Would You Bet Your Career on That Contract?
A few years ago, I watched a high-stakes deal unfold—one that could have ended a senior executive’s career if it had gone ahead.
It was a major managed services contract worth hundreds of millions of dollars. Internal pressure to reach down-selection was intense. The client was a government entity, and securing this deal would have been considered a marquee win. But behind the scenes, a critical decision had already been made.
A senior executive had quietly agreed to a condition that would have put us in a catastrophic position if a particular risk materialised after the initial contract term. The deal included options for extension, but if the client chose not to renew, we would have been left with millions in unrecoverable sunk costs. His decision was not communicated to the risk team or governance committees. When it eventually came to light, it triggered a detailed investigation.
The executive had gambled on the assumption that the contract would run its full course. If it didn’t, we would have been left holding a multi-million-dollar liability. The contract terms explicitly stated that we were responsible for meeting the client’s requirements, meaning any unrecovered investment was on us.
When Winning Becomes More Important Than Surviving
I’ve seen this happen more times than I’d like to admit. The drive to win a contract can override proper risk assessment, especially when a deal is seen as “strategic.” The excitement of landing a major client often blinds decision-makers to potential risks—until they materialise.
It reminds me of my early days at IBM, where we had a term for certain pricing decisions: “Executive Wedgies.” A crude but accurate way to describe situations where a senior leader would cut costs from a deal to win the business—without a viable plan to make it work. I can’t count how many times I’ve heard, “We’ll make it up with in-account growth!”—as if revenue magically appears just because the customer gets a deep discount on the base service.
This mindset regularly leads to contracts that are profitable only if everything goes perfectly—which rarely happens. More often, these decisions result in account losses, financial black holes, failed contracts, and job losses.
Had we won this particular contract and the worst-case scenario played out, the financial impact would have been devastating. The executive who made the call moved on not long after, but if the deal had collapsed before the full extension period, his career would have ended on the spot.
Fortunately, we weren’t down-selected, so the contract never proceeded. But the fact remains—this kind of hidden risk has sunk companies before.
How to Avoid Signing a Career-Killing Contract
Before locking in a deal, a few critical questions must be asked:
What happens if the contract is cut short? Are we left exposed with immovable assets or obligations?
Are we relying on customer behaviour we can’t control? If the business case only works if the customer makes a specific decision, that’s a gamble—not a strategy.
Who has the authority to make critical risk decisions? If key risks are being negotiated behind closed doors, is there proper oversight?
Have we ever walked away from a bad deal? If the answer is “almost never,” that’s a sign of a dangerous sales culture.
One of the best ways to mitigate these risks is through a separate group of experienced professionals who can challenge assumptions, uncover hidden risks, and push back on decisions made under pressure.
The Shipley Model and Why Independent Reviews Matter
The Shipley Proposal Development Process is one of the most structured methodologies for developing and reviewing complex sales deals. It’s designed to improve bid quality and ensure deals are both winnable and deliverable.
It follows a series of colour-coded reviews, including:
Blue Team – Develops the bid strategy, ensuring alignment with the client’s needs.
Black Hat Review – Analyses competitors to position the bid effectively.
Pink Team – Reviews the initial draft to refine messaging and compliance.
Red Team – Provides a rigorous, independent challenge to the deal’s financials, risks, and execution plan.
Gold Team – Conducts the final executive approval, focusing on financials and risk governance.
Among these, the Red Team review is the most critical for risk assessment—yet it’s often the one companies get wrong.
What a Proper Red Team Review Looks Like
A Red Team review should serve as a final line of defence before a deal is approved. It must be conducted by independent reviewers—people who were not involved in preparing the bid and have no personal stake in its success. Their role isn’t to make the bid look good; it’s to tear it apart and expose weaknesses.
A strong Red Team review will:
Ask uncomfortable questions – What happens if the client walks away? Are revenue forecasts built on best-case scenarios?
Look for hidden risks – Are there contract clauses that could leave the company financially exposed? Are projected cost savings realistic?
Challenge optimism bias – Is the company pushing forward due to pressure to win, rather than confidence in execution?
Identify gaps in the execution plan – Does the delivery team agree with what’s being promised, or are they being set up to fail?
Push for clear risk ownership – If something goes wrong, who is responsible? Is leadership fully aware of the exposure?
Why Most Red Team Reviews Fail
Despite their importance, Red Team reviews are often ineffective. Common failures include:
Lack of independence – Too often, the review is conducted by the same team that developed the bid. That creates a conflict of interest—they’re incentivised to justify decisions, not challenge them.
Being rushed or ignored – Under time pressure, organisations often treat the Red Team review as a formality rather than a serious challenge.
Lack of authority – A Red Team should have the power to stop a bad deal. Too often, their concerns are overridden by executives under pressure to hit revenue targets.
I’ve seen this happen firsthand—deals that should have been stopped at Red Team were pushed through because “we can’t afford to lose this opportunity.” The irony? Companies that believe they can’t afford to walk away from bad deals end up paying for them later in losses, disputes, and failed contracts.
A Deal Should Be Worth Winning
Winning business isn’t just about signing contracts—it’s about signing the right contracts. Any deal that depends on perfect conditions to be profitable is a bad deal.
If a single overlooked risk could wreck financials, careers, or even the company itself, it deserves far more scrutiny.
An Independent assessment of your bids by experienced reviewers can stop these disasters before they happen—but only if it’s done properly.