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Chris Duprey

By Chris Duprey

Oct 2, 2019


Executives and Leaders
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Executives and Leaders

To Be the Leaders Our Teams Deserve, We Must Address Our Fears

Chris Duprey

By Chris Duprey

Oct 2, 2019

To Be the Leaders Our Teams Deserve, We Must Address Our Fears

Why do we do certain things?

Why do we feel obligated to do to attend this meeting rather than that one?

Why do we feel guilty about taking time off?

Why do we feel guilty not responding to work emails on vacation or over the weekend?

Why do I care how many minutes or hours of meditation I’ve logged?

Other than the last one (which I'll get to shortly), these are all questions we ask ourselves a lot — especially as leaders and aspiring leaders.

We ask these questions because there is a never-ending series of “things” that present themselves to us, minute after minute. These questions and the feelings they produce can make us feel like we aren’t in control, that we don’t have the power to choose.

We spend most of our time focusing on others.

That's a great thing, in theory.

But if we don’t focus on ourselves, understanding the underlying motivations that makes us feel guilty or obligated, we will never be able to show up in a whole-hearted way to truly impact the lives of those we serve.

That's a bold statement, so let’s dig in a bit

When we allow guilt (or its step-siblings regret, fear, delusion) to guide our decision-making as leaders, we are letting negative motivations direct our actions. We show up with a sort of armor on to protect ourselves from whatever has led to our feelings of guilt

When this happens, we don’t show up as our true-self, but rather as a partially sealed off version of ourselves. 

This is not the version of us that our teams need. They need the whole person. The leader who is truly present — not in armor, but open, transparent, and ready to lead.

By truly understanding our underlying motivations and becoming aware of them we can show up in this way, we know we have the power to choose, that we control the actions we take.

🔎 Related: How an Obsession with the Success of Our People Creates Success for Our Organizations (Advanced Leadership Guide)

I’d love to tell you all that there are five things you need to do and once you’ve done them you will show up in this way, but there aren’t. I’d also love to tell you that I figured this out a long time ago or that I have it all figured out. The truth is, this is an ongoing process of self-discovery and self-awareness that each of us needs to take on ourselves.

With that said, I’m going to tell you a few stories that will I hope will do a few things:

  • Prove to you that you’re not alone.
  • Show you some ways you can look inside to find the answers for yourself.
  • Change your perspective or open up to what’s possible.

The two stories below may not relate exactly to your lived experience. So, what I ask here is that you look for the theme. Rather than saying, “I’m different,” look for what could be possible in  your life, your experience. 

The first story is a very personal one that dives into how I discovered that fear was a driving motivator for me in many decisions and actions I've made over the last 20 years. 

The second focuses on how we tend to let stories and our own perception guide our actions in ways that could actually lead to harming ourselves.

OK, let's talk about that meditation question from the beginning

Why do I care how many hours I’ve meditated for?

Weird question, right?

I’ve been meditating for the last 2.5 years, pretty intensely for the last year and half, meditating for more than an hour each day. 

Am I trying to win at meditating? Is that even a thing?

Of course not. But that didn't stop me from measuring and tracking my meditation "performance" through apps and other means, as if I could.

Then, a few weeks ago, I was having a session with my meditation teacher, JoAnna Hardy. We were talking about my practice and she decided it was a good time to change up my daily routine, as I had been dealing with some heavy stuff going on in my life.

Instead of sitting (seated meditation) for an hour, twice a day, and solely focusing on mindfulness of feelings — the practice of identifying phenomena as it arises as either pleasant, unpleasant, or neutral — she wanted me to do 10 minutes of walking meditation, 40 minutes of mindfulness of feelings, and 10 minutes of loving-kindness practice — a practice where you send good vibes, over and over again, to the subject of your practice — directed towards myself, once or twice a day.

It was not a huge shift to add a walking practice and some loving-kindness, as both are types of practice I had done before and found useful. 

However, as she shared with me what she wanted me to change, I started to feel physical symptoms of anxiety. More specifically, I felt my stomach tighten a little and my upper body got a little tense.

How was I going to log my time? Now I’d have to start and stop my practice to adjust my timer... and so on.

I tried to simply not be mindful of this, but I was. So, now I had to deal with it. Which, of course, is the goal of the practice.

JoAnna asked how I felt about it, and I think I said something about how it sounded good, but... 

"I have to figure out how to handle the timing since the app I use to track my meditation only had a countdown timer with a starting and ending bell," I said.

We then talked about how there were other apps that could handle it, meaning that I could set up bells to ring at 10 minutes, 50 minutes, and at the end of my hour. 

I knew this, but I didn't want to use another app.

JoAnna sat with that for a second and while she did that, I shared how much I liked seeing how many minutes I’d sat for on the app I used. 

This started a conversation about being attached to achievement and how at least I was aware of this attachment. At that moment, JoAnna lobbed in a hand-grenade of wisdom, in the form of a question:

"Knowing that you're attached to achievement is good, but we really want to know why you're attached — so, what's that about?"


