When I was at IBM, and now at CGI, reviewing the pipeline has never simply been a matter of saying, “I’ve got a big deal and I think we’re going to win it.”

The bigger and more strategic the opportunity, the harder the questions become.

What is the client actually trying to achieve? What value will matter enough for them to act? Who really makes the decision? Who supports us, who is unconvinced, and who have we not met? What is the competition doing? What could stop the deal? And what has the buyer done—not just what have we done—to show that the opportunity is moving?

For significant opportunities, that thinking has to become explicit through a Win Plan and the deal-management discipline we called CVDM.

At times, it can feel like governance.

Looking back, that is exactly the point.

A Win Plan doesn’t exist to prove that Sales is busy. It exists to expose whether we actually know how we’re going to win.

Activity is easy to document. Meetings were held. A proposal was sent. Executives were introduced. Technical workshops happened. None of that, by itself, proves the client is closer to a decision.

A credible Win Plan forces a different conversation. It connects the client’s desired outcomes to the people shaping the decision. It makes the decision process visible rather than assumed. It tests whether our value is meaningful to each stakeholder, whether our competitive position is real, and whether the client believes we can deliver what we are promising.

It also makes uncertainty harder to hide.

Perhaps we have strong technical support but no access to the economic buyer. Perhaps the business case sounds compelling, but the client has not validated the assumptions. Perhaps the close date depends on procurement, security, funding, or an implementation dependency that nobody owns. Perhaps the next step is really a seller follow-up disguised as buyer commitment.

These are not reasons to punish the salesperson or automatically downgrade the deal. They are reasons to improve the plan.

Good deal governance creates a shared view of what we know, what we believe, and what still needs evidence. It turns risks and dependencies into actions, actions into ownership, and ownership into observable progress.

That improves more than the opportunity. It improves coaching, resource decisions, executive support, pipeline progression, and forecast quality. Leaders can decide where intervention will help. Account teams can see where optimism has outrun buyer evidence. Delivery can challenge promises before they harden into commitments.

The Win Plan should remain alive as the deal changes. Stakeholders shift. Competitors reposition. Priorities move. New risks surface. The plan earns its value when those changes alter what the team does next.

A big number can get an opportunity into the spotlight.

A disciplined Win Plan determines whether it deserves to stay there.

Discussion question: In your largest opportunities, does the Win Plan describe the work your team has done—or the evidence that the client is moving toward you?

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