Issue #111

Why Big Deals Die

A Diagnostic for Salespeople Who Dare to Go Big

Most big deals don’t die with a bang, they die with a polite email or worse - total silence.

If you’re chasing enterprise revenue and your deal has gone mysteriously cold, it’s probably not about price or product.

That may be what they tell you and what you put in the CRM, but it's because you missed one of the real reasons big deals die.

Here’s a framework based on ten fatal flaws I’ve seen kill great deals. You can use them as a scoring tool to see where your deal might be in danger.

There's a download presentation to keep, at the end of the article.

The Big Deal Danger Scan.

Each one has a name, a short diagnosis, and three actions to either fix it or avoid it completely.

1. Wrong Risk

You’re solving for efficiency. They’re worrying about existential threats.

Is your pitch aligned with the actual risks they name in public or in private?

Fix:

Ask: “What would cause their board to intervene right now?”

Map your solution to risk reduction, not just efficiency gains. Use their language, not yours.

2. Weak ROI

The return is positive but irrelevant to them. Does your ROI impact the metrics tied to their bonus or career?

Fix:

Tie benefits directly to EBITDA, margin, or top customer metrics. Ask how decisions are evaluated internally.

Rework your case to show personal stake and company impact.

3. No Narrative

They like you, but can’t explain you to their CFO. Could they pitch this without you in the room?

Fix:

Build a defendable internal business case that they can use themselves.

Write the email they’ll forward. Anchor to hard numbers and key initiatives.

4. Category Complacency

They don’t care about your space or they see it as yesterday’s priority. Have they cut similar vendors or deprioritised the function?

Fix:

Reframe your solution in terms of today’s strategic moves. Show how ignoring your category creates future risk.

Tell a story of someone like them who made the shift and won. And a story about someone who didn't and lost.

5. Political Blindness

You’re treating it like a deal. They’re navigating a power map. Do you know who loses budget or influence if you win?

Fix:

Ask who needs to be convinced, not just who needs to sign.

Co-design a stakeholder plan that minimises the fall out as well as talking about al the benefits. Offer to help manage internal politics, not just the business case.

6. Shallow Prep

You ask questions a 10-K or their website could answer. Have you earned the right to ask strategic questions? You do that by offering deep insight in return.

Selling requires insight, here's a great example of how to do that, click here.

Fix:

Read earnings calls, analyst reports, and exec interviews. Come in with a view, not a blank sheet. If it's right you look great, if it's wrong, you've started a conversation and look interested.

Make insights, not interrogation, your default.

7. Soft Impact

You’re vague about numbers or choosing the wrong ones. Are you quantifying value in metrics they care about?

Numbers need to be translatable into hard money or they are just colour.

Fix:

Anchor your value to metrics with board-level visibility. Build a simple spreadsheet model showing impact.

Replace adjectives with numbers.

8. Mismatched Timing

You’re selling to your timeline, not theirs.

Do you know their planning and budget cycles? When are contract renewals happening that will affect you?

Fix:

Ask: “What’s your internal process for allocating funds?” Align next steps to their gates, not your quota deadline.

Use their urgency, not manufactured urgency (because that is just icky).

9. Sponsor Drift

Your internal champion just went quiet but you don’t know why. Has their influence dropped or their role shifted behind the scenes?

Fix:

Map the stakeholder power landscape again. Ask directly: “Has anything changed internally I should know about?”

Backfill support with adjacent execs if the original sponsor weakens. Never have just one contact in a key account. I know that is easy to say and hard to do, but the alternative is resurrecting a dead deal half way through the pursuit..

Here's an idea you can use to get people on side, click here.

10. Low Personal Upside

Your champion believes in the project but gets no personal win from it. If the project succeeds, do they get promoted, recognised, or enriched?

Fix:

Ask: “What does success look like for you personally in this role?”

Shape the project to give visibility, ownership, or leverage. Make them the hero of the success story, not just the person who signed the contract.

Final Thought

You don’t lose big deals because you’re bad at selling. You lose them because you failed to see how they buy.

This framework isn’t meant as a post-mortem tool, it is a pre-flight checklist.

Run it before every board-level sale, and if you spot danger, don’t push harder, adjust your approach.

Here's the presentation summarising the framework, so you can impress your boss.

​Big Deal Danger Scan- Avoiding Fatal Flaws in Enterprise Sales.pdf​

If you want to get your team trained up in the basics of enterprise sales, get my course.

You'll find loads of 5 to 10 minute videos that you can use to hammer home the foundations of enterprise sales.

Integrate them into your team meetings and coach your team to excellence, step by step.

"I showed them the video about the nine elements of a sale and I couldn't shut them up for an hour..." Simon, VP Sales. He uses the course to focus his team on a different skill every two weeks.

Email or DM (Linkedin) me if you want to discuss coaching or consultancy for you or your team.