Career AdviceCareer DevelopmentBosses and Coworkers

Setting Expectations with Your Boss

By Bruce Tulgan, RainmakerThinking Inc.

Based on It’s Okay to Manage Your Boss (Jossey Bass, September 2010)

Real power in the workplace rarely comes in the form of being left alone to do whatever you think should be done however you think it should be done. Rather, power comes from having the responsibility to accomplish specific tasks and projects in certain ways at certain times delegated to you. To move swiftly in the right direction, you need clear marching orders.

At the very least, you need to know the minimum requirements and the gold standard of performance, the cardinal rules of conduct and the outer limits of your discretion. No matter how self-sufficient, responsible and hard-working you may be, nobody can function successfully for long without some structure and boundaries.

So what do you do if you are working with a boss who has a hard time spelling out expectations in clear, specific detail?

Maybe your boss isn’t spelling out expectations because he is trying to follow a “facilitative approach.” Maybe the boss is trying to lead you 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. While the ongoing conversations you have with every boss should be interactive, 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 answer -- are:

  • "Can you complete this assignment? What do you need from me to complete this assignment? What additional information, training, tools, materials, space, money or people do you need?”
  • “What is your plan for completing this assignment? Have you set a schedule for meeting interim deadlines? What is the date and time of 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 of the project? How long will the first step take? What guidelines are you following for this step? What about step two, three, four and so on?”

When you are able to answer these questions about an assignment, 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, you know for sure that the two of you have the same expectations. If you and your boss both take notes while you talk through the answers to these questions, then you can both check that you are on the same page.

If your boss isn’t asking you these questions, then these are the questions you should be asking and answering yourself -- or asking your boss to help you think through the answers to. Listen carefully to your boss’s input and take notes. Use those notes as a tool in your next conversation with your boss to further clarify expectations for your performance on this assignment 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.

[Bruce Tulgan is an adviser to business leaders and a sought-after speaker and seminar leader. He is the founder of RainmakerThinking, a management-training firm. Tulgan is the author of Managing Generation X, It’s Okay to Be the Boss and many other books, including It’s Okay to Manage Your Boss. He has written pieces for numerous publications, including The New York Times, USA Today, The Harvard Business Review and Human Resources. He can be reached via email, on Twitter and on Facebook. His free weekly workplace video is available on his Web site.]