How to Adjust Your Selling Approach to Build Trust With Skeptical Execs

BY Jessica Helinski
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Sellers may be surprised that building trust with executives isn’t as difficult as many think it is. If you follow best practices when working with these sellers, you should be able to establish a trusting relationship. But every now and then, reps will encounter an exec who is a bit tougher to reach. This is when a more concentrated effort and an adjusted selling approach is required. 

Your C‑suite selling approach won’t always work

Most sellers know that when working with buyers at the executive level, they need to shift their process. And usually, if they follow best practices for working with these buyers, reps can successfully engage and sell to them. But not every senior executive is easy to sway. “When faced with a skeptical executive, you might be tempted to give up and invest your time and effort elsewhere,” writes RAIN Group’s John Doerr. “In some cases, moving on may be the right answer. But often, building a close, trusting relationship with a skeptical executive can be a catalyst to your success.”

How to reach these executives

Doerr goes on to explain that these executives are skeptical for a reason and understanding these reasons can help your approach. Some execs have a large mistrust of competence, often due to bad experiences in the past. The more issues they’ve had, the tougher it will be to prove your abilities. To demonstrate credibility and competence, sellers should be especially mindful to: 

  • Be ready with case studies, testimonials, social proof, and data. Sellers will need to prove their history of success to overcome skepticism. 
  • Show that you know their business. Having knowledge of their company and industry, as well as what their successes and challenges have been, will surely impress. This means do your research and do it well. “Create experiences that demonstrate your competence and allow buyers to get to know your content and capabilities,” Doerr advises. “Webinars, white papers, research, speeches, and seminars can help.”

And for more tips for successfully showing dependability and credibility to these buyers, check out this episode of Manage Smarter. In it, Jeffrey Hayzlett discusses the “Secrets of the C‑Suite” and how to earn their trust. 

When they question your professionalism and dependability

A different selling approach will likely be needed when the executive is skeptical of professionalism and dependability. They’ve likely worked with someone who didn’t do what they’d promised or been inconsistent with delivering results. Or they may even have acted inappropriately or not presented themselves professionally. 

At the C‑suite level, expectations are higher, not only for the executives but also for whom they give their time. This is especially true for those who are extra skeptical. Doerr recommends:

  • Learning what professionalism means to the executive. As he explains, “Some are sticklers for complete sentences in emails. Others might value appropriate language or presentation and collateral materials that match their standards.” Pay extra attention to how you speak and your body language. 
  • Delivering on everything you promise. Even if it’s an offer to share more information later or just send a follow-​up email, get it done, and in a timely manner. 
  • Owning any mistakes or missteps. 

You can also demonstrate your professionalism by engaging in the S.A.L.E. selling approach: “Speak Authoritatively and Listen Empathetically.” Johnny-​Lee Reinoso, C‑Level Partners, explains that this practice helps sellers adopt the C‑suite mindset while still respectfully listening. Adding a tone of authority to your voice portrays a polished confidence that is relatable. But sellers also must listen emphatically, which also demonstrates maturity and a true interest in what they are saying. This combination is a winner when it comes to connecting with these buyers, turning their skepticism into both respect and interest, thanks to the “refreshing mix of confidence and empathy.”

Connecting with executives isn’t easy when they happen to be highly skeptical. With this slight adjustment to your selling approach, you boost your chances of impressing these buyers and scoring a win at the highest level.

Photo by RODNAE Productions