How to Manage a Boss Who Doesn’t Provide Clear Expectations

Questions your manager should be asking and the questions you need to be answering in dialogue with your boss.

If you are working with a boss who has a hard time spelling out expectations in clear, specific detail, then you might need to help him or her out. Many bosses follow a “facilitative approach”; that is, they have been taught it is better to ask employees questions to lead them to the right answers rather than being directive. Unfortunately, the three most common questions managers ask their employees are exactly the wrong questions:

  • “How is everything going?”
  • “Is everything on track?”
  • “Are there any problems I should know about?”

These questions take you nowhere, because they are not specific enough. Indeed, the conversations between bosses and employees should be an interactive dialogue. But they should never turn into guessing games. If your boss is going to try to manage you by asking questions, then help that boss ask really good questions.

The questions your manager should be asking and the questions you need to be answering in dialogue with your boss are:

  • “Can you complete this assignment? What do you need from me in order to complete this assignment? What additional information, training, tools, materials, space, money, or people might I need? If I’ll be lacking in any necessary resources, what workarounds might I consider? How much discretion do I have to try workarounds as I go?”
  • “What is your plan for achieving this assignment? Have you set a schedule for meeting deadlines along the way? What date and time is the first reporting milestone? What initial steps will you follow? What will be the benchmarks for success at that milestone?”
  • “Have you created a to-do list or checklist for each step one of the project? How long will step one take? What guidelines are you following for step one? What about step two, three, four, and so on?”

When you are able to answer these questions about an assignment, then you know you have clear expectations about the work that needs to be done. When you are able to talk through the answers to these questions with your boss, then you know for sure that you and your boss have the same expectations. If you and your boss both take clear notes while you talk through the answers to these questions, then you and your boss can double check that you are “on the same page.”

If your boss isn’t asking these questions of you, then these are the very same questions you should be asking and answering yourself—or asking your boss to help you think out loud through the answers. Listen carefully to your boss’ input and take notes every step of the way. Use those written notes as a tool in your next conversation with your boss to further clarify expectations for your performance on this work and to make sure you are “on the same page.”

Maintaining clear expectations is an ongoing process of clarifying and fine-tuning, working and taking, getting on the same page and staying on the same page.

Managing Expectations in the Midst of Constant Change

Often people say to me, “Even when I spend time talking with my boss about the work in advance, the problem is that things so often change. What we decided yesterday no longer holds today.”

Maybe once in a while (or often, depending on your job or the industry in which you work), your boss says to you, “Yesterday I said the most important things were A, B, and C. Well, from now on they don’t matter. Sorry about all that work we started doing on them. Now the most important things are X, Y, and Z . . .” Is that somehow evidence your boss didn’t really know what the heck was going on yesterday? Maybe so. But probably not. The reality of today’s workplace is constant change. When priorities change, expectations change. That’s why it’s even more critical for you to be engaging in an ongoing management conversation with your boss. Every time there is a shift or change that requires a significant adjustment or course-correction in priorities and expectations, you need to make sure you ask your boss the following questions:

  • What has shifted and changed and what adjustments and course-corrections do I need to make?
  • How do I need to change or adjust my resource plan?
  • How do I need to reprioritize my to-do list of concrete actions?
  • Has the checklist to ensure quality control for every concrete action changed as a result of this shift in priorities?
  • What priorities should I be focused on as of right now?

Bruce Tulgan is an adviser to business leaders all over the world and a keynote speaker and seminar leader. He is the founder and CEO of RainmakerThinking, Inc., a management research and training firm, as well as RainmakerThinking.Training, an online training company. Tulgan is the best-selling author of numerous books, including “Not Everyone Gets a Trophy” (revised and updated, 2016), “Bridging the Soft Skills Gap” (2015), “The 27 Challenges Managers Face” (2014), and “It’s Okay to be the Boss” (revised and updated, 2014). He has written for The New York Times, the Harvard Business Review, HR Magazine, Training magazine, and the Huffington Post. Tulgan can be reached by e-mail at; followed on Twitter @BruceTulgan; or via his Website,


Bruce Tulgan
Bruce Tulgan is a best-selling author and CEO of RainmakerThinking, the management research, consulting, and training firm he founded in 1993. All of his work is based on 27 years of intensive workplace interviews and has been featured in thousands of news stories around the world. His newest book, “The Art of Being Indispensable at Work: Win Influence, Beat Overcommitment, and Get the Right Things Done” ( Harvard Business Review Press) is available for purchase from Amazon, Barnes & Noble, and all major booksellers. Follow Tulgan on Twitter @BruceTulgan or visit his Website at: