Ask the Career Consultant: How to Not to Annoy Your Boss

Dear Lisa:

I'm a brand new administrative assistant. I want to do the best possible job, but I'm worried about my boss. He seems to be moody, and I'm getting signals that I'm annoying him. He's tough to read. I'm his first real assistant and he hasn't been in this position long. It's important to me that I start out on the right foot. Do you have any suggestions on how to maximize the first few months on the job?

- Worried, but Willing

Dear WBW:

Congratulations on your first experience as an administrative professional! It's a challenging and rewarding career. It's great to hear that you want to give it your best. That's one of the most important attributes an admin can bring to the office every day.

Your question is a good one, and I've got a few suggestions to get you started. Other OA members will also provide you with some words of wisdom and offer you support and encouragement. If your boss is new to his position, understand that he also wants to do his best - and there's a learning curve. Fortunately, you have a wonderful opportunity to build a partnership from the ground up. So, take advantage of that by implementing a few of the following ideas for new assistants:

1. Weekly standup meetings (aka: "WhatSUP meetings"):

It's critical that if you're not meeting regularly with your boss, you take the initiative to schedule a weekly meeting with him. In this meeting, you can review tasks, discuss projects, set timelines, plan ahead, learn his expectations, and ask questions. This will also give you the opportunity to get to know your boss better.

Even if it's only a 10-minute standup meeting, it's worth the time. If the meeting gets cancelled, get it back on the calendar as soon as possible. Let him know how important it is to you. In the beginning, he may offer excuses or reasons why he can't get together, many of which may be justified. Don't get discouraged. Just continue to schedule a weekly agenda and be prepared. With time, he will see the benefit of meeting with you. Remember: This is your meeting - make it happen.

2. Watch. Look. Listen.

In the first few months of a new job, these three things will enable you to gauge your boss's moods and preferences. Observe his management style. Is he a morning person? What are his best and worst times of the day? What approaches work best when he's experiencing a moody moment? It's up to you to discover your boss's style - and it's impossible to do that unless you're paying attention and responding accordingly.

3. Timing is everything.

This tip helped me tremendously as an assistant, and I learned it the hard way early in my career. I would often try to catch my boss right after a meeting. I would follow him to his office and try to get my questions answered before he could jump into the next project or task. I thought this was pretty tricky tactic!

After a few attempts at this, I sensed some frustration. I soon realized that I wasn't paying attention to timing. Instead, I should have been more sensitive to the fact that his meetings were challenging and required tough mental deliberations and leadership decisions. As a new assistant, it's important to pay attention to timing. Try not to unload the day's problems or ask the tough questions when your boss needs a few minutes to regroup.

A savvy assistant is aware when the boss needs a break. Later in my career while working for a busy, ambitious CEO who had especially tough meetings, I would often follow him back to his office, smile, and say, "Take 10." I would then shut the door quietly. That was also a signal to the other office staff that he needed a few minutes of downtime. When I left that job, he commented on how much he appreciated that; it showed that I was in tune with him. Also, be aware of when and how you approach your boss.

4. Be a relationship engineer.

One of the best ways you can be the liaison your boss needs is to build strong relationships with your coworkers, vendors and customers. Be dependable, trustworthy and credible in all your relationships. Give others compliments and find ways to initiate bonds. Be diplomatic and professional, and represent your boss well.

5. Organize yourself first, and then organize your boss.

Many assistants get this backward! They want to organize their boss without considering the tools and self-management skills they personally need. Take a day or two to assess how you're maximizing your resources. Are you practicing solid organizational behaviors? Do you set goals, keep timelines, and have your files and office well-planned? A great boss/assistant relationship begins with mutual organizational respect. If you're not dedicated to effective self-management practices, you will not be as productive for your boss as you need to be.

Career Challenge

Start with these five ideas and build on them as you gain experience and confidence. Recognize the value you bring to the position and be proud of what you can contribute. If you're willing to be your best, there's no need to worry about your success as an assistant. Your boss may still get moody, but once you learn how to lighten his load, he will truly appreciate your efforts.

Lisa Olsen provides OfficeArrow members with down-to-earth career advice from her extensive experience as a Career Consultant. An author, trainer, speaker and consultant, Lisa's dedication to building relationship chemistry and helping people power up their potential has been the catalyst for her own success. Learn more about Lisa and her services, including keynote addresses, resume revision, and on-site professional development training here.