March 26, 2026
Hi Everyone,
Pipeline reviews are one of the most important recurring meetings on your calendar, and Gartner found that fewer than half of leaders have high confidence in the forecasts those meetings produce.
A big part of the problem is that the meeting is built around "what's the status?" when it should be built around "what do you need?"
Today, we'll walk you through a 30-minute weekly meeting format that solves the issue.
The meeting is producing the wrong behavior
Sandler Training found a consistent problem with pipeline reviews. Pressure to forecast accurately teaches reps to play it safe. Safe estimates make the forecast worse. A worse forecast triggers more pressure.
The deals where executive involvement could change the outcome are the ones least likely to come up.
Here's how to fix it.
The Win Room
The format is called a Win Room. It's a 30-minute weekly meeting focused on five to ten of your most important open deals. The whole point is one question: "What do you need to close this?"
Before each session, your sales leader prepares a ranked list of the deals that will be discussed. Each deal should have a short summary covering:
- The deal size and likelihood of close
- Current state and what's blocking progress
- Who else the buyer is talking to
A line gets drawn under the must-win deals, so nothing below that line gets discussed until plans are locked for everything above it.
During the meeting, reps walk through their deals and present what they need to move them forward. The ‘ask’ needs to be specific.
For example:
- A meeting between your CEO and the person who signs off on the deal
- A technical demo from engineering
- A pricing breakdown from finance
- A case study or side-by-side comparison from marketing
The room then figures out who can help on which deal, and every commitment gets written down before the group moves on.
How the meeting works
Keep the room small – five to eight people, with your sales leader running the conversation and the CEO there to offer help, not run the show.
Start every session by checking last week's commitments. If nobody tracks follow-through, the meeting loses credibility fast.
Then move through the deals. Each rep gets about five minutes to make their ask, and someone captures every commitment in real time.
Matt MacInnis, COO of Rippling, describes the right approach for executives well:
"I'm not a micromanager, but I'm microinterested."
Go deep on the deals where you can genuinely help, then step back. The moment you start questioning a rep's judgment instead of offering resources, reps will stop bringing you their hardest deals.
To make it easier to get started, we built a template with two sheets to track deal prep and commitments.
Go deeper
👉 AlixPartners: Winning Tactics for Revenue and Profitability with a Revenue Win Room – the full white paper on how to structure, staff, and measure a Win Room
👉 Costanoa Ventures (Mark Selcow): How to Close Your Quarter and Hit Plan – a step-by-step guide to running a deal-focused War Room, with agenda, prep, and participation rules
👉 SaaStr: How to Transition from Founder-Led Sales – when to stay involved in deals, when to step back, and how to avoid becoming the bottleneck as your team grows
👉 Sandler Training: Sales Sandbagging Explained – how pipeline review pressure teaches reps to hold back and what structural changes fix it
Coming up tomorrow
Tomorrow we'll cover why your worst decisions tend to happen right after your most stressful moments and share two breathing resets that work in under 90 seconds.
P.S. What's the biggest deal your team closed where exec involvement made the difference? We'd love to hear what you did.