If you’re a founder selling your own offer, it’s easy to fall into the traps of the over-eager salesperson. Instead of asking open-ended questions in sales conversations, you might find yourself losing good deals or closing bad ones because you’re not asking the right questions.
Selling is a noble art, and you don’t need slimy tactics or manipulative scripts to do it well. What you do need is excellent communication skills and the confidence to ask questions.
Without those, you end up guessing what the prospect wants instead of discovering what they actually need. That’s why learning to ask great open-ended questions in sales (and in life!) is one of the highest-leverage skills you can build early on.
It turns sales from a guessing game into a real conversation. And real conversations are what lead to real deals.
The Power of Open-Ended Questions in Sales
Open-ended questions invite your prospect to tell their story in their own words. They can’t be answered with a simple “yes” or “no.”
Instead, they give you insight into motivation, context, risk, urgency, and hesitations—none of which show up if you’re doing all the talking. You’ll also build more trust and rapport than you would by asking leading questions, such as, “Wouldn’t it be better if you didn’t have to deal with that?”
Most people have to say yes to a question like that, but it doesn’t mean you are qualified to solve it for them. Instead, asking something like, “How would the right solution impact your business?” provides helpful clues as to what they are looking for and whether you can offer it.
Here are a few more simple examples:
Closed Question:
“Do you have a budget for this?”
Open-Ended Alternative:
“How are you currently budgeting for solutions like this?”
Closed Question:
“Are you the person who signs off on this?”
Open-Ended Alternative:
“What does your decision-making process usually look like for something like this?”
What Happens When You Don’t Ask Great Questions
It makes sense why new founders struggle with asking open-ended questions in sales conversations. Because of the drive to grow your business and excitement about what you’ve built, navigating the selling process takes practice, especially when every lead seems so crucial.
But that excitement and limited mindset lead to several conversational roadblocks, including:
- Jumping to the pitch too quickly, either because you aren’t comfortable guiding the conversation or because you’re making assumptions about what they need,
- Spending more time talking than listening,
- And asking leading questions designed to give you the answers you want.
Whether you’re talking to prospects or networking with potential partners or investors, these mishaps can cause numerous problems.
You spend too long with the wrong people.
Without good questions, unqualified leads slip through the cracks.
You either find yourself chasing people who were never going to buy, or you take on a client that becomes a nightmare to deal with. In both cases, you’re wasting time and resources that you could have spent on better, more qualified leads.
You get ghosted after “great” calls.
You walk away feeling confident, but never hear from them again. Although it occasionally happens to the best of us, it can become a consistent issue if you don’t uncover your leads’ actual priorities or timeline.
You oversell and talk yourself out of the deal.
You pitch too soon and/or talk too much, the prospect feels steamrolled, and the trust you were building evaporates.
Or, you ask leading questions that make the prospect feel manipulated, and building trust becomes impossible.
Every founder has been there. Open-ended questions are how you avoid being there again.
Questions That Get Real Answers
The best sales questions are simple, honest, and focused on understanding, not convincing.
Here are a few founder-friendly prompts that reveal urgency, clarity, and buying readiness:
- “What does the right solution look like for you?” (Helps you uncover whether or not you can meet their needs and expectations)
- “How has this problem been impacting your business?” (Reveals need and urgency)
- “What’s been getting in the way of solving this already?” (Uncovers potential objections)
- “What would need to happen internally for this to move forward?” (Highlights buying readiness and helps avoid conflict within the company if other people/departments need to be involved first)
- “What’s at stake for you or your team if nothing changes?” (Reveals readiness for both you and them)
These are the kinds of questions that move a conversation forward without making anyone feel pressured.
They also help you avoid wasting time on people who are still just browsing or aren’t problem-aware enough to invest in your product. (That said, great open-ended questions in sales conversations can absolutely take a lead from completely unaware to fully aware. But it depends on the prospect and the situation, and rarely happens in a single conversation.)
How to Use Open-Ended Questions in Your Sales Process
Asking better questions isn’t about being clever; it’s about being intentional and communicating more meaningfully and helpfully.
Here’s how to build this into your sales conversations:
- Start every call with curiosity. Treat the conversation like a joint problem-solving session, not a performance.
- Ask fewer “check-the-box” questions. Focus on emotional drivers, timelines, and constraints instead of surface-level data.
- Pause and listen. Don’t rush to fill the silence. The good stuff often comes after a beat.
- Avoid yes-or-no questions. The devil is in the details, and that’s where you’ll close good deals and dodge unqualified ones.
The Beauty of Open-Ended Questions in Sales
Even for the most natural communicators, selling isn’t easy, especially with a new company and role under your belt. However, when you ask open-ended questions in sales conversations, it can create a more authentic and comfortable discussion, providing the foundation for a better relationship.
With prospects who aren’t qualified, that level of trust can still turn into referrals later on.
Think about it like this: When you talk to your best friends, they spend time listening to what you really care about. And you do the same for them. A sales conversation doesn’t have to be any different. They are simply centered around different priorities while being just as natural and human.
Plus, the right questions give you the insight you need to sell without pressure and genuinely help people.
Best of all, the better you get at asking questions, the easier it becomes to build a repeatable, coachable sales process. Remember, as a founder, you’re not just closing more deals—you’re building the foundation for a team that can sell just as clearly and consultatively as you do.
The way you sell often reflects the way you communicate with everybody, including your team. Therefore, learning to switch from yes-or-no questions to open-ended questions in sales will help enhance your communication skills both within and outside of your business.
