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Not So Breakfast Show - Episode 249: How to Be Agreeably Disagreeable

Sacha's experimenting with fake tan for the first time at nearly 53 (she looks like a giraffe's coat of many colors, according to her assessment), while Ish is fresh from the gym, sweaty and smelly (lucky they record on line). Today's topic: How do you disagree without becoming a career-limiting liability? How do you challenge ideas without tearing people down?

Main Topics

• The Contrarian Personality -- Sacha admits being disagreeable is almost a central trait - always looking at arguments from both sides, naturally questioning everything, enabled by upbeat personality that masks how disagreeable she actually is
• The Power Balance Reality -- Before disagreeing, assess: Is this your boss? A colleague? Someone who reports to you? The approach must shift based on power dynamics.
• The Three-Phase Framework -- Start with alignment (find common ground), ask clarifying questions (joint problem-solving), offer next steps (pilot tests, comparison options)
• Separating Ideas from People -- Pressure test ideas, not individuals. The sooner teams learn to separate their ideas from themselves, the freer everyone feels to contribute and challenge.

The Disagreement Framework

PHASE 1: START WITH ALIGNMENT

Find what you agree on before highlighting differences:

Examples:

• "I understand what we're trying to do here. I know we're aligned on the end result being X..."
• "I'm with you on the outcome. I just see the path to get there a little bit differently."
• "We all agree we want to live in a country where every child gets opportunity..."

PHASE 2: ASK CLARIFYING QUESTIONS

Get more information without setting people up to fail:

Good Questions:

• "Help me understand what you're optimizing for"
• "Help me understand what factors you're prioritizing with this idea"
• "Can I offer another angle? I'd like to present a few other ways of looking at it"
• "Is there more data we need to collect to give us better sense of which way to proceed?"

PHASE 3: OFFER NEXT STEPS

Suggest ways forward that don't make it winner-takes-all:

Examples:

• "How about we try both approaches and determine which gets best result?"
• "Maybe we should spend time exploring both options equally, then decide"
• "I'd love to work with you on this - if we could have half an hour tomorrow, let's find where the issues are"
• "Let's pressure test these ideas to see how they stack up"

Bottom Line

Being disagreeable effectively requires starting with what you agree on, asking questions that truly seek understanding, and offering collaborative next steps. Separate ideas from people. Build reputation for helpfulness. Accept defeat graciously. 

If you haven’t come across it yet, Working Genius is one of the simplest, most practical models I’ve seen for helping teams understand how they actually get work done. Not personality. Not fluff. Just clarity on where people thrive — and where they get frustrated.

 If you’re planning your next team day, offsite, or work event, I’d love to bring this to your crew. 

Find out more at IshCheyne.com