Following Your Internal Compass with Laura Shepherd

In this episode of Uncover the Human, Alex and Cristina sit down with leadership coach Laura Shepherd for a rich conversation about following your internal compass. Laura shares her journey from corporate success to scuba instructor to coach, describing what it feels like when the compass spins, how she learned to recognize misalignment, and what it’s like to step into the “exciting discomfort” of growth. Together, they explore the power of weekly reflection, rewarding progress along the way, and the courage it takes to leap when the next step isn’t clear.
Listeners will hear how authenticity, reflection, and self-leadership intertwine to create alignment that fuels both personal energy and effective leadership. Laura explains how leaders who do their inner work show up more fully, set clearer expectations, and create safe, trusting environments where teams can thrive. With metaphors ranging from compasses and mirrors to buses and statues, this conversation invites you to reflect on your own path—and consider whether you’re moving toward possibility or simply checking boxes.
Credits: Raechel Sherwood for Original Score Composition.
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00:00 - Introduction to Internal Compass
09:40 - Laura's Corporate to Coaching Journey
15:47 - Recognizing When Your Compass Spins
24:16 - Authenticity and Reflection in Leadership
31:24 - From Checkbox Living to Meaningful Direction
37:25 - Leadership Through Self-Understanding
44:38 - Taking the Leap: When to Leave
“Laura Shepherd: Before, which was very true, I checked off all the boxes, and it's like the reflection of check, done that, versus the reflection of, okay, that worked, and I did it, great. Is it what I still want to do, or how do I want to evolve it, or what else do I want to add to it, or take away from it?”
[OVERVIEW]
Alex Cullimore: Hello, Cristina.
Cristina Amigoni: Hello. It's Friday, our normal recording day.
Alex Cullimore: Our normal recording day, which also means our normal recording brains, which are just about flat by this time of the week.
Cristina Amigoni: Yes, yes. Somehow, it was a coherent conversation, I think, because the listeners will have to share whether it's coherent or not.
Alex Cullimore: Yeah, please let us know if this is not coherent. But I think Laura saved us on this one. Laura has some really powerful ideas. Laura was our guest this week. Laura Shepherd, who has really powerful ideas on following inner compasses, understanding your inner compass, and what happens when you align and don't align with that. I thought it was a fascinating conversation on the ways in which you get to trust yourself and what happens when you do.
Cristina Amigoni: Yes.
Alex Cullimore: I thought it was a much more hands-on conversation that sometimes it's easy to access when you start to realize, “Hey, I could align myself. That's great.” This felt more, what does that look like in an application?
Cristina Amigoni: Yes, definitely. Yeah. It also feels a little bit of a bingo board of monopoly items. We talked about mirrors, we've got compass, we've got nets, we've got statues, we've got buses. It's all in there.
Alex Cullimore: These all sound like important items in a Jumanji film, or something.
Cristina Amigoni: Exactly.
Alex Cullimore: Please, enjoy this conversation with Laura, especially if you're thinking about your own internal compass and whether you're on the right path.
Cristina Amigoni: Yes. Enjoy.
[INTRODUCTION]
Alex Cullimore: Welcome to Uncover the Human, where every conversation revolves around enhancing all the connections in our lives.
Cristina Amigoni: Whether that’s with our families, co-workers, or even ourselves.
Alex Cullimore: When we can be our authentic selves, magic happens.
Cristina Amigoni: This is Cristina Amigoni.
Alex Cullimore: And this is Alex Cullimore.
HOSTS: Let's dive in.
Authenticity means freedom.
Authenticity means going with your gut.
Authenticity is bringing 100% of yourself. Not just the parts you think people want to see, but all of you.
Being authentic means that you have integrity to yourself.
It's the way our intuition is whispering something deep-rooted and true.
Authenticity is when you truly know yourself. You remember and connect to who you were before others told you who you should be.
It's transparency, relatability, no frills, no makeup, just being.
[EPISODE]
Alex Cullimore: Welcome back to this episode of Uncover the Human. Today, Cristina and I are joined by our guest, Laura Shepherd. Welcome to the podcast, Laura.
Laura Shepherd: Thank you, Alex and Cristina. I'm super grateful to be here.
Cristina Amigoni: Welcome.
Alex Cullimore: We're excited to have you. If you wouldn't mind giving the audience just a little background, what's your story? What brought you here?
Laura Shepherd: Yeah, absolutely. I'm excited to share. I am a leadership coach and my background is corporate. I was in marketing in the consumer package goods world. I'm Canadian, and all of my work has been in Canada, but with global brands and Canadian brands. I worked my way up the ladder, had an amazing journey. Really was a high achiever. Went for the goals, got the goals and kept doing that. Then one day, I woke up and went, is this all there is? I was doing what I wanted to do. I was achieving the goals and looked around and went, it's not really meaningful anymore.
