Dear Dan, My Boss Didn’t Keep His Promises

Dear Dan,

I have to have a difficult conversation with my boss about promises made that have not been kept or fulfilled.

Any thoughts about how to properly challenge up?

Ready to Challenge Up

Dear Ready,

Thanks for your email. This situation is more common than you might think. Bosses disappoint.

When I receive emails like yours, I often begin with don’t shoot yourself in the foot by giving less than your best at work.

Disappointed expectations make the heart sick. When that happens, people often engage in self-defeating behaviors.


#1. Don’t challenge your boss if you have the reputation of being a complainer. After reflection, if you aren’t sure if you’re a complainer, you probably are.

Shift your reputation to a positive contributor before challenging anyone.  

#2. Don’t challenge your boss publicly.

Protect your boss’s reputation unless they’re engaged in illegal or immoral behaviors.

  • There’s a difference between publicly challenging your boss’s performance and offering alternatives for discussion in meetings.
  • Don’t copy the team when you challenge the boss in an email. Embarrassing the boss is petty revenge. If the boss made a public mistake, let them publicly fix it. Drama is a distraction.
  • Don’t go to your boss’s boss until you speak directly to your boss. If you can’t find resolution, explain that you’re escalating the issue. Don’t sneak behind anyone’s back.

#3. Don’t speak for others when challenging the boss.

Avoid saying, “Everyone thinks you’re making a big mistake.” When you complain to the boss on behalf of capable others, you encourage gossip, disloyalty, and complaining. In addition, you put yourself in a losing position.

#4. Don’t globalize by using terms like, “Always.”

#5. Don’t use a boss’s blunder as an excuse to violate common courtesy. You don’t have the right to be a jerk-hole because you have a jerk-hole boss.


#1. Define the win before you begin.

What are some good outcomes? Sometimes people are so consumed with what they don’t want that they forget to define what they want.

#2. Make “I” statements, not “You” accusations.

#3. Work for the advantage of your boss and your organization. Self-serving confrontations lower your standing. How is your boss advantaged by listening to your challenge?

#4. Assume they’re trying to serve well.

#5. Give your boss a heads up. Let them know what you plan to discuss BEFORE you show up. No one likes feeling blindsided.

#6. Stick to one issue. Your boss may have made the same mistake several times. You waited hoping things would get better but they didn’t. Stick with the most recent offence.

#7. Practice curiosity. Ask questions that begin with ‘what’ or ‘how’, not ‘why’?

#8. Offer solutions and alternatives.

#9. Get right to the issue. Don’t beat around the bush. Declare your concern at the beginning. Spend most of your conversation generating and exploring solutions.

#10. Test drive your confrontation with an unbiased outsider. Don’t use your spouse or friends.

Broken promises:

Some bosses make foolish promises. The promise of a promotion, for example, is a foolish promise. The future is uncertain.

Don’t stay with a job because you were promised a promotion. If the only reason you’re staying is the promotion, seek a promotion elsewhere. If you find an opportunity, TAKE IT.

You may say, “But I like my company.”

Decide what you like more, a promotion or your current company.

Understand that your boss probably made the promise sincerely. This goes back to item #4 on the ‘Do’ list. If your boss is intentionally deceptive, find a new boss.


Finally, I just finished The Courageous Follower by Ira Chaleff. Ira has studied followership over 20 years. His work is powerful. He has a guest post scheduled for this Wednesday here on Leadership Freak. His latest book is Intelligent Disobedience.

What suggestions do you have for Ready to Challenge Up?

*I suspend my 300 word limit on weekends.