As an administrative professional, you are expected to be a communicator, liaison, accountant, courier and sounding board, just to name a few of the responsibilities involved with assisting the corporate world’s most important executives.

sparring with your boss

As a gatekeeper, it is your duty to maintain perspective with regard to duties assigned, set realistic expectations for deadlines, and understand what truly can and can’t be done at your boss’s request.  While assistants aim to please at every turn, sometimes, remaining on your boss’s side is simply not the best option.  However, disagreeing with your boss definitely takes a certain amount of finesse, and it’s important to tread lightly, even if you think you’re right; remember, at the end of the day, your boss is your boss.

Step 1: Build a Credible Relationship

You would never walk up to a stranger and tell them you didn’t think the color of their shirt was unflattering, but you wouldn’t hesitate to tell your best friend the same.  Likewise, you must be sure to build a relationship with your employer before you deliver any harsh truths.  At the same time, remember that your employer is your boss and not your best friend, so find a steady middle ground to deliver any unfavorable news.

Step 2: Ask Permission to Give Feedback

Imagine you’ve decided to go to Italy.  You’ve wanted to go to Italy, you’re excited about going to Italy, and you’re going to Italy.  You tell your friends you’re going to Italy, and suddenly, one of them gives you their unsolicited opinion and essentially ruins your excitement.  Similarly, it’s important to know when your opinion will be received openly.  Do not assume your boss wants to know or cares about your opinion on a plan or procedure, especially if the plan or procedure is thoroughly fleshed out.  It’s best to tread lightly and ask outright if your opinion is welcome.

Step 3: Be Clear with your Disagreement

When you don’t agree with a policy, procedure or decision that has been made, be clear with why you don’t agree with it.  I don’t like that is not a reasonable remark.  If you disagree with a deadline, explain why you feel the project needs more or less time to complete.  If you disagree with a procedure, highlight the exact step(s) you feel are/are not necessary.  Simply stating that you like or dislike something adds absolutely no value to a project, and does not give you the credibility that, as a professional, you deserve.

Step 4: Lead with Value

When in doubt, always start a dissenting opinion with a positive statement, and always offer a solution.  For example, say, “I understand this project is important, however, to me, this approach (solutions) is a bit clearer. Beginning the conversation with a positive and offering a solution right away shows a proactive approach and can be a really effective way of getting your point across.  You have stated that (positive) the project is important but that (negative) you’d like to discuss other, potentially better solutions.  Offering a solution is always important when you don’t like or disagree with something

Step 5: Know When to Back Down

Just like personal relationships, professional relationships are about knowing when to pick your battles.  As strongly as you may feel that the color for a poster is incorrect, or that a different word choice would be more effective, or that your time would be better spent on a different project, it’s important to understand when to just let it go.  At the end of the day, there’s one person who calls the shots: your boss.  Read their body language, tone of voice and mood, and try to quickly judge whether you’re pushing boundaries for better or worse.

As your boss’s confidante and sounding board, it’s extremely important to lead an open and honest relationship with him/her, but that relationship has its limitations.  Expressing a dissenting opinion takes tact and professionalism, just as many of the other responsibilities within the administrative realm do.  If you use discretion, diplomacy, and awareness when disagreeing with your boss, you will worry less about the consequences of what you say.

Find Your Executive Assistant Now

If you're interested in hiring an executive assistant, personal assistant, office manager, or other support staff, we can make finding the perfect candidate fast and easy. Contact us to get started.

Find My Assistant