What’s on my Mind: The Remix: The Lessons I’ve Learned (and the mistakes I’ve made) in Business, Volume 1

Jeff Cherry
9 min readJun 13, 2023

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Yesterday, I had the pleasure of listening to a short but incredibly engaging presentation by SHIFT CEO Joe Mechlinski, who happens to be my business partner, investor, and portfolio company CEO. (Yes, he is all three of those things!)

I’ve been wanting to get away from writing about all of the political issues I see in society — not sure how long that will last but let’s give it a try shall we — and starting to write more about the useful lessons I’ve learned, taught, experienced of mistakes I’ve made, in building businesses over the last 37 years.

Joe’s message today was so powerful that I thought I’d start this series — to be dubbed: The Remix: Musings on the Lessons I’ve Learned and Mistakes I’ve made in Business — with some of his wisdom from today. (The Remix also happens to be the name of my podcast. If you haven’t checked it out please stop by!) So yes, some of this new series will be my own thoughts, and a lot of it will be me expanding upon and evangelizing about the ideas I’ve gotten from many smart people. People I’ve learned from in the past, and continue to learn from every day.

If you’ve listened to any of Joe’s talks or read any of his books (you can see his latest Ted Talk here and find his New York Times and Wall Street Journal best sellers here) you won’t be surprised that the theme of his talk today was The Future of Work.

If you’ve ever listened to Dan Pink, one thing he talks about often is that great leaders have “a sentence”. He says that anyone who has or is trying to achieve something great in life has a purpose-focused mindset that points them towards doing one or two great and transcendent things. And that the best leaders have a similar and singular focus. You can imagine those one sentence lives: Abraham Lincoln freed the slaves and preserved the union. Great sentence. FDR Lifted us out of a depression and helped win World War 2. Another great sentence. The notion that a great man is a sentence strikes me whenever I hear Joe speak. Now I’m not claiming Joe is the next Lincoln or FDR. But for us entrepreneurs here, this is an informative idea and one we might want to explore.

Joe’s sentence has been something similar to the following since I’ve known him: “I want to change the way people work, so that it transforms the way they live.”

His talk yesterday highlighted five situations and reiterated five ideas for a better way forward when it comes to work and organizational culture, that I thought would be great to share with you.

But before we get to the situations and ideas, let’s talk about a fundamental and foundational cause for all of what I’m about to show you:

Stakeholders or Shareholders? The answer is yes!
Much of the issues we see at work, how we experience capitalism and how we experience work on a day-to-day basis has to do with the ongoing and seemingly never ending tension between capital and labor. The notion that the only purpose of business in society is to create value for shareholders is at the base of this idea. It leads us to think about capital providers as the “risk takers” as if the only risks that matter are financial. And it diminishes the fact that without labor of some sort, capital cannot be expanded. This idea sets up a perverse relationship that in my mind actually over-values money and undervalues all of the other stakeholders (like employees, customers, suppliers, communities, legal structures, material inputs etc.) that commercial entities actually require in order to create value. It forces management in these entities to think about shareholders as being at odds with all those other stakeholders. The key to success in this scenario is diminishing what some see as the “natural” tradeoff between shareholders and everyone else. As opposed to thinking of a business as a system where ultimate success comes not from extracting what you can at the cheapest cost in order to create returns, but rather understanding that the greatest value — both societal and financial — is created when we see business as a systematic and mutual exchange of value between a interdependent web of stakeholders. Who rise and fall in connection to each other. This is the mindset in which the following situations flourish.

Why Work Can Suck:

Situation #1:
This capital — labor tension and the command and control structure it necessitates between management (the “thinkers”) and labor (the “doers”) causes almost a parent-child type relationship within many organizations. (Adult)

Situation #2:
Given this management and labor relationship dynamic, management feels as if a big piece of their job is to create rules to ensure that employees will do all that is required of them. We use rules, carrots and sticks, crime and punishment analogies (Freedom)

Situation #3:
Despite the obvious contradictions with Situation #2, business owners and managers are constantly asking us as consultants questions about employee engagement. As business people it is of course in our best interest to have highly engaged employees who are willing to go the extra mile for the company. We all want discretionary effort from our colleagues. But as we have seen in the “quiet quitting” revolution employees are asking themselves: “Under these circumstances, why on earth would I ever do more than the minimum that I am paid for? What’s my upside for working harder?” (What’s my Upside)

Situation #4:
The capital — labor tension and the management-employee relationships it engenders again rears its head, manifested in the way we both direct and reward work. We focus on the lowest common denominator of metrics when it comes to letting people know if they did a good job today or not. It’s all about the numbers, which often can obscure the actual strategy that we’re trying to achieve for those most able to influence those strategies. We hoard information and have a “need to know” mentality. (what is good?)

