Sign up for my newsletter and receive your guide to 4 Key Actions for Managing a New Team!

Connect through curiosity: Cindy Carless

Michael Hunter


Welcome to Uncommon Leadership.

I’m Michael Hunter with Uncommon Teams.

Today I’m talking to Cindy Carless.

Cindy has been described by her daughter as a rolling stone that gathers no moss related to her work history. She’s enjoyed multiple career changes and is currently transitioning to work as a death doula, freelance coach, and facilitator. In contrast, she’s lived in the same house for over twenty years, except for a two-year attempt to settle in Fredensborg, Denmark.

Welcome, Cindy.

Cindy Carless 0:38

Thank you so much, Michael.

Michael 0:43

As you reflect on your journey to seeing people as people, and learning to leverage their unique gifts to best accomplish your goals, when did you first recognize this might be a valuable approach?

Cindy 0:59

Well, it’s such a great question to contemplate.

I started out life as an accountant, so in a financial surrounding.

I was very soon tired of the digital or the number aspect of the work and more interested in the people elements.

That was back in the late 1990s.

I then embarked on a training, or a way of working with people in training, that became the thing that I thought would address the need of working with people.

It was interesting to make the shift.

I did a train-the-trainer diploma so that I learned a lot about what the training methodology was all about and how to engage with people.

It was a long process that took me through almost wanting to full-speed people with information and get them to the destination that was perceived as the desired outcome for the training initiative.

Over many years, I started to realize that that was exhausting.

And, that I got a sense of fulfillment from people growing and developing and learning things.

The process was not the best one.

So slowly, it evolved into more of a pull methodology or focus on the people themselves and where they were at and what methods would work to engage with them in the learning as opposed to force-feeding the change or the information onto them.

Michael 3:17

As you made that transformation, what signals did you use, how did you know that you were adjusting your alignment in the direction that you wanted to go, that was working better for you?

Cindy 3:33

I think essentially, it became about my energy levels.

I found that I was becoming exhausted by wanting to give so much in a training room.

It almost felt like a performance in some ways, which just didn’t feel authentic and didn’t feel real to me.

That was probably the signal that this was not sustainable, this was not something that felt aligned with something that I could continue with, I suppose.

I started investigating and exploring what that could possibly mean for me and how I could do it differently.

Michael 4:37

When you say that you were feeling exhausted and your energy levels were completely drained, how did that show up for you?

Cindy 4:46

Days were just feeling longer and longer, and by the end of it, I felt completely depleted.

I also had a sense I was taking ownership for where somebody else was at, and that felt like I wasn’t honoring the person on the other side who was receiving the training.

It really was that sense of, I was taking on the world’s problems, feeling responsible for making this shift.

At the end of the day, there wasn’t much evidence of that information being received and being utilized.

So, there was a key for me as well: that everything was designed for the person to grow and learn and develop, and I was giving my all, and yet there wasn’t much evidence of all of that information, all of that initiative, bearing fruit from the other’s perspective. Of them really showing that they had taken some of that on board and were able to use it differently.

Michael 6:13

How do you evaluate how well someone is absorbing what you’re offering them and how well they’re integrating that in and actually making that part of them?

Cindy 6:26

That is such a great question.

It’s one that has plagued me particularly on this journey of making the switch.

Obviously, formal training is very much, there’s an assignment or there’s some kind of exercise that gets graded or marked or assessed, and a percentage allocated as to how much information the person has actually taken on board.

That has always felt hollow to me in so many ways.

People can either do really well at that and then go into their day jobs, where you see them interact, and you’re not seeing any of that come through; or they can be really bad at their assessment part, their practical part, and yet as time goes by, you start to see that actually they took on more than was evidenced in their so-called formal assessment.

So, I started to realize that measuring learning in that way, with a mark or a percentage or something like that, was definitely not something that aligned with actually seeing a shift in the person’s abilities in the way they think, in how they approach things.

I started to realize that when somebody is engaging with you, when they’re asking questions, when they’re finding things on their own and coming and saying, “Oh, I found this book or this podcast or this bit of information,” that for me was a higher indicator of the learning or the shift taking place within the person as opposed to a single assessment or assignment designed to test somebody’s knowledge and skills.

