Have you ever found yourself wishing you would have had a conversation that could have made a difference for you and for the other person?

Maybe you wish you had told that wonderful colleague you appreciated her but were afraid it might be taken the wrong way or “go to her head.” Or you resisted telling a relative how his attitude was negatively affecting the whole family. Maybe you wish you had found the courage to sit down with your defiant teen to say what was really worrying you about her behaviour. Or, as a manager, you avoided dealing with a workplace bully and ended up losing a couple of talented employees who couldn’t take it anymore. And maybe you didn’t start because you didn’t really know the direction you wanted to go.

Most of us have regrets about the conversations we didn’t have. And the reason why we didn’t have those conversations can usually be traced back to one main emotion: fear. Fear of repercussions, fear of the unknown, fear that we wouldn’t have control over our own emotions or that we would be run over by the anger of the other person. Fear that we would look stupid, make the situation worse or open up a situation that would not be resolvable.

Starting courageous conversations

Although it is true that many confrontations should be avoided and we should pick our battles, it is common to spend more time avoiding the conversations we should have than regretting the ones we did initiate.

Step #1: Have the right intent

The key to having a courageous conversation is a sincere desire to improve a situation. If you find you want to win or score points against the other person, your intention is not pure and you will find the situation gets worse rather than better. Examine your intent closely, and once you are fully committed to finding the solution or improving the situation above all else, you’re ready to move to the next step.

Step #2: Determine and communicate your ideal outcome

Once you have established your intent, set up the desired outcome and how to get there. Make sure you state your intention and the outcome you are looking to reach in the beginning, and then assume a position of curiosity. If you ask questions and show you understand the other person’s take on the situation then it is easier to find mutual points of agreement.

Step #3: Follow through

Inevitably after a conversation like this there will be actions you’ll need to take to show that you are committed to enacting the ideas that were generated, even if the only agreement you have been able to reach involves seeking out more information. In any case, after the conversation it is important to consistently do what you have said you will do and to share the results of your actions.

Step #4: Remember you are dealing with a person

When you are deciding to have a courageous conversation with another person, it’s easy to use a typical lens and see the other person as a villain and you – or the person who brought the problem to you – as the victim. If you fall into this trap, it will be hard to come up with a viable solution because a victim is powerless and a villain has only evil intentions. Putting others into a box of judgment is not conducive to resolving the situation.

So why do people do it?

Because people need to have a sense that there is a way out – an opening to reframe their actions so they can move forward without losing their sense of dignity. If they see that they are being cornered, trapped in their behaviour or judged for their intent, they are likely to strike back, freeze up or argue to prove you wrong.

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I used to work for a school principal who would always start a student disciplinary conversation with, “I know you are much bigger and better than this incident we are going to talk about. And I know that you are going to show me the real you as we move forward.” He would then describe the action (for example vandalizing the school with spray paint) and ask the student to assume the role of principal and explain what he or she would require a student to do deal with the damage.

After establishing that the action was required and a responsibility was imminent, he would start asking questions about what was bothering the student and how the student ended up getting into this situation in the first place. Throughout the conversation, he always reinforced the dignity and nobility of the student and provided the student with a way to see him or herself in that same light. The issue was crystal clear and the intent to resolve the issue reinforced numerous times.

At the end of the conversation, he would look the student in the eye and say, “Can you explain to me why we discussed this and what we both agreed to?” He would then end the conversation with, “I am trusting you to stick to your word on this. The most important part of this conversation is that we are rebuilding trust between us. Trust is like hunger, you need to feed it daily.”

In the courageous conversations literature, this is approach is a perfect example of starting from the heart, being very clear about the intent, keeping the responsibility where it lies and then getting the other person to close the loop by agreeing to rebuild or maintain the relationship. If after this process the other party proves to be incapable of showing trustworthiness, you will have a record of the steps taken and it will be easier to move to the logical conclusion without drama.

Margie Warrell, in her article, “Is it past time you engaged in a courageous conversation?” wrote:

“The conversations that take the most courage – those in which you speak candidly and listen openly – are those which make the biggest impact.”

When you are in a management position, the actions you take to have courageous conversations define you as a leader. They show your team what your values are and set the tone for how you expect others to act. The example of the school principal is one that has stayed in my mind for over 15 years because it was such a powerful demonstration of the power of his belief that people can rise above their mistakes. I have since worked for and with many managers, but it is only those who showed courage that I remember and can call to mind when I need an example to follow.

