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As things go, one of the more difficult things to do is to confront or push back on the boss.  A lot of people won’t do it because they fear it would cause them to get fired or minimally get on the bad side of the Boss

While it’s an understandable concern, its also unfounded.  Your brain is making up false assumptions appearing as real (F.E.A.R.).  Unless you know without a doubt that your boss is too sensitive for well-executed confrontation, you need to add this to your toolkit.

Let’s first look at reasons why Standing Up to the Boss, can be a good skill:

a) The Boss isn’t always right 

No one is ever 100% right all the time. On those occasions when the Boss is about ready to drive you, or others over the metaphorical cliff, you are obligated to say something.

b) Self-respect 

You teach people how to treat you and if you allow the Boss (or anyone) to trample on your values, you are teaching them to disrespect you. Also, they will respect you for standing up for yourself.

c) Unaware 

You can’t assume the Boss knows all the facts or factors impacted by a decision. The Boss may make a decision that has consequences that they simply don’t know or understand.  The world is so complex these days that you can never fully grasp all of the implications of some decisions.  Do the Boss a favor and let them know.

d) Not a mind reader

If you were somehow ignored, disregarded or otherwise personally impacted by something the Boss did: you might be upset and they may be completely clueless.  This is not the time for passive-aggressive comments.  Those are unhelpful and often more offensive then coming right out and airing your grievance. 

Also, many people are very unaware that their behavior might be taken negatively so you will be helping the Boss to develop greater insight on their own actions.

Let’s look at things you can do to confront the Boss and keep your job:

i) Keep it private

One of the reasons why anyone including the Boss will think you’re a jerk is to air your concerns in public. Always take any confrontation into a private setting.  It will be safer for you both to fully explore whatever concerns you have if they aren’t trying to “save-face”.

ii) Keep it unemotional 

Being emotional when you confront them will only set up the situation to go poorly. All humans have an innate tendency to mirror the person they are with.  If you approach them in a red-faced rant, you will be met with the same or worse.  Do your confronting when you can be level headed.

iii) Don’t make it personal 

Don’t do or say anything that disparages the Boss. Focus totally on whatever the issue is and leave personality out of it.  Also, don’t make the assumption that whatever your issue is was done specifically to negatively impact you.  Even if a decision did negatively impact you, the decision was made for different reasons.

iv) Focus on the issue

Approach the Boss as if you are there to solve a problem. If you focus on problem solving, you will greatly avoid the Boss getting offended.

v) Be specific 

You must present the issue in very specific terms. If you are too general or vague, you have nothing to solve and cause more confusion that you intend.

vi) Talk about impact 

If there is a problem that impacts you or the business, make sure to outline what the impact is to whatever problem you bring to them.

vii) Stay upbeat 

It helps to take a positive view of working with the boss to create a solution.

viii) Accountability 

Make sure that when you have reached solutions that you build in follow up to keep you both accountable to each other in the process.

ix) Pick your timing and your battles 

Just like with anything else you know timing can be everything. Don’t do something like confronting the Boss when they are ready to head out the door or in the middle of a crisis.  Also, keep in mind that not all issues are worthy of the confrontation compared to other issues you do want resolution on.

Make the Boss your partner.  Take the perspective that you are both there to get the work done and enjoy it at the same time.  If you can develop this skillset, you will be well regarded by every Boss you will have.

Brought to you by Dorothy Tannahill-Moran at Introvert Whisperer  .  Dedicated to your professional success.

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Brought to you by Dorothy Tannahill-Moran. Devoted to your professional success by providing unique, actionable career advice at Introvert Whisperer .

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