Highly Successful Professionals Use Five Proven Strategies to Handle Difficult Bosses, Says Career Expert

Working under a boss who insists on approving every detail can be exhausting, but career expert Melody Wilding says that employees need not despair. Wilding, an executive coach, human behavior professor, and author of “Managing Up: How to Get What You Need from the People in Charge,” has spent over 15 years coaching leaders at major corporations including Google and Amazon.

Drawing on her experience, she outlines five evidence-based strategies that professionals can use to work effectively with controlling or overly demanding managers—without burning out or compromising their performance.

Wilding emphasizes that while such situations can be challenging, they are also manageable with the right communication and mindset. “I’ve seen firsthand how difficult it can be for people to navigate the challenges of working with a control freak,” she notes. “I teach them simple strategies to make the situation work in their favor — without leaving them exhausted and frustrated every day.”

A work team | Source: Pexels

1. Run with Rough Drafts

Instead of spending days perfecting a project before sharing it, Wilding recommends submitting an early version for review. “Do a first pass and say, ‘Here’s what I’ve put together so far. It’s a bit rough around the edges, but I wanted to capture the core ideas and structure so we can shape it into something outstanding,’” she advises. This approach satisfies a boss’s need for involvement and saves employees from unnecessary overwork.

2. Reinforce Their Authority

To reduce tension and gain cooperation, Wilding suggests affirming the manager’s position. Employees can use phrases like, “What we ultimately do is up to you,” or, “I’ll share my two cents so that you can make the final decision.” Presenting ideas as questions—such as “What if…” or “How about we…”—can also be effective. Wilding explains that this method draws on the “question-behavior effect,” a psychological principle that increases a person’s sense of control when they are invited to respond to inquiries.

3. Overshare to Build Trust

Providing regular updates can ease a boss’s need for oversight. “Send a breakdown of items you plan to tackle each week every Monday or shoot over a quick heads-up if you’ll be late to a meeting,” Wilding says. She recommends phrasing updates positively, for example: “To keep you in the loop about our progress, I’ve prepped a weekly status memo with a snapshot of recent developments.” Proactive communication helps prevent misunderstandings and reduces the need for repeated explanations later.

A work team | Source: Pexels

4. Get Ahead of Criticism

Anticipating feedback before it arrives can turn critique into collaboration. Wilding advises initiating discussions about upcoming work: “I’m planning to approach [X task] this way. Do you have initial thoughts?” When a boss offers corrections, she recommends the classic improvisational technique “yes, and…” — acknowledging their input while integrating one’s own perspective. For example: “Yes, I appreciate the need to be more concise in my emails, and I believe a brief context section is still beneficial for clarity.” This approach shows receptiveness while subtly asserting one’s expertise.

5. Ask for the Praise You Need

Through these five practical steps, Wilding argues that employees can transform a difficult working relationship into a productive partnership. Her message is clear: while managing a demanding boss is never easy, it is possible to do so strategically and successfully.