Remote Work Isn’t an Option, It’s an Evolution
Mandatory Dos and Don’ts for the inevitable future of work in tech
I have a love/hate relationship with remote work. Personally, I am a huge fan of the increase in productivity that comes with a lack of commute. And to be honest, I also value the increase in creativity that comes with the comfort of working from home.
I guess I do my best work in shorts and a baseball cap. Cargo shorts, if I’m being honest.
But on the flip side, I also love a good strategy room. And I’ve been on the management side of remote work more than a few times. I’ve had to deal with the rare flake, slacker, and miscreant. This is never fun to manage, and there are no easy solutions.
I’ve done a couple of company-wide remote work pivot projects as a C-level executive. One to prepare a company to be able to accommodate remote work for the first time — this was before the pandemic. Then I did another project for a different company, post-pandemic, which was a thoughtful but failed attempt to bring locals back to the office. Finally, I’ve had a ton of honest, open discussions with other leaders of remote, hybrid, and all-in-office workforces.
What I’ve learned is that remote work isn’t an option or a perk. It’s the future. There are just too many concrete pros that outweigh theoretical cons — from the lack of commute to the increase in talent pool to the reduced real estate costs to, quite frankly, a healthy reduction in in-office politics and drama.
It’s an evolution. It’s literally the difference between giving all your employees desktops or laptops. Or requiring formal office attire.
So why doesn’t every tech company embrace remote work? Well…
Because Too Many Companies Do Remote Work Wrong
Let’s take out the sunk corporate lease reasons and the CEO’s personal bias reasons. While those are indeed valid reasons, I’d rather focus on the problems we can solve.
That leaves two primary reasons. One is that, obviously, some tech jobs just can’t be performed remotely, just like some tech jobs require the processing power of a desktop or other less-than-mobile hardware. But this reason is kinda moot, because there was never any grand call for remote work from this class of worker. They took the job to have access to the tech they don’t have at home.
The other reason is the one we need to talk about. It’s that leadership at tech companies keep doing remote work wrong, and middle management keeps getting called out for what looks like incompetence, but is often just a lack of leadership-defined management structure.
Told you it would get real.
So here are several rules for remote work for every company to consider, small or massive, new or ancient. They have proven to be mandatory, and I’ll list them in a fun Do and Don’t format.
Do: Become location agnostic
Don’t become “remote work friendly,” that’s just a marketing slogan to attract talent. If you’re going to offer remote work at all, your entire company needs to be location agnostic — not “full remote,” but location agnostic.
In other words, it doesn’t matter if the employee lives five walkable minutes from the office, they can work remotely too, if they choose. But they must choose one or the other because location agnostic is not just something you say, it’s something you manage.
If you can’t be location agnostic, you can’t offer remote work universally. Well, you can, but it’ll fail.
Don’t: Think remote work is just going to happen
Now we get to the meat of the issue. I’ve found that almost every single problem with remote work falls squarely on leadership and management for not anticipating and accommodating the challenges that come with it. There is no “flaw” in most remote work that can not be preempted or solved.
But without preparation, accommodation, communication, and proactive management of the remote workforce, the risk for failure increases exponentially.
Simple example: If you have someone on the east coast who is hard to reach until 11:00 am EST, then you’ve got a gap to close. The worst thing to do is to try to solve this individual’s behavior with policy. That’s the folly of RTO in the first place. Your company has a management structure. You need to use it.
Do: Form teams around both projects and people
At smaller companies, these might be the same teams. But once you get to 20 or maybe 50 people, this will no longer be the case. The benefit here is that once you solve this problem for 50 people, you solve it for 50,000 people.
Here’s an option. Everyone reports to two people. One person is in charge of what the person is working on, the second is in charge of the person as a resource. At higher levels of the organization, this “boss” may be the same person. At lower, more hands-on levels, a worker might have one “career boss” and several “project bosses.”
This can present a host of its own problems, unrelated to remote work. But let’s fix those too.
Don’t: Arbitrarily leave this to middle management
The biggest lapse in workflow productivity happens when no one knows who is supposed to be doing what, when, and for whom. It all gets agreed on in principle, a lot of times verbally, then people forget. In a remote work environment, this mistake gets amplified, and leads to big problems quickly.
The direct manager for the talent should be involved in their day-to-day availability and priority, and that’s it. The project lead should be guiding their day-to-day effort on that project, and that’s it.
In terms of the worker’s time and commitment to any specific project, don’t use percentages, use priorities, handed down from leadership, with a clear delineation of what is expected from each “boss” in terms of management of the worker. If a worker isn’t spending enough time on a higher priority project, this is management’s problem, not the worker’s.
