Dealing with a Difficult Boss ( or Client )

Written by
Michael Wells

Dealing with a Difficult Boss ( or Client )

Written by
Michael Wells

Dealing with a Difficult Boss ( or Client )

Written by
Michael Wells
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"I have a difficult boss... no matter what I do, it's not good enough. I'm continually challenged, called-out on good work, asked to re-do it. It feels impossible to impress them, or even to satisfy their requirements. How should I handle this?"
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No matter whether you work for someone, or run your own business, difficult work situations with difficult bosses and clients are a fact of life.

There are a lot of reasons a boss or client might be difficult to work with, so it's essential to start with some deep reflection.

Know Who You're Working With

"Did I drop the ball here, or under-deliver on my responsibility in some way?"

"What expectations does my boss / client have, and are they reasonable?"

"How does this person deliver their complaints and criticism? Is it respectful, or abusive? Is it directed at the problem [the work], or at people? Is it designed to remedy the problem, or to provoke emotions?"

"Does this person give compliments equally, when they are pleased with work that has been delivered?"

"Do they treat others in this same way that they treat me?"

These questions will help you analyze and identify the type of situation and person you are dealing with.

I classify difficult bosses and clients as being in one of 3 categories;

  1. Challengers. People who demand a certain level of quality, both from themselves and others. They are difficult in that they are demanding, and can push you to your limits of capability.
  2. Dreamers. People who have completely unrealistic expectations, and usually no understanding of what they are demanding in work deliverables.
  3. Abusers. People who use complaints and criticism abusively, as a way to suppress others and validate themselves. Largely this is about control and power, through suppression. This is a classic bully.

Each situation and type of person has a different root cause, and demands a different approach to resolution.

Dealing with Challengers

"We can do it!"

Challengers validate through difficult achievements.

Challengers are a great category of people to work with, even though you may feel pushed to the limit of ( or beyond ) your capabilities.

However, they can make projects far more difficult than needed, deadlines and budgets tighter than necessary, and be exceptionally demanding quality and over-emphasize minor details.

  • Make certain that you did your part 100%. Where could you have done better? Use this as an opportunity to improve your skills.
  • Be honest about your skill level and concerns on delivering to their expectations.
  • Ask for help, guidance, training, etc when needed.
  • Learn to say NO, to the most unreasonable demands.
  • But when you're able, demonstrate your willingness to face the challenge, provided they understand your concerns and give you the full support you need.

Dealing with Dreamers

"Wow, wouldn't it be cool if ..."

Dreamers validate through ideas more than actions or results.

They have a vivid imagination and a strong fantasy life, and in work this translates to giant project specifications with lots of expensive-but-meaning

Dreamers are great fun to work with, provided that they are well directed and carefully managed. They are enthusiastic supporters of the project and that means they are motivated to support you and provide you with the resources that you need.

Key tips;

  • Manage expectations.
  • Formally document requirements, so they know clearly what's going to be delivered under the current budget and deadlines, and what's "phase 2".
  • Learn to push back, and even to say "no." Often when people are dealing with a client or boss, they misunderstand the relationship as "I must do what they want..." but if you're the expert here, then you're expected to identify the areas of a project's requirements that are unrealistic. Help the client to understand the costs, risks, and consequences of what they are asking for, and to find alternatives for things that are important to them.
  • Don't allow scope-creep. Dreamers tend to continually add new requirements mid-project. Document these, but...
  • Organize projects into phased deliverables. Protect your ability to release working results by phasing them.
  • Stick to budgets and deadlines for your releases, even if a release never becomes public. Then, adjust course for the next set of requirements, dates & budget.

Dealing with Abusers

"You didn't do what I told you to."

Abusers validate through maintaining superiority by controlling and diminishing others.

They don't care as much about a successful project, as they care about control, power, and making themselves look "good."

This is a no-win situation for you, because the harder you try, the more fiercely you'll be targeted for suppression. The only way to win is not to play.

Key tips;

  • Just don't work with these people. Fire their asses... Life is too short and you deserve better. Be picky about who you work for, otherwise it's impossible to do your job well.
  • Cover your ass. Document and track everything. Log dates, discussions, deliverables. Consider using email read-receipts and sign-offs to ensure your deliveries are recognized.
  • Go above and beyond. Deliver more than expected, and make sure deliverables are excellent.
  • Don't take the criticism personally. Abusers are classic bullies, motivated to make your life difficult. It's a dash of sadism, coupled with a need for validation by trying to establish superiority. The abuse isn't about you, it's about their own insecurities and need for validation.

In the right circumstances, it may be advisable to involve another person in authority that you can trust. For example, if your client is difficult, involve your boss so that they can monitor the situation, help manage expectations and support you effectively.

If your boss is difficult, then - as a last resort - you might be in a position to go to their boss. Generally, you should consider this a career ending move, because it often is... however in the right circumstances that's exactly the right card to play.

Although it's rare, It's possible for someone to be in more than one category, so be mindful of the type of people and situations that you're dealing with.

The Golden Rule

"Avoid enabling disruptive leadership patterns."

This is essential to understand.

All 3 personality types share a common feature which we often miss- which is that "solving the problem" will not satisfy the person you're working with.

  • Challengers will simply increase the challenge, because it's what excites them and you are enabling them to challenge you more.
  • Dreamers will dream up something new, because it's what excites them and you are enabling them to dream further.
  • Abusers will find new ways to diminish and abuse you, because it's what excites them and you are enabling them, by scrambling to meet their demands.

In all 3 situations, doing exactly what they ask for - without question - simply enables their disruptive leadership pattern.

Your most effective tool is to learn to wield the word "No," and it's cousins...

"I'll need more resources and budget."

"We'll need to extend the deadlines."

"This will introduce a lot of complexity / instability / weakness / support cost into the product."

"I can add this to the requirements for Phase 2."

"We'll need a specialist."

I find it helpful to think of the Company, not the person, as my client. My job is to deliver a good, working project, even if the person who assigned me that project is disrupting my ability to complete it.

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First published on 
. Last updated on 
May 8, 2020

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