How to Build Trust with Skeptical Executives

Sometimes, talking to the C-suite is easy. Conversation flows. You find common areas personally and professionally. Ideas bounce back and forth. Before you know it, work is underway.

But sometimes, it isn’t easy—even if you’ve been following the tips for selling to the C-suite. Maybe the executive is all business, guarded, and hesitant to share. When faced with a skeptical executive, you might be tempted to give up and invest your time and effort elsewhere. 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.

Keep in mind, skepticism isn’t necessarily about you. Some people simply have an overall preference for trusting slowly. We call this buyer persona a Skeptical Steve.

To build trust with a buyer who is skeptical by nature:

• Find areas of commonality and discuss them, but don’t get too personal too fast. Skeptical Steve is willing to open up, but he takes a while. Get to know him over time. Move too quickly and you’ll get rebuffed.
• Face-to-face time will help—either in person or via video. When setting meetings, make sure there’s a compelling reason to meet that goes beyond “getting to know each other.”
• Don’t embellish or be “larger than life” as this will turn him off.
• Don’t be too demonstrative, and don’t read too much into his lack of gestures and feedback.
• Give a Skeptical Steve time to respond. Press him too hard, and he’ll disengage.
• Focus your interactions in smaller groups, preferably one on one. The larger the group, the more Skeptical Steve is uncomfortable.

Know that if you build trust with Skeptical Steve, you’ll find yourself with a very good long-term business relationship. Your competitors will also have a tough time getting close, and they often won’t put in the effort.

When you meet a Skeptical Steve (or, indeed, anyone) for the first time, their initial skepticism will often focus around three areas: mistrust of competence, mistrust of professionalism, and mistrust of motives.

Make sure you figure out which areas are most important for your various relationships and focus your trust-building efforts where they’ll be most helpful.

1. Mistrust of Competence

In this case, it’s likely an executive has been burned in the past. Sellers may have sold their ability to get something done and were unable to deliver or achieve as promised.

The more executives have experienced this in the past, the larger a barrier they erect for new people and companies to prove their mettle.

If you’re selling something new—a new idea, new product or service, new company—buyers may be naturally skeptical because of your lack of track record.

If you’re selling the ability to achieve something with an uncertain outcome, such as increases in revenue, reductions in cost, the outcomes that'll be the result of a major change initiative, or anything that could be a real breakthrough, buyers will be naturally skeptical.

How to build trust in the face of mistrust of competence:

• Use your historical success as a proxy for future success in stories, case studies, and references.
• Demonstrate deep understanding of their businesses, their challenges, their opportunities, and their markets.
• Know your content cold.
• If you don’t know something, admit it.
• Create experiences that demonstrate your competence and allow buyers to get to know your content and capabilities. Webinars, white papers, research, speeches, and seminars can help.
• Package services and products in pilot tests or phases that can prove the case and prove your ability to deliver.
• Oldie-but-a-goodie: under promise and overdeliver.

2. Mistrust of Professionalism and Dependability

In this case, it’s likely an executive worked with a seller who either didn’t do what they said they’d do or did something that reflected poorly on the executive.

You might think this isn’t that common, but it happens all the time. Sellers say they’re going to do something and they don’t follow through. They’re unreliable, inconsistent, and sometimes act inappropriately in front of the decision makers’ colleagues.

How to build trust in the face of mistrust of professionalism and dependability:

• Make and keep promises. Even little things like, "I’ll get you that by Tuesday," have to come on Tuesday. If it comes on Wednesday, it’s a signal about how you operate.
• Ask yourself what tests of professionalism might be important to this decision maker. Some are sticklers for complete sentences in emails. Others might value appropriate language or presentation and collateral materials that match their standards.
• If you make a mistake or have a misstep, bring it up yourself. Don’t hide from it—apologize, and move on.
• Build your personal brand and reputation. This will help with building your reputation in both professionalism and competence.

3. Mistrust of Motives

In this case, it’s likely an executive has experienced self-focused or deceitful sellers. This happens to many people, but some are more sensitive to it than others and erect higher hurdles for others to jump before they let their guard down.

You'll need time and consistent behavior to help the client succeed, and to prioritize authenticity and genuineness in interactions.

In the area of motives, trust goes hand-in-hand with vulnerability. People need to know if they trust you enough to let their guard down. Will you take advantage of them, or will you protect their interests?

Ask yourself what it would take to make them feel more faith than fear.

One way to build trust and show your motives are in the right place is to trust the decision maker first. Show that you’re willing to be vulnerable and trust them and you’ll find reciprocation.

In the same vein, it’s also a good idea to give before you get, and don’t necessarily expect something in return. Again, reciprocation will happen, but if you expect it to happen and people sense that, they’ll question your motives. It shouldn't have to be an obligation.

Often, the test of your self-interest is revealed when you could do something that wouldn’t be in the executive’s best interest so you don’t do it, even if they might never find out. You act as a good steward of their trust, keeping your ethical compass pointing north when it might be more convenient for you to point it someplace else.

Keep true, and over time, people will notice and appreciate it. Then they’ll begin to trust your motives as well as your professionalism and your competence.

Then the word integrity will start to follow you around.

Keeping It Honest

You might have noticed that various ways to build trust aren't mutually exclusive to these three categories. They all work together. Building trust is like filling a bucket with water—it happens slowly, drip by drip. Eventually the bucket fills and you achieve trust. At the same time, you build a reputation for being trustworthy.

Take care not to spring leaks in your bucket. For any of the various pieces of advice in this article to work, you have to actually be honest and trustworthy. If at any point you’re not, your bucket will, indeed, spring leaks. And what took years to build will drain away quickly—and the damage to your reputation will take much longer to overcome.