My Boss Doesn’t Like Me

Problems with aligning

Problems with Alignment in the Team

Some relationships just start out rocky. Maybe they misread a facial expression, or perhaps they just had a huge argument before they left the house that morning, and the residue is still on their attitude towards, well… everything. It seems that at certain points in life, we have all had that unfortunate experience of working with or for someone who just doesn’t seem to have any bit of desire to accept us, much less like us. However, in the business world, and especially in the workplace as an Administrative Professional, when these situations arise, it is a test of our patience as well as our skill set.

As an Administrative Professional, there is a certain responsibility to finding ways to deal with and solve difficult situations. Whether it is a double-booked event, people not showing up to meetings on time, dealing with rude vendors, or just keeping tabs on the office inventory, Admins are always expected to be on top of it. While this is quite manageable in nearly every other situation, having to convince your boss that it would be to their advantage to try to like you can be a little overwhelming. Here are 5 Points of Wisdom (POW) to identify and deal with those difficult circumstances.

POW #1 Watch for Warning Signs

Sometimes you won’t need any assistance in deciphering this attitude flaw, but even when it isn’t apparent, you should always be cognizant when you are in a new role for a new boss. So, what should you be on the lookout for? How can you tell if trouble is brewing? Here’s what you’ll notice.  If they start to lose trust in you, they’ll become very prescriptive in their guidance—they may say, “Make sure you do x, y, and z as you are completing this project.” or “Don’t book any travel until I approve all the arrangements first.”

They’ll start checking in sooner and more frequently to see how you are progressing on assignments: “Give me a daily status update on all your projects.”  If they start to think the misfit is serious, you’ll observe them correcting what you say or how you say it. They won’t let you finish with your status update before jumping in and telling you you’re doing it wrong —a very bad sign. You will no longer be invited to certain meetings you used to attend. At this point in your employment it’s too late. If you get a negative performance review, you are probably close to getting fired. If fortunate, your employer will offer a performance improvement plan. But even if you turn around in 30-90 days, they will still find fault and you may well be gone.

POW #2 Act Quickly

Pay attention to that first time the boss’s guidance feels very prescriptive or more precise than you expected. You’re still in what we call the “forgiveness zone,” which means you can regain their trust through quick corrective actions. Ask them whether there was something you did recently that triggered their feedback. Have them explain what they would have done differently in that situation. Listen carefully. They are describing their expectations about the right approach to how they want things done or the real priority they want you to focus on.  


Adapt your workflow to meet their expectations and make sure to demonstrate, in ways that are highly visible to them, your new behaviors or your heightened emphasis on their priorities. This may seem unwarranted to you. But it’s important to remember that if you want to succeed in your job, it will always be your responsibility to adapt to your boss.


POW #3 Discover Your Boss’ Priorities

So, what’s the most likely cause of a perceived misfit? It usually starts with one event. You likely hit one of your boss’s “hot buttons”—their critical performance priorities or style imperatives. For one boss, maybe you didn’t provide timely updates on project status. For another, maybe you met the criteria for the offsite, but they expected you to exceed it.  Perhaps you spoke out of turn at a meeting – something they consider a sign of disrespect. Or maybe they wanted a simple one-page itinerary and you provided a five-page itinerary with details he didn’t want or need – and they interpreted that as a sign you didn’t listen or, worse, that you can’t get out of the weeds. Maybe you simply didn’t keep them informed of an important set of events that was unfolding, and it took them by surprise.


As soon as you start working with a new boss, one of your priorities should be to understand their buttons. Ideally, you should ask them directly: What are your absolute priorities for your performance and mine?  What criteria should I always consider in decision making? When it comes to style, you should ask: How would you prefer I work with you? What do I need to avoid doing that would really bother you? Find out how they’d prefer to work with you, such as how often you two should meet, whether they prefer formal or informal meetings, if you should always be reachable by email and cell, and how they will measure your performance.


POW #4 Observe Your Boss’ Non-Verbal Cues

As an Administrative Professional, you are sometimes asked to be a mind-reader. How to become a mind-reader of course is to stop talking, listen and observe. Not every boss will convey what’s important to him or her publicly.  So, in addition to asking directly, watch their actions in meetings. Observe what annoys them. Observe what they praise. See which individuals engage them well and ask yourself what it is about them that the boss finds so engaging. Look at the boss’s style of running meetings and the level of candor and pushback between the boss and the meeting participants.  Look at their office – what does it tell you about their lives, their needs for organization, the demands on them, and their preference for scheduling versus spontaneous interactions. If the boss had a previous administrative assistant, ask that person what really irks the boss – they’ll know better than anyone.


You should wait to solicit feedback on your behavior until you’ve worked with your boss for a little bit. We’d recommend doing so immediately at the end of a meeting where you played a major role.  Ask them directly, “What did I do well and what can I improve upon next time?” The most developmentally focused bosses will usually give you concrete guidance about what they want to see from you. Ineffective bosses may not. With them, you’ll have to pay far greater attention to their non-verbal behavior for that feedback.


But if you don’t ask directly, your boss usually won’t tell you the first time you trigger a hot button. They may assume it was unintentional on your part, but you’re now on notice – you just don’t know it yet. The second time you trigger them, however, the boss will begin to doubt you. Certainly, by the third time, you’ll hear from them. But at this point, you are now identified as a problem in their minds.


So, in those early days with your boss, ramp up your observation skills. The first time you trigger one of their hot buttons they’ll send you a non-verbal signal.  You’ll see a raised eyebrow or grimace or hear something like “I personally wouldn’t have done it that way.” Do not ignore that statement — have a conversation about it afterwards.


One quality that distinguishes individuals with successful careers is an attitude that there isn’t a boss you can’t win over – you must understand why they act the way they do.  Remember that all bosses want to be successful in some form or fashion. Your mission is to figure out how to help them succeed.



Meet Joanne Linden, CPS, CEAP, CWCA, President and Master Trainer, who was an administrative professional herself, and her teaching style is grounded in authentic office experience. AdminUniverse™ can help you improve yourself, widen your skill set, and advance your career.