Challenging Executives Without Damaging Trust

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A career mistake high performers make is confusing being “right” with being effective, especially when challenging executives. I’ve seen talented managers trigger defensiveness in execs, publicly corner leaders with data, and thus unintentionally damage trust. Not because their point was wrong. Because their communication delivery was. In our latest executive coaching breakdown, we unpack: 1/ How to challenge executives without triggering defensiveness 2/ Why timing and framing matter more than most people realize 3/ Specific phrases you can use Worth reading if you work with senior leaders: https://lnkd.in/gCGXC_pT

For PMs and TPMs, this plays out almost in every exec-facing conversation around roadmap, resourcing, or strategy. Before you decide how to challenge, understand what they're protecting - It's often a stakeholder commitment, a resourcing constraint, or a narrative they've already told their own leadership. Frame your challenge around that and you give them somewhere to go without losing face.

Jason - “It is dangerous to be right in matters on which the established authorities are wrong.” (Voltaire) Solid advice - and it'll also help business performance by tapping into insight of people at all levels.

"They incorrectly think, “If I present undeniable evidence publicly, leadership will have to agree with me.” Usually, the opposite happens." Oof. Been there, done that.

Confusing being right with being effective is a sharp distinction, since the strongest argument still loses if the delivery makes a senior leader feel cornered. Timing and framing carrying more weight than the data itself is the part most high performers learn the hardest way, Jason P. Yoong

Adrian Ho Kiu Cheng

Raising atm! ex-Amazon GM - built a 0 to $500M business | Electrifying SEA’s 20M motorcycles

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Also - don't confuse being 'right' within your level of context with being 'right' at the executive's level of context. Executives, by definition, know more about the business and objectives than you. So, it's a bit arrogant to assume that what's an optimal solution for you and your business unit might be right for the company as a whole.That's why it's better to approach the situation with humility, and go in with the assumption that there's context that you're unaware of.This is professional maturity.

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There is a big difference that you can make by saying the thing the right way versus only saying the right thing in the wrong way

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Being correct is valuable, but influencing decisions at senior levels often depends more on how the message is delivered than the message itself.

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You're right Jason. Sometimes unpleasant deliveries deliver a higher impact because it sticks and weighs more. Sometimes it's needed for things worth taking more seriously, beyond emotions. It understands the importance of respect at that level, and also the ability to communicate important information. Good food for thought.

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