Highly successful people do 5 things when dealing with a difficult boss, says career expert: ‘Don’t despair’



Working for — or alongside — someone who insists on reviewing every detail and requires approval for each step can test anyone’s patience. But don’t lose hope.

As the author of Managing Up: How to Get What You Need From the People in Charge, a professor of human behavior, and an executive coach who’s spent the past 15 years advising leaders at Google, Amazon, and other Fortune 500 companies, I’ve seen firsthand how challenging it can be to work with a controlling manager.

The good news? With the right strategies, you can turn a difficult dynamic into a productive one — without feeling drained or defeated.

Here are five proven techniques to make working with a demanding or controlling boss easier — and even beneficial:


1. Share Rough Drafts Early

Instead of perfecting a deliverable before sharing it, start with a solid draft and say,

“Here’s what I’ve put together so far. It’s still in progress, but I wanted to outline the core ideas and structure so we can refine it together.”

This approach gives your boss a chance to weigh in early — which they’ll appreciate — and saves you from spending excessive time perfecting something that may need reworking anyway.


2. Reinforce Their Authority

Small verbal cues can make a big difference. Use phrases like:

“Of course, the final call is yours,” or, “I’ll share my thoughts so you can decide what works best.”

This subtly acknowledges their position while easing their need for control.

When presenting ideas, frame them as questions — for example:

“What if we tried…” or, “How about approaching it this way?”

Psychologically, this “question-behavior effect” gives your boss a sense of agency while still allowing you to contribute meaningfully.


3. Proactively Share Information

Provide regular updates before your boss has to ask. For instance:

“To keep you in the loop, I’ve prepared a weekly status memo summarizing key progress and next steps.”
Or:
“I’m confirming we’re moving ahead with [X]. Please let me know by Friday if there are any changes.”

Consistent communication satisfies their desire for oversight and reduces the likelihood of micromanagement later.


4. Anticipate and Neutralize Criticism

Get ahead of feedback by inviting it early:

“I’m planning to approach [X task] this way. Do you have any initial thoughts?”

When your boss offers corrections, use the classic “yes, and” technique from improv:

“Yes, I see the importance of keeping emails concise, and I think including a short context section could still help newer team members follow along.”

This approach acknowledges their input while tactfully incorporating your perspective.


5. Ask for the Positive Feedback You Need

Everyone benefits from knowing what they’re doing well. You can say:

“I value your feedback on areas for improvement. It’s also helpful to hear what’s working so I can build on those strengths. Would you be open to sharing both?”

This encourages balanced feedback and reinforces a more collaborative tone in your relationship.


You may not be able to change your boss’s personality, but you can manage the relationship strategically. By anticipating their needs, reinforcing their authority, and maintaining open communication, you can protect your energy — and even thrive — while working with a controlling leader.


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