A Roadmap to Challenging Conversations

Published: Jan 24, 2019
Modified: Mar 25, 2020

By Rob Fazio, Ph.D.

Most of us welcome a conversation when things are going well. However, it’s those tough conversations we hesitate to have that are the most important ones. It’s completely normal for us to shy away from those interactions, but to succeed, we have to say what needs to be said; we must move the ball forward or risk the ball being dropped.

The trick is to balance your behavior between achieving two goals: nurturing your relationships and a getting to a tangible result. Every interaction is an opportunity to grow and to help others grow. If you take the approach of learning then leading, you will decrease stress and increase solutions.

Now that we’ve established why challenging conversations are essential to optimal performance, let’s get down to the “how.” It’s best to break down the approach into three sections:

  1. Before the conversation: Prepare, Plan, and Practice
  2. During the conversation: Listen, Leverage, and Lead
  3. After the conversation: Evaluate and Empower

1. Before the conversation: Prepare, Plan, and Practice

  • Prepare. Know your objectives and anticipate responses. Have a strong sense of what makes you uncomfortable and lessens your confidence. The more confidence and comfort you have, the better chance you have of facilitating a successful conversation. Pay attention to your emotions, thoughts, and typical behaviors. Ask yourself, “How can I make this conversation comfortable, yet clear?”
  • Plan. Develop an approach, based on what you want and what you know. Plan how you want to start the conversation. Go as far as writing your opening and closing.
  • Practice. Rehearse your opening and closing. Practice what you will say if things go off track. Transitions are often the toughest part of conversations for leaders.

Questions to ask yourself before your conversation:

  • What is the current situation?
  • What do you want to accomplish?
  • What are three key messages you want to get across?
  • How is the person likely to respond based on previous experiences and their personality, that is, will they be defensive, open, angry?
  • What questions may the other person have during the conversation?
  • How comfortable are you feeling entering the conversation? What would make you more comfortable?
  • What are your weaknesses related to this conversation: becoming too emotional, coming across too forcefully, already frustrated?

2. During the Conversation: Listen, Leverage, and Lead

  • Listen. People want to be heard and understood. Be present during the conversation. Have a mindset that allows you to temporarily suspend your agenda and understand the other person’s perspective, motivation, concerns, and abilities. Many people get this part wrong and don’t truly take the time to engage the other person. Having the wisdom to see the situation from their perspective will get you to your objective sooner. Many people think active listening is common sense, but most people don’t put this into common practice. Maintain eye contact, pay attention to your nonverbal messages and the other person’s response. Showing respect for their position is a catalyst to moving forward for mutual benefit.
  • Leverage. Once you listen you will be able to key into what is important to the other person and what drives them. The more you use their language and integrate their views, the better chance you have of gaining their buy in. Summarize their points of view demonstrates to show that you understand what they are saying.
  • Lead. Communicate your key messages clearly. Work with the person to develop a plan and to identify practical next steps. Then set a time to follow up. It’s important to remain confident, clear, and compassionate as you lead the person, maintaining a balance between maintaining your relationship and moving toward results.


3. After the Conversation: Evaluate and Empower

  • Evaluate. Ask yourself: What did I want? What did I get? What do I need to revisit or adapt? Has the other person bought into the identified next steps?
  • Empower. Help the person succeed by supporting him after the conversation. Follow up within two weeks and ensure that the person understands the key messages and next steps. Ask if he needs any assistance from you as he moves forward. Make sure you are both on the same page.

Possible Approaches to Starting a Challenging Conversation
Option 1: Direct

“I wanted to talk with you about something that I view as important to our success. I know this isn’t the most comfortable situation, but I want to ensure we have it on the table, because it’s critical. I have given some thought to this. Here is how I view the situation….
What are your thoughts?”

Option 2: Appreciative Inquiry—Gathering data through questions
“I’d like to get your input related to X. What are your thoughts?”
“How do you think things are going related to X?”
“What impact do you think it has had?”
“What would you do differently?”
“What can you do differently in the future?”

Option 3: Inquiry plus your input
“I’d like to talk with you about something that’s important. Is now a good time? Over the past X amount of time, I have noticed X. I wanted to first get your thoughts on this and then share my thoughts.”

Option 4: Indirect
“I want to start off by letting you know that I value your contributions related to X. I also want to talk with you about something that is important. I know these conversations aren’t always the easiest, but let’s do our best to talk this through. I know we both want what’s best for the firm. Here is my thinking…”

When Giving Feedback:

  • Use an “I” message: “I noticed that…”
  • Use an observation first rather than an impression. Keep it fact-based.
  • Include how it impacted you (how it made you feel, think, etc.): “My impression is that….”  “The impact it has had on me is….”
  • Ask for or suggest a solution

The Bottom Line:
Challenging conversations are like road maps. If you don’t use them you will get somewhere, but it probably won’t be your desired destination. Just like that little voice on your GPS, it’s often necessary to do some “recalculating.”

So, what conversations are you avoiding today that are important for a successful tomorrow? Time to enter your destination…

About the Author(s)

Rob Fazio, Ph.D. is a talent strategy and leadership consultant with Leadership Research Institute (www.LRI.com) where he specializes in executive coaching and tough transitions. He  is a co-founder of Hold the Door for Others (www.holdthedoor.com), a nonprofit dedicated to empowering people to grow after experiencing loss and adversity.  Contact him at [email protected] or (215) 514-5113.