Wednesday Walk: How Not to Manage
The future of work and the importance of systems
Welcome to the Quarantine Creatives newsletter, a companion to my podcast of the same name, which explores creativity, art, and big ideas as we continue to live through this pandemic.
Every Wednesday, I share random thoughts and tidbits with links to let you do some exploring. I call these Wednesday Walks, as it’s the type of conversation we might have walking down a path in the woods- the topics are free flowing, sometimes related, sometimes not.
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Happy Wednesday folks!
Usually, these Wednesday Walk columns share a few articles, tweets, or videos that are pretty unrelated. Today, I wanted to tie a few random ideas into a thought about a particular worldview in this (semi-)post pandemic time.
I wanted to open this week talking about Donald Trump and his style of management. News just broke that classified documents stored at Mar-a-Lago were hidden and deliberately concealed. That’s a separate matter to dig into another time, but the focus for today is the general chaos of how these papers were organized.
I think there can be some lessons from the former president as we think about the implications of a distributed, remote workforce. Stick with me.
‘The Right of Kings’
Let’s start with this video from The Problem with Jon Stewart where Stewart and writers for his show Robby Slowik and Maria Randazzo dig into the news of the FBI raid at Mar-a-Lago.
The first two minutes of this video were interesting to me, where Jon describes the difference between a public company that is subject to scrutiny and a private company that can operate on the owner’s whims (edited slightly for clarity):
“If you run a public company, you have shareholders… I always found this when I watched ‘The Apprentice'… When [Trump] would sit there at the table and he would have the two, it would be stereo sycophants, one on one side, one on the other… And whatever happened on the show… Donald Trump would do his thing and he would sit back, and then he would turn to one side and go like ‘That was tough’ and then whoever was on the right would go like ‘You did the right thing, boss. Great job.’ And then the other person would be like, ‘What else could you have done? That was a great decision.’ And you realize, oh, his worldview is the right of kings. If I do it, it is in fact correct and just.”
Of course, Jon Stewart is describing a semi-fictionalized portrayal of Trump’s management style, but I do agree that he seems to have a habit of surrounding himself with “yes” people that aren’t willing to challenge him on hard decisions.
‘No Rhyme or Reason’
This perception of Trump was on my mind as I was reading the mind-blowing article Inside Trump’s War on the National Archives by Jacqueline Alemany, Isaac Arnsdorf, and Josh Dawsey in The Washington Post.
As accusations are swirling that the former president may have shared or sold intelligence information to foreign adversaries (including possibly the identity of spies working on our behalf), this revelation late in the article was especially troubling:
“Boxes of documents even came with Trump on foreign travel, following him to hotel rooms around the world — including countries considered foreign adversaries of the United States.”
I don’t want to get too distracted by all of the former president’s misdeeds, and instead want to make a larger point about how businesses adapt to this new world. This is the paragraph that follows the bombshell one above in the Post article and it is more relevant to our discussion:
“‘There was no rhyme or reason — it was classified documents on top of newspapers on top of papers people printed out of things they wanted him to read. The boxes were never organized,’ [former senior White House staffer Stephanie] Grisham said. ‘He’d want to get work done on long trips so he’d just rummage through the boxes. That was our filing system.’”
Small, private companies often operate in a chaotic way like this. They may have a system of organization in place that is based on “how they’ve always done it.” Or it’s a process that makes sense to the owner but would be nearly impossible for an outsider to grasp or understand.
At any rate, it seems that in the Trump Organization (at least by Jon Stewart’s telling of it) and in the White House, having strong systems of organization in place were not the priority.
‘Newfound Flexibility’
On what at first seems like an unrelated note, there was a great Washington Post article from Andrew Van Dam looking at how remote work is reshaping our cities. (Hat tip to Addison Del Mastro for calling it out in his newsletter last week). It’s a really interesting read and worth your time.
This passage stood out about how remote work is expanding beyond tech, finance, and other white collar jobs:
“The data hints that the real remote revolution is taking place not at tech giants but at firms like the Inside Out Co., an Illinois construction, roofing and painting outfit that has found it provides a competitive advantage.
Inside Out had never considered a hybrid or remote model for the 40-plus back-office employees in its Batavia headquarters. But when the pandemic hit, the company adapted, jettisoning cumbersome workflows that required staff to pass files around the office, and adopting a streamlined cloud provider. Management learned to work with employee schedules and child-care needs, and didn’t lose a single worker to the Great Resignation.
Now, said Christie Allen Mortimer, the firm’s chief financial officer, they’ve seized on that newfound flexibility to take on projects from Florida to Tennessee. A business that just two years ago was hyper-focused on the Chicago area now would see no problem hiring back-office personnel who could work remotely from anywhere in the country.”
It sounds like this company had an outdated, inefficient, paper-based workflow (which sounds similar to how both the Trump Organization and the White House were being run). The pandemic forced them to invest in productivity software that improved their efficiency to the point that their staff has been able to continue to work remotely and have expanded their footprint far beyond what they thought was possible.
This was the point I was making on Sunday when looking at Apple’s return to office plans being out of sync with their stock price, which has doubled since the start of the pandemic. Companies that have adapted to new ways of working have seen growth and success over the last two years. If you’ve found a new system that works better, why go back to the old way?
Whether your company is just one person or you employ thousands, the same lessons seem to hold true: systems matter, and investing in the right ones can lead to big productivity gains and improved performance.
Adaptation looks like the building supply company in Illinois that met the challenge of the pandemic and thrived. Not adapting is being an old man lugging boxes of random papers to hotel rooms to “get some work done,” then being raided by the FBI for the mishandling of those documents.
The connection here may be tenuous, but it’s at least where my mind went as I was watching and reading these disparate pieces of content this week. I hope these little ideas may bloom into something bigger for each of you!
Have you worked at a place where the whims of the boss dictated the systems in place? Have you worked somewhere that was well organized and efficient? Do you own or manage a business and struggle with organization? I’m curious to hear your thoughts in the comments.
Other Wednesday Walks
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Stay Safe!
Heath