It was at the start, like I learned so much, got so much out of learning business, learning branding, learning marketing, learning a whole lot out of my career path. I just, it wasn't satisfying anymore. My compass was spinning. My internal compass was spinning going, what do I find next? It took me a while to figure that out. I did a couple of exploration side launches. I left the corporate world and went to the Caribbean for 40 bucks a day, plus tips, to teach stupid diving and drive boats. I'm like, yeah, why did – Everyone's like, why did you come back?
Cristina Amigoni: Yeah.
Laura Shepherd: I have an entrepreneurial spirit. I've always had it. My dad was an entrepreneur. I wanted to open my own scuba business, but I wanted to go live it, breathe it, feel it, see if it really was. I did a path along that for about four years. Loved every minute of it. Knew it wasn't the path that I actually wanted to be in from a business point of view. Came back to the corporate world. Got back into marketing. My compass then started spinning yet again. I found that ultimate path that I found now is coaching. I've done a lot of coaching in my life. I teach scuba diving. I teach skiing. I also coach my staff and my team in corporate.
When I actually started working with the coach myself to figure out my own direction, it came through loud and clear that I'm supposed to help people find their own path and help them with communication and leadership, and how they can be aligned within themselves and live from an energy of authenticity, so that they can be the best that they can be. I know that sounds hokey, but it’s so rewarding and I love it, and here I am now doing it.
Cristina Amigoni: That's a wonderful story. I love the internal compass piece that you brought up a couple of times, because a lot of that coaching, especially it's teaching people, or helping people understand when they hear, and acknowledging and have the awareness of that internal compass ringing the bells and saying like, this is not right. What's happening here? How did you realize that that was happening and what did it feel like? What does it feel like when the internal compass is off?
Laura Shepherd: Oh, that's such a great question, Cristina. Thank you. Because I didn't listen to it for the longest time. For me, the internal compass spinning felt just like I was tired. I was working hard, but I wasn't feeling I was making any progress. It was hard to get out of bed in the morning. It was like, what am I here for? But it took me a long time. It took me a lot of energy, wasted energy that I fought against myself. It was this negative internal conflict that I felt, before I woke up to say, “Huh. I got to do something about this.” What do I do about it, right?
I think when I just said that, like what do you do about it? I didn't know, right? I didn't know what to do, but I didn't know how to figure it out. Because strong, independent woman, I have all the answers. I can do this.
Cristina Amigoni: You’ll figure it out, because you have to.
Laura Shepherd: I’ll figure it out. That was my identity. It was a lot of internal struggles, how I really felt when I stepped out of my zone. I met a coach and I start – she was being coach with me and was being curious and asking me questions. I went, “Whoa, I need help.” It's okay to ask for help. That was my first step of trying to figure out how to stop the spin and find the direction.
Alex Cullimore: Yeah. That's it. I don't think anybody can relate to that feeling. Nobody has internal struggle. Only you. No, that is absolutely a good description of what the internal tension that you can feel when you start to have that inauthentic drift, and you start to move into like, “Hey, wait. Was this right for me? Is this what I actually want to be doing?” I'm curious how it started to feel when you started to feel like you were on the right chart, on the right path with that compass when you felt you – What does it feel like that?
Laura Shepherd: Oh, you guys are good. Another good question. All the real stuff out. Because what I want to say is, it's amazing, and I'm aligned. That is amazing.
Cristina Amigoni: It is amazing.
Laura Shepherd: It is absolutely amazing, the feeling of alignment on the path. It's a knowing for me. My visualization and my feeling is a knowing. It's an internal in my gut, in my chest, I feel aligned. The tension goes away, so it's really powerful and it's really hard. Because I am now in a – I'm aligned, but it's uncomfortable, because it's more uncertain and I'm figuring things out. It's an exciting discomfort. Whereas, before I was uncomfortable, but comfortable in my discomfort, if that makes sense.
Cristina Amigoni: Yes. Yes.
Laura Shepherd: Now, it's like, I'm uncomfortable in a good way for growth and learning, but it doesn't make it easy. In the back of my brain, I was like, well, once I find my purpose and my direction and I get aligned, it'd be all rainbows and unicorns. It wasn't.
Alex Cullimore: It's a great way of describing it. I like the idea of a comfortable discomfort, where you're starting to drift into – You've made your life comfortable, but you don't feel good about it, versus an exciting discomfort, which is, this is still really hard, but I'm glad I'm on this path.
Laura Shepherd: Well, there's a lot more reward, and it's not all hard. There's a lot more reward, and I know I'm on the right path. Now I look at the discomfort is, ooh, I'm growing. This is good. Where I'm finding what I need to remind myself of sometimes is, okay, when I'm in a zone of, it's still gross, enjoy and celebrate and reward myself along the way, because this is what it's about for me. I've released that. Well, I say, I've released the attachment to outcomes. I continue to release the attachments more accurately.
Cristina Amigoni: It's a muscle. It's not a metal.
Laura Shepherd: It's a muscle. I get it, and then it comes back. I get and it comes back. It's rewarding yourself along that path, because it really is the path. It definitely feels totally different than the comfortable discomfort. It gives me energy. Then I remind myself when it's hard, yeah, I know. I'm choosing this hard and I'm loving it. Versus just going, letting life happen. I'm choosing.
