Gaining and Keeping the Confidence of Senior People

If you want to be listened to and have an impact, start where the boss believes they are. Focus, first and foremost, on establishing the relationship of trust and common direction with the boss. These are the relationship elements that matter. It is the mutual recognition of common direction that provides the platform for fixing various other shortcomings that may indeed be present.

Work Against the Patterns That Bother Bosses

In talking with chief executives and leaders, specifically about advice they get both internally and externally, a pattern of frustrations surfaces relatively quickly. These are the most frequently mentioned frustrations. You would be well advised to avoid them.

1. Unintelligible, therefore unusable, approaches.

If you want something done by an operating person, you need to describe it appropriately. Speak management’s language

2. More ideas and concepts than can possibly be achieved or even considered.

Remember the most important reasons CEOs lose their jobs relate to failure to perform. If your methodology is to suggest new ways of doing things, or simply new things to do, you would be well advised to emphasize what needs to get done smarter, in a more focused way, and that is doable. And what has yet to be completed rather than putting even one or two new ideas on the boss’s desk.

3. Time wasting and non-specific (purposeless) conversations.

Even if it is the boss who brings up vacations, the family, what seems like chit chat, the trusted advisor’s role is to keep these encounters focused on what truly matters when getting things done. Yes, it is true, over time, you will develop a relationship where a lot of personal information is known and seems appropriate to discuss, but our advice remains, keep these meetings and encounters as focused and professional as possible. Keep your actual role in focus at all times.

4. Information that is late, incomplete, and with some key facts and data or interpretations apparently being purposely withheld.

Senior executives already know that the information they get is filtered, detoxified, and often pretty harmless. One of your most important currencies is candor: this important, concise, prompt dis-closure of things you know that the boss should know. Information withheld or that is late for whatever reason reflects on the trust in your relationship. Even just a couple of incidents where the feeling persists on the part of the boss that you are intentionally failing to be forthcoming, and your invitations will decline.

5. Information that is already known or could be thought up independently.

Stick to what matters. If it is something you know they know, move on. Count on it; you are wasting their time. Avoid doing that or risk losing a good part of your relationship.

6. Giving only partial input, apparently on the assumption that the boss knows more than they do, or should know more than they do.

Use a structure for giving advice with options to prevent providing only partial information. To avoid leaving out key information, talk in terms of timelines or priorities. What should be done first, second, or third, or apply a calendar or a clock to the information you have to share. This way, things the boss already knows get put in a new, useful, more strategic context.

7. Reluctance to be candid.

This behavior is a relationship killer . . . Whether it is fear, lack of preparation, or simply timidity, lack of candor is the fastest way to become disemployed as a Trusted Strategic Advisor. If you want to be there, be ready, be actively engaged, and tell the truth promptly.

The problem with these behaviors and approaches is that they distract and irritate top executives and erect barriers to taking your advice or even taking you seriously.

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©2026, James E. Lukaszewski, “Influencing Leaders, The Seven Disciplines of the Trusted Strategic Advisor,” Wiley. Contact the copyright holder at jel@e911.com for information and reproduction permissions. Editing or excerpting forbidden.