Difficult Boss? How to Get Out of Hot Water Now!


No one manages to go through an entire career without having a difficult boss.  Maybe it’s a new boss, or the same person who just became more difficult to work with.  Or your boss may be the type who runs hot and cold – some days they’re in a great mood and others they’re just looking for things to ding you on. 


Whatever the circumstances, it can cause a lot of stress at work and at home and erode your confidence.


Every situation is unique, but there are some common threads that can greatly improve your relationship with your boss. 


Here’s our “Take Five” on how to get off the hot seat:


  1. Anticipate His/Her Needs – Assuming you’ve been working with your boss for some period of time, you should know the kinds of questions they will have, how they think and what’s important to them. The ability to anticipate needs demonstrates your ability to think like your boss.  As a result they will have more confidence in you and be less inclined to micromanage.  
  2. Clarify Expectations – This is more of a problem than you might think.  Many times people walk away from a meeting believing they understand their marching orders, only to find later that they are confused about some aspect or all of it.  It’s critical that you understand upfront what your boss is asking of you AND when it’s due.  Your boss might be the type of person who “fires away” instructions faster than you can think.  If this is the case, follow up with an email to make sure you are on the right track.   It is worth taking the time to clarify their expectations, otherwise you can waste a lot of time and effort going down the wrong road.
  3. Give Bad News Right Away – If you can’t meet a deadline or some unexpected problem has surfaced, let your boss know right away.  People tend to hold on to bad news, believing they are sheltering their boss, when in effect they are making their bosses vulnerable.  Bringing bad news to the attention of your boss right away allows for more time to develop an appropriate response.
  4. When Presenting a Problem Have a Solution – Bosses really appreciate when you take the time to think through a problem and construct potential solutions.  Even if your boss has a better one, it will still demonstrate your critical thinking.  Bosses often complain that they don’t like to do all the thinking for their team.   If you really want to hit a home run, offer multiple solutions and your rationale for the best of the alternatives.
  5. Frequent Communications – Provide frequent updates on key projects.  Don’t wait for your one-on-one or for your boss to call asking what the status of a project is.  If your boss is calling to ask the status of something, it’s a sign that you are under-communicating.  Keep a steady flow of information to your boss so that they always know where the key projects stand.   


Here Are Two More Because We Can All Use a Little Extra Help:


  1. Keep Things at a High Level – Most bosses don’t have the time or desire to get mired in the details.  After all, that’s your job.  Provide overviews on the most relevant things, for example, “Project’s on budget, there’s one issue that might affect the timeline, however, I’m already addressing it”.  Don’t take your boss through all the minutia of what happened, who was involved and how late you had to stay to get it done.   
  2. Look for Ways to Bond with Your Boss – Sometimes we think of our boss as being a one dimensional person – only interested in work.  We forget they have lives and that there may be things we share in common.  Kids the same age, pets, sports, etc., can all be vehicles to strengthen the relationship you have with your boss.  Make sure you pick the right time to bring these things up.  The last thing you want to do is ask “How’s your cat doing?” when you’ve just missed an important deadline.  



Incorporate these steps and you should see an improvement.  Work doesn’t have to be a four-letter word.



Whelan Stone


About whelanstone

I'm originally from New York - lost my accent when I moved down to Florida - and made San Francisco my home in 1985. I've been recruiting & coaching for 12 years, with the best partner (Fred) you could ask for, and love what I do. When I'm not busy working I write screenplays (haven't sold one yet) and travel - Morocco this past summer was fantastic. Fred and I started this blog because we wanted to share what we've learned along the way. Hope you enjoy reading it as much as we do writing it.
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3 Responses to Difficult Boss? How to Get Out of Hot Water Now!

  1. Sandra Martinez says:

    I have found these tips to be valuable and highly effective. I especially favor tips #2 Clarify Expectations and #5 Frequent Communications.

    I believe it is highly important to have a clear understanding of the task your boss has given you. First and foremost, when a boss has called you in their office to discuss a project, always have a pen and paper with you. This demonstrates that you are prepared to take notes, which is always appreciated.
    Additionally, don’t forget to communicate! I find that it is vital to keep your boss informed of the status of the project and although the task was assigned to you, your boss will welcome the updates. Consider setting up scheduled follow-up meetings at the time the assignment was given to you. However, be cognizant of those unforseen events that may require you to initiate a special meeting with your boss.

    These tools are essential, now is good time to implement them!

  2. Pingback: Fred Whelan and Gladys Stone: How to Plan Your Exit and Not “Just Quit” | Atomic Stock Picks

  3. Pingback: How to Plan Your Exit and Not “Just Quit” | WHELAN STONE

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