Striking a Balance Between Yes Man and Doubting Thomas An executive who serves a CEO's inner circle should not shy away from sharing well-reasoned opinions

By Joel Trammell

Opinions expressed by Entrepreneur contributors are their own.


Doesn't everyone want to be a CEO? Because of my personal aspirations, I used to assume that everyone does. Then one day I realized that many people are happy to remain in an executive role without rising to the chief so that their responsibilities and stresses are not quite as demanding as those of the top boss. But how does one play that role well?

If you find yourself in an executive position directly reporting to a CEO, here are some behaviors to avoid and others to cultivate if you want to be successful.

Yes men. What does a CEO look for from his or her lieutenants? Bad CEOs often look for "yes men," executives who will respond to every directive with "Yes, sir" (or "Yes ma'am"). If you find yourself working for this type of CEO, begin looking for an alternative.

Related: Are You Surrounded by "Yes" People? 3 Steps to Straight Talk

Some executives serving a CEO are natural "yes men." Indeed, a recent Harvard Business Review article referred to this as "violent politeness." These people feel they should always agree with their CEO: After all, he (or she) is the boss. Executives like this are redundant, however, and a good CEO will realize that they provide no value to the team. An effective CEO encourages the participation of members of the team despite not always taking their advice.

No one person is smart enough to know all the right answers, and any CEO who doesn't encourage input from the executive team will eventually make a big mistake. I have seen organizations in which the CEO indeed knows more than the rest of the executive team; but this is just the result of the hiring of weak managers. And if you are part of a team like this, your chance of success is almost zero. Better to cut your losses and find an organization with a truly competent leader.

Doubting Thomases. On the other hand, you may find yourself in the position of disagreeing with your CEO most of the time. This is often a sign that your values are incompatible with the CEO's. It is not a question of right or wrong but rather a matter of disagreement over the most important priorities. If you find yourself in this situation, it's often better to find a different organization with a leader whose approach is more aligned with your values.

When you accept an executive position, you are taking an oath to support the company line -- assuming it's not illegal -- once a decision is made. The challenge for some executives lies in becoming too emotionally attached to their position and not actively supporting a final decision counter to their thinking. In addition, executives who try to secretly undermine decisions that they don't agree with are cancers in any organization and should be removed.

Related: An Exercise in Compromise: How to Agree to Disagree

Debbie Downers: Another troubling quality often seen in members of an executive team is an inability to actively engage in a discussion when they don't agree. It is often obvious that they have some reservations but instead of offering a diverging opinion, they just comment on the difficulty of the chosen course of action -- without elaboration. The conversation might sound something like this:

CEO: "I think we should take that hill."

Weak executive: "Are you sure you want to take that hill? It seems hard."

CEO: "Do you think we shouldn't take that hill?"

Weak executive: "I am not saying we shouldn't take the hill, but it seems like it could be really difficult."

Such a conversation provides no value to the CEO and indicates that the executive is uncomfortable with his or her position.

Good executives. The right executives serving a CEO will find themselves in agreement most of the time but able to openly question the boss when they disagree. Good CEOs recognize that such questions from an executive make the decision-making process better -- even if they don't end up siding with the person pushing a particular issue.

A good executive will answer the hill question with one of three positions:

  1. "I agree. Let's go take the hill."
  2. "I disagree. I think we should take a different hill or not take any hill."
  3. "I need more time to examine the situation. May I work on it for 24 hours and give you my recommendation then?"

All these answers are valuable to the CEO and demonstrate the proper role of an executive. Every CEO needs a strong executive team. Don't allow yourself to be a weak executive.

Related: Build Your Management Team

Joel Trammell

Veteran CEO; CEO, Black Box; Founder, Khorus

Joel Trammell is CEO of Black Box, which provides IT infrastructure services, and the founder of CEO software company Khorus. He is also the author of the The CEO Tightrope.

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