Remaining Positive When Faced With Skepticism as a Salesperson

If you want to be a successful salesperson, you need to get comfortable with scepticism. Why? Because people have doubts about one another. Pew Research Center found that 71% of Americans think interpersonal confidence has worsened in the past two decades. And the distrust isn’t only in strangers; it also extends to people we know well, like colleagues and family members.

Embrace Being Wrong

Instead of fighting off doubts and anxieties, salespeople should get comfortable with being wrong. Admitting you’re wrong puts you on common ground with your customer, who also has doubts and insecurities. Be honest about your concerns; learn from each other, share ideas—and move forward. Sales don’t have to be a competition or dog-eat-dog fight. But it does require overcoming an inherent human resistance toward uncertainty and change.

Ask Questions

A willingness to ask questions goes hand-in-hand with scepticism. People will always be more comfortable with someone who's willing to listen and learn. In addition, asking good questions helps you establish rapport, determine where your prospect is in their decision-making process, and figure out what needs to happen next—all of which are critical aspects of successful salesmanship. To keep your customer open and engaged, ask Positive Questions. Positive Questions engage the pre-frontal cortex of a persons brain and ensure a deeper connection between you and your client.

Think Positively! The power of the right question – points to think about.

  • The person who sets the question sets the direction and has the power of a change agent.

  • Images of the future are powerful. We can only move in the direction of what we can imagine.

  • Human systems want to move in a positive direction (like plants seeking the sun). Positive questions and feedback create energy — like the sun, they make it more possible to live and grow.

  • It is essential to name and claim what's working as well as what needs work. This is a trustworthy foundation on which to build.

  • Negative images and conversations weaken us mentally and physically; positive images strengthen us and what we can accomplish.

  • Positive communication is essential to mental and community health and requires practice.

Unfortunately, we are surrounded by negative vocabulary. We can choose to replace it with affirmative communication and community affirmation.

To design good sales questions, remember to:

  • Ask about ultimate concerns (e.g. What do you value most?)

  • Use positive questions that build on optimistic assumptions; (e.g. What about your current solution makes you especially glad you bought it….?)Present questions as an invitation using expansive, positive, feeling, experiential words. (What has inspired you to speak to us? What do you most hope to achieve from the change?)

  • Enhance the possibilities of storytelling by asking questions about trusted personal experience. (Thinking back on your use of…., please share a high point when.…)

  • Phrase questions in a conversational, friendly tone (and listen eagerly as to a friend.)

  • Ask open questions to which you do not know the answer, and expect to learn something interesting and important. (Open-ended questions cannot be answered “yes” or “no”)

  • Good questions invite thinking—they stretch the imagination and inspire new thoughts without evoking defensiveness or hostility.

Listen and Analyse

The key is not just asking questions. It’s asking questions that solicit answers that lead you toward discovery. Here are two examples: When your prospect says they’re happy with their current solution, ask why. And when your prospect says they have no problems, ask what would happen if they did have problems. These questions are more than polite chit-chat—they will help you determine where sales opportunities may lie and how to address them moving forward.

Demonstrate Value

When it comes to winning someone over, being trustworthy is usually more important than being liked. That's why salespeople need to be knowledgeable on their subject and explain how their product works quickly and easily. Take some time before every call or meeting with a client (or potential client), so you can speak confidently about your product in relation to their business. Practice talking about its features in an easy-to-understand manner that people from any background will understand.


Being comfortable with scepticism is not about changing someone's mind. Instead, it's about acknowledging that people have doubts and showing that you're secure enough in your product or service to withstand questions, criticism, and doubt. This posture communicates confidence – which is persuasive in its own right – and allows you to move forward in sales interactions while minimising your customer’s resistance.