Josh Allan Dykstra
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Josh Allan Dykstra

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Future Of Work
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speaking@joshallan.com

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Lessons From A CEO: The Typical Path Is The Worst Path

Lessons From A CEO: The Typical Path Is The Worst Path

I always wanted to be a CEO.

Well, when I was a kid, I would have said “President,” but the idea was the same — I wanted to be the guy “in charge.”

This feels a little scary to admit, because I know the adage: “Don’t give power to people who want it!” but it’s the truth. For whatever reason, I’ve always been attracted to this particular challenge.

Actually, as a kid my ideal grown-up profession was one of two things: 1) President or 2) Architect — and at least in my mind these have pretty striking similarities. Not because I think the public sphere should be run like a business (I don’t), but because I see both these jobs as helping to create environments where people can thrive.

In 2015, my wish came true for the first time… almost.

I had merged my consulting practice with my friend Mike’s practice, and we agreed to Co-CEO the new entity. I went from solopreneur to CEO of a small team overnight, and it was honestly kind of jarring. I now had to spend a lot of time getting input and building consensus (something a solo owner never has to do because, well, there are no other people to involve).

The trickiest part, though, was probably that Mike and I had agreed to own and lead things 50/50. This arrangement meant I wasn’t ever REALLY the one calling the shots. This was operationally risky, of course, but we believed we could do it kindly and fairly, and we did, parting ways amicably 3 years later with each of us taking a half of the business, which had by then grown into 2 companies.

So now it was 2018, I was a decade into my entrepreneurial adventure, and I was finally “the CEO.”

My business partner Anissa and I agreed to bring on 2 more partners for the new venture, and I got to work, crafting the brand and culture I could finally build. I had gotten a taste of this, of course, over the past 3 years, but now all decisions ultimately came back to me.

We grew that service-based company for a few years and then pivoted into the tech company that became #lovework.

I learned many, many things in that roughly 7-year season, and someday I will write the full book.

But one of the largest lessons is what I told you in the title — that when it comes to designing process and policies for your organization, it’s good to start with one assumption:

The typical path is almost always the worst path.

Why?

Because the vast majority of our organizational systems are descendants of one guy — Frederick Winslow Taylor — who, in 1911, essentially based his entire organizational and management theory on two fundamental assumptions:

  1. Most people are dumb, and
  2. Most people are lazy.

Follow that path for over a century and see where it gets you.

Oh wait, that’s exactly where we are.

The outcome of this belief system is a workplace operating system that is overwhelmingly top-down, laden with fiat power for a small few and mostly-blind obedience for everyone else. It’s full of processes and procedures that are designed to “check” the dumbness and laziness of the people who work there.

Important note: it doesn’t matter if you don’t believe people are dumb and lazy. The system believes it, and the system always wins.

What I discovered over and over as CEO was that almost every “default” path in the way organizations ran was difficult at best, and utterly inhumane at worst.

Sound extreme? I don’t think it is. Why? Because my litmus test is one simple belief:

Work should energize you.

Not one ‘part’ of work. Not that fun task you get to do once a week. Not that great conference you get to go to once a year. More. WAY more. As in: as much as humanly possible. Will you ever get to 100%? I don’t know, but at multiple times in my career I’ve been pretty darn close for pretty long stretches of time so I know it’s quite possible.

But I learned one of the biggest obstacles to this being possible for everyone is the default operating system of work.

As CEO, at every turn, I needed to help lead the team to do ‘something’ in our business: we needed to hire a new person, we needed a new communication platform, we needed to explore health insurance, we needed to recruit developers, we needed an international payroll system, we needed to assess performance, on and on.

Not to mention we also needed to have meetings with each other and actually build something people wanted to buy from us and then serve those customers well and continually test and refine the product…

You know this stuff — it’s the stuff we all do at work.

But what I found time and time again is that when I reached out into the universe of business for a tried and true process I could “plug and play” to do the above tasks, I couldn’t use it. Why?

Because it invariably sucked.

I mean this quite literally, as I have for a very long time — almost every single “plug and play” process out there sucks the freaking life out of people because it’s built on a faulty operating system that’s actually designed to suck.

This meant I spent an insane amount of time trying to research and think and craft a new way to do almost everything… to create some path that would be energizing for humans instead of draining.

Think about it — in your organization, can you say your hiring process is life-giving? Can you say your expense report process is simple and effortless? Can you say your meetings are energizing? Can you say your payroll system is beautiful? Can you say everyone loves your HR information system?

These thoughts might feel crazy… but should it be crazy for the things you spend the majority of your life doing to be more energizing than draining??

Personally, I think it’s crazy to put up with it the way it is.

This means, when it comes time for your organization to think about…

  • How you hire new people
  • Vacation policies
  • Compensation methods
  • Flexible work policies
  • Your office locations
  • The way you run meetings
  • How you organize teams
  • How you allocate work projects

…and just about everything else in your organization, take a good, hard look at the way you’ve seen it done.

Chances are, it’s not even close to the best way to do it… and it just might be the worst.

//

P.S. If you want to start exploring new pathways that create energizing ways of working, please watch this video and/or send me a note. I’m always happy to do a chat or two pro bono!

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