Ep. 109 - Managing Expectations Without Being a People Pleaser

Are you saying "yes" just to avoid a difficult conversation? Being a people pleaser might feel safe in the moment, but it's destroying your credibility in the long run...

In this completely unscripted, sunset-turned-nighttime "Walk & Talk", Gary and George tackle the fine line between professionally managing expectations and falling into the people-pleasing trap. It’s incredibly easy to promise the world to avoid disappointing a client or a boss, but kicking the can down the road with unrealistic deadlines always bites you in the end.

Gary breaks down why delivering bad news honestly is the ultimate trust-builder. We explore how to "clean your own house" so you can push back constructively, why fake promises (like the police looking for George's stolen car) ruin your reputation, and the simple "pause" technique that recovering people pleasers can use to stop overcommitting.

Key takeaways from this episode:

  • The truth will set you free: Don't invent fake deadlines just to soften the blow. Tell the honest truth, set a realistic timeline, and then work hard to overachieve on it.

  • Clean your house first: Before you push back on a client or colleague (like asking for missing data), make sure you and your team are executing flawlessly on your end first.

  • The People Pleaser's Pause: If you naturally hate confrontation, stop committing in the moment. Simply say, "Let me look into it and come back to you," so you can gather the facts and set an expectation you can actually meet.

  • Trust earns you the tent: When you consistently do what you say, you build trust. Once you have trust, you get "inside the tent," meaning people actually care about your opinion and give you leeway when things go wrong.

Links & references:

Highlights:

  • “The truth will set you free. So somehow you've got to be truthful. And what people worry about is, 'I'm going to piss them off and they're going to shout at me'...” - 03:13 - Gary Gamp

  • “Being a people pleaser is more about you capitulating because you're too scared to tell them the truth. It'll bite you in the ass.” - 07:28 - Gary Gamp

  • “Once you've cleaned your house up... now you can push back constructively.” - 15:08 - Gary Gamp

  • “If you're a people pleaser, it's because you're a certain personality where you don't want to upset people and you care... but actually, what happens is you're on a journey of disappointment for yourself and for them.” - 18:25 - Gary Gamp

  • “If you can manage expectations as in commit to something that you can actually do and do it, your credibility, your opportunity, your chance of promotion... will make a massive leap.” - 20:00 - Gary Gamp

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Ep. 108 - The Evolving Role Of The COO Linked To Diversity In Tech