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Building Trust with Skeptical Executives

blog author
Written by John Doerr
Co-Founder, RAIN Group

Sometimes it’s just easy. You meet a person and connect. Conversation flows. You find common areas professionally and personally. Ideas bounce back and forth, and you start talking about how you can work on something together. Before you know it, work is under way, and the collaboration is the definition of one plus one equals three.

Sometimes it ain’t easy. You meet a person, and they’re all business. Getting them to engage with you in any sense is slow. Painful. You open up and share, provide great ideas, and work hard to get the other person to see the value in working with you. It should be plain to see, but it’s not. You’re met with aloofness and suspicion.

You try to engage on a personal level and ask, "How was your weekend?" His reply, "Fine." Then dead air.


And even if you get a sale or project started, the pace of progress is slow not because you can’t move fast, but because the other person keeps their guard up and action stays at a relative standstill.

When faced with the skeptical executive, you might be tempted to give up and invest your time and effort into something else. In some cases, you might be right. They may need more investment than is warranted.

But often building a close, trusting relationship with a skeptical executive is not just necessary; it can be a catalyst to your success.

To do that, understand that their tentativeness is not about you. It’s about them. Some people have an overall preference for trusting slowly. This doesn’t mean they don’t ever trust and don’t have intimate relationships. They do. It just takes a while to get there with them.

Treat this preference with respect, and tackle three common but distinct areas of mistrust, and you’ll be well on your way.

For those executives whose overall preference is to trust slowly, know that they are hard wired to erect trust barriers and take their time before they let their guards down. And it’s usually not just with you. It’s true for their personal relationships and relationships with their colleagues.

We call this person Skeptical Steve. Skeptical Steve is one of the 6 Buyer Personas you’ll commonly encounter when selling and in general working with clients.

To build trust with people who are skeptical by nature:

  • Find areas of commonality and discuss them, but don’t get too personal too fast. 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.
  • Live, face-to-face time will help. When setting meetings, make sure there’s a compelling reason to meet in person over and above "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 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 Steve is uncomfortable.

Know, as well, that if you do 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 in his inner circle, and often they won’t put in the effort to get there. He’s all yours if you don’t mess things up.

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 sellers have sold their ability to get something done in the past to an executive and were unable to deliver what they said they could deliver and unable achieve what they said they could achieve.

Buyers can be burned by this. The more they’ve been burned, the larger a barrier they erect for new people and companies to prove their mettle.

As well, 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 that is not certain in its outcome, such as great increases in revenue, reductions in cost, the outcomes that will 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 deeply. 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 over deliver.

2. Mistrust of professionalism and dependability: In this case, it’s likely a seller either didn’t do what they said they would do for this executive in the past or what they did reflected poorly on the executive in the eyes of other people.

You might think this is not that common, but it happens all the time. Sellers say they’re going to do something, and they don’t do it. They are not reliable, are not consistent, and sometimes interact 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. Shined shoes, pressed suits, and straight ties. Appropriate language. 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 sellers have been either too self-focused or deceitful to this executive in the past. This, of course, has happened to everyone, but some people are more sensitive to it than others and erect higher hurdles for others to jump before they let their guards down.

Time and consistent behavior to help the client succeed, as well as authenticity and genuineness in interactions, are major factors here.

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

If they were to think about letting their guards down with you, 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 they sense that, they’ll question your motives.

Often times, the test of your self-interest comes out when you could do something that wouldn’t be in the executive’s best interest – and they might never even find out about it if you did it – but you don’t do it. 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.

You might have noticed that various ways to build trust are not mutually exclusive to the three categories. They all work together. Building trust is like filling a bucket with water, 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, however, 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 right away.


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Topics: Sales Conversations