Alex Cullimore: I think it's really important distinction on the separation of rewards. You talked about the first part of your story. You're coming up and you're going, you're just wanting to achieve all the goals, checking the boxes, making sure you get the, hey, this is the next thing I want to do. You get there, get there, get there, and there's that feeling of external accomplishments. Then this path you're talking about, you're finding these internal rewards of this feels good, this feels right, and finding the ways to celebrate that for yourself, so that you remind yourself, hey, that's important. It's important to continue to check in with, “Hey, this feels good. This is good for me.”
Laura Shepherd: Absolutely. Well, I think in our world today, we forget to reward ourselves. It's so busy. It's so chaotic. The world is still telling us we're supposed to be doing things. It's a constant muscle, as you said earlier, Cristina, to actually practice and work through that. We need to reward ourselves. That's what life's about. It's not about all rewards, but it's about when you do something, celebrate. We forget, it's too busy.
Cristina Amigoni: Well, and I find that rewarding ourselves during the journey in the progress, instead of at the end, or hoping somebody else would reward us at the end, because we're never good enough to be rewarding ourselves. I think it helps with that awareness of realizing like, “Oh, the compass is pointing in the right direction, or it's not.” Without that pause, as things are happening, it's harder to recognize like, am I in alignment? Is this not in alignment? Is it internal or is it external? What can I do here? Where's my choice, if we don't actually pause to recognize what's going on?
Laura Shepherd: That's a wonderful distinction, because it is the rewarding in the journey, not at the end. That's where true, for me, anyways, that's where true alignment comes from. It's like, it is the process. It's in that life. The end game, there is no end game.
Alex Cullimore: That brings up one of the things you brought up. You said, you found a coach, and that coach was helpful in realizing, “Hey, maybe I need some help.” I think that personally, yeah, I find that coaching is useful, particularly in providing that reflection point of not only helping remind you when you should do things like celebrate, reward yourself. You have some third-party perspective saying, “Hey, this is big.” But also, just that reflection point of being able to look at yourself and say, “Oh, this compass seems out of alignment.” There's something profound about somebody who's able to reflect accurately enough that you can comfortably, or at least without totally turning away, face yourself in the mirror.
Laura Shepherd: Oh, yeah. Having a coach to be that third-party safe, non-judgmental space, to hold the mirror up for us, and they do more than hold the mirror. They hold the mirror and challenge you in a way that, to open you up, to help you look at yourself to get to what the root is of what's going on in your journeys and your choices. When you get there, I mean, that's where that support and accountability, right? It's accountability as well. It's powerful. It's a powerful, powerful place to be for, have someone hold space for you. It's only about you. It's like, you're seen, you’re heard. It's all you. You get to be you. So many people in our world are not seen and heard in the way that they need or want to be.
Cristina Amigoni: Very true. Very true. Yeah, that mirror, it's interesting because it is more than just a mirror. It's like, yes, you see your reflection, but you also see the cave behind you. You're like, “You see that? You need to walk there. Can we go walk there?”
Laura Shepherd: The answer you need is in the cave. You need to look at life. I totally didn't do that, right? But that's that approach. Love that approach.
Cristina Amigoni: Yes. Especially when there's a lot of, “I'm fine.” I'm like, uh-huh. Sure, you are.
Laura Shepherd: Well, that word fine and the word should are two red flags, I've found with my client. It's like, oh, yeah. Okay, let's dig in here.
Alex Cullimore: When you’re thinking about the journey that you've taken, how is that coaching both inform your own personal compass that you're currently on the trajectory of making sure you're in this leadership coach position? How do you see that helping other people?
Laura Shepherd: Great question. Yeah. I mean, I think for me personally, because I'm more aligned with where I am, I am showing up everywhere, more authentically me. I used to be work Laura and life Laura. Now I'm all. No matter what situation I show up in, I'm all me. When I show up as all me, people that resonate with me resonate with me. Not everybody's going to resonate with me, and that's fine. People that I can help, or that can help me alignment of myself personally helps that, that connection.
Then, helping others, it's really, leadership starts with ourselves. When you are aligned with yourself, you can communicate better. You understand different things. You understand what you do and say, impacts others. We can't change anybody but ourselves, and we can influence through how we show up and how we communicate and how we lead as people. Then that can help you in your careers, right? It's like, how do you influence to get what you want? It starts with a clarity of alignment of what you want.
Cristina Amigoni: Yes. Well, I'm looking inward and understanding that self-leadership of like, okay, how do I lead myself? How do I communicate with myself, so that then, I can understand how to do it with others? A lot of times, especially when we think about leadership, or in most definitions of leadership, it's always outward. It's like, it’s about others. I'm like, is it about others?
