How to Disagree with Executives Without Losing Trust
Why “being right” can backfire — and how to challenge senior leaders productively in high-stakes rooms
Hi, it’s Ethan & Jason from Level Up: Make career breakthroughs with AI-proof leadership skills.
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Today’s Level Up: Inside Executive Coaching scenario spotlights how to challenge leadership thoughtfully and without triggering defensiveness.
In most roles, there comes a time when you need to challenge your leadership.
This could be a single executive or an entire team.
This can be difficult to do in a way that is both productive for the company and not actively damaging to your reputation, especially if your challenge to them is some version of saying “Your idea sucks and here is why.”
It is extremely important that you are able to challenge your leaders without coming off as difficult, disrespectful, and damaging to their efforts or reputation.
During a recent executive coaching session, “Kalyani” (Director in a Fortune 500) asked me how to do this.
Her question was:
“When you’re challenging senior leaders (SVP and VP) or surfacing an uncomfortable truth, how do you balance that impact with respect?”
The reality is that many people will fail to balance impact with respect.
They will either avoid challenging their leadership and thus fail to be impactful, or they will challenge them in a way that comes across as pompous or downright rude.
This will trigger defensiveness in leadership, stalling your impact and giving you a reputation that you do not want. Especially with those who hold your career progression in their hands.
Mastering the ability to be both upfront with your leadership and respectful of them will become more important the farther along in your career you get.
Here is how you can do it at any level.
Label the Conversation Up Front
The first thing I told “Kalyani” in our coaching session was that one of the best ways to handle difficult conversations is to tell people up front what is happening.