Tips for Managing a Difficult Boss | Managing Up Tips

Tips for Managing 4 Varieties of the Difficult Boss


As a corporate trainer and professional speaker, I speak on various topics (e.g. communications, meeting facilitation, team development, project management, etc.) to a variety of different audiences around the country and beyond.  Over the past few years I’ve noticed something that stops me in my tracks every time it happens.  Invariably, during my Q&A after my talk (irrespective of the talk topic) one of the first three questions is….”But what if the problem person/behavior is my boss???”  This insane consistency just reminds me that the idyllic inspirational supportive manager is in many ways the chupacabra of our time.  Instead, most of us find ourselves struggling to succeed in spite of our boss not because of our boss.  Sad, but all too often true.

In defense of bosses everywhere part of the problem may be that expectations are not always realistic.  I think that bosses are like doctors in many ways in that patients walk in with the completely erroneous assumption that just because someone has an MD behind their name, they’re all knowing and all powerful…this simply couldn’t be further from the truth.  There are great doctors and horrible doctors – the same is true for managers and executives.  Unfortunately, too many of us get stuck with the difficult boss.  The good news is that you really can manage up and not just succeed in spite of the difficult boss but maybe teach him/her a thing or two in the process and earn their respect!

Clearly, there are many permutations of the “difficult boss”; however, the following four types seem to appear with unsettling frequency.

The Tornado – “I hope you don’t mind me intimidating everyone with my overbearing nature at your team meetings…I’m just trying to help you speed things along.”

Sometimes our boss can become the “problem participant” in our meeting and that can be difficult to manage.  Try these meeting facilitation techniques if you find yourself in this situation:

  • Meet with your boss prior to the meeting and specifically discuss what you need from them in the session. Possibly write out talking points for them – many will appreciate it if it’s offered in the spirit of helping take one more thing off their plate (not telling them specifically what to say).  Ask them to withhold their opinion until others have weighed in to avoid tainting others’ input.
  • If you sense others may be intimidated by the boss’ opinion, suggest the group do a round robin and start at the opposite end of the table as the boss (so that their opinion comes near the end).
  • Stand up! Whenever you stand when everyone else is seated, you immediately regain control of the group (temporarily). Thank the boss for their input (even note it visibly) and redirect the conversation as needed.
  • Repeat their point and write it down – this may sound counterintuitive, but oftentimes someone will get on their soap box (and not get off it) because they don’t feel heard. When you repeat the point back to them and then write it down for all to see (on a flip chart or whiteboard), it reassures them that they have indeed been heard and immediately communicates an appreciation for their point.

The Wishful Thinker – “Would you please boil the ocean…and solve world peace too while you’re at it?”

We’ve all encountered the boss who expects you to achieve the impossible.  They somehow think you’ve got a magic wand tucked away in your cubicle and can move mountains.  When you encounter this boss, don’t fall into their haze of wishful thinking.  Instead, try these techniques.

  • Try to identify the specific mandatory requirements (and separate the “wants” from the “needs”). Sometimes they will ask for a Porsche when a skateboard will do.  Also, there may simply be a knowledge gap and they don’t realize that there is a quicker, easier way to get them what they really want.
  • Quantify anticipated risks. Instead of lying awake at night and wringing your hands thinking about risks associated with a particular project or tasks, put pen to paper and attempt to quantify them.  One simple formula for risk analysis is multiplying anticipated probability times estimated impact if the risk event occurs – resulting in a calculation of estimated severity.


Probability of rain (.25%) x Financial impact if it occurs ($10,000 for inside venue) = $2500 anticipated severity

If you calculate severity amounts for all anticipated risk events, you can easily estimate total risk for the project or task.  Keep in mind that these calculations can be quick/back of the envelope but having conducted some written risk analysis will position you well to bring the concerns to your boss.  Now when you approach him or her, you’re not whining.  Quite the contrary, you’re raising well documented concerns and providing them ample opportunity to change course, apply additional resources/funding, or even pull the plug on the project.  If you’re concerned about moving forward, ask them if they’re comfortable with that level of risk.  Finally, use this as an opportunity to ask for support in developing mitigation strategies and/or backup plans proactively (e.g. Jim, I know that if we lose our lead system architect, it will severely impact our timeline.  In an effort to be as proactive as possible, I’d like to find out from you what we can do in the event that that does happen?)  Even if they insist that you proceed without providing much support, having documented and communicated these risks not only provides you  some cya in the event that the task or project does implode but it also shows that you’ve done your homework and elevates your credibility with the boss.

