7 Planning Questions for Coping with a Difficult Boss


How do you prepare for a coping conversation with a Difficult Boss? While there are times and places for spontaneity and unrehearsed candor, a coping conversation with a Difficult Boss is seldom one of them. Knowing that you’ve worked out a handy map for finding the best path through the unknown territory will lessen your apprehension and add to your confident that you can cope with your boss effectively and safely. Equally important, a plan will avoid your applying the wrong technique to the wrong problem. In Coping with Difficult Bosses, Robert Brahmson provides seven planning quesitons for plotting, planning, and protecting yourself.

Seven Planning Questions
Bramson provides the following seven questions for preparing a coping conversation with your Difficult Boss:

  • Planning Question 1: What Does Your Boss Do That Bothers You?
  • Planning Question 2: How Have You Both Reacted?
  • Planning Question 3: What Kind of Difficult Boss Problem Is It?
  • Planning Question 4: What Are Your Specific Goals?
  • Planning Question 5: What Is Your Action Plan?
  • Planning Question 6: What Other Players Need to Be Involved?
  • Planning Question 7: How Will You Monitor Your Plan?

Planning Question 1: What Does Your Boss Do That Bothers You?
Bramson writes:

“What behavior has led you to characterize your boss as difficult? Be specific and descriptive as possible. Pick some of the worst instances and describe just what your boss has done and said that you find objectionable.”

Think through what and how you plan to say to avoid triggering more explosions. Consider a writing a script to avoid hints of accusing, nagging or complaing. For example, “When this happens, I react in this way, and it has these effects.”

Planning Question 2: How Have You Both Reacted?
Bramson writes:

“How have you both reacted to your boss’s difficult behavior? How did you feel? Whad di you say or do? How did your boss react to what you said and did? As much as you can, try for detail. Did you stand up? Did your boss point a finger? Did you look down? Specifics of that sort identify ways in which you may have unwittingly reinforced your boss’s difficult behavior.”

Planning Question 3: What Kind of Difficult Boss Problem Is It?
Bramson writes:

“Think broadly about your predicament, and probe for underlying causes that might not be apparent when your sole focus is on what hurts. Are there confusions about expectations and levels of authority, do you have a behavior blindness problem, have interactions gone sour? Do you simply have a boss who fits one or more of the specific difficult behavior types? (Keep in mind that about 35 percent of the Difficult Bosses you might be unlucky enough to encounter bring at least two of those behavior patterns into play, although seldom both at the same time.)

It is possible, if unlikely, that all of the underlying causes will apply to your boss. Don’t give up. Instead, rank each one of them from most applicable to least applicable and plan to work from the top of your list.”

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Planning Question 4: What Are Your Specific Goals?
Bramson writes:

“The main question here is, what do I want my boss to do more of, less of, or do differently? Resist the temptation to wish your boss into a paragon of virtues. Reflect on what really hurts the most, or interferes most with your own best performance. Do you value your boss’s honest feedback, but wish that it would be delivered in a way that was less sarcastic, or in other ways demeaning? If you could count on your boss to actively support your next promotional opportunity, would that take the greatest edge from your having a boss who’s otherwise not very strong?

You may find it helpful to start with a wish list of adjectives – stronger, less hostile, less indecisive. However, your final statement of your goals should also include the clues, subtle or obvious, that will tell you when those goals have been reached.”

Planning Question 5: What Is Your Action Plan?
Bramson writes”

“To the point you’ve assessed, as best you could, the nature and causes of your boss’s difficult behavior. Your next step is to decide which actions offer the most chance for improvement … Note what you will say to your boss, how you will try to say it, the most suitable timing and settings, and how you expect (not hope) your boss will initially react.”

Planning Question 6: What Other Players Need to Be Involved?
Bramson writes:

“At times, your coping plan may need to include fellow workers, human-resources people, or your boss’s boss.”

Additional Considerations:

  • Be realistic about your goals. Start off your sentence with “What I would like” and focus on specific changes that would clearly enable you to be more personally effective on the job.
  • Ask the senior manager to setup a three-way conference – you, your boss, and your boss’s boss – focused on how you and your boss can work together more effectively.
  • Indicate you will not let the matter drop. Offer to let your boss’s boss know that you will let them know how things are going in a month.
  • Stay focused on problem solving language. For example, “Can we leave this all in the past? Tell me specifically what you expect from me and what stands you’ll use to judge me against. I’ll do my best to meet them. In return, I’ll expect …” or “It’s what will happen from now on that I’m interested in …”

Planning Question 7: How Will You Monitor Your Plan?
You’ll need to answer questions like these:

  • Am I actually doing what my plan called for?
  • Did I, perhaps, peg my boss as the wrong difficult type, confusing a constantly bullying Ogre with a Fire-Eating monster who only attacks when I overrun a deadline?
  • Can I see any results? What seems to be working well? What is not?
  • How should I modify my approach, given my boss’s reactions to my first efforts?
  • How am I doing personally? Am I feeling more or less powerless to deal with this situation?
  • Would my obtaining counseling or training – on how to communicate more assertively, say – be helpful?

Bramson also suggests reviewing your your plan with a friendly counselor.

Key Take Aways
Here’s my key take aways:

  • Build a roadmap. Having a sketch of a plan is better than shooting from the hip where emotions and sensitive areas are concerned.
  • Get specific. Generalizations don’t help. To turn insights into action, use concrete examples, stories to exemplify, and get specific on what good will look like or what your “tests for success” are.
  • Do a dry run. Doing a dry run of your conversation should expose some things you might have overlooked and help you anticipate a variety of your boss’s potential responses.
  • Test your assumptions. When you’re analyzing it’s important to be able to separate your conclusions from the underlying facts and assumptions. To get the fact on the table, ask yourself, what did you see, or what did you hear, so you can get a firm foundation. Simply doing this might give you new perspective on the problem.
  • Involve others. Use others as a sounding board and for reality checks as well as additional perspective and insights.
  • Focus on problem solving. Problem solving is about getting clarity on the problem and focusing on how to move forward while throwing solutions at the problem until something sticks and proves effective.
  • Stay focused on your personal effectiveness. At the end of the day, if something’s holding you back from your best you or your best work, own it and focus on reducing friction, barriers, and hurdles to your success.

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