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By October 5, 2017August 23rd, 2021No Comments

It’s 5.30am on a Tuesday morning and I’m rather red-faced, having a quiet, semi-composed cry in the gym. And it wasn’t because I’d pumped out too many squats.

I was completely blown away by being on the receiving end of what I call a ‘caring conversation’, delivered so eloquently at this most unexpected hour of the day. Specifically, my trainer had taken a moment to notice how I was doing energetically and offered some kind, heartfelt advice about looking after myself.

Now, as a leadership expert I like to believe I have self-awareness and self-care sorted (who am I kidding, nobody is completely sorted, right?!), so his comments took me by surprise.

I was most touched by his courage to have a caring conversation with me. The kind where he unhurriedly asked questions without presuming any answers, simply being present while I responded and then being brave enough to gently but clearly shine a light on some behavioural patterns that are not serving me.

All of which hit me right between the eyes and made me rethink my self-care mojo from that moment forward.

And it also got me thinking about the value of caring conversations in leadership…


Leaders who have the courage to have caring conversations with us are special,

and we want to keep them close.

Caring conversations in leadership are powerful – but most leaders will shy away because it can feel vulnerable and awkward to show our colleagues we really care, especially considering the possibility that uncomfortable emotions might surface.

So, how do we deliver these conversations without it getting emotionally ‘sticky’?

First, as a leader in caring conversations you must completely set aside your own agendas for what you might want from the conversation – which in itself, is liberating – to meet the person where they are and ask questions that help them identify their overall thinking patterns, or ‘meta-programs’ as we call them in the leadership business. Simple, respectful questions like: “Tell me what’s happening for you?” and “How is that impacting you and your life?” are super powerful – but subtle enough to allow the recipient to disclose what they’re comfortable discussing with their leader.

Next, we get present – that means we shut the heck up, tune in and just listen. When we are energetically available and ready to truly listen, with no agenda or desired outcomes planned, our people sense openness and feel increasingly safe to tell us what’s on their mind. Sure, some gentle questioning can help things along. But mostly we need to be okay to ‘hold the space’ for the conversation – which means not filling in the uncomfortable and emotional silences with small talk, but simply being present for the other person. Critically, there’s no advising, telling or directing in caring conversations – just a few kind, considered questions which help our people get to the heart of the matter.

When done right, with presence and a sense of service, we can attain a whole new understanding of what is driving our people.

Further, when we release the need to ‘fix’ discomfort or rescue our people from emotional experience, and simply be present in the conversation, we’ll be able to help them notice patterns which may not be serving them. Basically, it comes down to having the courage to offer our insights in a supportive, caring but challenging way. For example, we might notice a pattern of overcommitting to work – and we could simply offer “I wonder how your life might be different if you weren’t fully allocating your time each and every week?”.

Delivered well, caring conversations can open a new realm of possibility in the thinking of our people.


Holding the space for caring conversations is a critical role of a leader. When we consider that less than 44% of employees believe their leaders are effective (from a 2017 global survey by professional services firm, Towers Watson), it’s clear we must find new and more meaningful ways to connect with and engage our people.

By making caring conversations part of our leadership mojo, we can start to address the common problems that leaders so frequently complain about – that our teams aren’t delivering consistently, or our bosses don’t ‘get’ us, or we’re concerned that our people aren’t bringing the desired level of energy and enthusiasm to the business. All of this simply points to the need for us to have better quality connections with our people.

There’s nothing as refreshing as a conversation where the other person is acting in complete service to you – so go do that for someone else today. And when you’re done, let me know how it felt for YOU to be acting in complete service to your people… I’ll bet you’ll be surprised at the rewards.