Dear Dan: My Boss Feels Like a Limiter

Dear Dan,

I’m wondering how to push through when I have a challenging leader?

My boss gives me space to do what I need to do, but is very unpredictable in approach, response, and feels like a limiter to me being able to lead my own group.

Anyways…you are always a wealth of resource & help so just wanted to reach out.


Feeling Limited


Dear Limited,

Your email reminds me that lousy bosses make performance difficult and satisfaction unlikely. (Atlantic)

Here are a few points of reflection. I warn you that I’m focusing on you more than your bad boss.

#1. Build the strongest possible relationship with your boss.

Influence begins with relationship.

On a scale of 1:10, how strong is your relationship with your boss? What might you do to take that relationship up a notch?

One a scale of 1:10, how confident is your boss that you have their best interest at heart?

How have you communicated your commitment to seek your boss’s best interest in the last week?

#2. Commit to character development.

How might you re-frame this situation as a learning experience?

  1. How might learning to navigate a lousy boss make you a better person and leader?
  2. What positive qualities is this situation calling you to exhibit or develop?
  3. How does learning-through this experience expand your potential?
  4. How might you include your boss in your character/skill development?

I hope this is the last frustrating boss you ever have, but chances are, there are a few more in your future.

#3. Notice when your bad boss is bringing out your worst.

It doesn’t help you, your team, or your future to let a negative boss turn you into a negative person.

#4. Look in the mirror.

How might you have some of the same frustrating qualities your boss has?

Sometimes our frustration with others is frustration with our self.

#5. Speak up in the moment.

If you give your boss constructive feedback, do it in the moment. Delayed feedback is like spanking a dog the day after they made a mess.

Tell your boss the impact of their actions.

“It seems like yesterday you said, ‘xyz’. Today it seems like ‘abc’. What am I missing?” (I wouldn’t say this unless #1 is fully in the bag.)

I realize I’m dumping the load on you and I know it can be a heavy load.

I wish you well,


What suggestions do you have for Feeling Limited?

Added resources:

The Art of Coping (Positive Psychology)

How to Handle a Bad Boss (Forbes)

How to Deal with a Bad Boss (NBC)