Nowadays, every startup, especially in tech, follows the exact same boilerplate, using all the same buzzwords, all the same marketing, all the same tools, and all the same methodologies. And whether they intend to or not, every “new” thing they add back into the structure of the company, is just another bar on the cage of the cubicle that they’re putting us back into.

Hiring

Job Listings

We Work Remotely has become one of the most popular go-tos for posting tech jobs. Luckily, this at least ensures that jobs really will be remote, as opposed to companies that only wish to appear innovative and flexible, but actually pull a bait-and-switch along the lines of “Oh sure, the job can be done remotely, but you still need to be local to our city.”

The problem starts with the actual listings, where they all use the same kind of job titles and outline language. Titles like: “Developer Ninja” or “Design Rockstar” or “Customer Happiness Engineer” . Outlines include language like: “We need someone who wakes up with a smile everyday, and doesn’t look at problems as something that holds them back, but challenges they’re excited to conquer!” or they try to be hip and funny “Bob’s our senior developer, but don’t ask him questions too early in the morning before he’s had his coffee… unless you have a cat gif ready to go. He sure likes his cat gifs.”

Most job listings read like the person who wrote them just looked at all the other listings to see what they said, as opposed to actually having something original of substance to say, based on a company that really has true freedom and values to talk about. They all talk about how cool they are, what a great culture it is, the flexibility they offer, and make the same “we’re a fun and friendly place to work” cat jokes.

Job Applications

They then send you to a third-party form to apply, one of several commonly used like Workable, because modern startups have an unhealthy addiction to adding yet another app, service, or piece of software to handle some menial task (more on that later). The application itself usually has all the same questions: “Where do you see yourself in 5 years?,” “What’s an exceptionally tough problem you had with a customer and how did you overcome it?,” “Why do you want to work here?,” or “What salary are you looking for?”

And look, not all clichés are bad; sometimes there’s a good reason that something is a cliché, because it’s useful, but there are always a few questions on these applications that are rude or pointless, meaning they’re only asking it because they’ve seen that it was asked on other forms, not because they have some deep, psychological analysis that they’re doing.

I’d confidently put money on the fact that they quickly skim over some of those answers because it doesn’t actually mean anything to them or whether they’ll hire you or not, because they themselves were only trying to appear “smarter” or “professional” to someone above them by padding the listing and asking what other popular companies ask.

The Test

Next up, you’ll receive a follow-up email after about a week (after sorting through the often hundreds of applicants), letting you know whether they’re interested or passing. In my case, they’re almost always interested because I generally only apply for gigs that I’m perfectly suited for, if not over-qualified for in the first place.

I would only be guessing on this part, but I think the fact that I don’t care whether they hire me or not (I’m usually just taking a flyer on something to see if it’s a good fit and somewhere I might actually enjoy working), helps in terms of confidence, as opposed to the desperate “I’ll jump through any hoop.” mentality of a normal candidate.

At this phase in the process, they’ll typically give you one final test before getting to the true interview. The test is usually designed to give them an idea of your skills or common sense. In other words, they’re weeding out the dumb-dumbs that lied about their experience.

The Interview

If you make it past the Indiana Jones like booby traps, you can now set a day and time through yet another third-party app (something like Calendly) before moving onto the final boss, which is the inevitable video interview (which is almost always done through Zoom) with the big man himself, which is often the CEO (on a side note, can we stop with all these archaic, overblown titles — I’ve started many businesses and I’ve never once called myself the “CEO” of it).

A Word About Zoom

This should really be its own article, but seriously, fuck Zoom; we need to talk about this. Would you install a mandatory keylogger on your computer imposed by a company? No? Then why in the hell would you ever install Zoom, a far worse form of malware. Zoom records your “private” meetings. That means video and audio of you, and everything you’re doing and saying, and outright using and selling that data. This is common knowledge and most people in general heard about it in 2020 during the massive uprise in its popularity due to the virus, which came with much more scrutiny of its weak security (Zoom is not end-to-end encrypted) and its even weaker company policies.

I can understand how a lot of organizations like companies in non-tech industries, schools, churches, etc. continue using the software because they may not know any better, but tech companies who definitely do know better, also continue to force their employees to use this software. I’m really not sure how that’s legal to endanger your people’s right to privacy like that, but I’m no lawyer. I’m not a fan of this style of communication for all my own reasons anyway, but there are always safer alternatives.