Specifically, the “career boss” in middle management is tasked with loaning out talent to “project boss” teams. In an ideal world, you want to write something like a short contract of when, how, and how much this talent is going to be used. If your org structure is really good, the “career boss,” the “project boss,” and the worker are going to discuss this together in five minutes.
If your org structure is not really good, you’ve got bigger problems than remote work.
Now that we’ve aligned the org structure to close the gaps, the rest of it is execution.
Do: Extend the workday
The single biggest friction with remote work is bringing the team together at the same time. However, this is not just a remote work problem, this is also a globalization problem. Extend the workday from early to late. If we’re working from home, the concept of work/life balance is different, and remote workers should expect and embrace that.
Don’t: Require butts in seats
But none of us are naive. If you tell a worker they will be required to be fully available from 6:00 am to 8:00 pm their time, they will quit. But they won’t quit right away, they will do all those things you see in headlines of HR articles — like quiet quitting — and then you’re spending all your time fighting that. Expect some waste in the day, but focus on hitting goals, not filling hours.
Don’t replace the in-office desk chair with a camera. Replace it with the calendar. Get people in the habit of mapping out on the calendar where they are going to be, what they’re working on, and when — this can be in really loose terms. Then, everyone’s calendar needs to be visible to their manager(s) and vice versa. And preferably, leadership’s calendars should not be set to block out details of meetings. Find a way around it.
Do: Use every communication channel at your disposal
Text, phone, slack, email, collaboration software, video — in that order. The expectation is that all of those are set to “on” during the extended workday.
Don’t: Do this without guidelines
I know. You’re going to push back against that last one. Here are some basic guidelines that, at a minimum, need to be followed. This should be common sense on paper, but in practice it rarely is.
Text: You need me immediately. If not, use Slack.
Phone: You’ve already asked me if you can call. For you oldsters, this is not how the phone used to work, but now it is. I can’t remember the last time I listened to a voicemail.
Slack: This needs a little more explanation because Slack gets to be a problem quickly. Slack, or any instant messaging, is for communication that you would use in an in-office environment. I don’t care what Slack tells you Slack is for — that’s where the problems begin.
If you Slack an entire channel, that’s the equivalent of standing up in a cube maze and shouting. Use sub-groups or direct channels often. Channels should never be formed around projects or topics, but around teams and sub-teams.
Never use Slack for work communication that is not critical-work-related, like birthdays or hobbies or whatever. Find another platform for that so people can turn it on and off.
Email: Any communication you need a record of to refer to later, including that for which a response is required. And again, do not use Slack for this. It is not email. Shit gets lost easy.
Collaboration software: Any communication that is an official add to a task or a project or one that needs an add. Do not, please do not, use Slack or email or God forbid text for this. I’m looking at you, upper management.
Video: We don’t need video for 99% of video calls and people are over it. Even when you require video for collaboration or presentation, do not require the camera be on.
Speaking of collaboration software, you can see where this can get expensive quickly. If you can’t spend the money to create this location agnostic infrastructure, don’t go remote.
Oh, if you want to save money to fund the software, you don’t have to bring everyone together every so often for that “personal touch.” It’s expensive, it’s stressful, and it doesn’t accomplish anything that you can’t accomplish otherwise. I’ll get pushback on that, but it is what it is.
If we were all family we wouldn’t be firing people as quickly as we do.
Do: Have an open door policy for 1:1 communication
I’m sorry folks, here comes my management side, but we need to kill the concept of “focus time.” All time should be focus time. Developers have been struggling with this for decades and I can’t help but believe in 2025 that this is just how software development works. We’re not making art, we’re making tech. If we want to make art, we need to start our own tech company and then yell at our own developers when they want more focus time to make art.
Don’t: Communicate — unless absolutely necessary
That sounds antithetical to productivity, right?
Again, with decades of experience in my rearview, I am very confident that there will be enough absolutely necessary communication in a healthy work environment to have to promote it. And this goes for meetings too. We hated meetings before remote work, why do we miss them now?
Then make your adjustments
Here’s why this works.
Some people just can’t handle remote work. Be prepared for that. But guess what? That same individual is almost always the pain in the system, the monkey in the wrench, the ghost in the cube maze, in an in-office environment.
On the other hand, almost anyone can be a remote work expert and increase their productivity if the environment exists for them to be able to do that. If you create that environment proactively and manage it with good leadership, think of all the concrete benefits your company can enjoy.
I’ll keep riffing on how the tech industry is changing, in small and big ways. Please join my email list and complain along with me.
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