- Learn how the CBDD process works — and when it's applied
