Ask The Experts: How Can I Deal With Having 3 Demanding Bosses?

One demanding boss is enough. Three is a nightmare. An overwhelmed assistant writes in for help managing her managers.

Ask The Experts: How Can I Deal With Having 3 Demanding Bosses?
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Managing your own work priorities can be overwhelming. But what if your job is to manage the competing priorities of three bosses? This reader is in that unfortunate predicament.



I’m an administrative assistant at a large company and I’m having trouble prioritizing the work that I get from the three Senior Vice Presidents that I work for.

Not only do they work in different divisions of the company, but they are also each located on different continents. They are not interested in each other’s priorities, and each report to separate C-level executives. Each of them thinks that I should make their work a top priority and gets frustrated with me when I work on a project for another one.

They are all my bosses so I have a hard time saying no to them, but it’s really difficult to manage so many requests that are all treated as urgent.

Need A. Win
New Haven, CT

Leadership coach Lolly Daskal offers her advice.

Dear “Need A. Win,”

I can imagine how frustrated you must feel and how distressing it must be. We live in a culture where urgency is the new norm and the demands are never-ending. And on top of that you have three bosses, all in different time zones with different priorities–nothing I can say will make that situation not a challenging one.


The best way to confront difficult people is to have a courageous conversation. And the best thing you can do for yourself is not to delay this conversation another minute.

Here are the steps you can take to make a difficult situation easier:

Gather the Facts
The key to managing a difficult situation is to stay focused and objective. Start by gathering all the facts of the situation and getting to know them well enough to bring them into the conversation concisely and clearly. Find statistics, numbers, specific examples.


Open a Line of Communication
Next, set up a time to have a conversation. You may want to do this separately with each of your three bosses, or with all of them together via a video chat or conference call. Give them all the facts and information you’ve gathered.

Make it clear that they matter
Stay focused not on your frustrations but on your bosses and their needs. While this may be the last thing you feel like doing, it is the most effective way to get what you need.

Clarifying that your top concern is being able to meet their needs and help them fulfill their mission within the company will prevent the perception that you’re just venting after a bad day or week, and it give you the best chance of launching successful change.


Encourage questions.
Encourage your bosses to raise their own concerns and ask questions. When you give them a voice in the situation, it will help them become part of the solution.

Rephrase what they say
After you have stated the situation and the questions have been asked, rephrase the key points to help clarify what’s been said and foster listening and understanding.

Work together on developing solution.
Now work together on a solution that includes everyone involved. Ask each your bosses to help you figure out a balanced solution to the situation. Involving them in the process reduces defensiveness and gives them an investment in the outcome.


Once you’ve put together a solution that everyone understands clearly, commit to making it work. Set up a system and timeline for keeping everyone accountable.

Follow up
Schedule a time within a few weeks to take stock. If you can see positive change–or even small improvements–acknowledge and show appreciation of the progress.

If there is no change, start the process again, and again be as honest and as courageous as you have to be. Until when? Until you see a change happen.


Being able to resolve a difficult situation is not easy. Having a courageous conversation is even harder.
But it’s one of the most valuable tools we can acquire for any relationship.

Let me know how it goes.

To much success,
Lolly Daskal


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