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Dear Dan – I Feel Caught Between the Boss and Fellow Employees

Dear Dan,

I wonder if you could provide me some guidance with what I call “The curse of the middleman.” I’m a member of two teams. The team of leaders that run our organization, and the team of people that report to these leaders.

A leader on my team is often hurt when employees approach me with questions, instead of going to them directly. The irony is this same leader tells employees that I am a leader in our organization and to utilize me as a resource.

I strive to build strong relationships with employees, but the success of that work is causing me to fail in another area. At times, there is concern from employees that if they approach the leader, they will get an immediate smack with a bat. Some have been smacked enough, they’ve learned not to approach.

I don’t want to violate the relationships I’ve built, but I’m trying to navigate these waters. 

What advice would you give?


The Middleman

Dear Middleman,

Like you, people usually try to do the right thing. It’s always disheartening to have good intentions misjudged. This happens more frequently than you might think. Intentions are invisible. Behaviors are all we see.

We are judged, not by our intentions, but by the intentions others impose on us.

Biggest challenge of feeling misunderstood:

The biggest challenge you face isn’t a fearful boss. It’s loss of enthusiasm.

Loss of enthusiasm becomes discouragement. Eventually, we give less than our best. Winston Churchill said, “Success is the ability to go from one failure to another with no loss of enthusiasm.”

Tighten your belt and keep doing the right thing with enthusiasm.

Doing the right thing matters most when you’re  misunderstood or underappreciated.

The higher you rise in an organization, the more you will be misunderstood. The best you can do is apologize when appropriate and press forward with unaltered enthusiasm.

Adapt to the leader:

People who don’t adapt to the leader always struggle and often flounder.

Perceived threat invites fearful bosses to attack like caged animals. Forget about instilling confidence in a boss who feels threatened, but don’t turn a blind eye either.

  1. Don’t tell the leader, “You seem threatened by my relationships.”
  2. Seek advice from your leader. Ask, “What are some ways to respond to co-workers who come to me with their concerns?” Eliminate any resentment or resistance in yourself when you ask for input. You may or may not receive useful advice. It doesn’t matter. You asked.
  3. Show respect to your leader in public ways. Notice positive qualities. Honor successes.
  4. Encourage co-workers to go to the leader, even if they feel smacked down. Nothing good comes from undermining your boss, even if they seem inconsistent or oversensitive.
  5. Send a message to the boss. Ask your co-workers to tell the boss you sent them for input. Give them words like, “I brought this up with ‘the middleman’ and he suggested I should bring it up to you.”

Get out of the middle:

It might be unintentional, but you are the middleman because you put yourself there.

  1. Release self-imposed pressure to solve other people’s problems for them.
  2. Reject any internal pressure you feel to speak for others. Speak for yourself and help others do the same.
  3. Refuse to build relationships for others. Help others build their own relationships.

4 questions for coworkers:

Use questions frequently. Offer advice reluctantly.

  1. What kind of relationship do you want with the boss?
  2. What are some possible ways to build a strong relationship with the boss? (Brainstorm ideas. Don’t offer THE solution.)
  3. What are YOU willing to do to move toward that relationship? (Watch your pronouns. Don’s say, ‘we’.)
  4. What’s something useful to say when you feel smacked down?
  5. How can I help? (Be sure to reject any subtle attempts to make you responsible for things THEY need to do.)

Facing the future:

As a rule, the person who gets in the middle – without also having positional authority – loses.

Leaders say they want the truth, but often bristle when they hear it.

Make it a personal challenge to build the strongest possible relationship with the leader. Build a relationship with the leader that allows constructive feedback.

High-level leaders often help others navigate relationships. Use this situation to learn what works for you.

Don’t take sides.

Always act in the best interest of your organization.

Find a new position if you feel you are sacrificing your future.

You have my best,


What would you like to adapt about my suggestions?

What suggestions do you have for the ‘man in the middle’?

Note: I relax my 300 word limit on Dear Dan posts.

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