Difficult conversations: Planning your route to success

head in sand

Scott Van Ness, Colorado Springs Business Journal


Having difficult conversations to improve employee and work group performance is a necessity in today's competitive business environment.


Problem: As a manager with multiple direct reports, I find that I often avoid difficult conversations with my employees. Although I don't know for certain, I believe I avoid difficult conversations because I fear that my relationships with others are or will become strained. I also tend to avoid difficult conversations when the stakes are high and I'm less confident in my conversational skills.

Having difficult conversations to improve employee and work group performance is a necessity in today's competitive business environment. However, if the employee or work group is defiant or non-responsive many leaders choose to delay or avoid the difficult conversation. How common is this avoidance? A 2012 study from the Learning Consultancy Partnership showed that 60 percent of leaders "often or sometimes put off difficult conversations." Leaders have a lot of reasons for avoiding difficult conversations. Some of the reasons leaders avoid difficult conversations include:

  • Not wanting to make someone (or me) feel bad.
  • Talks like this never solve anything - they only make it worse.
  • Fear of interpersonal conflict and tension.
  • Fear of sabotage or outright retaliation.

As much as leaders may want to avoid difficult conversations, it is best to develop the resolve and conviction to engage in them. Over my many years of practice and research I have learned that avoidance usually leads to poor outcomes. When I was a supply chain manager for the military, it became clear that planning for my difficult conversations greatly improved my chances for successful outcomes. My current research continues to demonstrate that mapping your conversation in advance will help you get to where you need to go. Below are some practical tools that any leader can use to map their personal route to success in their difficult conversations.

Here are three ways you can get on the road to success with difficult conversations.

  1. Plan your trip. Just like if you are planning a road trip, you have to determine the route you want to take. One company I worked for had a human resource system where we documented all employee conversations - good or bad. In an effort to help new managers engage in difficult conversations with employees, I encouraged them to document the conversation ahead of the meeting. Reversing the system by writing the conversation documentation before the meeting forced the new manager to plan the route (how the conversation will unfold) and the destination (the goal of the conversation). Using this approach, leaders anticipate what should be said and what could go wrong. This vital step ensures the leader is prepared for the difficult conversation.
  2. Look out for roadblocks and detours. Knowing the route for your trip and checking for road conditions ahead of time will ensure the driver is ready for roadblocks and detours. The same thing can happen in a difficult conversation. If the leader practices and role-plays the conversation ahead of time, challenges and attempts to take the conversation in directions it does not need to go (detours) can be avoided. The leader will be ready for those roadblocks and detours and can return the conversation to the planned route. This can be as simple as an acknowledgment of a problem - "I understand that was difficult for you, but right now we are talking about your performance on this project." or "I agree that is a problem, but right now we need to address your late deliveries." Using this strategy for roadblocks and detours acknowledges the employee's issue but brings the trip back on the route for success.
  3. Watch out for potholes. Potholes often seem to just appear out of nowhere while we are driving. It is difficult to anticipate them, but when we are focused on our driving and on the road ahead, we have a better chance steering around them. Potholes in conversations can be words or terms that could offend or distract the conversation, and maybe bring it to a complete stop. Accusatory language or harsh words can deviate or halt a conversation. Knowing who you will talk to and how they respond enables leaders to maneuver through accusations or vulgar language. Curse words or shouting in a conversation might offend, but if the leader is ready for these potential potholes they can be steered around to get the conversation back on track. Leaders need also to be aware of their own potential to create conversational potholes. This might take some self-examination and reflection on past conversations. Leaders need honestly to determine whether past conversational strategies have introduced needless potholes into a difficult conversation.

Scott Van Ness is an instructor of operations management in the UCCS College of Business. He is a U.S. Air Force retired lieutenant colonel with more than 21 years of service in the area of operations and supply chain management. Scott is also an executive education facilitator through the college's OPED office.  He is also a small business owner of National Loan Clearinghouse in Colorado Springs. He can be reached at  OPED@uccs.edu.

[ Scott Van Ness, MBA. ]