Right now, like always, every shot counts when you're running an enterprise deal cycle.

I've been at this for over a decade, and if I am being honest, I've lost more enterprise deals than I have won. That's just the math of long sales cycles, complex buying committees, and competitive landscapes.

But enterprise sales has a funny way of making the wins matter a lot more than the losses.

One good deal can change everything. Your bank account. Your confidence. Your company’s valuation. Sometimes even your customer’s stock price.​

That is why the details matter so much when you are trying to move a deal into the coveted Closed Won stage.

If you are working an enterprise opportunity right now, here are the things to keep a close eye on during the deal cycle.

These are the areas where deals quietly stall, slip, or die altogether.

The Deal Killers to Watch For:

1. No clear next steps

If you are not continually establishing clear next steps, you are drifting. Enterprise deals do not move forward on vibes. They move forward because someone owns the next action and the timeline.

2. Weak discovery early

Poor discovery always shows up later as a pricing objection, a surprise stakeholder, or a sudden loss to status quo. You earn the right to close by asking better questions up front.

3. Single channel communication

If all your communication lives in email or scheduled calls, you are fragile. Strong enterprise deals usually involve multiple channels like Slack, text, onsite meetings, and executive conversations.

4. No access to power

If you do not have a real sponsor or decision maker, you are playing telephone. Influence matters, but authority closes deals.

5. No multi-threading

If your entire deal depends on one person, you are one calendar conflict away from disaster. Enterprise buying is a team sport.

6. Skipping executive peering

This is still one of the most underused levers in enterprise sales. When executives talk to executives, things move faster and with more clarity.

7. Ignoring personal motivation

WIIFM matters. What is in it for your buyer personally? Career growth, visibility, bonus protection, or risk reduction. If nothing changes for them personally, why should they push?

8. No mutual action plan

If you do not have a shared plan that outlines how the deal gets done, you are guessing. Guessing is expensive in enterprise sales.

9. A weak business case

You need to quantify value early and revisit it often. If the value is unclear, the deal is fragile.

10. No friction

This one surprises people. The right kind of friction helps you qualify the deal and your odds of winning. It forces clarity and protects your time. The worst outcome is spending six, nine, or twelve months chasing a deal that was never real.

Enterprise sales rewards patience, discipline, and intentionality.

Pay attention to these details, and you give yourself a much better shot at winning the deals that actually matter.

If you want more enterprise frameworks like this, hit reply and let me know what you are working on right now.

Cheers!

-Jesse

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