I think they’re basically encapsulated.

This whole coaching return on investment was something that then plagued me as I evolved into that being part of my work life.

It’s very hard to show that your coaching is giving a return on investment if you’re in a corporate environment, which is where I found myself then.

It’s something that I still spend a lot of time thinking about, and wondering how we can actually measure the impact that has been made on somebody else.

Michael 9:29

It sounds as if your intent shifted from learn this material and prove to me that you understand and you’re going to use it to I’m using this material as a proxy to engaging your curiosity and your openness, and increasing that is really the goal despite the surface or proxy intent of here’s some material that will help you do your job better.

Cindy 10:05


Michael 10:10

You mentioned that when we’re coaching, it’s challenging to really prove the impact that we have on a person on a team, the people that we’re working with. As you made that shift, did you come across any proxy measures that you use as some signal that you were having an impact you wanted to have?

Cindy 10:44

I must admit, as I said to you, it’s been a continuing exploration for me.

I definitely realized that anything that you put a number to is open to misuse by anybody interpreting it or wanting to put it into a spreadsheet and add it up and say, “Oh, cool, this means you achieved this amount of something.”

I explored various different things.

I even went with the karate belt scheme of different colors. Trying to work through the novice to mastery kind of elements.

Mostly, I think you hit the nail on the head when you said it’s about curiosity and creativity from the other person and engagement from them.

Those are difficult things to measure.

But they do come across for me in whether the person is seeking out new information, which obviously you’re not always going to know about. It’s very seldom that somebody will come back to you after a coaching session and say, “You know what? After chatting to you, I actually went and did this.”

It’s a really challenging part of coaching in a corporate environment, because it’s a very elusive measure.

It’s also very long-term something that happens.

Change doesn’t happen immediately.

Part of the things that were expected of me as a coach was that I would have this magic wand, and I would just touch somebody in one hour, and they would be remarkably changed forever and completely different.

I’m sure as you know, that’s not the experience.

It can take time.

When I reflect on my life and look back, there are many times where I’m going, “Wow, that took me a long time to really take that information on board and understand it and make it part of how I now approach life.”

It’s not something that can be measured in hours or weeks or years. It’s more like years.

Michael 13:24

As you’re working with people now, when you have your first conversations about, “What are you the client struggling with? Here are ways that I can help you achieve what you’re trying to achieve.” How do you talk with them about how you and they will measure their progress and know whether working with you is having the impact that you and they both want it to have?

Cindy 14:01

I have sort of let go of that part of being outcomes focused and of late have tried to be much more interested in being present with what is, and making sure that the person themselves is conscious of what it is that they’re working towards, and how they would be able to describe what that would mean to them. Being very open and candid and honest about the fact that it isn’t a magic wand, that it can take time, that you definitely will have sabotages and roadblocks along the way, and that that’s all part of the learning.

I am very much engaged now in learning something and then trying to put it into practice.

And then reflecting. Coming back and talking about how it felt to put that learning into practice.

Very much about the engagement.

Not looking for that measure, but looking for that continued engagement.

Often, I have found that people would tend to disappear as a result, because it’s hard work to work on yourself. It’s hard work to achieve outcomes. So, often your next session would be canceled. Or there would be some reason why you can’t meet.

That is an indicator of both the person not really being ready, or possibly feeling a little bit intimidated by the extent of the change.

So, I keep trying to go smaller and smaller with, as you say, the little steps that can be taken.

Those actually end up being giant steps at the end of the day.

If you try to take a giant step, often that’s what creates a whole lot of issues.

Michael 16:29


We take too big of a step, we lose our balance, and fall down.

If instead, we take twenty smaller steps that add up to the same distance as that big step, then we can stay stable.

Each one is a lot easier to digest.

And we may actually get there faster.

Because we’re not trying to stabilize.

Not having to expend as much energy stabilizing and working through fears and whatever else may be coming up because it’s just all such much smaller scale.

Cindy 17:09

Exactly. Very much so.

