Make Challenging Conversations Stress-free

We have all been in situations where we have had a coworker who interrupts us constantly, a team member who isn’t living up to their potential or a supervisor who maybe isn’t supporting our career goals.

Whatever the situation, two things remain the same…

  • They are very stressful situations
  • They won’t get better unless you start a very difficult conversation.

We all have our own individual comfort level when it comes to disputes and how to talk to our colleagues about them. There are going to be times when we need to overlook minor differences.  It’s when the behavior is repeated over and over again that if the problem does not get dealt with, the situation as well as the relationship will become unpleasant and destructive…to you and the office environment.

No one wants to make things worse but they won’t fix themselves without intervention.

You can follow three key steps before having difficult conversations…

  1. Prepare: Be conscious of where you decide to have your discussion.  If this conversation is very important or unpredictable, try practicing what you need to say with another coach or mana  Be clear-cut about your goals for the conversation and be able to describe the specific behavior you’d like to see change.
  2. Focus:  Don’t get distracted, keep your eye on the goal!  If you maintain your focus, you will remain calm and keep the discussion to the issues at hand.
  3. Follow up: It could be a simple note, additional paperwork or for more serious conversations, formal documentation.  Make sure to set up future meetings to review progress if needed.

Some leaders can really struggle with their emotions and they do tend to arise during these difficult conversations.  You also want to create an environment that your staff can receive your feedback openly.

As coaches, managers and supervisors, we have all had our fair share of difficult and uneasy conversations.  Those conversations are never easy or enjoyable but it comes with the territory.

If you are able to handle these discussions positively and effectively you will show your skillfulness and proficiency as a successful leader.

Difficult conversations are a way of life but they don’t have to disturb your life in or out of the office.

How do you handle challenging conversations?


Dave Baney is the founder and CEO of 55 Questions, LLC and author of “The 3×5 Coach: A Practical Guide to Coaching Your Team for Greater Results and Happier People”, which is now available in Paperback or a Kindle version at

At 55 Questions, we work with successful top executives with a driving ambition to crush their competition.  We help CEOs and Entrepreneurs improve alignment, communication and accountability throughout their organization.

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