If an SE can’t get a sense of who the prospect is and what they’re looking for, it’s almost impossible to deliver a live demo that lands.

Particularly now, when buyers are more discerning than ever.

They’ve already read reviews, played around with your competitors’ free trial, and have a healthy sense of skepticism that your product will actually fit their use case.

Asking the right questions – in a way that doesn’t alienate or frustrate potential customers – can help you zero in on what truly matters to them and present your product in the best possible light.

Here are three questions to help you sharpen your discovery approach.

To frame the value of your product in a way that’s convincing to a buyer, you have to know what other tools they’re already working with day to day.

Otherwise, you might design a demo that doesn’t show your tool slotting seamlessly into their existing workflow – something they might very well expect to see.

You might also overlook important blockers that derail the deal later or miss upsell opportunities for integrations, custom builds, or services.

To uncover what’s really going on behind the scenes, start broad with a question like, “What tools do you currently use related to [insert your product’s core focus]?”

Then go more specific:

• “How do these systems connect today? Are there any integration pain points?”
• “Where are you seeing the biggest gaps or inefficiencies?”
• “Have you tried other tools that didn't work out? What went wrong?”
• “What would swapping or adding a new tool require (technically and politically)?”

Listen (and very gently probe) for workarounds, data silos, or workflows that aren’t currently built to scale so you can position your product as the solution.

Tip

If you want to get a head start on your discovery, try building an interest-level interactive demo and sharing it ahead of your call.

That way, you know, going into a disco call, what products or features they might be most interested in.

And you can use that data to tailor your line of questioning about the prospect’s current tech stack. The team at Haloo takes this approach.

Emily Casaccio, Haloo’s Commercial Director, shares:

“We created a kind of monster master demo that we now distribute to prospects before they meet with sales. In the sales call itself, we can say, ‘I see that you spent a lot of time looking at comprehensive search. I would love to talk to you about that.’”

Your main goal as an SE is to prove, without a doubt, that your product can solve a buyer’s problem.

To do that, you need to go deeper than surface-level pain points and figure out:

What the primary stakeholder(s) is goaled on → Can your product help them measure it? If not, what KPIs can your product contribute to?

What they’re worried about → What risks is their company facing (or them personally) that your product could help mitigate?

When they need it solved → Are there any ways to speed up the onboarding? Perhaps bundling services or doing a phased launch?

As Mark Rida, Director of Solutions Engineering at Saviynt, puts it:

“You want to ask, ‘What's the big strategic initiative that's occurring in the business that we can start to attach our program to?’ That includes what are they doing today, what’s the impact of what they’re doing today? What do they want?”

Get them talking about outcomes with questions like:

• “How will you know this solution is successful?”
• “What’s something you’d be proud to say related to this project in 6 months? Next year?”
• “What metrics do you discuss in your internal QBRs?”
• “Who else needs to see results from this? What do they care about?"
• “Are there any upcoming deadlines or initiatives that depend on solving this?”

Tip

Michael Ammaturo, Head of Solutions & Partnerships at Experience.com, recommends looking at LinkedIn, press releases, and using AI to understand what's happening at the account ahead of any conversation.

“You should know if, for example, you're going into a call and there's a merger that's been announced. That's happened to me, where it was good that we knew that this merger was coming.”

This will help you ask even more pointed questions about stakeholders’ wants and needs.

Enterprise deals rarely have a single decision-maker. Often, it feels more like there are ten.

Understanding the buying committee, at least at a high level, can help you engage with each person on the call, asking questions that pertain to their role and requirements.

Knowing who’s who can also help you multi-thread the deal.

Your champion is a great person to start with. Ask them:

• “Who will actually be using this once it’s implemented?”
• “Can you walk me through the decision-making process and who needs to weigh in at each stage?”
• “Who is most likely to have concerns or objections about moving forward?
• “Is there anyone on the team who’s evaluated similar tools before? Especially anyone who’s had a bad experience?”
• “Any internal politics or priorities I should be aware of?”
• “Are there any other teams that need to be looped in (legal, security, IT)?”

Tip

Interactive demos are another way you can identify key stakeholders early.

In a tool like Launchpad, you can create and send multiple personalized demo flows to the entire buying committee.

Whenever someone enters the demo, they provide their name and email address, allowing you to track their behavior (and put new important people on your radar). They can also share it with their colleagues right from inside the demo.

Watching where users spend their time can help you anticipate objections during your live demo and personalize your post-demo follow-ups.

It can also help you ask even more detailed questions of your champions, like:

• “How will [insert name] be using this tool?”
• “What matters most to [insert name]?”
• “What role does [insert name] play in the evaluation?”

Want more intel before you hop on your next discovery call?

See how other leading SE teams are uncovering new buyers, gauging intent, and freeing up time for strategic deals with Navattic.