The problem, as is usually the case when it comes to privacy issues, is complacency. People don’t care about their own privacy, let alone other people’s. It’s also harder. I’m not perfect; there are many ways I could improve upon my own bad habits, but acknowledging the problem is at least better than nothing, and it’s never too late to improve, even if it’s a slow process.

One of the best parts of working on a remote team was getting to work at home, rolling out of bed, not worrying about how you look or your stinky cat walking around in the background, playing in your unmade bed. But now, in this new move to devolve remote teams back into “the office experience” as much as possible, we’re forced to stick a camera in our face to do our work? It’s just creepy and I refuse.

And we’re back.

Aside from the technology being creepy, I can at least understand that the main point of this step is that they want to “meet” you, see your face, hear your voice (though for my own privacy, I’d rather they not). While I personally don’t give a shit about this (when I hire someone all I care about is that they can do the work and have a good work ethic), I’m not a complete monster; I get it. It really is just the tech that makes it creepy.

Imagine going into a real, physical office to have an interview. Sure, you might be nervous, but it’s a fairly innocuous experience overall. But, now imagine that there’s some lady standing in the corner with a camera on a tripod recording you, while she also takes notes. This is going to be pretty awkward and you’re definitely going to ask.

You: “This is being recorded?”

Them: “Yes.”

You: “Why?”

Them: “Oh don’t worry about it. We record all of ABC Inc.’s meetings.”

You: “Do you work here? Is this for training purposes or something?”

Them: “No, we don’t work here. ABC Inc. has just given us permission to record all their meetings.”

You: “For what purpose?”

Them: “For marketing and research purposes. By entering this room, you too have agreed to these terms.”

You get the idea. It’s definitely not okay. Not to mention that the company you’re working for itself is likely keeping a copy of the recordings (they legally have to disclose this by the way — that doesn’t necessarily mean they will though), and storing it forever for reasons that benefit you in no way whatsoever, including for potential legal purposes to be used against you later if there’s a dispute.

Another big purpose of the video interview is as a precursor to the unwritten policy of…

Company Culture

Because of discrimination and harassment laws, they can’t come right out and say it, but another common theme in this new startup boilerplate model is culture. That is, more or less, you need to be able to be friends with your co-workers in order to be accepted onto the team. Rather than being something that occurs naturally among co-workers if it’s going to happen or not, which is fine too, it’s now kind of a requirement.

If like me, you’d rather just keep your head down, get your work done, and keep your personal and work life separate, it could honestly mean you’re not getting hired or you might not last there very long.

Retreats

A major new fad for startups, but an age-old staple of the corporate world is the retreat. Flying the team out for a week-long work vacation to some domestic or exotic tourist destination. There are a lot of things at play here. Most likely, the boss has read about how team-building exercises out in the wild can improve productivity in the “office.”

I’m not going to argue the pros and cons of this. Certainly, there may be benefits for a certain kind of company, but tech teams really don’t work shoulder to shoulder together where those benefits would be most useful. In a tech company, everything is extremely compartmentalized, and everyone is doing work that’s highly specific and tedious to just them. The only communication really needed is just to let each team member or department know your ETA for X or if you’re having issues with Y.

In any case, I don’t care what the benefits might be, I’m not into it. And even if the retreat isn’t mandatory (it often is outright stated that it is in fact mandatory), going back to culture, it really just is. If you don’t “fit in,” you might find yourself being pushed out or just quitting because you’re tired of being forced to have play dates with your co-workers.

There’s a reason I work remotely in the first place. Having to leave home, travel to the airport, get on a plane, and then spend a week in a house or hotel with what are essentially strangers is the absolute antithesis to the joy of working from home. I’d rather they just took that couple grand they spent on each of us for a retreat, and give us half as a bonus, gaining happier employees and saving money at the same time.

The Work

This is what it was all about, the work; the joy of the project. But, being able to do that work with complete autonomy and time flexibility. Not being micromanaged; not being fixed to any kind of 9-5 like window; just being able to work in your own way, using the tools you like to use, and in your own time. It didn’t matter where you were in the world, what your sleep schedule was like, as long you got your work done within every 24-hour period, and as long as you checked in every now and then and obviously respond to any direct communications to you.

Autonomy

The freedom to keep it simple and use the tools you want to use.

