Administrative Assistants: Techniques for Assisting Multiple Bosses

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August 15, 2018
Author: Tamala Huntley
Organization: Tamala Huntley International


Assessing Working Styles

Managing multiple bosses requires understanding how each one operates and how that relates to your own working style and needs.

“Learning” your boss happens naturally over time as you get to know them. Even still, the process can be a challenge when dealing with one boss so imagine the degree of complexity when you support more than one.

Often, more is caught than taught. This simply means, you’ll learn more by just being present. There are a few things you can do to assess the style of each of your managers and flow smoothly with each of them:

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  1. Have a conversation with each of them and simply ask what their expectations of you are and what their preferences are.
  2. Be impartial in how you split your time between them so that you can spend adequate time learning from each of them.
  3. Be available and willing to participate in meetings so that you can see each manager in action and see how they handle various situations.
  4. Understand your company and department goals so that you can understand what drives your bosses and what pressures they may face.
  5. Look for areas of strength and weakness and determine how you can support the weaknesses without magnifying them.

Without doing these assessments, you put yourself at a disadvantage and increase the chances for misunderstandings and conflicts to arise.

Negotiating Conflicting Schedules & Priorities

Ask Your Bosses to Resolve Who Gets Priority
When you receive conflicting assignments, schedules or priorities, let the bosses establish the priority.

Create Prioritization Levels
Create standard levels of prioritization and ask the managers to assign a priority to their requests, based on your scale. Then handle conflicting deadlines or schedules based on which has the highest priority level.

Do Your Research and Decide
Do your own research on the assignments and gather all of the relevant facts. Based on your research and understanding for each assignment, set your priority.

Don’t Cave Under Pressure
Learn how to pace yourself and refuse to be afraid to speak up. Many times it just takes one conversation to resolve a conflict. And if you go off thinking you have to do all of the tasks, whether they conflict or not, you do yourself and your managers a disservice because you won’t be able to give it your best.

Staying in Sync with Your Bosses

Understand that challenges will come and the best way to stay in sync with your bosses is to be quick to communicate. Recognize the challenges and develop a “pre-made” script for how you will them:

  1. Know that you will be overloaded at times. Take time to step away and regroup.Stick to your prioritization rules and keep at it.
  2. Know that you will receive conflicting messages. And oftentimes, the more bosses you have, the more opportunity there will be for messages to get crossed.
  3. Know that you may be expected to put one boss before the other. Establishing a consistent track record for impartiality will help.

Be Self-Motivated
One of the worst things you can do is require your boss to tell you when, how and why you must do every assignment. Be proactive and resourceful. I can’t repeat enough that you must ask questions. Seek out information. Go the extra mile and dig deeper when given little information with great expectation.

Be a Problem Solver, Not a Problem Announcer
Your bosses will appreciate this. When you do have a problem, try to come up with your own solutions and when you go to your boss, present the problem with the solutions.

Establish Boundaries and Stick to Them
People tend to treat you how you allow them to treat you. Everyday you educate your bosses on how you want to be treated, by what you allow.

If you have personal convictions that conflict with requests, make them known. If you have time constraints and family obligations that are important to you, make them know. Don’t be afraid to establish new “rules” for getting work done. Talk to your bosses about your established “Power Hour” and refuse to bend for co-workers or anyone else during this time, unless it is a genuine emergency.

Just get the job done, with excellence while sticking to your boundaries. If you can show that your boundaries actually help you be more productive, then the better off you’ll be.

Ask for Feedback and Don’t Take Offense

Ask your bosses for feedback on how you are doing. Ask if you are meeting their expectations and if not, what they would prefer to be done differently. Don’t wear your heart on your sleeve and take offense to their personality traits and flaws. It’s a fact… when dealing with other people there is always opportunity for offense. Be very careful in this and don’t harbor ill feelings. Communicate and get them out so the air is clear and your work environment isn’t strained.


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