‘What if…?’ 10 Coaching Questions to help you prepare for your next ‘Difficult Conversation.’
What come to your mind when you have an important but tricky conversation to have with someone?
‘Stressful’
‘Heavy’
‘Can I just… not do it?’
Whether around feedback on performance or conduct, negotiating pay, or incidents of exclusion or discrimination, this is what I hear from my coaching clients about upcoming ‘difficult conversations’ in their roles.
It’s normal.
As humans we’d rather not experience the discomfort, vulnerability, and frankly, unpredictability that those conversations require.
Our minds catastrophise. We stray towards the worst possible outcome. The goriest ‘What Ifs.’
And yet…
In the following session, after they’ve had the conversation, clients come back with a different story to tell.
‘It went surprisingly well.’
‘It wasn’t as bad as I thought.’
‘I feel relieved - it was surprisingly refreshing.’
As Karla McClaren writes in her excellent book, ‘The Language of Emotions’, uncomfortable emotions aren’t pesky flies to be swatted or suppressed. Each one is a messenger with important data to deliver to us.
So I’ve been wondering this week about what message surprise has for us about challenging conversations. Maybe to balance out the risk of these conversations, we need to lean in more to the possibilities they bring, too.
Here are 10 ‘What If” questions to wonder about before your next Difficult Conversation, to help you entertain the possibilities alongside the risks…
Why am I having this conversation? What bigger purpose am I standing for?
What values do I want to embody in this conversation?
What do I hope to Discover from the other/s in this conversation, and what messages do I want to Deliver? How can I maintain a balance of both?
What new possibilties do I hope this conversation opens up?
What do I know about my body’s tendencies during difficult conversations? What might I do before, during and after to loosen physical tension and stay grounded?
What would I say if I weren’t afraid?
What boundaries can I set or requests can I make if it gets too much?
What data and learning might I gain from this conversation, even if my outcomes are not achieved?
Who can support me to prepare and debrief this conversation behind the scenes?
Whatever happens, how might this conversation be a ‘crucible moment’ that makes me a better leader and human being?
How does your next ‘Difficult Conversation’ look through this lens?
Let's Talk Possibilities
Imagine if you could approach your next feedback, conflict or money conversation with clarity and conviction.
If you want to feel more confident (and less anxious) in leading conversations that facilitate lasting change, I’ve got you.
Rebel Courage on the Leading Women in Tech Podcast
Anti-Oppressive Leadership & Doing Hard Things
Yes, I used the word ‘Refreshing’ to describe a conversation about addressing systemic racism on this podcast.
If you enjoyed this week’s newsletter on Difficult Conversations, or you’re looking to step up your allyship of marginalised folks, this conversation on anti-oppressive leadership with Toni Collis on the Leading Women in Tech Podcast was everything.
Debbie Danon
Founder, Rebel Leadership
Debbie is the founder of Rebel Leadership - a developmental practice serving leaders and teams of change-making organisations. She is a certified Integral Coach, inclusive leadership facilitator, and sought-after expert in personal and professional development.
In a world where burnout is too common among activists and change-makers, Debbie is passionate about supporting leaders to build their capacity for Rebel Authenticity, Balance and Courage - so that they and their teams can feel energised and fully resourced to navigate even the most complex challenges.
Clients recognise Debbie for her ‘deepest emotional intelligence’, ‘extensive leadership knowledge’ and ‘total unshockability.’
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