Michael 17:24

Is there anything that you’re struggling with today that showed up like, “Oh my gosh, I didn’t know that would be an issue?”

Cindy 17:42

It’s quite challenging to go, “Oh my gosh, I didn’t know that would be an issue.”

But there are many things related with the challenges.

One is how the person wants to actually make the change, wants to achieve something, and then becomes fatigued or disengaged or isn’t quite ready for it.

That’s one that I didn’t really expect to come across.

Thinking that most people would be interested in making changes and committed to making them, forgetting how fatiguing it can be to constantly be working on yourself and constantly be changing.

Also, that you’re working within a system.

Whether it be your family, whether it be your colleagues at work, there are many people actually almost invested in you staying the same and not really wanting you to be any different. Even though it’s better or best maybe for you, because you decided this is where you want to go and this is an improvement that you feel you can make.

It often is not as welcome or achievable, even, in the system that you find yourself operating in or the environment that you have.

You almost have to consider the conduciveness of the environment to the changes that you’re wanting to make and the shifts that you are wanting to make.

And realize how uncomfortable that can actually be, not just for you, but for many others too.

Michael 19:52

Are there specific tools you found that help you and your clients deal with that uncomfortableness?

Cindy 20:03

I’ve recently started to experiment with celebratory retros and joy rituals.

I’ve always been a fan of retro—well, probably the last ten or fifteen years.

The idea was always to try and identify those little steps that you could take and continuous improvement.

I realized that what we don’t do enough of is spend time on the celebrations. On the things that went well. On finding the joy. On finding the elements that we even take for granted.

So, I now particularly try to at least once every now and then focus on just pure celebration.

Don’t worry about what’s next.

Don’t worry about what we’re going to improve.

Just, let’s look at where we are and what we have to celebrate.

It may not even be an improvement.

It can just be something that you’re grateful for in the particular situation.

That, for me, really builds energy.

That focus on gratitude and the joy element.

The rituals around joy are something that I’ve just recently started exploring.

It’s so important to be able to remember those.

The importance of the ritualization is that you can quickly then grab onto that energy upliftment and build from there.

It gives you an inner resource almost, that you can grab on at any time when you’re feeling depleted, when you’re feeling slightly overwhelmed or exhausted.

If you’ve ritualized the joy, it’s there more easily for you to bring into your life as an energizer.

Michael 22:20

Do you have an example of what a joy ritual might look like?

Cindy 22:25

A joy ritual? Yes.

It could be something as simple as enjoying your coffee.

You could have a specific ritual around how you make your coffee and bringing your mindfulness to it.

It doesn’t even have to be anything special.

Just a special cup, maybe, that you use.

Or just paying attention to the ritual of making your coffee.

Then, sitting down and making sure that you literally enjoy each sip.

You can even count the sips.

You will realize that the more mindful you become of taking each sip, the more joy you actually get from that cup of coffee, which on any other day could be quickly taking down your cup of coffee.

That’s the kind of thing: really focusing on how you can bring joy into this simple thing of the coffee.

Michael 23:30

Seeking out and highlighting an activity that brings you joy.

Cindy 23:37


That’s gonna be different for everybody.

Michael 23:43

I was just going to say that for some of us, the joyful aspect of that cup of coffee may be selecting the cup. After that, it’s just a cup of coffee.

For some of us, it will be the process of making the coffee.

Or all the senses that are activated as the coffee is being made.

And for some of us, it’s the drinking, or just holding it.

I have a friend who doesn’t drink coffee. Yet she makes coffee every day because she loves the smell. It is the sense of holding that mug. Then she puts it down the drain.

Cindy 24:30

Yep, yeah.

Michael 24:33

That’s a great example of how the same activity brings joy in different ways to different people.

Cindy 24:45

It points to the uniqueness of each of us.

There’s so much that is our shared common humanity that I think is important for us not to lose sight of and not to forget about.

That is how we connect with each other and how we relate to each other.

There’s also a very important part of remembering that each and every one of us is unique, and it’s about finding what works for you at the end of the day.

I can share my experience and suggest certain things.