Laura Shepherd: I agree that it is not about others. It's only about others after it's about you, right? The beauty of humanity is connection is what we all need, right? You're not alone living in a cave, even if you have to go search the cave. You're not living alone in a cave. We're in community. How we lead ourselves is and it is a reflection of how you impact others. If we just look at the externals of how we should be and how, okay, are you authoritative? Are you collaborative? Are you all those things? That's one thing that's all external, but how do you show up naturally within you?
When you understand how you are actually, versus what you think you should be, then it just changes everything. It changes how you show up. It changes how you communicate it. It's powerful, because you're not chasing something. You're not chasing, or running away from something. You're working towards something. If that to me, that's where it all comes together. It's like, I want to be moving towards possibility, and that's alignment with who you are and how you lead yourself and others, versus running away from something, or chasing something.
Alex Cullimore: It's a good way of putting it. That’s what I was thinking when you're talking about the idea of running to your compass and then being in uncomfortable discomfort. You're trying to, in a life when you're living a little less authentically, you're trying to pat away all those pieces of discomfort. You're making comfort by running away from that discomfort. Whereas, in the exciting discomfort that you're identifying of moving towards your internal compass, this is something where you're pushing towards this thing you want. You're pushing towards it. It doesn't mean that it's easier, but you have a direction you're moving towards, instead of something you're moving away from it.
There's something really powerful and the continual reevaluation of your life in that. When you start to reflect that on a leadership perspective, we've seen this over and over again, there's so much projection. When we're really worried about others, we're painting this just really great silhouette of exactly ourselves that we just don't see.
Cristina Amigoni: All the time.
Laura Shepherd: It’s so true. All the time. We're all humans. I'm not by no means perfect. I still have a coach, and I will always have a coach, so that I can sanity check myself, and keep growing and learning. But the energy of moving towards gives you possibilities. You see possibilities and creativity in front of you, versus the energy of moving away from is like, it's tight and closed and not – you don't see what's around you. What I like about when you're on your compass path, the right direction, it doesn't mean that's the direction forever.
It means that's the direction you've aligned to and find now. As you start down that path, if you're moving towards something, all of a sudden, other possibilities come up along the way and you get to choose. Maybe that's where, I want to go off to the northwest right now, versus the east, because there's something interesting over there that I want to explore. Or, maybe you don't, but you see it and you choose, and then you keep moving, or you realign your compass to a new direction. There's no straight line either, right? It's going to take us all over the map. It's about choosing. Yeah.
Cristina Amigoni: That's a great distinction. Also, elaboration on the compass. Because there is this sense of wanting to be in the comfort zone and wanting to be, as much there as possible, it's just like, “Oh, okay. Let me get this uncomfortable for a little bit. Move the compass, figure out the alignment and I'm done.” Having that attachment to like, this is the direction. Then a lot of the, what happens is the more we stay in that direction, especially when we start feeling that it's not aligned anymore, it's like, oh, but I can't change now, because of the sun cost. Because I would have wasted all these years, or all these months, or all this energy into this thing that was, that was the direction. I have to pour more into that direction, as opposed to go back to, what's the compass telling me here?
Laura Shepherd: Agreed. It's like, what's really important? That's a constant reflection, right? The other thing that I find leaders and most people don't do is reflect often enough and reflect with the purpose of, what did I learn? Where do I want to keep going? Versus just a reflection of, okay, here are the routes, here are the steps, here's what happened. Blah, blah, blah, blah, blah, blah, blah. They do all the checkpoints. Check, yes, I did that. It's the checkbox. Like, Alex, you said, I did before, which was very true. I checked off all the boxes. It's like, the reflection of check, done that, versus the reflection of, okay, that worked and I did it. Great. Is it what I still want to do, or how do I want to evolve it, or what else do I want to add to it, or take away from it? All of those things. And reflect often, so that it's not this one big, massive thing.
I make it a weekly reflection for myself and it's as simple as like, how do I look at my week? How do I look at my week going forward? What do I want to accomplish this week? Then at the end of the week, what did I accomplish? Not from a sense of judgment, or I didn't get that done. I didn't get that done. It's like, okay, I put too much in that a week that I thought I could get done. I'm starting to get this energy of not achieving something. It's like, wait, okay. So, moving forward for less in my week and do better, do more quality work, or do more focused work. I adjusted every week, depending on what happens, and every week's different. It's like reflecting and learning. Taking it as feedback is learning. That's it, right?
Alex Cullimore: That's really great. We are just explaining more productive reflection, rather than just there is the reflection that's natural in so many workplaces and so much leadership. That's just, are we on track for this project? What is our status? How much percentage are we complete? Where should we have been by now? How do I make up that delta? Whatever it is, there's that focus on – It again, feels like running away, versus running towards. We're trying to avoid the failure of feeling like, “Oh, I didn't do this right.” Versus like, well, what are all the possibilities of how I'm going to do this differently and better? How are we going to – are we even on the right path? Have we reevaluated that in a little bit? Is this the right way to do this?
