What are the best ways to build trust with skeptical executives?

This may sound like a captain obvious, however the best way to win over skeptical executives and skeptics, in general, is by doing, suffice to say... be authentic say 'what you mean, mean what you, then do what you said you would do... this is a time tested centuries-old best practice method of charming a skeptic.

Authentic rapport and time, everyone is hesitant around strangers. You must educate first and never sell until there is a known pain/trigger that you solve and the person has agreed to talk to you about it.

If We Know For Sure They Are Skeptical Sometimes, asking them directly is the only way to determine if they are. Anyone else is secondhand information. Perhaps I'm a naive executive, or maybe because I work in the jungle where efficiency is critical and sometimes life or death. We skip the formalities and simply go to the person, asking them directly, respectfully, Why?

You should try to understand their priorities. Among those priorities select those that are low hanging fruits for them and that you can easily deliver. Under promise and try to over deliver on their expectations, especially those that add more value to their functions or that help them to discover new perspectives and new possibilities

Does Their Skepticism Bring Pros Or Cons Pay attention to whether their skepticism aligns to meeting the goals. It's about assessing if their questioning contributes to the overall success of our objectives. What if they are skeptical and meeting goals, and everybody else is falling in line and not? I will closely examine whether the skepticism brings out the best in others. If it's about getting them to fall in line being a hindrance, they run a risk of being replaced. Consistent skepticism with no purpose is not skepticism at all, but a distraction or disturbance. People can be skeptical and still follow the plan; it's just part of their character. Know them and why they think the way they do is more important than them being skeptical.

I Wont Put It On You I have a friend from college, and we are still close friends today. Many people ask why you are friends with him. He is an azz, and my replies have always been the same for years, "Yes, he's a butt, but he's the same butt every time you are around him." I know people who, if they are mad at their spouse or children, are angry at the world. The ability to hold constant is very needed in the workplace and society. You can have a group of people who always fall in line with what you want as an executive, but outside forces constantly change their mood. In my opinion this is more damaging than a skeptical person because you don't know what the energy is going to be today. No matter what happen to me I wont put it on you.

Two Are Different But Are The Same It is a severe statement I am making. What if the skeptic is meeting goals, hitting the objectives, and always calling it even though they focused on the negative aspects, or is it? I bring this to your attention because I know situations where everyone falls in line and does not truly contribute. However, their attitudes are so team-oriented that the leaders don't want to eliminate them even though they are not performing. Closely examine whether the skepticism brings out the best in others. In some cases, both are a problem.

Sitting On The Toilet Or At 2:00 am Yes person or skeptical person: Build trust gradually with small talks and diverse conversations to understand their perspectives and personalities. In my experience, skeptics value evidence, facts, and consistency. Yes people are not allows saying yes when they sound like they agreeing, listen for when they say "or, but, and, what if, you can also, etc." They are just not confrontational in any way, so they do these things instead. Keep open communication and let them be in contact with you outside normal hours. In my opinion, one of the worst things about corporate is having to do everything within an 8 hour block. Sometimes the best of a person don't come until sitting on the toilet or at 2:00am.