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Leader Fails First

Every day I push our Team at SoWork to reframe how they think about failure, to see it as signal — just like success — on a learning journey to excellence.

And every day, I try to do what I ask them to do. I try, fail, learn, get up, and try again. And while I’ve always tried to show this, to be open and authentic about the messy journey that is progress, I’ve realized as we’ve gotten bigger that I spend less and less time failing alongside my Team. And more and more time failing alone. And while I’m intentionally and deeply modeling the behaviour I ask of them, I hadn’t adapted to make sure they still see it.

I’ve started to get more intentional about exposing my failures and messy growth journey as a founder. Not for me. For my Team. Because what business do I have asking them to do it if they can’t see me doing it, too?

I share my failures here to turn up the intensity of sharing the messiness that is living up to our Cultural Principles. When it comes to asking our Team to trust, open up, push themselves, and fail… leaders need to go first, and they need to go harder.

Below is a message I shared with Team Sophya in a company-wide reflection page after asking them to focus on channeling the mindset of excellence over the mindset of perfection.

“Someone brilliant asked me a wonderful question the other day. They asked me why I don’t write in Preflections. I told them that when we switched to squads, it mattered deeply to me that we were consistent in showing teammates that squads were theirs to own and shape within the guardrails we provided (piece, prompt, purpose). So I wanted to be consistent in showing that. They asked me why that stops me from writing in preflections, through, if every Theme I, too, do the same work the Team does, I just do it on my own. Can I not share that, without detracting from the consistent message I wanted to send? Yeah, I totally can. Especially for a topic I chose because I believe that it’s such a critical mindset shift for healthy, impactful high performance.

I grew up on Perfection Lane. I was a competitive gymnast, competitive horseback rider, ballerina. I went to strict schools and was pushed to be perfect in my environments, and I translated that directly onto myself. From my younger years, I have countless examples of taking perfectionism to the extremes. And then life smacked me down. One day in Australia, I ran a marathon. It was a horrendous marathon. I was so sick, I never should have run it. And my reasons for doing it all came from perfectionistic head spaces. I knew something was horribly wrong with me physically, but I forced myself to run it anyway, for all the wrong reasons. The next day I was hospitalized with meningoencephalitis.

On day 6 in the hospital, after a terrifying near-death journey, I got my vision back. And I remember looking out the window for hours, hating myself for not loving myself. Not just in that moment, when I ran the marathon instead of taking care of myself. That was stupid, for sure. But it was looking at that, which felt so fucking stupid relative to lying in bed not knowing if you’re going to die, and realizing how many years I’d wasted not loving myself.

It wasn’t overnight from there. It never is. I had more pivotal life experiences that challenged the shit outta me, I read life-changing books, went through rough experiences with loved ones… but it all took me firmly off of a path where I channeled all my grit, energy, competitiveness, and relentless drive against myself to instead channeling it for myself, in a loving, forgiving, but still healthfully demanding way. Relentless AND loving. Driven AND forgiving.

I said this to an amazing teammate recently:

You are worthy. You are valuable. You deserve to love yourself. You are the only person who can give this to you

To me, personally, excellence > perfection is the balancing act of pushing yourself, channeling your drive, always growing and reaching for more, failing hard when you miss, getting up again… AND being your own biggest fan on the sidelines along the way.

As for preflecting, many months ago I flagged that, as I played time forward, I wouldn’t be in my highest performing leadership gear without making some big shifts. Leading in startups is funny, in that every time you successfully get the Org to the next phase, the skills or methods that allowed you to do that can suddenly become the exact things you need to pivot away from, otherwise they’ll slow down, confuse, or hurt the Team/Org in the new environment. Or, you just make yourself sick in the process of trying to do it all. So I had a feeling I was about to enter a new phase, and if I didn’t get ahead of how I’d need to adjust, I wouldn’t walk us into it clicked into my most effective gear.

I’m a super intuitive person, so i’ll often flag things in feeling before I know what actually needs to be done about them. At the time, I just kept saying it. I had no idea what I meant, what I wanted the change to look like.. nothing. And when I was pushed on it more recently, I couldn’t share the signal I usually have to ‘prove’ that I need to adjust. I was really frustrated. I demanded more from myself, and I had moments where I doubted my own ability to intuitively spot that I needed to grow because the answers that usually just present themselves for me weren’t coming.

In the end, they came. And most importantly, I learned why they weren’t coming, and that itself was a huge part of the big new gear shift that I sensed I needed to make. If I take the lens of excellence > perfection, I temporarily lost the love of the journey piece, and I did that because I was putting immense pressure on myself to get into my next leadership gear ahead of the Org’s needs, so I would be ready to guide the Org through the next phase. And the biggest cost was energy, which just means I have less of myself to give to the same thing I was focused on when I was applying pressure to myself. How funny.

Going forward, I’d sit my ass down earlier and remind myself how much I love the messy journey, to tone down on the unnecessary pressure, because I know that all the best gifts are there in the journey, and I’ve already learned that my life is too short for me to veer off of the excellence path.”

Written with ❤️ by Emma Giles, Co-Founder & COO of Sophya

Emma spends her days designing an Organization that unlocks teams to work from anywhere, empowers them to do impactful work, and ensures they feel connected to each other and the Organization, no matter where, when, or how they do their best work.



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Emma Giles

Emma Giles

COO & co-founder of SoWork ( Ultra runner & caffeine lover.