Entering that non-judgmental evaluation space is incredibly powerful. Without thinking like, oh, what are all the ways that I haven't made the goals that I have meant to in a week? What am I learning this week? What did I take on that was just too much? We can't know what we don't know going into it. I had so many plans for this week, and this week has gotten absolutely away from me. That's how this week was going to go. I can't change that. It wasn't something that was anybody's fault. It's just how the week laid out. If we can actually enter that and then decide, “Hey, what are we going to do about this?” That gives us so much more foothold and adaptability in life going forward, rather than just, “Oh, I'm not doing this right and I need to correct.”
Laura Shepherd: Yes. It's not about not doing anything right or wrong. I love that. It's not about right or wrong. It's about what's working for me based on what I want and my objectives and my goals and what's not working for me. A lot of times, I'm finding in my own life, it's like, what do I need to take away, versus what do I need to add? Because I'm like, how do I strip it away? To me, it's the Michelangelo and David, right? It's like, how did you carve David? Well, I didn't. David just came out of the stone, right? He took away what wasn't David, and David appeared. How do we take away?
I've just been reflecting on this and acting on this for the last month, and it's really been powerful. It's like, what do I need to take away, versus what I need to add? Because usually, I have to-do list. I've got all of these things and it's all of this stuff that I want to get it done and I'm excited about it. I'm like, it's not practical. Instead of setting myself up for failure, I want to say, which there's nothing wrong. Again, no right or wrong, no failure. It's like, my version of success is looking back and going, I had a good week. I had a bad week. It's okay. Either both are okay, and I'm going to keep moving forward.
Cristina Amigoni: Well, and the challenge. I love the David image, because the challenge is as we're chipping away to our authenticity, which is the avid, if we are not aware of what's too much, then we also risk taking away David's hand. That was supposed to stay there. That wasn't covering David. That was actually necessary.
Alex Cullimore: Then you got stone glue. You’re trying to reattach.
Laura Shepherd: That is so true.
Cristina Amigoni: Exactly. Now you're trying to reattach it.
Laura Shepherd: That's so true. That's so true. To me, it's about being that, how am I living up to myself and my expectations with the understanding and realization that I'm not at my highest best? I know what I am when I'm at my best and I'm performing and everything's – I'm in flow and everything's happening and all of that. Everything's working in the way that I want it to work. That doesn't happen every day all the time. It's reflecting and giving myself grace that I did 100% of what I was able to today, now present. Tomorrow will be another day and I will be 100% at that day. That doesn't mean that it's at my best all the time, or the top of my game. I'm always at my best, but I'm not at the top of my game all the time, if that makes sense.
Alex Cullimore: Absolutely, absolutely. That one is a huge lesson that everybody at some point, I think, learns when we try and test our limits and believe that we should be at 110% at all times. That's a really good example of one of those reflections that helps us in leadership, too. Once we realize that I can't run at 100% all the time, then we might lose in the expectation a little bit, take the foot off the gas a little bit overall, all of our people and saying like, “Why haven't you done this? Why aren't you going at 1000% all the time?” Those are the narratives that end up having people separate their work self and their life self, because their work self is supposed to be this 100% person, and their life stuff just will have to absorb whatever is left over. I'm curious, what else you see as far as self-reflection, powering that leadership muscle and that understanding, the leading from self that helps others?
Laura Shepherd: Yeah, that's a great question. It's a great reflection, what you said on we work our teams too hard at times, because of our own expectations. There's nothing wrong with having high expectations for your team. They're people, right? How do you lead your people? Well, you lead yourself and give yourself a break and you set clear expectations. I mean, expectations have to be set, and everyone has to understand them. Recognizing that your team actually understands them, I think, is powerful too, because a lot of people go, “Here's the expectations. Great. Go.” It's like, wait. Let's have a conversation. What does that actually mean, and what does that look like?
Because it's like, it’s one thing to have a number that you got to achieve, right? Or whatever that is in your business. Then there's how you get there and the how, what I think from a leadership point of view, the challenges I've personally run into, and I've seen some of my clients run into is they expect the how to be done the way they would do it. There's many hows. It's like, I believe there's many ways to live your life. There's many hows. Your team, you got to empower your teams and your people to do the how, the way that they will excel at it. This is where I'm releasing the outcome, but the result is here, the goal is here.
It's like, how you get there will come at it from many different angles, and your team knows how they can. Then you support them in that, right? You support them in how it's working for them. It doesn't mean let them go off and be willy-nilly. It's like the check-in points. It's communication, right? It's making sure you're checking in and communicating and not just having, here's the status report, boom, boom, boom, right? It's like, how is it working? Being open and curious with your team on where are your problems? How is this working? Then, you can co-create. You can let them open up, and you can co-create together.
Cristina Amigoni: Yeah, for sure.