Situation #5:
All of this leaves a question in the heads of all of your employees as they walk out of the door each night: “Was today worth it?” Each day we ask them to spend the most precious thing they possibly can — a day of their life — in service of our organization’s goals. Whether they are contemplating this directly or not, it impacts how they feel at the end of the day and how they show up in the world. Thus we have a restaurant called TGIF (“Thank God it’s Friday”) and a real condition called the “Sunday Scaries!”

So much to unpack! But to make it simple, here are a few ideas from Joe (with some editorializing by me) that you can use to help make work a source of joy and fulfillment, and a little less sucky!

Photo by Clark Tibbs on Unsplash

How to Make Work Suck Less:

Idea #1:
How about we recognize that all of these people working for us are adults and we start to treat them that way?

It seems to me that almost every employee I’ve ever come in contact with (I said almost!) wants to do the right thing at work. They want to come in and do a good job, be treated with respect, be honored for their contribution and intelligence. Oftentimes they have studied long and worked hard to be in a situation where they are then treated like children. We think that Adult-to-Adult conversations are tremendously rare, and tremendously empowering. The separation between thinkers and doers in today’s modern workplace is less evident than ever and recognizing this could go a long way towards reducing or removing that parent-child dynamic.

Idea #2:
COVID show’d us all that the rules and regulations we labored under for years aren’t necessarily the only way to get things done. We believe an approach of Freedom inside a Framework has the power to unleash all sorts of new types of creativity inside organizations. At Conscious Venture Partners we have been thinking about how we get back to being together in the office — with the obvious benefits it brings — while also honoring the new ways of working, and living, that have emerged from the pandemic. What we came up with was a system in which we ask people to be in the office 3 days a week, but give them the freedom to do whatever is best for their situation and their families. So if this week you can only be in the office for one day because of whatever you have going on, that’s fine. Just let the rest of your team know, be available and get your work done. So the framework is: in the office for 3 days, and the freedom is make the best decision you can about your work situation on a daily basis based on the trust and respect you have for your team! And know you won’t be penalized for using the freedom nor will you get special treatment for living in the framework. Oh, and we also don’t do meetings on Fridays nor is that one of the “in office” days.

Idea #3:
If you want employees to be highly engaged and give discretionary effort, it’s pretty obvious that you have to answer one simple question: “What’s in it for them?” If you’ve answered, “Well your paycheck!” well be prepared to lose the battle for talent. That’s just the ticket to the dance. And we all know that. To make work joyful — and reap the rewards of doing so — you need to bring more to the table. You have to care about the things your employees care about, you have to give them a stake at the table. That doesn’t always mean a piece of the profits — although that’s certainly a good approach — but at the very least you need to make sure they see an upside — and in most cases it should be more than or in addition to money — that makes them feel like they are a part of something and not just a cog in a shareholder machine.

Idea #4:
Highly correlated to the Adult-to-Adult conversations we should be having inside organizations, we should be giving out as much information as possible so that everyone can help row the boat in the right direction. In other words, get really serious about “What does good look like?” That means having deeply strategic conversations with as many people inside the organization as possible and letting them know not only about the number metrics, but about all of the things that drive those numbers. And related, what the world looks like everyday if we are great at executing on our strategy. We all want to be a part of something impactful. Most of the time money metrics don’t tell that story. Tell me what good REALLY looks like for us and I will help get us there.

Which leads me finally to…

Idea #5:
from an employees perspective: If you treat me like an adult, with dignity and respect in every situation, provide me with some freedom and autonomy to make decisions that help us win, show me how it all helps make me better, my life better, my family and my community better, and be open with me about what we’re trying to accomplish and how my position aligns with and contributes to that mission, more often than not, I will walk out of the doors at the end of the day feeling energized and grateful that I spent this day of my life — which I will never recover — on something meaningful and fulfilling. Show me it’s worth it!

Joe and I both believe that these are some of the ideas we can implement as leaders as a path towards making work a source of joy, fulfillment, and personal growth for employees while achieving greater success as organizations.

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Jeff Cherry

Dedicated friend and serial entrepreneur. I am the founder and Executive Director of Conscious Venture Lab and Managing Partner of the Conscious Venture Fund.