Episode 299: How do you use your problem-solving skills to tell your boss “no”… without risking your job?
We’ve all been there—your boss makes a decision that feels wrong, risky, or just totally off. But speaking up? That feels like walking a tightrope over a pit of career-ending lava.
In today’s fast-paced, high-pressure environments, staying silent when you disagree with leadership can hurt your integrity, your team, and even your performance. But pushing back doesn’t have to mean burning bridges—it can actually boost your influence and credibility. This episode gives you the exact words to say and the approach to take.
Here’s what you’ll walk away with:
- A powerful mindset shift to move from emotional reactivity to strategic influence
- Specific, non-threatening phrases to open tough conversations with senior leaders
- A step-by-step approach to disagreeing without drama—and maybe even strengthening your relationship
Building the Foundation with Problem Solving Skills
00:57 – The moment of conflict that started it all
David opens up about a time he was asked to execute a plan that went against his values. This real-world scenario sets the tone for learning how to navigate disagreement with influence.
02:28 – Why staying silent costs more than you think
Avoiding conflict may feel safe, but it erodes your credibility and surrenders your opportunity to be seen as a strategic thought partner. Leaders need your perspective—even when you disagree.
03:19 – The conversation that comes first is with yourself
Before you say anything to your boss, you’ve got to check in with yourself. David shares a key question to ask that sharpens your intent and strengthens your problem solving skills under pressure.
04:17 – Reframing your mindset to lower emotional heat
Instead of reacting out of frustration, reframe your boss’s decision with curiosity. This shift helps you return to your values while staying calm, focused, and solution-oriented.
05:07 – Prepare like a strategic thought partner
This isn’t about complaining—it’s about presenting a compelling case. David walks through how to assess business risk, align with strategic goals, and strengthen your influence.
Phrases, Pacing, and the Power of Listening
05:41 – The magic of aligning with what your boss values
Start the conversation by connecting to shared goals. David gives examples of language that shifts the tone from confrontation to collaboration, creating space for honest dialogue.
06:28 – Setting the stage for productive conversation
Timing matters. Don’t ambush your boss—schedule time and open with phrases that show you care about the team and the outcome. This respectful setup builds trust and lowers defenses.
07:46 – Listen deeply and reflect for mutual clarity
Want to really elevate your problem solving skills? Practice reflective listening. Use check-for-understanding phrases to confirm what you’ve heard and co-create a path forward.
08:23 – A surprising outcome that preserved integrity
David shares how his CEO responded with unexpected openness when approached the right way. The result? A solution that honored both perspectives and deepened the relationship.
09:26 – Even if you don’t “win,” you still grow
Not every conversation changes minds—but everyone reveals insight. Whether it’s alignment or a values clash, speaking up gives you the data you need to decide whether to stay or go.
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