Exec Conversation

Exec Conversation

An executive is not a more senior version of your champion. Different time horizon, different vocabulary, and a different definition of a good meeting. Your champion wants to know what is happening. The executive wants to know whether to keep spending money on it and what it is costing them not to.

The failure this exists to prevent: the product tour. Fifteen minutes explaining what the platform does to someone who does not care what it does, ending in a warm handshake and nothing at all.

What this needs

Shared context. If an account-context document exists, read it first, particularly the value metric and who signs in this business. Where it is absent, carry on and name the assumption.

Minimum: their title and roughly why the meeting exists. That is enough for a first sentence, one ask and two questions.

Better with whatever the champion can tell you about this person: what they were hired to do, what they have said about your product, and what they are under pressure about this quarter. Ten minutes with the champion beforehand is the highest-return preparation available here.

Best with the account's outcome data in their unit of measure, their public commitments, and the original business case. Those turn an assertion about value into a number they recognise.

Nothing here is required.

When this runs

Any meeting where a senior customer-side person is the point rather than an attendee. A sponsor check-in, a first meeting with a newly arrived executive, an escalation that has gone up, a fifteen-minute slot granted at the end of a longer visit.

Do not run this for: a QBR or EBR with executives present, which business-review owns end to end, or a meeting whose whole content is bad news, where hard-conversation governs and this skill only shapes the room.

Step 1: Find out why this meeting exists

Someone put it in the calendar, and the reason changes everything you should say. Ask the champion outright.

• The champion arranged it to show progress. You are supporting their internal position. The most useful thing you can do is make them look right, and take no credit
• Your own side arranged it for coverage or relationship insurance. Then the executive is doing someone a favour and the bar is that they do not regret the fifteen minutes
• The executive asked for it. Something is being reviewed. Find out what before you walk in
• A new executive is auditing what their predecessor bought. The most common version of this meeting, and the highest stakes. They are deciding whether you are inherited value or an inherited cost

If you cannot find out, ask them in the meeting. "Before I start, what would make this fifteen minutes worth your time" is a strong first question and it beats guessing for ten of them.

Step 2: Work out what they are measured on

Not what they are interested in. What they are accountable for this year, in the terms their own board or boss uses.

Everything you say has to connect to one of four things: cost, risk, revenue, or time. If you cannot connect your point to one of them, it does not belong in fifteen minutes.

Where to find it without asking: their own public commitments, their company's stated priorities for the year, what they have posted or said publicly, what the champion says they are under pressure about, and what changed when they arrived.

Then translate. Your usage numbers, adoption rates, feature releases and support metrics are all inputs to something they care about, and none of them are the thing itself. Do the translation before the meeting, because doing it live sounds like improvisation.

Drop your vocabulary. Product names, module names, internal acronyms, your company's language for its own tiers and stages. All of it costs a sentence to explain and buys nothing.

Step 3: Write the first sentence

They will be late, distracted, and deciding in the first thirty seconds whether to give you their attention or their phone.

Lead with the conclusion. No agenda, no company overview, no build-up to a reveal. The first sentence is the thing you would say if you only had one.

The shape: the outcome so far, in their measure, then the one thing you need from them.

Test it against two questions:

• Would this sentence be interesting to someone who had never heard of your company
• Does it contain a number they would recognise from their own reporting

If the honest answer to the first is no, you do not have a reason to be in the room yet, and it is better to find that out now.

Step 4: Pick the one ask

One. A meeting with three asks produces zero, because a busy person defers a list and acts on a single clear request.

Good asks of an executive are things only they can do: sponsor a change inside their organisation, unblock a budget, put their name on an internal communication, introduce you to a peer, agree to be a reference, make a decision their team has been circling.

Bad asks are things their team could have done, which tells them the meeting was unnecessary.

Make it specific and small enough to say yes to in the room. "Would you be willing to open the session at the January kickoff" gets an answer. "We would love your continued support" does not.

Have the ask ready early. Fifteen minutes is realistically eight: they join late and leave early. Front-load, and put the ask before the material you could send instead.

