coach coaching conversations courage culture resilience May 22, 2023

Imagine courageous conversations as the norm for retaining talent in the workplace. Talent comes in all forms, shapes and sizes, and team leaders need to be willing to have those courageous conversations to retain high-achieving and value-adding employees. Doesn’t everyone want a thriving, diverse, and resilient space to work in?


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“Coaching is unlocking a person’s potential to maximise their own performance.” Let’s take this concept, and apply it to the corporate world. Hold this question in your mind, what are some of the things that stop people from being courageous? Think about your clients or yourself, what stops you from having those difficult conversations in the workplace? Some of the potential reasons that I have experienced and observed include;

  • Fear
  • Ridicule
  • Fear of failure
  • Fear of judgement
  • Other people’s responses
  • Fear of the unknown
  • Other people’s judgement

I was always super curious as a kid, and yet I didn’t want to upset the apple cart, or say the wrong thing, for fear of being shamed and embarrassed. Have we knocked our curiosity out of the workplace? Curiosity allows space for different opinions, which can be perceived as creating unnecessary conflict. Yet, this is healthy and much needed for continual growth and improvement as long as everyone has a voice at the table. Some of the challenges that I have seen, around taking the next steps needed to have those challenging conversations with a fellow workmate, are our own belief system, feeling resigned to the status quo, sheer exhaustion, and knowing that leaders often step in for under-performing employees, rather than overwhelm team members.

There’s never a good time to have a challenging conversation. More often than not, there’s no time at the end of the day, we don’t want to offend people (and upset the apple cart), and think we’re better off saying nothing.

What if we flip this around?

Imagine a future that presents challenging conversations as a starting point for ‘unlocking a person’s potential to maximise their own performance’. Claude Silver, the Chief Heart Officer of Vayner Media, has the awesome job of making people feel valued and empowered. She blocks out time to deliberately have those curiosity-building, creative conversations in the Vayner Media workplace.

I’m going to reveal and share with you a courageous conversations tool, a practical coaching tool that you can walk away with right now, tried and tested.

But first, let’s start with a positive role model. Starbucks’ CEO, Howard Schultz, came back to steer the company forwards, after listening to the challenges and problems facing employees working on the frontline. Really hearing, listening and seeing what frontline workers were experiencing. True leadership starts with being heard and understood; it is happening out there, and this is one company leading the way.

After thirty years of being in the coaching industry, one of the reasons that conflict surfaces in the first place can be summarized in the Conflict Resolution formula below.

Conflict = Expectation ÷ Reality

When somebody’s expectation of their role and job, doesn’t match their reality, it becomes an area for future conflict, something that I see time and time again, both in business and in coaching. Do you see this conflict formula out there in your workplace?


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In what ways as managers, leaders, and coaches, do we create a safe environment for team members to be heard and understood?

Strategy 1: Guiding Principles

As coaches, we see greatness in others, so it is important that we first grant trust and assume positive intent, before launching into a courageous conversation. Start by having a set of guiding principles within your organisation;

Guiding Principles

1.     Grant Trust

2.     Assume Positive Intent

3.     Rapport Building

These three things are needed, in order to begin having courageous conversations within your organisation.

Strategy 2: Listening & be Understood

Have a think about your answer to this question;

"In a maximum of one to three words, what makes a great coach?"

Each week, I alternatively interview sports and business coaches on The Coaching Podcast – you can find links to over 100 podcasts with coaches and fast-track to what makes a great coach. In addition, I have a new book coming out soon called, "What Makes a Great Coach?" that examines over 500 responses from the world's leading coaches based on the question; in a maximum of one to three words, what makes a great coach? The third top response to this question is listening! Being understood, and not just heard. If you are curious to learn more, check out the show as I will never stop collecting this data and will continue to share this knowledge with my listening audience; check it out HERE.

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Strategy 3: Resilience

One of the most common characteristics, found in both male and female champion tennis players (top ten in the world), was resilience! For example, Roger Federer and Serena Williams both finished world number one in 2016, winning a large percentage of their matches within that year, yet how many points did they lose overall? They lost 45% of the points. Let that sink in for a moment.

Micro-moments of resilience. Watch this link to a Ted Lasso clip. What is the happiest animal in the world? A goldfish – and the 10-second memory rule, remember a goldfish has a 10-second memory. The faster we can get over ourselves in the workplace, and on the tennis court, the faster we can move forwards.


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Are you ready for the courageous conversations formula?

Credit for this coaching tool goes to one of my mentors, and co-author, Natalie Ashdown, who is the CEO of The Open Door Coaching Group. Natalie's vision is to create a culture of coaching conversations in the workplace. This coaching tool can be easily retained and remembered by using the following initialisms — TFFI We Can Fly. Initialisms are abbreviations that are pronounced one letter at a time, and it goes smartly with this graphic to help you associate this coaching tool with the idea of an airline tagline!

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TFFI We Can Fly! The key is to get through the entire formula before the respondent is granted the right of reply.


T – Topic 

This is the issue. Assume positive intent and check-in first; is this a good time or block out a time to meet. What I want to talk to you about today is…

F – Facts

What I have observed is, the facts are…

F – Feelings

This is how I feel, or this made me feel upset, this made me feel really frustrated…

I – Impact

Here’s the impact on the team, organisation, the business…

When you get through the first part of TFFI, briefly pause and take a deep breath. It’s not easy to have this type of conversation and this is not an opportunity for them to respond. Remember to assume positive intent, show that you care and continue to move through the entire formula before asking them for their reflections.

We Can Fly

WE: WANT – This is what I want, here are the options, provide some solutions, moving forwards…

CAN: CONTRIBUTE – This is where I acknowledge how I have contributed to the situation, and take responsibility for my role in the issue. Note that this is how you take responsibility and acknowledge your contribution to the situation, to really open up some healthy dialogue.

FLY: FORWARDS – So moving forwards, this is what I am proposing... I would love to hear your thoughts.

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Share this formula with the people in your team, everyone in the crew benefits; allow them to map it out for themselves.

NOW - Game Plan

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Call to Action – What are you going to take action on? What insights and opportunities can you see as a result of using this courageous conversation coaching tool in your workplace? I’m asking you to take action, after reading this article – What are you going to do for yourself in the next 24 hours? Share this article on your social media pages, with your crew and work colleagues.

What are you going to do for one of your team members in the next 7 days? Is there a situation where a client would benefit from hearing the steps outlined in the TFFI – We Can Fly formula?

Finally, in the next 30 days, what conversations (that you have been avoiding) are you going to have with someone in your community? Are you part of a community group or sporting club that could use this courageous coaching tool in their leadership structure?

What is your game plan? What are you going to take action on? Step into your courageous self, and share your game plan.

Remember; Talent isn’t nearly as important as execution.

The ball is in your court to take action.


Email [email protected] if you are curious to discover the Top 5 qualities that all champions have in common (remember No 4: Resilience) and bring out your best today.

Read more about What Makes a Great Coach? and learn about how you can access The Coaching Toolkit to empower your team.

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