Startups no longer build their own tools or methodologies to keep it all sane and less convoluted. They all just use the same obligatory third-party services:

• Google Workspace
• Slack
• Basecamp
• Zoom
• Help Scout

I’m not saying that I don’t also use some of these tools, or that there’s inherently anything wrong with them, but the point is all about how every startup now is just a carbon copy of one-another, instead of doing things in a smarter, simpler, more minimalistic way. To stop doing things like the corporate dinosaurs of the past.

Flexibility

The freedom to wake up at whatever time you wake up wherever you are in the world, whether that be 7am, noon, midnight, or whenever.

And it didn’t matter because you got your work done within the 24-hour work cycle. You don’t need to commute anywhere, you work with people all around the world with all their own varying schedules, so it just didn’t matter. That’s how time management is supposed to work.

Now, the modern startup keeps chipping away at those freedoms to return to the traditional corporate regime of being available between 9-5 in whatever timezone they decide to designate (usually where the boss lives) and to attend incessant meetings, that have been proven to not increase productivity, and in fact, just waste time.

Conclusion

What the hell happened, why, and can anything be done to stop it?

What?

Whenever there is some kind of anarchy or push back against the ways of old, those systems eventually catch-up and find a way to appear as the new thing, while still implementing their control to serve their bottom line. It happens with all things, from cable to streaming, from books to audiobooks, from radio to podcasts, and from corporations to startups.

In the end, the old always finds a way to get its claws into the new.

Why?

I think the fact that being a nerd has become cool plays a big part in this. There’s Nerd Classic and then there’s the new class of nerds, who are often just Jocks 2.0. Originally, the Jobs and Wozniak dynamic was common among tech companies, but for a short while the Wozniaks took over, and everyone on the team was a Wozniak.

Where rebelling and quitting your day job to revolt and go into business for yourself, to show the dinosaurs in suits that you could do it better, with less bullshit and red tape used to be what a startup was all about, but the suits and conmen caught on and now they play the part of a Wozniak and call their corporations startups for the trendiness of it.

But, while no one’s looking, they keep peeling back the ideals of a true startup, and still touting the claims about being open, fair, free, autonomous, flexible, original, and innovative, are sneaking all the old ways in through the backdoor. The reason for this I think comes from two places, money and ego.

Money

There have been a lot of innovations in business, mainly what a waste of money it is to lease office space. If they can cut costs on all that, but also keep tabs on you with tools like Zoom (the modern equivalent of taking a stroll through the office and watching people work over their shoulder), win-win. Save money, but also keep control? Sure sounds good for the bottom line.

Ego

Admittedly, we might have taken the whole “everyone is equal, no one has a job title” thing in the beginning of the revolution a little too far. I think there has to be some kind of hierarchy to keep the train moving, but there’s definitely a balance. On the opposite spectrum, we see people starting very small independent projects and giving themselves the title of CEO.

It’s just a little much. I think there are people who start projects that already have delusions of grandeur and then sometimes, a Wozniak becomes a Jobs type character after making a lot of money. Money changes people, and they suddenly feel self-important. I think there’s a certain make-believe aspect to it. To appear cooler, more sexy, I think a lot of these people like to play the role and be seen as aggressive, business-savvy operators.

Stop?

Can it be stopped? I don’t see how. That said, I’m sure there are still rare gems out there that really are a joy to work for and truly offer freedom instead of a corporate repackaging of it where all the same buzzwords are used, without any of the actual freedoms.

Of course, history repeats itself over and over and over. At first, innovations like tiny houses, nomadic van life, and startups say “Fuck you and fuck your rules; we’re going to do it our way.” But eventually, the monster catches you and eats you and the revolution is now just the new norm, and it too, will need to be rebelled against.

All I can say is that whenever I hire someone, I do my best to get the hell out of their way. That’s my idea of win-win.

The reality is working remotely is working in isolation, and you will drive yourself and your team crazy if you just create busy work for the sake of creating busy work. You have to take responsibility for how you prioritize your time and effort when working remotely, as well as to research and understand the best tools for resolving communication issues.

For example, some people use a linear process for how they manage tasks. In fact, most people do this without realizing it. They reply to emails or messages in the order they are received. They start from the beginning over and over again without any consideration for timeliness, priority, importance, or productivity.

