How to Run Deal Reviews that Change the Forecast (Instead of Just Reporting the Weather)

I used to think the point of a deal review was to figure out where deals stood. 

Turns out, that's the least valuable thing we can do with our (rep’s) time as sales leaders. Because here's what typically happens:

1. Your rep walks you through the deal.
2. You ask some good questions. Identify a few gaps.
3. Then your rep walks out with… the same deal they walked in with. And a to-do list.

Nothing actually changed in the deal. 

So the shift that changed everything for me was simple to describe, and hard to practice: 

I stopped trying to gain information from my AEs, and started trying to gain traction with them. Which is the difference between reporting the weather and changing the forecast.

What "Going Deeper" Actually Looks Like

Early on, I'd hear something like: 

"We don't have any engagement with the Economic Buyer," so I'd respond with questions:

• "Have you tried…?"
• "What about…?"
• "Who else could you…?"

All reasonable. But also, kinda useless.Because our AE’s already knew the gap existed. I was just making them narrate it. Which, if anything, made the deal feel more stuck, not less.

What I've learned to do instead is go multiple levels down. Not in the diagnosis, but in the action:

Level 1 is the gap: "We don't have any engagement with the EB."

Level 2 is a direction: "Based on what your champion said last call, here's how we could connect this back to the data modernization initiative the EB's funding…"

Level 3 is the move: "Here’s a forwardable email that matches how your champion talks, framed around that initiative. Let's ask her to send before their 1:1 on Friday."

Most of us have the instincts to get to Level 3 here, but what I didn't give myself permission to do or create the space for was to actually go there inside the deal review itself.

I thought my job was to coach. Turns out, the coaching is in the doing.

Which is actually a big reason we built Olli the way we did. Getting to Level 3 means someone has to actually produce the thing:

• The forwardable email.
• The business case.
• The exec brief.

That work used to fall on the AE after the meeting, which meant it often didn't happen.

Olli can draft that content during or before the review, using your champion's actual language and context from across the pipeline on what’s working. So the deal review becomes the place where you review, edit, and send — not where you add it to a list.

The 3 Habits for Winning Deal Reviews

Habit 1: Use pre-reads to skip the recap.

I resisted this for a while because it felt like extra process.

But the math is brutal: if you're spending the first 15 minutes of a 30-minute deal review just getting oriented, you've got 15 minutes left to actually help. That's barely enough to get past surface-level advice.

So now, context goes out before the meeting:

• Deal summary + stack-ranked risks
• Where the business case stands
• What's changed since last time

It goes right in the calendar invite. Nothing fancy.

One thing I love about how the Enterprise team at Informatica, under Peter Sheehan does: they start their internal deal reviews at :05 after the hour.

Those first five minutes are a silent refresh on the pre-read. Without the, "let me walk you through where we are." The conversation starts at the point of what’s next..

📎 If you want a framework for the pre-read itself, the 60-Second Deal Review is a good starting point. And this crash course breaks down restructuring your deal review rhythm more broadly.

Here's the thing I didn't expect either: pre-reads don't just save time, they change what you do with the time:

• You can ask questions about the pre-read before the meeting.
• You show up with a point of view, not just a blank slate.
• The live conversation becomes about making moves, not catching up.

That's a completely different meeting.

Where Olli fits in here: He generates deal summaries that pull from every source — calls, emails, Slack threads, CRM — into one continuous view.

Not another dashboard. An actual written brief, with:

• Top risks stack-ranked
• A point of view on what to do next
• Enough context that leaders can read it in 60 seconds

That way, you’re walking in at Level 2 or 3. Taking a pre-read from "nice to have" to "we can't run a deal review without this."

Habit 2: Surface what's working — and replicate it.

This took me a while to internalize, but it's become one of the things I lean on most.

As a sales leader, you've seen hundreds of deals across reps, segments, and years. You know — even if you can't always articulate it — which moves tend to show up before closed-won and which ones show up before a deal goes dark.

Your newest AE has seen, maybe, 10-20 deals. That gap is enormous.

