Leadership Retreats Resources

4 Tips for Having HARD Conversations - WinShape Teams blog by Charles Hooper, Jr.

4 Tips on Having HARD Conversations

October 11, 2022
Lead Teams
Charles Hooper, MCC

“We need to talk.”

Those four words are so terrifying to hear and speak.

“We need to talk” is usually code for “I need to have a hard conversation with you.”

Fear, confusion, anxiety, overwhelm, and insecurity usually follow that four-word phrase. This is true if we hear it or if we say it.

Let’s face it, we all say those four words and hear those four words.  Some people actually like having those hard conversations, but most of us don’t.

The key is how we can be more effective in having hard conversations. As leaders, we also need to know how to help others have hard conversations with others when needed.

Here are four tips for having HARD Conversations: Heart, Affirm, Recognize and Discover.


1. Heart Preparation

Preparing for the hard conversation will help you and that person have a positive experience.

Principles to affirm

  • Do not delay in having the conversation; the longer you wait, the more intense it will become.
  • Talk to the person directly.
  • Commit to not talk about the person to anyone else, which can cause gossip and drama.
  • Commit to not listen to someone who wants to bad mouth someone else.
  • If someone tries to tell you about someone else, ask them, “Have you talked to them directly?”
  • Remember that you are not responsible for their reaction but only for your attitude, behavior, and words.

Reflection: Which heart principle is most helpful to you now?


2. Affirm the Person’s Potential and Positive Qualities

The goal of having hard conversations is to ultimately help the person and their team/organization to flourish. Many times, a person’s weaknesses are actually their strengths taken to the extreme. If you can find the positive behind the poor attitude and behavior, you can navigate the hard conversation with grace.

“When you have to have a hard conversation, be sure to do it with a KISS: Kind, Intentional, Simple, and Short.”

~ Charles Hooper, Jr., WinShape Executive Coach

We can affirm the person’s potential and positive qualities when we choose to “call up” rather than “call out.”

When we “call out” a person they will become defensive because of pride or insecure because of fear.

This usually causes discouragement, stunted development, quiet quitting, conflict, decreased productivity, and they will ultimately quit or be terminated.

When we “call up” a person they will become open because “perfect love casts out fear.”

This usually causes encouragement, accelerated development, active engagement, cooperation, increased productivity, and they will ultimately flourish.

“Make praise such a common part of your personal style that when you do enter into a crucial confrontation, you’ll have built a safe, trusting and respectful relationship. Balance confrontations with confirmations.” ~ Crucial Confrontations: Tools for Resolving Broken Promises, Violated Expectations, and Bad Behavior

Reflection: As you prepare for a HARD Conversation with someone, what potential do you see in them? What are the positive qualities which may be taken to the extremes?


3. Recognize the Issue for What It Is

In most cases, conflict stems from unmet expectations. We all have expectations of those around us, even people we don’t know. We have even higher expectations for people who serve on our team. The discrepancy between our expectations and the reality of the situation causes us to react in an attempt to close the expectation/reality gap in ways that can often be destructive.

~ Team Work: 13 Timeless Principles for Creating Success and Fulfillment as a Team Member by Russ Sarratt and Rusty Chadwick

Prepare for the conversation by asking these questions and writing down your answers.

  • What are my expectations?
  • What are their possible expectations?
  • Is this a personal issue or situational issue?
  • What is the issue in one sentence? Reduce the story to a sentence for clarity.
  • What is the goal of this conversation? Go beyond petty reasons to find a win/win for both.
  • What to talk about? Writing down talking points keeps you clear and honest.
  • How much do I need to say? Less is more.
  • What will I NOT say? Write it down then cross it off.
  • When is the best time and place to talk? Be private without distractions and interruptions.
  • What method is most effective for communicating? 70 to 93% of communication is nonverbal.

Best methods of having a hard conversation from worst to best

  • Social Media = 5%
  • Text = 10%
  • Email = 15%
  • Phone Call = 35%
  • Video = 70%
  • In-person = 95%

Which is adapted from a resource by GiANT Worldwide and 100 X Leader.

Reflection: Which of these ideas will help you the most in preparing for the HARD Conversation? Which of these will help the person you are training?


4. Discover Solutions Which Will Promote Flourishing

We want to flourish in our life, work, and relationships. Successful hard conversations can build relationships and increase results. When two people work together to discover solutions, good things can happen!

WinShape Teams & H3 Leadership

Questions to ask to discover solutions in hard conversations

  • What is the best result we can strive for?
  • What would you need to flourish in this situation?
  • What can you do to help me/us flourish?
  • What changes in my beliefs, desires, attitudes, and behavior am I willing to make?
  • What changes in your beliefs, desires, attitudes, and behavior are you willing to make?

Reflection: What is the best way you and that person can discover solutions together?


Start Having HARD Conversations Today

Hopefully these four tips for having HARD Conversations will give you some ideas so you and the other person can flourish. As a leader, these ideas and questions can help you train employees.

Our world needs leaders like you who have a heart of kindness, can affirm people’s potential and positive qualities, can recognize issues clearly, and can discover solutions that promote flourishing.

Creating Clarity: 5 Tips on Getting CLEAR

Discover more about creating clarity with the help of Team Work

Unlock your potential as a team member with thirteen timeless principles for creating success and fulfillment.