Running discovery with executives

Running discovery with executives:

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⛔️ Don’t: Ask a ton of questions

✅ Do: Bring proof points and insight

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Your champion did a great job of introducing you to power.

It’s your first time meeting with a senior executive at this account.

We meet with dozens of VP of Sales & CROs every quarter at Outbound Squad.

Here’s how we make sure not to blow it:

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✅ 0/ Prep with your champion (15-30 min.)

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This extra step almost guarantees that the call will go well. Your champion has insider info that you don't. Take advantage of it.

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Questions to ask your champion:

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- What is [senior exec]s' top two priorities that align with this project?

- What could take a higher priority than this?

- Why might they shoot this down?

- What do you think they'll be most skeptical of?

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✅ 1/ Get agreement (1-2 min.)

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Let the exec know exactly what you plan to cover and the intended outcome for the call.

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Tips:

- You're a peer, act like it

- Be very clear with the objective for the call: to earn their buy-in

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Example: “I imagine you want to get caught up on what we’ve discussed so far...See a proof point or two with similar customers we’ve partnered with. And then a quick run-through of how we plan on partnering with you. Our goal is that by the end of this, you feel comfortable sponsoring this project. Does that work for you?”

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✅ 2/ Summarize (1-2 min.)

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Share a one-page slide with the business case:

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- Everything you know about their key priorities

- Challenges you uncovered that could get in the way

- What they might not be thinking about

- What you understand to be their desired future state

- Key timelines

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Frame the conversation as ""we"" not ""I."" Make sure the exec knows this is validated by your champion.

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Then ask for their feedback.

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✅ 3/ Share proof points and insights (3-5 min.)

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Pick 1-2 similar customers. Similar industry, company size, and a similar situation. This builds credibility and shows you’ve seen this situation before.

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Then share a few insights that were key to these clients getting the result they wanted. Executives love this.

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The key is to share insights that challenge common thinking.

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Example:

- "Surveys don’t work. XYZ COMPANY found that only their vocal minority of customers (less than 2%) actually completed surveys. And the feedback wasn’t representative of what their more typical customer was experiencing. And they kept spinning their wheels to find the root causes behind customers calling in. They started collecting information OUTSIDE of surveys—messages, chats, emails, phone calls, etc—and used this to reduce cost to serve by 19.2% per customer."

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Take 5-7 min. to run through these three steps and execs will be way more open to doing discovery with you.

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What's your best pro tip when meeting senior execs for the first time?

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