Alex Cullimore: Yeah, I really like that. Reminds me of the idea of you're saying like, “I set this compass direction. Maybe I feel I'm closer to it.” That's not the same thing as setting it forever. When we're setting expectations for our team, we have this idea, and it's good to have that high expectation. I think we can do this. I have faith in the team that we can do these things. That doesn't mean that's what reality is going to be able to deliver for us. Anything could happen in our general human lives, to the team, or to any individual that just changes what's going to be possible. Or maybe we did happen to set those expectations too high. It's like, your weekly reflections. “Hey, I put too many things on the to-do list and it just wasn't going to happen this time.” That's okay. Just, I had expectations. As long as I can approach those with grace, that's going to be okay. We can approach that as a team and say, “Hey, we had this goal. We're not going to make that goal, and that's okay. Here's what we learned. Here's what we could do, can't do.” Having that adjustment is super important. Instead of just having like, “Hey, I finally figured out I can just demand things and then just be upset if they're not that level.”
Laura Shepherd: Very true. It's the reflection along the way, right? The adjustment and the – That's where communication amongst leadership and team and cross functionally and however it works, the communication has to be open and based on trust, so that people can be, I hate to use this word, but things can fail, right? Because failures feedback. It's like, what does that mean? This is what we thought. That's the part of reassessing and reflecting. It's like, hey, we did this, because we thought it was going to work along the way. It didn't work. Do we need to change direction? Or is it just, what are the other possibilities that help it work? Or do we need to tweak something that it's not exactly the outcome we thought, and we tweak it this way, because now we know better. Because what we thought would work didn't work. I'm talking a lot around about, sorry.
Alex Cullimore: Yeah. No. No, that absolutely is it. The other thing, too. I don't want to sound like it's all just, “Oh, hey. We want to make sure we manage expectations for when things don't go well.” When you have that openness and that communication you're talking about, you access the opportunity to get more than you thought out of this. Suddenly, you've got the communication points. Somebody brings up some idea, or some new thing comes through, and now you've accomplished more than you thought you were going to in this period, or whatever. That's only accessible if you've allowed for that space, that grace and that adjustments to have that open communication, to have those dialogues, so that it's not just, I said expectations and try and march to that expectation.
Laura Shepherd: Absolutely. Because you don't know what other people know and you don't know how creatively they can come to the table and say, “I did thought about this direction, right?” If they have that space of safety where they can communicate that, things can be, it's always about making it better overall, right? How do we make it a bigger whole, right? Allowing input across the board.
There's times where you got to say, okay, no, we got to just keep moving. Your leader also to take accountability and show up and lead. Sometimes you have to say, no, we have to move this way and we have to keep going, and that's where it is. Because sometimes our leaders, our visionaries and they see the vision, they just – sometimes those visionaries have to bring people along and they don't know how to do that, right? It's about, still, having that balance between the, we need to go on this direction, versus, and allowing people to contribute in a way that supports everybody.
Cristina Amigoni: Well, and that balance, it's really tough from a leadership perspective. Because without the self-reflection, without the awareness of how we're thinking about things, how we're showing up, how we're communicating, and hopefully, with the definition, the communication is not like, I told you the expectations, let's go. Because that's not communication. It's that balance of, “Hey, I'm also human, so I may not know everything.” If I don't allow for that dialogue, for that feedback, for everybody else's creativity and view of these things, I may be marching people off a cliff. You probably want to create an environment where others contribute to it, because they may see something you don't see.
Laura Shepherd: Absolutely. That just triggered a thought for me, where as the leader, who's your leader and boss, and you have targets and you have real-world corporate, you got targets, you got a hit and you're getting pressure from side. It's managing that balance on both ends, right? Especially as leaders, you have to up and down and figure out how. Keep moving the ship forward and not over a cliff.
Cristina Amigoni: Yes. Yes. Maybe it's just a tweak. If the dialogue is not there, if the communication and safety is not there, you're going to go off the cliff. Bring as many people as they're blindly following with you.
Laura Shepherd: So true, so true.
Alex Cullimore: It feels like, there's then all of the alignment of all of the compasses that, can I keep marching this path? As a leader, do I say like, “Hey, I know that that's difficult, but I think we're still on the right path. I'm going to ask people to keep marching on this one.” As the middle manager, at what point is your compass? I can't continue to walk on this path at all levels. Is this where I can keep going or not? Is this something that is worthwhile or not? If everybody can reevaluate that, we can at least all decide consciously whether to stay on the boat or, “Hey, this just isn't the boat for me. Even if this boat's going to be okay, I have to be on a different one.”
Laura Shepherd: Well, that's the self-awareness that we all need to continue to practice, right? It's all practice and reflect in action, both, right? It's really, the action steps along that way. The more you reflect to the fact you say, “This isn't the boat for me.” That can be super hard for someone to accept. They also, it could make them super – They can help them find their path in a way that's more powerful for them. Internal compass is not an easy path to follow, but it's the most rewarding from what, and it's the most rewarding from what I've seen my clients do and what I do for myself.
Cristina Amigoni: Well, because as you said, it's not just about staying on the path. It's about when the path continues, or changes direction is having that courage to say, “I'm glad I'm still on the bus. I'm glad there's a potential seat. But you know what? I actually don't want to be on this bus anymore. This bus no longer aligns with my compass. It actually stands for everything against what I believe in. So, I'm going to choose to get off the bus.” As opposed to hoping to get thrown off.