  • Remember the triple constraints of cost, time, and quality/scope – when they change one element, it impacts the others. If there is a reduction in time, emphasize the impact on cost and scope.  (e.g. Jim, I understand that you now need to roll out the new release a month earlier than planned and we can do that, but there will be an impact on cost and scope.  I can either reduce the scope and hold off on some of the features until the next release or spend about $50K more to expedite things.  What is your preference?)
  • Push back if it’s not realistic…(g. Jim, I would be irresponsible if I didn’t tell you that I don’t think this can be accomplished with the level of quality we would expect. I know you would prefer that I be very honest now (before any time and money have been invested) rather than hear a laundry list of apologies after an unsuccessful project.  I’d really like to be positioned for success, and I honestly have real concerns here).

The Clueless Chameleon – I’m not exactly clear on what I’m looking for, but I’ll be sure to hold you responsible when I don’t get it…

Too often bosses may have a vague idea of what they want or worse than that they may keep changing their mind.  When this happens, employees are sent on wild goose chases trying to reach a loosely or poorly defined objective.  Don’t fall into that trap.  Try these best practices instead.

  • Clarify the effort early and often. Identify in scope items and out of scope items (out of scope is even more critical), tangible deliverables, timing expectations, budget restrictions, roles and responsibilities, known risks, and key stakeholders.
  • Identify their soap box issue early and emphasize WIIFT (What’s in it for them). If they don’t understand exactly what they want, ask them to explain their motivation/driving factor.  Oftentimes, execs have a soap box issue, predetermined bias, or hypothesis they want validated.  Try to find out what this is as soon as possible.
  • Ask your boss to prioritize scope/quality, time, and cost (good, fast, and cheap) for important tasks or projects. Find out which criteria is most important (relative to the others).  Hint: The answer is not all 3 J Think fast food – the focus is very intentionally fast and cheap.  Be clear which constraints are really driving the effort.
  • Explicitly ask how they will define success. ALWAYS ask your boss to finish this sentence when he/she is assigning an important new piece of work…I will consider this task/initiative/project a success if…

The Naked Emperor – I love the sound of my own voice in particular because my ideas are brilliant…NOT!

Nothing is more frustrating than a boss that only sees what they want to see and seems to be blind to reality (particularly when that reality may reflect poorly on them in some way).  This type of boss is particularly dangerous because their blind spots could certainly derail your success as well if you become too closely associated with them and they go down in flames.  Don’t blindly go along.  Try these techniques instead.

  • Ask for permission to be honest early on. It’s always difficult to tell the boss that their latest idea isn’t actually that great, but sometimes we need to tell them they have an “ugly baby” and spare everyone wasted time, effort, resources, etc.  “Laura, I know that you’re really depending on me to help steer the group towards success and I’m more than happy to do that.  I do however want to respect your authority so I thought I should ask you how you want me to handle it if I think we’re headed down the wrong path or if I disagree with one of your ideas or assumptions?”  In virtually all cases, the boss will ask for your candor (whether they really want it or not).  This action won’t be a panacea, but it can be very helpful when you later need to deliver a difficult message since they’ve requested candor.
  • Avoid allowing bad ideas to gain momentum. In project management there is a mantra – “Kill what’s ugly while it’s young” which essentially means that the time to kill a bad idea is at the outset not later on when time and resources have been expended.  Ask your boss to define criteria early on for evaluating important ideas before they are implemented.  Frame this within the context of wanting to ensure that they don’t waste time on ideas or activities that might eat up valuable time and money.
  • If and when you need to deliver bad news or give them a reality check, frame it as your giving them the best information possible and leave the ultimate decision to them. It also doesn’t hurt to include a bit of a tease about potential consequences to instill some healthy fear.  “Laura, I know that you’re very excited about moving to the new organizational structure, but I just feel like I’d be doing you a disservice as your right hand not to point out a few potential concerns.  Ultimately, it’s your decision of course and I respect that, but I just want you to have as much input/data as possible and since I’m a bit closer to the customer.  A few key customers have mentioned that they might walk if the new org structure impacts response times and I know that would be devastating for our group’s metrics so I just want you to know what I know if that’s helpful at all as you refine the structure.”
  • If you sense that theirs is a sinking ship, get off! At least build a broad network and develop a “plan B” in case they are demoted or removed from the organization.

Dana Brownlee is an acclaimed keynote speaker, corporate trainer, and team development consultant.  She is President of Professionalism Matters, Inc. a boutique professional development corporate training firm based in Atlanta, GA.  She can be reached at