Six Waymarkers in the Landscape of Leading with Kindness…

…without being a pushover

Thank you Andrew Martin and Pixabay for the image

This post comes out of one of the Leadership Sessions I host. It isn’t a read-out exactly, nor a summary, but a few ‘highlights’ from the session, distinctions and pointers I thought it might be useful to share. Places, perhaps, to pause and reflect on the landscape.

1. Can You Feel It?

My words may not be your words but I suspect we will both know ‘kindness’ when we feel it.

I don’t mind whether you have a definition in words. Sometimes that’s important-when you need agreements, when you’re in cooperation and you need a shared understanding. Your context is your context and you don’t need me (or anyone) to tell you what to write down. For a session like the one yesterday, where my focus is on your self-exploration, we didn’t need a definition in words, the feeling was enough, and we all scored a perfect ten.

2. Can You Transmit It?

Does it transmit?

We tested this as well (although you may not have realised that was what we were doing at the time), and yes, absolutely, in an environment like this when we are settled, calm, curious and safe, of course.

The kindness is palpable…

But when I polled you to ask whether that’s always the case, we got a 90% no. You shared experiences of when someone doesn’t take your words the way you intend them. That’s normal too, right? Good to know.

We could have spent the whole session here, but I merely point you to the seeming paradox here, kindness ‘real’, we know it, we had it in our hands yesterday, but it doesn’t always transmit.

Why is that and what more can I do?

Again, a topic for much longer than we had on the call, but first of all, knowing and adjusting expectations can help here. Knowing you might not create the feeling in someone else that you intend. But also knowing that a kind and loving presence is one of the greatest gifts you can give someone-to really see them, to let them be with their pain or anger or frustration. That is kindness.

And stop listening to yourself.

A very normal response, me too, but when I put my attention on how settled the other person is, and what I can do about that, then the dynamic, and the outcome, shifts. You may not be able to achieve perfect peace on a customer service call when the whole IT system has just gone down (thank you for the example on the call!), but allow someone their experience and notice what you can do to settle them, rather than attempt to convince them.

3. Infinite Kindness, Finite Resources

If you’re the ‘yes’ person, this could be a big one for you.

It seems to me there is no bottom to the well of kindness. The more you draw on it, the more it multiplies, and, when we sit in kindness it seems as if anything is possible.

And, at the same time, we operate with finite resources.

I make a choice about how many hours at the weekend to go cycling with my husband-how many hours even to set aside for these calls-you too made a choice about that.

There’s a concreteness to this world we inhabit, something we can describe,

Will I choose to drop the bike ride with husband and take my son somewhere, just because he asks? Will I give the promotion to this person or that person, or indeed to no-one because it doesn’t feel like we have found the right person?

When we see the separation of these two parts to our reality, we can stop chasing the infinite in the finite. No amount of saying ‘yes’ will bring that shared happiness. Kindness exists all by itself, and we can apply it in the most difficult of circumstances.

When we think the kindness is in the ‘yes’, in the allocation and choices, we can find ourselves chasing something that is never to be found. Too say no to another is not to be unkind, and to say yes does not define, or create, kindness.

These are the choices of life and yours to answer for yourself but it’s good to know there is no ‘right’ answer in the finite world, only answers that have consequences, good and bad and likely unknown. And that kindness will flow alongside and guide both your choices and your behaviour.

4. Intention and Presence

As is typical on these calls, it’s as if someone is reading my mind, or has my notes in front of them, and shares something that is exactly what I am thinking of pointing to next-the distinction between kindness of intention and kindness of our in-the-moment presence.

I hope you set your intentions with kindness, you run your business, or you’re aware of the ‘kindness’ of the recruitment policy-are you setting someone up to fail or does the process support someone to be their very best given the resource choices we talked about above?

It’s easy to be kind when things are going well, but what about when someone else is frustrated, aggrieved, shamed? Are we being kind in the moment? Do we laugh off a bad meeting because we feel slightly self-conscious ourselves, or do we pause and let that person share how they feel and simply be with them.

I’ve made all your mistakes and probably more, which is why I’m highlighting them-I’ve been there before and I know what to look for.

5. Discernment

All of this is pointing towards a greater discernment of what’s going on for you. Whatever your objective in coming to the call, I point you to,

Refining your own discernment, ‘tuning in’, as I often call it, will be what takes you closer to your objective.

We already did activities to test our capacity to feel certain things and you’re good to go-no-one was ‘tone-deaf’ to kindness on the call, and I trust you to develop and refine this discernment. Don’t think about ‘what if’, think about ‘what’s going on now’.

6. Delight

An hour is a short time to even describe a topic that is a lifetime’s exploration let alone try to dip into some helpful activities. But, rather than see that as a challenge, let me pose it as a delight. An opportunity to uncover something that is so multi-faceted that every movement we make uncovers yet more surfaces to marvel and admire.

That’s all these topics are doing, these short sessions, revealing that there is more depth to see, and more of life to enjoy.

On kindness, we completed with Seneca,

Wherever there is a human being, there is an opportunity for kindness.

With love,


Cathy Presland

Here to help with leadership and impact. I have lots of additional writing here, including regular leadership seminars. If you’d like to explore more deeply or join a conversation check those out or contact me directly if there’s something I can support you with.

Originally published at on April 7, 2021.

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