Why do executive meetings go sideways?
Executive meetings are high stakes. I mean, you haven't really sold enterprise if you've never sweat through your shirt before an exec-level meeting. It's a rite of passage. And I've screwed up my fair share of those precious few minutes, much to the chagrin of past champions.
So before every key-account meeting with an executive, write one page for your side of the table, send the executive a different page, and then use your page to run the half hour itself. Here's each piece.
What goes in an executive brief template?
Eight blocks, on one page, for your team:
1. Meeting objectives. Three sentences:
We need to enable [ next best buying behavior ] to keep our deal on track.
If we see [ evidence ] by the end of the meeting, the conversation was successful.
We also need to ensure [ key contact ] feels [ emotion ] after, based on [ context ].
2. Threats and alternatives. Finish the template's sentence: if we lose this deal, and they don't invest in us, it'll be because... It might be a competitor, an in-house build their CTO is exploring, or a competing priority.
3. The customer's problem statement. "Despite trying [ failed solution ], the customer still can't [ desired outcome ] because of [ problem ], which is costing them [ cost of problem ]."
4. Why now. "[ Executive ] is pushing to reach [ strategic goal ], and sponsored a project labeled [ internal language ] to support this. Their goal is to reach [ project milestone ] by [ compelling event ]."
5. Customer impact. The one or two executive KPIs the meeting is really about, with the current measure and the target by a date.
6. The attendees, and the question in each head. For every person from their side, write the #1 question they're privately asking, like "How is this going to be any different than the last / failed time?"
7. Roles. The AE opens with the intro and agenda, the AE and your champion frame the context together, the discussion runs between the AE, your own executive, and the champion, and the AE closes on next steps.
8. A value map for your focus areas. For the one or two areas you'll steer the discussion toward, map the problem, its root cause, the impact, what's required, your differentiator, and the outcome. Here's the example in my template, from selling to sales teams:
- Problem: Slowing revenue growth is falling below plan.
- Root cause: Our close rate is too low, we only close 15 - 20% of our pipeline each quarter.
- Impact: Scrambling to build more pipeline, overspending on top-funnel that doesn't convert, driving up CAC.
- Requirement: Build compelling business cases that sell value aligned with priorities, not just product.
- Differentiator: [Feature] Messaging built with buyers, and using their own, internal language.
- Desired outcome: Close rates rose above 30% and spending on top-funnel slowed to get costs under control.
Underneath all eight sits the narrative you've built with your champion, compressed into a few sentences the executive can hear, retain, and repeat (the 4-sentence soundbite is how I'd build it). I learned that kind of compression early in my career, by the way, building valuation models that turned thousands of pages of legal documents into one line: "Your wireless technology is worth $4.00 per unit." That one line was the result of three months of work, lots of takeout, and a hundred Excel tabs.
What do you send the executive beforehand?
Never the brief, since it's full of your team's honest read on the deal, including how you might lose it. The executive gets a pre-read instead, and the best one is your 1-page business case.
An executive assistant taught me this one. She was helping me set up a conversation with an SVP at a top-five insurance company (we landed a multiyear deal, which I attribute to her in large part). Here's how it works:
- Set your calendar invite to start at :05 after.
- Attach your one-page business case to the invite.
- Let their assistant know there's a pre-read.
- Join the call at :05 after, and dig in.
Executives are sharp. They think clearly and process information far faster than the pace of a typical sales conversation. Which is why a pre-read, with no homework expected, lets you both drive toward what's most important. But not every executive will be a fan, so ask their assistant or your champion first.
Now, find the executive whisperer. A small handful of people hold a no-questions-asked level of trust with any executive, and if they nod "yes" during your meeting, the executive gets the confidence to push forward. If you don't get the nod, well, get ready for an uphill battle. If that person isn't already your champion, meet them ahead of time and ask: "What area of this project gives you the most concern? If it were to go off the rails, why do you think that would be?" Then address those concerns before you're all in the room together.
How should the meeting itself run?
Keep your prepared material to about 25% of the meeting time (that's seven minutes on a 30-minute call), because executive meetings always go off-agenda. Executives have strong opinions about where they'd like the conversation to go, and they're used to running it. So leave room, and plan the half hour in five pieces:
- :00 to :05, deliver a nonobvious insight. In the first few minutes, they decide whether you're more interesting than everything else on their mind. Fill in this sentence beforehand: "Most people believe , but actually, ."
- :05 to :10, adapt to their quirks. I've met with a CEO at a large payments platform who'd finish my sentences (he wasn't rude, he was excited, so I learned to talk in short, fast sentences), and an executive who sat with her back to the screen until she asked me to shut the screen share down altogether. If you're not sure how to adapt to their style, pose a question to your champion, watch how they interact, then follow their lead.
- :10 to :20, confirm or correct your narrative. Find out what they're on board with and what they'd change. And answer the question. As Dave Kellogg puts it, if an executive asks how the team is working on a scale of one to ten, the best answer is "7, but there [are] one or two key problems to work out." It answers the question, it's short, and it leaves them a thread to pull.
- :20 to :25, frame up the decision. Executives think in choices and tradeoffs, so ask: "Are there certain projects this discussion will need to take a backseat to?"
- :25 to :30, confirm owners and outcomes. The most likely outcome is an internal referral, and that referral is worth its weight in gold, because it brings priority with it. So leave with a specific name. "We'll just need to make sure you pass our security requirements" is a general action. "Jon Clark is our VP of info security. We need him to send you our evaluation forms" is a name you can work with.
What happens after the meeting?
Executive meetings usually kick off a new round of internal communication, starting with that referral. Keep the executive posted while asking almost nothing of them:
[Executive], no reply needed here, just keeping you in the loop. We also have Y planned for next week and will update you after. We're continuing to make good progress on X.
By the way, this is also a good question for the end of the meeting itself: "How would you like us to keep you updated?"
And remember whose house this is. You're a short-term guest, while your champion lives with that executive long after you've left. So your main goal in all of this is to create more internal standing for them, and you'll know you did if your champion tells you afterward they're grateful you were part of the conversation. Like bringing John Legend to a wedding to sing to the bride and groom.
"Isn't this a lot of prep for one meeting?"
Less than it looks, because most of the brief carries over from work you've already done. The problem statement and the why-now line come from your business case, and the people come from your account plan. What's new is the question in each attendee's head and who leads which part, and those are the two things nobody can improvise once the meeting starts.
Your move this week
- Before your next executive meeting, write the #1 question you think is in each attendee's head, then check it with your champion.
- Find the executive whisperer, and ask them what concerns them most about the project.
- Send the executive your one-page business case as a pre-read, with the invite starting at :05.