3 Questions To Ask Yourself Before Disagreeing With Your Boss

The art of picking your battles wisely and getting your voice heard at work

By Bryant Galindo

You will eventually disagree with your boss about something. Maybe his project or idea won’t produce the results he suggests or her management style will rub you the wrong way. The real question is: Should you bring it up? Employees who speak up usually thrive more in their workplaces, but not every disagreement is worth your time and energy (or that of your boss).

Take it from me. I once worked in an environment where going with the flow meant taking whatever was commanded of you and running with it, securing the intended result as fast and as cheaply as possible. What I disagreed with, in terms of my manager’s communication and managerial style, was just “company culture.” If I were to remain and thrive, I knew I had to pick my battles wisely and plead my case convincingly. Not all issues were won, and some even worked against me (I would get extra work all of a sudden).

The next time you find yourself disagreeing with your boss, ask yourself these three questions first:

1. Is it worth it?

Not every battle is worth the fight and, in the same way, not every workplace issue is worth being brought up, especially if you want to advance in the company.

Recognize which issues are important to you by identifying your own personal stake in the matter and the reason(s) why you disagree with your boss.

Post and graphics are adapted from the Workplace Collaborations blog and republished here with permission.

Picking your battles means that you should know exactly why you are disagreeing with your boss, basing that judgment on something concrete that impacts the workplace, the team, and not just your personal feelings.

I once worked with a coworker who would use watercooler time to vent about issues she had with her aging organization, which quickly became tiresome for me and everyone else around her. I soon realized her comments weren’t based on any substantial grievance but simply her own feelings of dissatisfaction over never having reached the professional level she had wanted.

Imagine bringing up an issue to your boss to only find out later your own personal feelings (and nothing he did) was the real issue. That could be an embarrassing mistake!

2. Is there a business benefit?

Your boss isn’t going to change his mind and suddenly accept what you say without some support for your position. This could be a fact, a statistic, or some alternative he hadn’t thought of, so long as it benefits the business in a way that will quickly make your boss more receptive to hearing what you have to say.

Sometimes having only one business benefit is enough to convince a boss but other times, especially if it’s related to an established company process, you’re going to need more than one.

If you want to suggest a better CRM tool for your organization but can’t back that up with some numbers as to how it could potentially be a cost-saving measure or increase efficiency then you probably won’t get much traction. When in doubt, get feedback from colleagues first.

3. Is my boss open?

If your answer is “no,” then (even if you may be right) it’s going to be a serious hassle convincing your boss otherwise. Most times, I have found bosses are a lukewarm mixture of open — receptive to some things but closed to others — and it’s up to you to figure out how to present the issue.

If your boss is the type that regularly invites comments in company meetings, but can be quite unapologetic, then it’s probably in your best interest to bring up the disagreement one-on-one instead of in front of everyone. That way you respect your boss’s position of authority without risking putting him or her in the hot seat around others.

That’s what I had to do when I wanted greater autonomy to work on a project without feeling micromanaged by my boss. I waited until the meeting was over and I could talk to him one-on-one. He had a condescending, “I know I’m the boss” attitude but, thankfully, because I had approached him directly and respectfully presented my case as to why it would increase my own efficiency, he understood and gave me the leeway I desired.

The bottom line is this: As with any battle, being strategic and correctly preparing beforehand can be the difference between life and death; and, while it is hopefully not that perilous of a situation in your workplace, it works to your benefit to forge an effective relationship with your boss where disagreements are well-received and your opinions are respected. Next time you find yourself in a disagreement with your boss, you’ll know exactly what to do.


Originally published on The Well, Jopwell’s digital magazine. Jopwell is the career advancement platform helping Black, Latino/Hispanic, and Native American students and professionals through all career stages. Sign up to unlock opportunity.

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