Position Yourself as a Trusted Advisor, Not a Salesperson

22 Sep 21

Key executives don’t want to be interrogated. Here's how to have a meaningful conversation as a trusted advisor rather than peppering them with questions.

“Do you mind if I ask you a few questions to understand your needs better?” This is the go-to line most salespeople use as they transition the sales call from building rapport to discovery.

But is this the best approach for selling to senior-level clients? Although asking questions is integral to any sales conversation, key executives don’t want to be interrogated. They want to have a meaningful conversation with a trusted advisor rather than be peppered with questions by a salesperson.

So how can you position yourself as a trusted advisor when you’re meeting with a senior-level executive?

First, consider that salespeople and trusted advisors ask questions for different reasons. A salesperson asks questions that demonstrate a low level of knowledge, focus on discovery, or help inform a proposal. By contrast, a trusted advisor asks questions that demonstrate a high level of expertise, are part of a give-and-take conversation, and are thought-provoking for the key executive.

A fundamental assumption is that as a trusted advisor, you’ve done significant pre-call research. You then need to strike the right balance between asking thought-provoking questions and offering insights.

Strategic Questions

A hallmark of strategic questions is that they move beyond seeking factual information or cliches (“So what keeps you up at night?”) and prompt strategic thinking on the part of the key executive.

Here are a few examples:

  • Given changes in the industry such as ____, how do you plan on maintaining your competitive advantage?
  • Your annual report indicates that you’re positioning your company differently in the next three years in terms of ____. Can you share your goals?
  • What do you consider the challenges [or opportunities] ahead?
  • What other challenges are you facing as a result of this problem?
  • What would be the impact on your organization of not achieving those goals?
  • Why is it important to solve this problem?
  • What would you like to have in a partner?
  • What would success look like in this case?
  • Why is it important to solve this problem?
  • How would this solution help other areas of your business?

These questions expand the conversation away from a typical discovery call by helping the executive share concerns and the impact of such concerns with you. These questions are difficult to think of in the moment, so you should prepare them before you meet with the key executive.

Yes! And …

It‘s challenging to find the perfect balance between asking insightful questions and contributing input during a meeting with a high-level executive. How do you tactfully share an insight, success story, or data?

Consider the concept of “Yes! And …,” a conversational technique that first accepts what the other participant has stated ("Yes!"), then expands on that line of thinking ("And ...").

Saying “Yes!” after the key executive answers a question demonstrates that you:

  • Are actively listening.
  • Appreciate the executive’s contribution.
  • Accept what they are saying.
  • Validate their statement.

“And ...” is where you add your own comments that:

  • Build on the key executive’s idea.
  • Corroborate what’s been said.
  • Demonstrate collaboration.
  • Inspire more conversation or ideas.

Here is an example of how “Yes! And ...” positions you as a partner rather than a salesperson:

Key Executive: “We’re thinking about moving our sales team to a 100% Work From Home model.”
You:Yes! And that can help you attract and retain great people.”
Key Executive:Yes, and that will boost our productivity.”
You:Yes, and our new employee engagement platform offers a better employee experience for remote teams.”

Focusing your conversation on high-value questions will help you have a strategic conversation that will help the executive feel that their time with you was well spent. Using the “Yes! And ...” technique is a way to share your own insights naturally, which positions you as a trusted advisor, not just a salesperson.

More information on how to become a trusted advisor in sales:


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