Laura Shepherd: Oh, wow. That's interesting. I love that, because I do actually think people, there's a lot of people out there that are waiting. They're hoping to get thrown off. To me, that's not a way to live. It's like, that is just passing time and stamping the time sheet. It's choose, choose. If you just wait, if you hope to get thrown off the bus, there's something misaligned within you, and you're not willing to look at it because it's uncomfortable. When you do get thrown off the bus, if you haven't looked in to get alignment, it's not going to be any easier, or any more comfortable.
Cristina Amigoni: You're going to get on the wrong bus again. It's going to be a different one, but it’s still going to be the wrong bus. And you're going to feel bad about all the time you spent in the first bus. I'm like, “Oh, I should have stayed on, because I spent years and I put so much into it, and what will people say about me? What do I feel about myself?” It's really all that. Just get off the bus and figure out. Be in alignment to know which bus you want to be on.
Laura Shepherd: It's doing the work, right? It's doing the work. It's the internal work. That's the hardest thing in our society today is to do the internal work, because the external society says, “This is what you need. This is what you want. This is where you should go.” Everybody is unique and everybody has their own gifts, and everybody has a path that will bring them to their biggest, their highest self. It's up to the individual to choose that they want to start working on that and figure that out. As they do and work and figure it out, this is where within as it relates to leadership and corporate, it's like, everything falls into place in an easier way. It really does fall. You have to do the work, which is hard. Things then start. You attract things and things fall into place, versus constriction.
Alex Cullimore: I agree. There's a lot of that, that power in that alignment. I think it's very hard sometimes if you're at the beginning of the journey, especially if you haven't done a lot of the work, if you feel – that feels like taking a giant leap of faith on something that you don't know and you can't see how that could be true, because it's hard to understand. Until you start to see those things and feel them for yourself like, oh, this does line up better. I feel better. I feel I can lead better. It's hard sometimes to take that jump. What advice would you have for people who might be feeling that internal worry?
Laura Shepherd: That's a great question. It's valid and it's true. It is hard. It is uncertain. There is no certainty, ever. Which is not good advice. I know. Yet, the advice that I would say is what my coach, the first coach I worked with said with me is like, “Laura, when you leap and that appears. If you're in alignment and when you leap, things start happening, people start supporting you, it comes out.” It's not like, sit around, do nothing. It's, you leap, you do the work and that appears and you keep along the path and you keep reassessing.
When I realized that it's a lifelong journey, it went damn, the high achiever in me is like, yeah, I want it done. This one done, and now I'm good. I realized that it's a lifelong journey, and that's exciting. I get to explore new sides of me, old sides of me, different things in life that are adding to my path, and not all of them work. I love seeing if it works, or it doesn't work, truly at this point, which when you're at the start of the journey, it's hard to see that. The start of the journey advice is actually, get help. Ask someone. Work with someone to help you, because you can't see the label from inside the jar. You need that person to reflect back to you. You need to see the cave that's behind you. Only other people can help you with that.
Alex Cullimore: Yeah. I think there's some understanding as well that just life, but I like to describe it, like things will just happen. It sounds hard to believe, because like, well, what things will happen? How do you know things will happen? If you look back at your life, things have always happened. They just haven't been always in alignment, but things have always continued to happen. There's always things happening around you. You'll pick up on this, this, that, the other thing. There's an opportunity to do these things. It's just, it's not about it magically happening. It's that life is always happening so much, that once you start to direct that, you'll find all the little pieces along the way. It's so hard to know that, unless you reflect on like, “Hey, this is actually already have been happening my whole life.” We've always had things happening and random currencies. That will continue to happen. We're just, we're getting hopeful for an outcome and it can feel really hard to attach yourself to that when you can't see the path.
Laura Shepherd: So true. I love what you just said is, when you look back, life is always happening. When you choose to direct it, that's the power. That's the power. It's still not always going to give you what you want, but to direct it. It's going to give you what you think you want. Then you get there and you reevaluate what you – it's not what you wanted. Okay. There's a new one and you keep choosing to direct it though.
Cristina Amigoni: That's very true. It’s choosing to direct it. Also, knowing that that part of that leaping is the more you've done the work and you continue the work to find that alignment, it becomes – it's never easy, but it does become more of a muscle to say like, I know I can leap, because the net is my internal compass that will appear. That's there. If I know what it is and I truly know what's in there, that's the net. Whatever the scenery will show, the net will appear.
Laura Shepherd: I love that. The net is the internal compass. It's so true. It's so true. It does get easier. It does get easier. It’s not easy, but it gets easier. It's also very simple. The simplest path is typically the one that we don't want to follow. It's the one we should. Not should. I was just going to say should. I hate the word should. The one we possibly could follow it and see what happens.
