Tackling the Fear of Challenging Conversations in Four Simple Steps

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By a Director of Marketing
for a portfolio of global hotels
Voices from the Trenches

Timing plays a role in just about every aspect of our lives – personally and professionally.  When it’s necessary to have a conversation with your boss, timing is huge.  While it can be a daunting task to be face-to-face with your superior to discuss your concerns, it’s always best to take a step back, assess the situation and figure out the best way to approach the conversation.  Just as with many business decisions, there should be a strategy behind your conversation:

  • Schedule and appropriate time and place
  • Set the tone/agenda for what you would like to discuss
  • Provide insight prior to the conversation so your boss does not walk in and feel blindsided
  • Dial down emotion and censor yourself as appropriate
  • Provide some possible solutions rather than just coming to the table with a problem

Be Prepared

There is always going to be some degree of risk and it’s wise to try and understand that level before you have the discussion. Would you be embarrassed if your conversation made its way up the chain or even made it to Human Resources? Would you be ok if it did? There may be some things that can be worked out by yourself or with co-workers directly, without escalating them to an entirely new level.  And that’s something you have to ascertain before your bring your boss or others into the mix.

While issues related to personnel may result in some fear of approaching your boss, there are other areas that tend to be easier to approach.  For example, if you need additional training, hopefully you have a culture where your superiors are receptive to helping you achieve success. If you reach out to your boss for help related to your professional development, chances are he or she would embrace it and help you however they can.

Be Your(work)self

Obviously you should be comfortable to be yourself at work, but there are some stipulations.  If you were going out to dinner with a bunch of girlfriends, you’re probably going to have a slightly different demeanor than if you were walking into a 9:00 a.m. management meeting, right? There’s a time and place for everything – your behavior, your choice in clothing, and even issues you want to bring up to your boss.  Always be true to yourself, but learn to do so while towing the corporate line. Be aware of the image you project and make sure it’s the one you want out there.  If you’re not sure about how you handled or should handle a situation in the workplace, ask your boss.  The feedback and advice they can offer is invaluable.

Be Flexible

Sometimes it is much easier to go with the flow.   As a leader, it’s aggravating when someone challenges every decision you make. Those who are constantly contrarian will get pegged as “difficult”.  As an employee, it’s important to be respectful of your superiors.  You should also think before expressing your concerns – pick and choose your battles.  Not every little thing needs to be discussed with your boss, so figure out the most pressing matters that require their attention.

Be a Positive Contributor

Establish yourself as a person who can command a room in a professional and positive way. There’s a huge difference between being someone who likes to hear themself speak and being someone others want to hear speak. It will always benefit you to be the latter.  Your colleagues will respect it and your superiors will appreciate it.  It builds your credibility in various ways but especially when it comes to approaching your leadership to have a conversation.

Most people have an innate fear of change.  Since having conversations with bosses, difficult or not, can likely result in some sort of change, it perpetuates that fear.  Change and evolution is a reality in our workplaces and in life.  The sooner you learn to accept it and develop sound approaches to work-related issues and conversations, the easier your transition through any conversation, and change, will be!