How to Tactfully Challenge Your Boss (4 of 5)

Reader question: “Do you have a blog post on ‘How to tactfully challenge your leader?” Why, yes. In fact, we have 5!


Your boss asks you to do something that seems bad for business or bad for your team. You want to speak out (and your peers are hoping you will) but you are not sure how to do it without the situation blowing up.

Every boss and every working relationship is different, but I can offer five tips that help me keep the peace while challenging the status quo:

((Read part 1part 2, and part 3.)) 

4 (of 5). Use humor. Not agreeing with your boss is almost always more palatable if you can have her laughing while disagreeing with her. Most people love to laugh and are more amenable to suggestions if they are at ease in a good mood. Here is a super secret pro tip I stole from James Altucher: if you know you are going to confront your boss tomorrow, spend today listening to comedians or watching stand-up comedy.

Think about it. Stand-up comedians are professional speakers who challenge conventional ideas for a living and they do it in ways broad audiences accept (and even laugh about!). Before having a challenging conversation, watch stand-up acts. Pay attention to their movements, mannerisms, and vocal cadence. Notice the pauses and set-ups for punch lines. Don’t steal their act. Steal their actions.

This tip is also great as preparation for public speaking, interviews, most social gatherings (if you feel nervous about crowds), or pretty much any speaking engagement.


Today’s Lesson: Laugh it up before putting yourself on the spot. It puts both you and the other person at ease. Also, learn from the people who do what you need to do best.

Tomorrow, I’ll share a dumb tip that works magic.



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Michael Salamey

People are made of many things, but only a few things define a person. For me, those things are Philosophy, Leadership, and Health. I help independently owned and ethically run businesses break through communication obstacles and challenge conventional thinking. Sometimes that means delivering insightful marketing content; sometimes it means having tough but compassionate conversations. All the time, it means communicating and building relationships with honesty and integrity. I am a vegan, an individualist, and occasionally a man willing to risk everything to reach a goal. I am known for being uncompromising in my values, and for being someone who dares to own his own life.

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