Published in the San Diego Union-Tribune, May 5, 2025
by Neil Senturia
From time to time, I draw on a bit of reality and confess my sins.
In this period of ecumenical reflection, I am being called to the altar by an executive coach, Melody Wilding, author of “How to Get What You Need from People in Charge.”
Wilding has framed a management puzzle, namely: Your boss is set on a strategy that he thinks is great, but it is a bet-the-farm decision, and you think that he is going to drive the tractor off the cliff. And maybe crater the company.
She explores how you go about telling the boss that a significant intervention is necessary without being confrontational. At the outset, “there is the inherent power dynamic,” she writes, acknowledging that you will worry and wonder about whether he will retaliate. Do I want to go all in, and potentially get tossed all out?
But avoiding conflict comes at a cost. If you don’t call it out, you will feel frustrated. But can you do it in a way that avoids direct conflict.
Still, on the way down, as the plane is auguring into the mountain, you will ask yourself, “should I point out that the wing is on fire, or just bite my tongue for fear of being dismissed.”
Wilding points out that in order to be taken seriously, you need to believe in your capacity to shape the outcome. You don’t want to go to the mat if you have no standing in the organization. Will you be heard?
Wilding says, “Being a truth teller is a smart career move.” Maybe, but the problem is, “whose truth.” Do not assert with absolute certainty, but also don’t roll over or easily back down or you risk being easily dismissed in the future. Frame the disagreement as a “necessary and appropriate” exploration, not the classic “existential threat.”
My bride and I are streaming “MobLand,” a companion piece to an earlier show, “The Sopranos.” My editor has forbidden me from writing about politics, but this whole speaking truth to power thing, well I’m, just sayin’.
Now, as promised, the confession. Our little AI company is facing an all-in, go deep, throw the bomb decision. While some on the team are trying to signal for a timeout, I am pointed toward pushing all the chips into the center of the table. Gunslinger, ace on the river.
So, how does an employee challenge timelines, priorities or direction, without ending up ostracized, marginalized and ultimately fired? The two sides of the triangle (I know, equilateral) are how can they say it and how can I hear it.
Wilding says, “stay strategic,” meaning don’t get confused by past interactions. Authority figures trigger intense emotional response. The boss is not your father or your mother. Focus on why the proposed plan in its current form is not good for the company, not why the old man is an idiot.
Hey, Senturia, do you really understand the granular workflow required in the software or are you flying along at 10,000 feet, head in the clouds, confused by ego and venture and going big?
Wilding wants the employee to shift from a “subordinate mindset to a partnership mindset.” This is critical because you have been in the big company meetings where the CEO gives the speech about how we are all in this together. Don’t be afraid to remind him of those words. After all, a crash landing takes you with him.
Remember the importance of time and timing. Is the house really on fire or is it only smoke from a burned chicken strip? Speaking to the boss in the hallway on Friday at 5 p.m. is not likely to get an adequate hearing or the best response.
Then there is the how to present your personal PowerPoint. Do you beat around the bush at the beginning or is it more effective to make a clear, single declarative sentence?
Regardless of the outcome, keep breathing. Present dissent as a team player. Find compromise if possible. And finally pick your battles — so that you win the war.
My team was persuasive. They convinced me. The plane has landed safely and come to a full stop at the hangar. Able to fly another day.
Rule No. 789: Full flaps and lower the landing gear.