Are You a Pushover Boss?

Learn how to be more assertive without alienating your employees with a few tips from performance coach and licensed social worker Melody Wilding.
Do you find yourself doing more work than you think you should because you don’t want to tell someone else to do it? (Photo: KieferPix/Shutterstock)

You’ve just returned to work from a 30-minute break to find that your employee has left early. That same employee is late almost every day, takes two-hour lunch breaks and frequently ropes in other employees to perform tasks that she should be doing herself. She’s rude to customers, messy, lazy and forgetful.

And yet, each time she missteps, you let it slide, don’t you? You’ve given her chance after chance to get her act together, and she continues her unprofessional behavior.

Come to think of it, she’s not the only one. Several other employees, subcontractors and partners of yours have let you down. So has your delivery driver, your landlord and your babysitter. Why does this keep happening to you? Is it just bad luck? Do you somehow attract irresponsible people?

It might not be conscious or intentional, but chances are, it’s because you’re a pushover. You don’t want to offend or upset the people around you, so you end up pulling double duty to cover for others. You don’t want to fire a longtime employee, so you forgive her when she apologizes, even though you know she’ll do it again.

Related: Are You a Jerk Boss?

It’s a totally understandable and utterly human reaction to want to please others. But the key, according to performance coach and licensed social worker Melody Wilding, is doing so without harming your small business, your relationships or your own well-being.


“Building a successful business or career takes a lot of self-respect and requires having a thick skin and knowing when to say no.” – Melody Wilding, performance coach (Photo: Melody Wilding)

Wilding, who teaches human behavior at Hunter College in New York, has identified four key steps to achieving this:

Identify your own habits

Think about your average day. How much time do you spend simply reacting to other people’s demands? Do you reflexively say “yes” the moment one of your employees makes a request? Do you find yourself doing more work than you think you should because you don’t want to tell someone else to do it?

Answer those questions internally, Wilding said, and own those answers.

“Recognizing what you’re dealing with is the first step to helping you identify and manage trouble situations in the future,” she said.

Related: The Friend Zone: Boosting Sales by Focusing on Relationships

Write a to-don’t list


Writing lists can be a great tool in helping you stick to your boundaries. (Photo: areebarbar/Shutterstock)

You’ve probably written a to-do list at least once in your life. But have you ever written a to-don’t List? This, Wilding explained, is a list of anything that does not align with your top priorities. From there, you can focus on achieving your goals without distractions or derailments.

“For example, if increasing revenue by 10% in the next quarter is your top priority, don’t agree to take on a pro bono project right now to ‘diversify,’” Wilding said. “If you’re looking to gain experience managing junior employees, anything non-essential that takes time away from working directly with your reports should be on your ‘to-don’t’ list.”

Ask for help

Delegate, delegate, delegate. You might think you can do it all, but you can’t – or you wouldn’t have adopted so many pushover tendencies. Your personal life wouldn’t be suffering, and you wouldn’t be wondering why you started your own business in the first place.

“Ambitious self-starters often get caught up on multiple projects, but if you don’t start passing off certain tasks now, it will only overwhelm you when it becomes too much,” Wilding said.

Instead, she advised starting with anything that comes across your desk that’s on your to-don’t list and see if there’s someone who may be better suited to take it on.

Related: How to Make Better Business Decisions

Practice saying no


Flex those self-respect muscles. (Photo: Kotin/Shutterstock)

This is the hardest step, Wilding acknowledged, but the most important one in learning to manage boundaries. “Next time you’re asked to take on a project that falls outside the boundaries you’ve identified, you need to say no and stick to it,” she said. “Not the next time it happens, not most of the time, but right now.”

If you’re really struggling with this part and you fear saying no would be too destructive, try to negotiate – for example, with an employee who’s making an unreasonable request. Offer a compromise, rather than fully picking up the slack.

“Building a successful business or career takes a lot of self-respect and requires having a thick skin and knowing when to say no,” Wilding said. “Fundamentally, it’s about learning to better set and manage relationship boundaries and flexing your self-respect muscle.”

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