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How To Hold Courageous Conversations

How To Hold Courageous Conversations

entrepreneur leadership Nov 17, 2021

Dear Reader

Undoubtedly, many of the problems I experienced as a Manager resulted from self-sabotage brought on by my lack of courage to have those difficult conversations with my team. I was worried about making things worse, I think!

If it is the same for you, you wonder why you put the conversations off. It is most likely that you have an active Inner Critic (Saboteur) or strong imposter who is telling you that tackling the issue will worsen everything. This is unlikely to be accurate, and it is not true in most circumstances.

Learning to coach had a significant impact on making this easier for me because I learned to listen deeply to the other person's perspective and trust my intuition to get to the route of the issue. I knew the SBI feedback model,  Situation, Behaviour and Impact. which would enable me to give great feedback. I just needed the courage!

The SBI model ensures we replace the personal feedback element with practical feedback about the topic. If you haven't already, check out my feedback training webinar for more on this.

In this blog, I want to add ten tips to prepare well for those courageous conversations to enhance giving feedback and address those issues we avoid tackling.

So here are TEN tips to consider before you have a courageous conversation

Speaking up about the issues weighing you down is essential to growing as a leader, so this is definitely for you if you are putting something off.


  1. Don't put them off – If you don't have the conversation, who will?  Don't let fear stop you. Explore the fear to the end game. What if?  Then what?
 Then What?  What is worse, the situation now, or what could happen if left unresolved?


  1. There's nothing wrong with a healthy ego, but your ego can get in the way of expressing yourself in ways that serve a positive outcome – for you and your team, family or relationships. There's a difference between speaking up and talking down to someone, making them feel insecure or putting them in a defensive mode. Before starting the courageous conversation, be very clear about why you are having the conversation and what you want the outcome to be. Check-in with your self-importance, self-esteem, respect, and self-pride, and set your intention. 


  1. Who are you trying to serve? If you aren't clear, discuss it with someone else or write it down, keeping in mind that if it's about you 'winning', that implies someone else must lose.  Speaking your mind is not fruitful unless the conversation is well-considered and entered into when you have defined why. It is ultimately of service to all parties.  It may sound like an adage, but the truth is that a message comes from the heartlands of the heart.


  1. Mean what you say.  Be candid in your feedback and honest in your opinion. Say what you sincerely believe needs to be said, even if you know others may not enjoy hearing it. People can intuitively tell when you are sincere and have good intentions. They can also tell when you aren't. Don't sugarcoat the truth in fluffy compliments and disingenuous flattery. But do keep it impersonal where possible. Ie. "The speech was rushed" Rather than "You went too quickly"  ( About the speech, not the person) 


  1. Share the facts:  In the aftermath of the Challenger disaster in 1986, NASA found that the engineers working on the spacecraft had concerns about the O rings when exposed to extreme heat. Still, their fear of passing on information kept them from passing it up to their supervisors. While your silence may not result in putting lives at risk, it does undermine your ability to succeed.


  1. Be vigilant of Victims and Villains. As human beings, we live in stories – about ourselves, other people, and the situations in which we find ourselves. The issue isn't that we have stories but believing that our stories are "the truth."  Be sure to check your facts.  Before you engage in a tough conversation, think about the stories you are carrying into it, particularly any that cast yourself as a victim or others as a villain.  Your own story can highlight productive conversation, and so too can your lack of understanding of others' stories. Taking the time to genuinely listen to and understand another's story builds trust and makes others more receptive to your opinions, growing your leadership influence.  Starting with perhaps "I realise I may be missing something, but from what I can see, it appears that " can be a gentle approach.


  1. Discuss the 'Un-discussable'. Issues that aren't discussed, especially in teams, can become more significant, resulting in higher absenteeism, turnover, and lower productivity and engagement. When talking about something sensitive, what is left unsaid is often what the conversation needs to be about. Trust your intuition - Skirting around the real issue is fruitless because it will not go away, which can be costly to the organisation. Acknowledge the unspoken; discuss the "un-discussable." The cost of engaging in difficult conversations far outweighs the discomfort you feel having it. Be aware of others limiting beliefs and values and respect their thoughts and beliefs.


  1. Be the change you want to see in others.  People don't always act as we'd like or how we'd expect them to. Don't let the work ethics of others be an excuse for you to follow suit.  While it's tempting to descend to the same pattern as your peers to fit in, it serves no positive purpose.  Be the change you want to see in others. It is just as significant to show as it is to lead.


  1. Be ready with humility. Just as you appreciate when others share their struggles openly with you, others will also appreciate your openness and vulnerability. When we share something with someone with implied criticism, we shouldn't be surprised when they get defensive. Counter their defensiveness by distinguishing the problem (behaviour or issue) from the person and inviting their input to address the issue. Often the solution to a problem is far from evident to you or anyone else. Be willing to ask for help in figuring out a better path moving forward, acknowledging that you don't have the answer but would like to work together to find it.


Lastly, it is not a tip, but staying future-focused is crucial. Many people excel at laying blame, throwing stones, and criticising others' mistakes because they focus on the past. It's easy. Staying focused on the future, what needs to change to keep the same problem from arising again, is more of a challenge.  If someone makes a mistake, they will already feel bad. It is ant helpful to make them feel worse.

Learning to coach will help you have more courageous conversations using the TGROW structure. You can learn about this in my "Coaching in the Workplace Course" check it out here.