Why Your Biggest Deals Are Stalling (And The 5 Hour Fix That Unlocks Them)

What's the biggest deal sitting in your pipeline right now that hasn't moved in 60+ days?

I'm betting you have at least one. Maybe more.

Here's what's happening across sales teams everywhere. Your reps are staying busy with the easy stuff. Singles and doubles. Quick wins that keep them comfortable and their activity metrics looking good.

Meanwhile, your million-dollar opportunities are collecting dust.

It's Not What You Think

It's not because your team can't close big deals. It's because they're not doing the deep work these deals require.

Complex deals need different skills. Different strategies. Different focus.

But your weekly pipeline reviews aren't built for this. Your one-on-ones focus on activity, not strategy. Your forecast calls are just status updates.

None of that actually moves the needle on your biggest opportunities.

The Real Problem: No Structure for Deep Work

Most sales leaders try to fix stalled deals with more meetings. More check-ins. More "accountability."

But you can't manage your way out of a skills and focus problem.

Your reps will always default to working the easy stuff unless you create structure that forces them to focus on what actually matters.

Enter Target Time

We call it Target Time. It's a 5-hour monthly war room that forces your team to strategically work their biggest opportunities.

One client went from zero deals over 500K in their pipeline to closing $2.1 million in big deals within 90 days of implementing this system.

Here's the exact structure:

The 5-Hour Format (4th Friday Every Month)

Hour 1: Targeted Training

Focus on complex deal skills. Stakeholder mapping. Multi-threading. Messaging for different personas. Economic buyer psychology. Whatever your team needs most.

Hours 2-3: Group Deal Strategizing

Each rep presents one stalled big deal. The team asks questions, identifies blind spots, and strategizes next steps. Multiple perspectives unlock what one person missed.

Hours 4-5: Execute Strategy

No more talking. Deploy the strategy. Make calls. Send emails. Do the work. Then report progress to create accountability.

The Secret Weapons

Include Operational Executives: Invite your ops leaders. They offer business perspectives outside the sales lens and often volunteer to help directly on deals.

Leverage AI Live: Run account plans through AI to identify red flags and missing information in real time with the team.

Breaks Every Hour: Everyone shares progress made. Nobody wants to report they did nothing.

Why This Works

Structure drives behavior. Without forced focus on complex deals, your team will always default to the comfortable stuff.

Target Time isn't just another meeting. It's a systematic way to:

• Develop complex deal skills through targeted training

• Unlock stalled opportunities through group strategizing

• Create accountability for immediate execution

• Build team collaboration on your biggest opportunities

If you're managing a sales team and not seeing movement on your biggest deals, this is the missing piece.

The deep work your team isn't doing is exactly what's keeping those million-dollar opportunities stalled in your pipeline.