The Discovery Questions You Should Be Asking

Effective sales discovery is about more than just ticking off a checklist of standard questions. The best conversations uncover hidden challenges, priorities, and motivations, helping both you and your prospect reach a clear understanding of whether a solution is the right fit.

To improve your discovery calls, here are some essential questions that go beyond the basics and help drive meaningful discussions.

1.⁠ ⁠Clarifying the Problem

“What’s something about this challenge that people you’ve discussed it with don’t seem to fully understand?”

This question gives your prospect a chance to vent frustrations and explain their situation in depth. It helps you position yourself as someone who genuinely listens and understands, which can strengthen trust and rapport.

2.⁠ ⁠Understanding Priorities

“I imagine this isn’t the only initiative on your plate. What else is competing for attention right now?”

Rather than assuming this project is their top priority, this question helps you gain insight into what else is happening in their business. It also allows you to align your solution with their biggest concerns rather than forcing it into an already crowded agenda.

3.⁠ ⁠Defining Success

“In your view, what would need to be true for a solution like this to be successful for your team?”

By getting them to outline their success criteria, you ensure that your solution aligns with their expectations. This approach also allows you to influence their thinking by reinforcing the key advantages of what you offer.

4.⁠ ⁠Exploring Budget Options

“I know most companies don’t have spare budget sitting around. If this was a priority, how would you go about securing the necessary funds?”

Instead of asking if they have a budget (which often leads to a dead-end response), this question encourages them to consider how they could make room for your solution if they see value in it.

5.⁠ ⁠Identifying Internal Drivers

“In recent company meetings or updates, have you noticed any recurring themes or priorities?”

Executives often repeat key phrases when discussing their goals. If you can tap into these, you can frame your solution as a direct contributor to the company’s broader objectives, increasing its relevance and urgency.

6.⁠ ⁠Uncovering Personal Motivations

“Everyone measures success differently. What key metrics are you personally focused on this year?”

People are often motivated by their performance evaluations, bonuses, or internal recognition. Understanding what drives them personally can help you tailor your approach to show how your solution supports their individual goals as well as the company’s.

7.⁠ ⁠Mapping the Decision Process

“Has your team taken any concrete steps toward solving this yet?”“Who else in your organisation would have useful input on this decision?”

These questions help you understand how far along they are in their buying journey and who else might need to be involved in discussions.

Final Thought: Focus on Understanding, Not Just Selling

The best salespeople don’t just present solutions—they uncover problems and work collaboratively to find the best path forward. By asking deeper, more thoughtful questions, you not only build stronger relationships but also increase your chances of closing deals that truly benefit both parties.

Next time you’re in a discovery call, go beyond the standard script. A well-placed question can change the entire trajectory of a conversation—and a deal.