That’s where that curiosity and engagement from the other, for me, is so important.

It has to be what feels authentic and unique for them. Is going to actually resonate. Form part of what is meaningful for them in their futures.

Michael 25:52

What other tools have you found or do you use to help build that engagement between people?

Cindy 26:06

That’s a really good question.

Nothing comes to mind particularly.

I have played a little bit with embodiment techniques and yoga breathing or mudras, taking positions with hands.

I’m not sure that was so much to achieve the outcome.

Those are tools that allow people to connect in their particular way.

If you can use whatever comes to you as a position of your hands to indicate your tension or your stress or your joy, that can be something unique.

But, I haven’t actually thought about it in the way that you’ve raised the question.

Michael 27:06

That’s a really interesting idea to me: signaling how we’re feeling with certain body postures, whether that’s hands, how we’re sitting, all of that.

That allows us then, while we’re interacting with other people, to provide information about what’s going on for us without having to verbally inject that into the conversation.

It lets us add a layer of richness to the conversation that the other person can utilize as they wish without forcing it on them.

Cindy 27:57


I have found that often I cognitively think something and try to put it into words. And sometimes I realize that that way of doing it is counterproductive and almost takes me too much into my head.

I’m often astounded at the wisdom that comes out of me when my body is engaged and I’m not letting my mind take over.

I’m a big fan of massages, and that for me is also really incredible.

I’ve recently found massage therapists who do the talking kind of massage. So, it’s almost like a therapeutic session, but you’re having a massage at the same time.

I’m often astounded at the words that come out of my mouth while my body is actually enjoying touch.

There’s definitely something about embodiment.

And to get out of our heads.

Michael 29:21


The more that we distract whichever part of us we’re used to working with, whether that’s our mind, heart, body, spirit, and allow all of them to work together, and to not filter what they’re trying to tell us, the more what really needs to be done to move us forward can happen.

Cindy 29:49

That’s definitely something that’s becoming really evident to me, the older I get, and the more I realize that my analytical past, having been a business analyst and a test analyst, is very much of disservice in some ways. Because it brings me up into my head and disconnects me from that holistic element that you were talking about, of your heart, your mind and your spirit needing to be just as involved for you to be able to show up authentically and really be there and be present.

Michael 30:34

This has been a great conversation today, Cindy.

What else should I ask you today?

Cindy 30:40

What else should you ask me today?

Well, interestingly enough, the transition that I’m currently going through is probably one that I wouldn’t mind talking about. And that’s related to embarking on the work as a death doula and end-of-life companion. So, I’m happy to chat about that, if you’d like to.

Michael 31:09

Please explain what that is, and how it connects with the work that you’ve been doing. How it connects from where you’ve been and where you’re going?

Cindy 31:24

The death doula work is around being the emotional and spiritual support that is often missing at end-of-life, where mostly there are doctors and nurses and social workers. There for the person’s physical and medical requirements.

But often the greater part, that holistic element that we were talking about, is neglected in the environment of end-of-life.

It is often that emotional and spiritual well-being that allows for a peace-filled end-of-life.

It’s been fascinating to immerse myself in the learning.

It has, in so many ways, brought together the coaching elements that I’ve been working with up until now, and facilitation, and literally being present with what is, and being able to reflect.

A lot of the work is around creating legacies for people as they are in their end-of-life phase, as a way to both honor their lives as well as leave something behind.

It’s a huge gift and a privilege to be able to work with somebody and pull all those things together that are probably going to be neglected due to all the medical and physical issues that are most prevalent at that time.

It brings together the creativity, the heart, and the curiosity about what was life like for this person. How to focus on living, right until that death moment. Really making the most of life up until that final breath.

Michael 33:57

Is this exclusively working with people who know they have a timeline to their death and what that is? Or is it also people who can be, “I probably have twenty years to go, and I just want to be ready for that when it comes, so help me work on this now.”

Cindy 34:17

It’s both.

Even more, I’ve realized that loss is something that is part of our human experience.

I’m constantly astounded that we don’t do it better, to be completely honest.