If you do this, you’re acting like a robot, and you’re creating more work for yourself. You’re not allowing yourself to prioritize or be creative. In fact, getting stuck in your own obsessive and compulsive processes prevents you from being creative and seeing the big picture of what needs to be done. Working from home is an opportunity to focus on the big picture, and not get lost in micro tasks.

While it is fine to have processes and systems for how you do your work, you cannot get stuck in them. If you’re still using the same systems you were using in 2019 in 2021 during a pandemic when almost everyone is working from home, then you need to take a step back and upgrade your processes to accommodate for today’s reality.

There are so many managers trying to duplicate in-person working conditions remotely. This is a huge mistake.

If you’re a manager hosting 8-hour Zoom meetings every single day, or even holding daily meetings for more than an hour per day with your team, you’re not working effectively, and your team is suffering because of it.

Video calls suck. There’s something weird about the latency and delay in visual queues and speaking during video calls that is just unnatural, draining, and exhausting. Video calls take energy without the endorphin boost of in-person, face-to-face interaction.

The first remedy is stop having so many meetings.

You need to adopt an asynchronous mindset. Most remote work does not happen in real-time. Most work happens between interactions. If you’re interacting all day, then you’re not actually giving you or your team any time to actually do any real work. You’re just having meetings to have meetings and you’re not actually achieving any objectives aside from appearing busy. In some cases, this is how people convince themselves that they’re working, when the reality is they’re not. DO NOT DO THIS.

Asynchronous communication is when you communicate in a way where you do not expect an immediate response back. This means taking time to thoughtfully craft what you have to say, and clearly defining context. It is more like sending a letter, or an email, vs having a real-time conversation. Spend more time articulating priorities, goals, and objectives asynchronously, and less time having real-time conversations.

Unfortunately, social media and modern communication tools have convinced us all that real-time communication is the only way to accomplish anything; but it is not. In fact in many cases much like real-time video calls, it is a waste of energy. You’re better off taking time to thoughtfully write a detailed message that clearly articulates what you want someone or your team to do, and then send it to them. If they have any questions then you can simply wait for a thoughtful response back without assuming you will have an immediate response.

The second remedy is to pick up the phone and actually talk to people.

Phone calls don’t require the same level of commitment as video calls and are not as draining. I can walk my dog and talk on the phone; I can drive while talking on the phone; I can pace around my living room like a crazy person while talking on the phone. Phone calls have less latency; they’re more natural; and you can multitask without having to worry about how you look, or being in front of a computer or camera. Learning how to have effective phone calls is an extremely productive remote working hack. Turn your camera off. Just talk to people if you don’t need to share your screen. A 20-30 minute phone call is more than enough to convey complex information or solve complex problems. A simple phone call can easily prevent miscommunication that happens over just text.

Next, ask yourself: is this meeting necessary or could this be an email or message on Slack?

Often, video or phone calls aren’t even necessary. Using an asynchronous method of communication, especially when there is not a sense of urgency, should be the default way to communicate remotely.

On the flip side, no face time at all, and only using email or Slack and never talking on the phone or video calls is equally as harmful to your team. A weekly or bi-weekly or even monthly video call with the entire team for an hour or two is a good morale booster. However, these meetings should be fun, collaborative, status-based, and objective-based. Video calls should be used strictly for “show and tell,” presentations, team-building, vision-setting, big picture, or just fun.

For detailed work, 1-on-1 or small group text chat is the most effective, or a phone call. When I have a direct report that I’m managing I usually manage them directly in a private or direct message. It is extremely counter-productive when you’re trying to get work done with a single person, and you’re using a channel or chat with multiple people who can read it, and randomly start jumping into the conversation out of context because they think you’re talking to them when you’re not. DO NOT DO THIS.

Direct Message the person you’re working with, and if there’s something the rest of the team needs to know after that conversation, summarize it and post just that summary in the group chat asynchronously. Use group chats for async messages and status updates, not 1-on-1 conversations.

To be an effective remote team manager you also need to understand some basic human psychology when it comes to text communication. There’s a very strange phenomenon that happens with text on a screen that we all experience and it can often cause significant harm and miscommunication.

You know when you’re in a really bad mood, in the middle of a thought, and you get a message from your significant other, perhaps a family member, or even a co-worker, and you immediately reply in a bad mood without considering the context of what the other person is saying? This happens all the time. It’s something everyone does. When we read text on a screen, we interpret it based on how we feel at that moment, not in context to what the message actually says. Our feelings cause us to immediately blame the messenger, and take the message out of context.

