You will eventually disagree with your boss about something – maybe his project or idea won’t produce the results he suggests or his managing style will rub you the wrong way – but the real question is: should you bring it up?

Employees that 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 was a disagreement for me, in terms of the communication and managerial style used, 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).

So, to know if you are pursing the right issue and, to learn from my own mistakes, ask yourself these three questions next time you find yourself disagreeing with your boss:


 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 with that company.

Recognize which issues are important to you by identifying your own personal stake in the matter (i.e., whether its personal or not) and the reason(s) why you disagree with your boss.

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 over only your personal feelings.

I once worked with a coworker that would use water cooler 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!


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 has a business benefit added to it 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 an established company process, behavior or norm, 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 better efficient program, then you probably won’t get much traction. When in doubt, ask colleagues.


If you answer “no” immediately to the question “Is my boss open?” 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. This way you don’t risk potentially putting your boss in the hot seat while “respecting” his position of authority.

That’s what I had to do when I wanted greater autonomy to work on a project without my boss micromanaging me. I waited till 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 to him why it increased my own efficiency, he understood me and gave me the leeway I desired.

Bottom Line: As with any battle, being strategic and correctly preparing beforehand can be the difference between life and death; and, while it’s hopefully NOT that perilous of a situation in your workplace, it only works to your benefit to forge an effective relationship with your boss where disagreements are well-received and your opinions respected. So next time you find yourself in disagreement with your boss ask yourself these questions.

October 4, 2016

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