Andrew Donato
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Episode 2·Sunday, April 12, 2026
Things I Learned the Hard Way

The best question I've ever learned

One question that completely changes the dynamic in any conversation — sales calls, consulting, or just talking to a friend about their business.

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TL;DR

There's one question I use in almost every conversation now: "What's the biggest problem I can solve for you right now?" It's not polite small talk — it's direct, it's generous, and it completely changes the energy of the conversation.

The Full Take

I've tried a lot of opening questions over 17 years in sales. Most of them are some version of "how can I help?" And most of them get a safe, small answer. People give you what they think you can handle, not what they actually need.

A few years ago I started asking a different question: "What's the biggest problem I can solve for you right now? Dream big. If I could make it go away, what would it be?"

The difference is immediate. It does two things at once — it signals that you're there to actually do something, not just have a conversation, and it gives the other person permission to think bigger than they normally would.

Most people hold back because they don't think you can actually help with the real thing. This question opens that door.

I've used it on sales calls. I've used it with my team. I've used it with people I'm meeting for the first time. Every time, the energy shifts. People lean in. They tell you the actual problem, not the polished version.

The key: you have to actually mean it. If you ask this question and then can't deliver — or worse, don't try — it backfires. But if you're genuinely trying to help, it's the fastest way to get to what actually matters in any conversation.

Here's why it works better than "how can I help": that question puts the burden on the other person to figure out what you're good at. They'll give you a small, safe answer. "What's the biggest problem I can solve for you right now" tells them to dream big and trusts that you'll figure out the how. You get the real answer, not the polite one.

Resources

  • This question works in sales, consulting, management, and personal relationships — anywhere you're trying to help someone
Try it this week. One conversation. 'What's the biggest problem I can solve for you right now?' See what happens.