Step 5: Prepare two questions worth their time

The highest-value output of an executive meeting is usually not what you said. It is what they told you, because they will say things nobody else in the account will: what is actually under pressure, what got deprioritised, what happens to their budget next year, whether the initiative you support is still the initiative.

Two questions, prepared, that only they can answer. Not "how do you feel things are going". Closer to "what has changed in your priorities for next year that we should know about", or "if this programme had to justify itself in six months, what would it need to show".

Plant the question you want asked. Leave one thing deliberately incomplete in the first sentence, so the natural question back is the one you are prepared for. A meeting where they ask a question and you answer it well is a better meeting than one where you present without interruption.

When what they say contradicts your champion, that is the most valuable thing in the meeting. Do not resolve it in the room and do not tell them their team said otherwise. Note it exactly and take it away.

Step 6: Protect the champion

Two rules, and breaking either one costs more than the meeting is worth.

Never take anything to an executive that the champion has not already seen. Not a number, not a risk, not a request. A champion blindsided in front of their own boss stops being a champion that afternoon, and they were the reason you had access in the first place.

Never surprise the executive with bad news in front of their team. If bad news has to be delivered, it goes to them separately and first. In the room, your job is to make the champion's position stronger, not to demonstrate your own value at their expense.

The related trap: letting the champion narrate the entire meeting because it feels supportive. If the executive hears only from their own team, you have not been in the room. Agree the split in advance, out loud, so neither of you is improvising over the other.

Step 7: Plan for eight minutes

Write the running order for eight minutes, and a second version for four.

• First sentence and the number
• The ask
• The two questions
• Everything else, in the order you are willing to lose it

Decide the cut line now. The failure is the version where the ask is at the end and the meeting ends before it.

Finish early if the content is done. Handing back four minutes to someone whose calendar is full is one of the few things that reliably earns another meeting.

Step 8: The follow-up

Same day. Five lines. To them, not only to their assistant, and not routed through the champion.

• What you agreed, in one line
• The ask, restated, with a date
• Anything you owe them, with a date
• Nothing else

Write it to be forwarded. If they pass it to their team as the record of the meeting, it should stand on its own without your explanation attached.

Send the champion their own copy, and tell them what was said. They will be asked.

Output

1. Why this meeting exists, and what they think it is for
2. What they are measured on, in their own terms, with what is fact and what is inference marked
3. The first sentence, written out, with the number in it
4. The one ask, specific enough to answer in the room
5. Two questions only they can answer, and the one you want them to ask you
6. The champion plan: what they have already seen, and how the meeting splits between you
7. The eight-minute running order, with the cut line
8. The five-line follow-up, drafted
9. What you could not check

Failure modes

• The product tour. Explaining what it does to someone deciding whether to keep paying for it
• The multi-ask. Three requests, and a busy person defers the list
• The no-ask meeting. Deference dressed as relationship building. They gave you fifteen minutes and you asked for nothing, so there is no reason to give you fifteen more
• The update. Everything that has happened since the last meeting, none of it connected to anything they are accountable for
• Your vocabulary. Product names, tiers, internal acronyms, adoption metrics. Each one costs a sentence and buys nothing
• The champion ambush. Raising something in front of their boss that they have not seen. It ends the relationship that got you the meeting
• Letting the champion carry the whole meeting. Supportive, comfortable, and indistinguishable from not attending
• Planning for fifteen minutes. It is eight
• Waiting for the number. Arriving without a figure in their unit of measure, intending to send it later. It never lands the same way
• Resolving the contradiction in the room when what they say does not match what their team said. Note it, take it away
• The follow-up sent through the champion. The record of the meeting should reach the person who was in it

What good looks like

• The first sentence would interest someone who had never heard of your company
• There is one number in it that they recognise from their own reporting
• There is exactly one ask and it is small enough to answer in the room
• They said something you did not know, which is what the two questions were for
• The champion was stronger at the end than at the start
• It finished early
• The follow-up is five lines and it went to them the same day

Related skills

• stakeholder-map for whether this person is the economic buyer and whether you have ever met them
• call-prep for the general shape of preparing any call
• business-review when the executive meeting is a QBR or EBR
• hard-conversation when the point of the meeting is bad news
• renewal-risk when a newly arrived executive is reviewing what their predecessor bought