Her point, I think, was that knowing or being aware of an attachment is great but when we understand the causes of that attachment, we truly awaken to it and have the ability to make a choice.

After she asked that question, our time came to an end. It would be two weeks of practice before we’d speak next…

Why was I attached to achievement?

As many of you who know me can guess, I sat with the question echoing in my mind for a while. Why do I care about how many minutes or hours I’ve sat for? When I reach a certain number, am I all of a sudden enlightened?

I then started to think more broadly.

Why has achievement been such an important part of my life? That’s when JoAnna’s hand grenade of wisdom went off in my head. 

I am trying to prove that I am worthy, that I belong, that I am valuable.

This was not an easy thing to realize. It made me see that I had been driven by fear for a long time. Fear that I wasn’t worthy, that I didn’t belong, that I wasn’t valuable.

That’s some deep stuff. Or, at least it was for me.

I started to think back to what could have caused this type of achievement conditioning or more importantly where did the fear come from.

The first thing that came up was not getting into West Point, which had been a goal of mine as a high school student. Then not being a ranger qualified infantry officer came up… I  remembered back to my time in the Army, and how I always felt obligated to work harder, to show my value, my intelligence, so that I would be accepted.

This may be why as soon as I finished graduate school, I put the M.S. after my name on LinkedIn and on my business cards.

To show the world I was valuable.

So, these things from 18 years ago were impacting my life right now. I was so concerned with the concept of self I had worked to create, that I was allowing it to control my actions.

I’m sure that some of you may be thinking that being achievement-focused is a good thing. I agree, but that’s not really the point here. 

The point comes down to the motivation. Why was achievement so important to me?

As I discovered, it was fear-based, for the most part for me. As I learned this I was able to start looking at all my actions and choices from a lens of, "What is the motivation?"

As I did this, I started to really focus on calling out fear and then making a conscious choice, rather than blindly following whatever story the fear told me to. I started to try to reframe things to bring love, happiness, joy, and compassion into play to be the motivations behind my actions.

How fear creates stress for us as leaders

The other day I was meeting with one of our teams, going through a refresher on communication. As the conversation was taking place we started to talk about fear, very openly. (As a note, this isn’t something I think is usual in many organizations, but is highly valuable.)

We were talking about how fear plays a role in why we aren’t as candid with our clients as we sometimes should be. So, being the incredibly curious COO that I am, I asked what were the things that made us fearful of being candid?

The team started sharing how some clients believe that the service this team provides is the only thing that affects their revenue. As a result, when a client is upset or sees a slow down in their sales, this team goes into hyperdrive to try to fix it.

Now you may be saying that’s exactly what they should be doing to ensure the client is successful. The problem is, a lot of the time it has nothing to do with the team's service — it is usually another issue or the combination of several

Still, this team puts in extra hours, scours numerous spreadsheets, schedules extra calls… 

This made me ask them why they were afraid to be candid with the client and pushback that the service they provide is one part of a  revenue strategy.

That's when our conversation got real.

The team wasn’t afraid of the client, they were afraid that if they were candid and the client left, leadership would place the team at fault.

Red star clusters started going off in my head as I heard this. This is a real problem. Instead of reacting, I started to ask some questions to help figure out what was behind this thought the team had.

As we talked, we uncovered a ton of stories that the team was telling themselves. They self-discovered that the extra work they were doing was totally motivated by fear and that it probably wasn’t going to actually help them or the client. 

As this became clear, we started talking about how if they were candid and educated their clients a couple of things would happen:

  • We’d actually solve the real issues.

  • If the client left, they’d know they did the right thing and would be able to articulate that to leadership.

Why do we let fear own us, and what can we do about it?

Because we do not realize that fear is behind our actions or motivations. 

I know this from my own personal experience. If you had asked me six months ago if fear motivated my desire to achieve, I probably would have laughed at you.

Here’s the thing, once we identify it, we get to make the choice how to act. I am still achievement-focused. I wouldn’t be a good leader if I wasn’t, but my motivation is different.

Rather than letting fear own me, I now let skillful motivations help drive me — happiness, love, compassion, etc.

“Great Chris, I’m so glad you found this out, but how do I know if I’m doing it?”

Whether that’s going on in your head or not right now, here are some things you can do.

Find some time to reflect on your motivations. This can be done in any way you like. For me, I find meditation and quiet time to be the best outlets for this. Think about the decisions you’ve made lately and ask yourself:

  • What led me to this decision?
  • What things were true that got me to where I am right now?
  • What was I or am I afraid of?
  • What is causing me to act this way or not to act at all?
  • What stories am I telling myself that may not be true?
  • What does success look like?
  • What does happiness look like?

Then you need to make a choice.

Believe the answers and do something about it, or continue to live a life where you have no choice.

When we become aware of what is motivating us and take action, we take control over our lives. We become the leader we aspire to be, rather than the leader we used to think we needed to be.

When we do this, we become the leader our teams deserve.

Photo courtesy of Connecticut Headshots.

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