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Becoming a Trusted Advisor To Your Boss


It’s a dilemma.  Imagine you are an engineer at GM having a concern about a defective ignition switch, or an administrator at the VA noticing strange scheduling cover ups, or perhaps you see something at work that disturbs you.  Speaking up candidly to your boss about something not working – or expressing ideas about how it could be better – can either fast track you to promotions or get you fired.  It all depends on how it is done. 

Most of the time people feel it isn’t safe.  Better to lie low.  They notice that when someone delivers unwanted news (especially repeatedly), the messenger may be “killed” (fired). 

Quick confession: early in my career I was fired.  At the time I assumed it was just the price I had to pay for speaking up—pointing out to my boss and others all the things that weren’t working or failing to live up to my “high quality standards.”  I believed I was “being brave and accountable.”  Later I realized this “bravery” alienated people because it came from a judgment: “I think you are wrong and I want you to do something about it.”  Yes, it was momentarily satisfying to feel righteous, and it was easier to be critical than to be constructive.  But it was also career deadening. 

My client Gail is known for her candor and is clearly a “trusted advisor” to the top executive in her organization.  Her boss sees her as someone he can trust, someone who reliably tells him her honest view, acts as a sounding board for new ideas and possible solutions to critical problems.  She consistently helps him peer into his blind spots and shares a new perspective.  Everyone knows she helps shape his thinking and has a quiet influential power, even though she never mentions it. 

In my work, I also play this role as an Executive Coach and organization effectiveness consultant.  Recently I invited Gail to collaborate with me on sharing the insider’s tips to becoming a trusted advisor.  I wish I could go back in time and given these tips to myself.


  • Invest in building a high-trust, long-term relationship:  High trust relationships are intentional.   The origin is a feeling of genuine caring about the other person (which can’t be faked).  The first steps of establishing a connection might be by simply emailing an idea, sharing an article, speaking up with a supportive view in a meeting or a lunch invitation.  The boss might not be as inaccessible as you think. It is this context of having a trusting relationship that makes a difficult message is easier to hear.

  • Intention of Service:  Shifting from an ego need to be “right” or pushing a self-serving agenda (I want my idea to be recognized so I will look good) to looking for ways to best support the aspirations, vision and values that serve the “greatest good of all concerned” makes the critical difference. This intent shapes how the message is delivered – such as, “Here’s something I think might be helpful…” 

  • Design the Conversation:  Be clear about what you want to say.  Introduce it in the context of what the boss cares about.  “You know how we want to improve employee engagement, I have an idea…” Make it vision focused, solution focused, rather than a criticism.  Talk in the boss’s language.  Create of mood of collaboration.  Make sure the timing is conducive to the conversation.  Be self-confident that you have something important to share.  Be prepared to share how you think your idea could be accomplished- practical next steps.

  • Trustworthy: What you discuss in private is never made public.  What you say is reliable – it is your most honest assessment of the situation or feedback about an idea, not what might be convenient or “politically correct” to say.  You can both express this view and be open to learning and changing your perspective.  You are authentic.

  • You have an expertise that is valued: The views you share are valuable, credible, based on sound data, not just your opinion.  When you don’t know, you say so or find out.  Over time your view is solicited because it often turns out to be just the right advice. 

So if you can be that person who cares, offers solutions (not problems), makes a solid point that is valued, supports your boss authentically (we all know the fake version) and is open, you will be appreciated (and promoted).  It really all depends on your intention – and your ability to communicate effectively.


Connie Meyer is President of Performance Partners and a trusted advisor to top executives as an executive coach, transition coach, or organization effectiveness consultant.

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