The pain of asking for pain

Build trust first, then ask about challenges

Founders often face pressure from investors, advisors, and employees to identify "pain and urgency," which typically results in awkward discovery questions like, "What are your challenges?" or "What pains do you have?" 

The issue here is that you probably haven’t earned the right to ask such questions, and people may not yet understand what your product does to answer clearly. Sometimes, people—usually seasoned or empathetic buyers—will grasp the question and provide some details about what they’re looking for in a solution, followed by a scenario. However, in most cases, you'll receive a blank stare or the response, "We don’t have any challenges at the moment. Just curious what you do. Demo, please."

Make the conversation productive and earn the right to uncover pains and challenges. Sometimes, you may discover that what you offer doesn't align with real pains and challenges, but you need to earn that knowledge too. Otherwise, you'll wonder why deals aren't moving forward.

There are many discovery guides and templates available (always happy to share examples and our perspective on best practices). However, as a Founder, what’s unique is that you're trying to identify a relevant need for your product, which means you need to dig for it. This effort will create the path for your future employees and the first version of your “sales playbook.”

Instead of asking, "We help companies create [X Workflow] for your business. Do you have any pains or needs that we can solve based on what I shared?"

Try this approach: "Introducing this type of workflow is likely new for your business. Based on what you've shared so far, how do you currently solve for [Y Use Case]?" or "When you tried to solve for [Y Use Case], what were the outcomes? Were they what you expected?"

With this line of questioning, the prospect now has the opportunity to share:

• What they have/haven’t tried and why: use cases, stakeholders involved 

• What were the results (good or bad): desired outcomes

• What they expected: desired future state and hopefully some success criteria 

• What they’re looking for in a partner or why you’re interesting based on what you’ve shared so far 

If the prospect didn’t like their outcomes and their expectations weren’t met, keep probing to learn about the challenges and pains in the area your product can address. If they don’t have enough pain, move on and continue searching for a relevant challenge with the same line of questioning.

This may seem straightforward, but you need to earn and build trust with prospects first. This involves demonstrating that you did your research before the call, showing your (earned) credibility and understanding of the core problem you aim to solve in the market, and presenting yourself as a trusted resource to help them solve a problem they feel comfortable sharing with you. Build the trust and ask questions that encourage people to share how you can help them. The rest will follow.