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why your deals keep slipping

Apr 22, 2026

You know the feeling.

You're 22 minutes into a sales team meeting and you are still on the first deal. Someone's gone down a rabbit hole. You realize you're not getting to the other 9 deals.

Or: you're in a 1:1 that turned into a meandering pipeline review (again).

Or: you're talking about the same 5 deals you talked about last week. And the week before. No progression. Just...more updates?

Week after week you are spending time in meetings but nothing’s happening. 

Here are the only three conversations you need keep your sales team on track:

  1. Team Sales Meeting (45 min/week)

What it covers:

  • What's going well
  • Roadblocks
  • Where each person needs support
  • High-level pipeline review of your top 10 active deals

The key is prep and structure.

Everyone adds agenda items in advance. 

You use a consistent framework for pipeline qualification (i.e. MEDDIC). For each deal, you're only covering: current qualification score, where the risk is, and brainstorming next steps to overcome it.

This is not a long conversation about the demo you just had or the internal meeting that needs to happen! Keep it focused.

You should be able to get through individual items and 10 deals in 45 minutes.

Tip: Looking at the agenda at least an hour before gives you time to triage anything that can be solved over Slack 😎

 

  1. 1:1s (30 min/week per rep)

This is not a pipeline review.

The team member owns the agenda. 

They come with their own items: career growth, blockers, feedback, skill development, whatever they need.

If they show up without an agenda, cancel the meeting. (I'm serious.)

Tip: Don’t let this become another pipeline review or random brainstorm. Half the value is in your reps thinking through their own plan. 

 

  1. Team Coaching Session (1 hr/week)

Pull sales calls from the last week. 

Identify common themes. 

Pick 1-2 to work on together.

End with specific action items the team can practice in the coming week.

Reviewing real game tape and iterating is the fastest way to improve skills. 

 

That's it. Three meetings, less than 3 hours a week.

 

TRY THIS WEEK:

Review the recordings (or your notes) from your last 3 sales meetings and aks yourself: 

  • Are you starting and ending on time?
  • How many agenda items are you actually getting to?
  • Is everyone leaving with solutions?
  • Are you seeing progression week over week, or coming back to the same things?

If you answered "no" to 2+ of these, try this system and let me know what happens! 

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