Where this gets incredibly dangerous is when someone is in a bad mood, they’re going to reply in a bad mood, and they’re going to assume the other person sent their message from a similar bad mood (when they likely did not). All tone, perspective, and context is lost. So many interpersonal relationships and communication suffers from this phenomenon, and it absolutely happens between co-workers, and remote teams on a regular basis. This is why hopping on the phone regularly is so important to be able to hear and understand the tone of the person you’re talking to. Context matters. Tone matters.

If you’re physically in the same room together you can visually see when someone is unhappy or distressed by their facial expressions, posture, and tone. None of this information is available via text on a screen.

It’s for this exact reason my significant other and I do not discuss feelings, or express complex information to each other via text message. We use texting exclusively for status updates and reminders (“Hey, I’m running 20 minutes late.”), or positive interactions like sending each other a emoji. We don’t discuss plans; we don’t talk about friends or family or important contextual information. We call each other and actually talk on the phone so we can hear each other’s tone and have more context for what we are discussing. We also seem to remember things better when we actually talk about them, vs a string of text messages.

The same is true for work. If someone is being rude, short, or saying things that you do not believe they would normally say to your face, then stop using text to communicate and call them. You have to break the cycle, get more context, and have a more human connection with someone in these moments. More text messages always make this problem worse. When a conversation starts to spiral and both people obsessively start arguing back and forth over Slack or text messages, the only solution is to break the cycle and have an audio or video call to resolve the problem. You have to get more context, and the only way to achieve that is through a more human connection with tone.

If one party is unwilling to talk, then just end the conversation entirely and revisit it when both parties are free to talk it out.

What do you do when miscommunications happen?

When miscommunications happen between team members there’s really only one solution. As a manager, it is your job to get both parties on a call or video to discuss what happened. In some cases, this can be resolved with a group chat. But a short call or video conversation is typically more effective. As a manager, your job is to be a leader and hear both sides of the debate and mediate a solution or compromise between the two parties. Most of the time, miscommunication occurs between team members when working remotely because they’re missing context that usually wouldn’t be missed if they were in the same room together. Although, honestly this happens even if you’re working in the same office, but it happens more when working remotely.

Half of a manager’s job is resolving miscommunications between teams or team members. These conversations typically require tone or even video to be able to read facial expressions and body language. Especially if you suspect one party is not being fully honest.

Let people make decisions on what they need to do their job.

Lastly, this is more of personal pet peeve than anything else, but don’t pick other people’s tools. It is fine to have shared collaborative project management or communication systems that are standard that the whole team has to use. That’s fine, but when it comes to specific tasks, I have never felt more frustrated or stifled in my life than when I was working a job or project and the person managing me wouldn’t let me use the proper tools for the job. This is like telling someone to only use a hammer when you really just need a screw driver. Or telling a graphic designer they can’t use Photoshop, and have to use MS Paint.

Autonomy is required for remote work.

You have to encourage and promote those who are able to work autonomously, and teach and coach those who struggle to work on their own. This means giving the people reporting to you the freedom to do things in the way they know how, even if you know another way, or don’t agree with their methods. What matters is the end result, not the path the other person chose to get there. Let your team do what is necessary, and trust them to get the job done. If they make a mistake, correct them until they get it right. If they do a good job, positively reinforce them. You don’t always need to understand how someone else does something as long as the end result meets quality standards and objectives.

When it comes to working remotely you really need to see yourself as more of a coach and mentor when leading a team, and less of a micro-manager.

Let people use tools they know how to use, and support them in whatever way they need to succeed. Your job is to support your team in getting the tools, budgets, or resources they need to do their job. You don’t need to understand why someone is using the tool or software they want to use, all you need to know is if it will help them achieve the goals and objectives of whatever you’re working on together. Focus on the end result, and do not try to micro-manage how people work.

The key to remote work is giving others autonomy, and enabling them to make their own decisions. The role of a remote manager is to support, coach, and define clear objectives and vision. Your job as a manager is to define priority, manage by priority, and clearly define and articulate what the priorities are for your team. Then give them the space, respect, support, and freedom to actually do their job.

I’ve managed teams remotely and globally for over 10 years now.