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Remote Leadership and how to normalize failure

Kerry Guard • October 7, 2022 • 5 minutes to read


At our annual summit last week, we went around and had everyone share a moment of failure.

It was a tall ask. An important task.

As leaders, especially remote leaders, we need to normalize mistakes so they come up more often, faster, when they're small and we can get out ahead of them.

But most organizations shame and blame. They don't seek to understand what happened. They don't take responsibility. They blame the single point of failure, point fingers and move on. Mistakes happen in a vacuum and we need to change the narrative.

So, at our Annual Summit I asked everyone, all 16 of us, Mike Krass and I included, to take three minutes each and share a moment of failure.

Below is mine...

Let's normalize being human and lean into the learning cycle.

The Money Movement Mistake

At the agency Mike and I met at, I came in around Q4. They were right in the middle of a big campaign with Western Digital. I took over the planning and budgeting from my predecessor who was out on maternity leave.

I couldn’t make heads or tails of how money was moved around. I consider myself pretty good at financial documents. I built a system prior to WONGDOODY at MEC where I took everyone’s hours, applied our hourly rate, and sent what was to be invoiced to billing every month. I recovered over $250k in the year I worked there. And most of it was relatively automated. Yay spread sheets with VLOOKUPS and SUMIFS. My favorite.

So the fact that I couldn’t trace the money for these Western Digital Campaigns was a head scratcher. Turned out they moved about $60k from one campaign that finished in September to Q4.

I didn’t catch it. And so, I did’t catch the $60k Google Invoice that was never received either.

My boss must have asked me so many time, “You’re sure. We have all the invoices? You’re sure?”

FFS, “Yes I’m sure!”

So my boss worked with the clients to close the books….

Then it came… an invoice from Google for exactly $60,000. After the books were closed.
I called Google and BEGGED them to rescind it. They refused, because well… they’re Google.

I had to tell and retell the story to my manager, to our boss, who then had to tell the CEO….

I never felt so alone. No one had my back. No one said, let’s figure out how to not have this happen again. It just a countless retelling of the same story of my failure.
10 years later, I see a lot from my boss's perspective that day. The weight of my mistake and how he needed to take it up the chain. I didn’t have empathy for him in that moment. Maybe because he didn’t have any for me and that I took something over that was a disorganized disaster.

Besides having slightly more respect for what I put him through that week, it’s why I rebuild finance sheets. I have to think them through the way I process them to then double check. There does need to be a source of truth that’s checked again, but taking the time to make sure I understand the path. And I still make mistakes. Our Account Director caught one just a few weeks ago when I was double checking capacity against Scopes of Work.

This is why part of our Big Picture value is that is no person is an island. Because especially with data sheets, it’s easy to overlook something, whether that’s $60k that moved from one campaign to another. Or a type-o on a spreadsheet.

Knowing what I know now and if I had been in my previous boss's shoes, my big aha moment would have been checks and balances. He should have had eyes on the financial spreadsheet and known how money was moving around. He should have double checked my spreadsheet to say, we’re missing something and then sent me to go find it. I’m taking that into my leadership journey in understanding more how my team does what they do. As well as the importance of empathy when mistakes are made. Especially if it’s the first time and especially if people are owning something that wasn’t initially theirs.

And I should have asked for help. We had this lovely finance person. I should have sat down with her and went line by line. Or asked Rob to double check it with me. A good chunk of my career was working as an island so I had the mentality that if I couldn't do it all then I wasn't capable or good enough.

I’m getting better. Sam found that error. I fixed it. We moved on and I’m grateful she did otherwise we’d be over extending your capacity. I’m grateful I was able to connect with Mike before the summit week and say, hey I need help next week in Chicago. Let’s talk roles and responsibilities.

I will continue to find opportunity to raise my hand and say, hey… check this out for me, because no person is an island… not even me.


We're human. We're accident and error prone. We are not robots or machines. Making mistakes is part of the active learning cycle. We can't learn without failure. Fail fast to fail forward. Learn and move through. My grandmother used to say, "The only way out is through." You can't go over, or under or around. Own it. Move through it. And you don't go at it alone.

If you'd like to join MKG Marketing, we're always actively looking. We may not have open roles.... yet. We'd love to connect, learn more about you, and when a position becomes available be sure to let you know. Connect with me on LinkedIn.

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