The thing is, most of us use that pattern recognition passively. We have a gut feeling that a deal is in trouble, so we ask more questions. But the real leverage is using it prescriptively:

"Sarah had a deal like this last quarter — stuck at procurement, no exec sponsor. She sent a 1-page business case tied to their CFO's cost reduction mandate. Procurement approved in 8 days. Let me pull up what she did so we can build something similar."

That's not abstract coaching. That's connecting what worked in one deal to what's happening in another. It's making your institutional knowledge portable.

And it compounds. The more deals you review through this lens, the sharper you get. You start to notice patterns:

• Getting a problem statement written early with certain types of data
• Multithreading in specific roles before Stage 3, in a certain order
• Anchoring to a funded initiative to engage the EB

These don't just feel right. They show up disproportionately in your wins.

But even the best leaders can only hold so many patterns in their heads. You've got the experience, but you're also:

• Running 30+ deals across a team
• Managing up
• Doing your own selling

Some patterns slip through.

That's the problem that pushed us to build Olli as a single agent across your entire pipeline — not one agent per deal, and not a bunch of disconnected workflow bots.

Because cross-deal pattern recognition only works if the system can actually see across deals. When a deal stalls at security review, Olli can surface something like:

"In 4 similar deals that got stuck at security, the ones that closed had direct CISO engagement by day 3..."

That's not a guess. That's pattern extraction from your own data: doing the comparison work that no human has time to do manually across every deal, every week.

It doesn't replace your instincts. It sharpens them. And it gives your newer reps access to the institutional patterns they haven't had time to build yet.

Habit 3: Do at least 1 thing during the meeting.

This one came from watching someone else, and it changed how I think about leadership.

When I ran a P&L for the first time, I had a weekly 1:1 with our CEO. And he'd do this thing that, honestly, annoyed me at first:

He'd effectively stop the meeting before I could deliver my full update, because he'd already picked out one thing that mattered and he started doing it.

He'd hear something he could change. Open his laptop. And execute.

So we never got to everything on my list. But I always left with one thing off my list.

That was the gift. And it took me a while to see it, but over time, I started to frontload where I needed:

• A blocker cleared
• An intro made
• A decision

And he'd handle it in real time.

When we started the enterprise segment, for example, I had to "borrow" CS resources from another P&L owner to service our first large customers. While we chatted, he emailed Finance to change how we booked those costs. It cleared up a bunch of internal tension. Done, in the meeting. The pattern I took from this: 

The best leaders I've worked with create momentum.

• A decision today vs. "I'll circle back."
• Cut scope vs. add requirements.

Which translates directly to deal reviews. Pick one thing and do it with your rep while you're together:

• Ghostwrite an exec-to-exec email for a stalled deal.
• Edit the POV your SE will use for an upcoming demo.
• Draft a forwardable business case for their champion.
• Send that intro to your contact at the prospect's company.

This is where all three habits connect.

When you have a pre-read that's already oriented you on the deal, and you've got pattern data showing what's worked in similar situations, the "one thing" becomes obvious. You're not guessing at what to do, you're choosing from a short list of high-leverage moves.

With Olli, that last part gets real. You can pull up a deal mid-review and have a draft ready to edit together in the room:

• A business case
• A multithreading email
• An exec brief

The rep doesn't walk out with homework. They walk out with something sent.

So don't just add to the list. Subtract from it while you meet. Your team will feel the difference — and I promise, they'll start bringing you their hardest deals instead of hiding them.

The Reframe

Looking back, the thing that held me back longest was a belief about what deal reviews were for. I thought they were for:

• Inspecting deals
• Getting the lay of the land
• Understanding what was happening across the pipeline

And that's useful. But it's not where the value is.

The value is in the meeting where an AE walks in with a stuck deal, and walks out with a sent email, a clearer strategy, or a decision that was holding them up.

Where you didn't just talk about what to do: you did it.

Which is the shift from reporting the weather, to changing the forecast.

And if you want to see how this works in practice — pre-reads, pattern matching, and producing the actual content that moves deals — that's what we built Olli to do.

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