More tools to help

Here is a modified version of Margie Warrell’s steps to having a successful courageous workplace conversation to provide you with a framework of principles almost identical to what the school principal story illustrated above:

  1. Set your intention: What comes from the heart, lands in the heart. Make sure it isn’t about you winning or getting points against the other person.
  2. Be fully present and in the moment. This is not the time to take a phone call or check your messages.
  3. Mean what you say: Dr. William Schutz, behavior specialist and founder of Human Element Solutions, once said “If people in business told the truth, 80 to 90% of their problems would disappear.”
  4. Hot issues need to have cool emotions: Hot issues with hot emotions are explosive. If you are feeling upset, name your emotion and call a time out.
  5. See the other person(s) as people: If you truly want to resolve the situation, don’t see yourself as a victim and the other person as a villain.
  6. Always get the facts first: There are two sides to every story.
  7. Name the elephant in the room: If you avoid the key issue, the conversation will not have any real effect.
  8. Be noble: Don’t give into petty insults and mean spirited digs.
  9. Realize your fallibility: When you feel defensive, autocorrect by adopting a position of humility.
  10. Be clear: Ensure your requests and your commitments have been understood well.
  11. Keep the end in mind: Stay future-focused and concentrate on the desired outcome, resist the urge to go back to past behaviours and past hurts.

Barry Moltz has a helpful set of 10 questions to use inside a courageous conversation to keep things moving towards the future. They can be helpful to have with you as a memory aid if you are worried your emotions might sabotage you. Barry’s list is:

  1. “I didn’t realize this was going on, so tell me more.”
  2. “I want to listen to your point of view, but I can’t do it when you are yelling at me.”
  3. “I understand your point of view, but I see it differently.”
  4. “I will incorporate your thoughts going forward.”
  5. “Both of us need to put more effort into this if it’s going to work out.”
  6. “Why don’t you agree with me?”
  7. “Since we can’t seem to agree, can we continue talking about it another day so we can think of more solutions?”
  8. “Let’s see what we can do to make sure it doesn’t happen again.”
  9. “What can I do to improve communications so this does not happen again?”
  10. “What can I do next time to make this less difficult for you?”

From a quick perusal of several other articles on courageous conversations I found a few more helpful tips for both setting up and keeping a courageous conversation on track:

  • Be clear in your own mind about the issue and know where to begin: Practice your opening sentence and write down your key issue. Make sure you are only staying with one issue, not a shopping list of problems.
  • Be comfortable with silence: If you stop talking and just wait, the other person will talk. The more you fill up the space, the less the other person is likely to talk.
  • Preserve the relationship: Try as much as possible to remember that all relationships will come back to you in some way. Ask yourself if what you are thinking of saying will result in the outcome you seek. If you thing your desired outcome will be compromised, don’t say it.
  • Keep things on track: Watch for and divert stonewalling, sarcasm and accusing. You started the conversation and you are responsible to keep things moving in a productive direction. Keep coming back to the issue and don’t let the other person try to deflect from the problem.
  • Be consistent: Whatever you both decided to do is something you have to consistently carry out or your word will not be taken seriously.

The value of making a start

In conclusion, most of the reasons we don’t have those courageous conversations can be overcome with some advance planning, a few key questions and little mental and emotional preparation. What is left is overcoming your own fear. I’m a big proponent of feeling the fear and doing it anyway. The more frequently you tell yourself that you are bigger than your fear, the more likely you are to overcome it.

Practicing courage fills you with a sense of purpose and power. You overcome your fear and gain confidence through practicing the principles of a successful courageous conversation which is why it is important to get started. If your intent is pure, even if you miss things or don’t get as far as you wanted to, there will be ways to move forward. Courage is like learning to walk: you have to keep doing it to find out how it works. Prepare, swallow your fear and trust in the process of heartfelt intent.

Here are a couple of quotes to help you find your inner courage and keep you focused on resolving conflict:

“That courageous conversation you have been avoiding is actually a leadership opportunity.”

– Anonymous

Life shrinks or expands in proportion to one’s courage.”

– Anaïs Nin

For a really useful guide to mentally preparing your upcoming courageous conversations, I recommend this article by the Government of Ontario:


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