How to Tactfully Challenge Your Boss (1 of 5)

Great question from a friend: “Do you have a blog post on ‘How to tactfully challenge your leader or something like that?” Why, yes. Yes, I do… now. In fact, we will have 5 this week!


I have definitely been there. My boss asks me to do something that either seems bad for business, bad for my team, or frankly, just sounds like a bad idea. I want to speak up (and sometimes my peers are counting on me to speak up) but I have no idea how to approach my boss without the situation blowing up in my face.

I do not think there is a good “fits all” cookie-cutter answer for this because every boss is different and every working relationship is different, but I can offer five tips that have helped me keep the peace while still challenging the status quo. I can probably also offer 100 tips of how I learned NOT to approach bosses and challenge them, but here are 5 that have not bitten me back so far in my career:

1 (of 5). Start with a request for help (even if you do not actually need help). “I need your help with…” or “Help me understand why…” is a more effective way to start the conversation than directly confronting someone who has power over your employment. Starting with a request for help is betterĀ than starting with, “Well, I just don’t agree with that…”

Requesting help puts the burden on your shoulders as someone who wants to do the right thing but is maybe not understanding how, instead of putting your boss in a corner and forcing him to defend his character or actions. Put another way, “I need your help with…” translates to, “I don’t get why you are asking me to do thisĀ AND… I want to get it right.” On the other hand, “I don’t agree with…” translates to, “I don’t get why you are asking me to do this AND… I think I can do your job better than you can.”


Today’s Lesson: Sugar is a better way to attract flies than salt. Sweeten your challenge to an idea by becoming a partner (asking for help) instead of by becoming a combatant (which at the very least tarnishes your boss’ opinion of you and at worst can lead to the end of your employment).

Tomorrow, I’ll tell you how to prepare yourself for any tough conversation, including challenging your boss.



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