Alex Cullimore: Yeah, it makes me think that we spent so much time avoiding that path. The hilarious part about avoiding it – Usually, I mean, internally, we have that dialogue of like, we've gotten so good at avoiding it, we pretend it's not there. Yet, we are so good at avoiding it, we know it's there. It's like this object in the middle of the room you never picked up, so you've just always been walking around it. In your mind, it's not there, but it's there. You're always avoiding it, so you always know it's present.
Laura Shepherd: Well, and what we avoid, what we resist persists, right? If you're avoiding something, if it's a pattern that you see that you're avoiding something, that's a signal for me to go, okay, I got to look at that. I got to lean into it, go through it and see what's on the other side. Then that pattern goes away.
Cristina Amigoni: It's like that lesson that keeps coming back over and over and over. I'm like, “Oh, I've been here before. Okay. Which means I haven't actually gone through it. I haven't learned enough, and I'm going to have to stop avoiding it, because it's coming back.”
Laura Shepherd: Yup. Yup. Sometimes we learn it, but not at a deep enough level as we're not ready yet. When it comes back at us, it's like, “Oh, I've seen this. I've learned this, but I'm at a higher level.” I like it a spiral. It's like you're going up the spiral. It's like, you come back on yourself, but you're at a higher level. It's showing you that sometimes, sometimes you just haven't learned a lesson yet, but sometimes it's like, okay, you're ready to go deeper.
Cristina Amigoni: So much to unpack.
Laura Shepherd: Yes. It is lifelong. We guess, it's what's so fun.
Cristina Amigoni: It is lifelong. Yes. It is lifelong. Yes. The more we avoid it, the harder it is to do everything else.
Laura Shepherd: Yes, absolutely. Absolutely. We think we're protecting ourselves, and that's when we have to rip the band-aid off.
Cristina Amigoni: Indeed. Yes. Yeah. We've talked about authenticity a few times, but what's your definition of authenticity?
Laura Shepherd: It's a great question. My definition of authenticity is finding your path. It truly is what's your alignment. Being in alignment, which just means being in yourself in a way that you're accepting of all of you, authenticity. When you accept all of who you are, what you feel, what you know, what you don't know, what you look like, what you don't look like. When you're fully accepting of who you are, then that helps you follow that path to say, “This is how I want to grow and be in life. This is who I want to be,” then you're authentic. That being can always be growing and changing. For me, it's based on acceptance of everything that I am as a person and as a human being. Then that's authentic.
Cristina Amigoni: That's powerful. Yes. Yeah. Where can people find you?
Laura Shepherd: Thank you. LinkedIn is my best contact. I mean, I have a website, nnwcoaching.com, but LinkedIn is where all my contact information is. That's always the best place. That's where I spend the most time.
Alex Cullimore: What does NNW Coaching say?
Laura Shepherd: North by Northwest Coaching. It’s my compass.
Cristina Amigoni: Yes. That is your compass.
Alex Cullimore: That's really good.
Laura Shepherd: Yeah. Yeah.
Cristina Amigoni: Yeah. That’s very, very good. Well, thank you, Laura.
Alex Cullimore: Yes. Thank you for sharing.
Laura Shepherd: Thank you. It's been a pleasure chatting with you guys. I love – I could talk about this forever.
Cristina Amigoni: I know. Yeah. Same here.
Laura Shepherd: Thank you for inviting me on your podcast.
Cristina Amigoni: Yeah. So much to unpack, and many tangents to go on.
Laura Shepherd: Yes.
Cristina Amigoni: And good lessons. Thank you for your time.
[END OF EPISODE]
Alex Cullimore: Thanks so much for listening to Uncover the Human. We Are Siamo, that is the company that sponsors and created this podcast. If you’d like to reach out to us further, reach out with any questions or beyond the podcast, please reach out to podcast@wearesiamo.com. Or you can find us on Instagram. Our handle is @wearesiamo, S-I-A-M-O. Or you can go to wearesiamo.com and check us out there. I suppose, Cristina, you and I have LinkedIn as well. People could find us anywhere else.
Cristina Amigoni: Yes, we do have LinkedIn. Yes. Yeah. We’d like to thank Abby Robinson for producing our podcast and making sure that they actually reach all of you. And Rachel Sherwood for the wonderful score.
Alex Cullimore: Thank you guys so much for listening. Tune in next time.
Cristina Amigoni: Thank you.
[END]

Laura Shepherd
Leadership Coach
Laura Shepherd is an accomplished executive coach and
marketing strategist with 30+ years of leadership
experience building brands and leading teams across global
organizations. She brings a unique blend of strategic insight
and people development expertise, having led brand
transformations and guided leaders through growth,
change, and complexity.
An ICF-accredited coach (ACC) with multiple certifications,
Laura partners with senior leaders and teams to unlock
clarity, alignment, and leadership effectiveness. Her work
sits at the intersection of business strategy and human
potential—empowering individuals and organizations to
thrive and create meaningful impact.
Specialties include executive coaching, brand and
marketing strategy, leadership development, team
performance, and organizational change.