Whether you’re leaving high school and going into university, or whether it’s the end of a relationship, or whether you’re changing careers or changing jobs, there’s an element of loss that is there.

Part of the learning for me is that, yes, it’s most prevalent when you only have a certain amount of time to live or you’ve been told that your life has an expectancy.

But, I definitely feel like we can all benefit from bringing those planning, bringing those elements into any transition. Any time that we are going from one thing to the next thing.

Needing to make plans.

Needing to look back and think about the lessons that we’ve learned from a previous career or a previous way of being.

I don’t think it’s end-of-life only related to death, but end-of-life as we know it.

And we’re constantly doing that as human beings.

So, if we can embrace that, and make it less scary as part of our lives, then we can start destigmatizing death and dying as part of life as well.

Because it certainly is.

Michael 36:05


The more we recognize that all these changes are a death to one life and birth into a new life, the more we can make that transition graceful and experience that the way that we want to experience it.

Cindy 36:29


I suppose, in essence, we get a false sense of control, because we are never really in control.

But by engaging with something, you start to take hold of what there is for you to be able to take hold of.

That in itself brings, as you said, some grace, some peace, and elements that allow or facilitate an easier transition.

Michael 37:05

That word “engagement” feels really key.

If we think of our life as, there’s this torrent of energy zooming past us, and we get caught up in that energy sometimes against our will, and we’re just tumbled about, and we feel like we have no control.

If we had total control, we would grab hold of that energy. Shape it exactly the way we want. Hold it and shove it where you want.

That would be really challenging to do.

We don’t have the ability to do that.

But by engaging, it’s not that we’re grabbing hold of that and forcing it to what we want. It’s not that we’re just being tumbled about helplessly. We’re grabbing hold of it and playing with it. It becomes a dance.

Cindy 38:13

Yes. Yes.

It almost comes back to that realization I had of force-feeding through training material is that element of trying to grab something and make it into something else.

And then the coaching part, where it’s more allowing and how the measurement of that is around engagement and curiosity and creativity related to what is, almost embracing what is, in each of the moments.

Michael 38:56

We stop trying to control whatever it is and start creating with it.

I love that image. Thank you.

What would you like to leave our listeners with today?

Cindy 39:13

I’ve been thinking about that one for a while.

What comes to me is the magic of moments.

Really engaging with those moments as much as you can.

Whether it is to elicit the joy from those moments.

Or it is to elicit a lesson.

Or it is to elicit the next small step.

What I would hope, or love to leave listeners with, is: if you become aware of the magic of the moments and being with what is, then your creativity and your curiosity can allow you to make the most of each and every one of those moments and build a magical life.

Michael 40:23

Creativity, curiosity, magic: sounds like a wonderful life to me.

For people who have been intrigued by what we’ve talked about today, who’d like to connect with you and learn more about how you work and the work that you do, what’s the best way for them to connect with you?

Cindy 40:51

Michael, I think the best way is via LinkedIn. I’m on LinkedIn. They can find my profile. It’s Cindy Carless.

I’ve tried to keep it up to date and include as much about my “rolling stone history” as I can.

I would love to engage with people on LinkedIn.

That would be great.

Also, Cindy’s website is

Michael 41:19

I’ll link to that in the show notes.

Cindy 41:23

Excellent. Thank you so much.

Michael 41:25

Thank you for a wonderful conversation today, Cindy.

Cindy 41:29

Thank you, Michael. It’s been such an honor and a privilege to be with you and to be able to share with you.

Michael 41:37

Thank you. You’re welcome.

And audience, we’re happy to have had you here today. Please let us know what resonated with you. Cindy on LinkedIn, me through my website.

Have a creative and curious filled day.

Cindy 41:58

I echo that.

Michael 42:01

Thanks for joining us on Uncommon Leadership today.

If you found these stories interesting, inspiring, and illuminating, sign up for my newsletter.

Use the form at the top of this page.

You’ll be the first to know about every new episode of Uncommon Leadership.

You’ll also discover how you can build uncommon teams.

Thanks so much!

Sign up for my newsletter and receive your guide to 4 Key Actions for Managing a New Team!