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Managing home workers? Here’s how to do it well…

This is a long read article: Approximate time to read is 15-20 minutes.

The COVID-19 pandemic has changed the way that many people work and, for some, it may never be the way that it once was.

Twitter just told employees they can work from home permanently

Business Insider

How ready is Twitter and other companies moving towards home working? Even if the employees are willing, how well are companies prepared to embrace this change?

Remote working requires changes to how you manage people. And it can benefit everyone.

In this article we’ll explore the changes that any business will need to make for this to work, from hiring people to managing them day-to-day. You’ll learn how effective remote working can be compared to working in an office and simple techniques that you can use to improve both environments.


About 5 years ago, whilst working for another employer, they decided to allow more staff to work from home. You see, they had a problem. They were consolidating various offices into one but they simply had more staff than there was space. To get around this, they introduced hot-desking, where nobody had an assigned desk and you sat where one was free.

The number of available desks was still not enough, so the only solution was to allow more staff to work away from the office. After all, most of them had work laptops rather than desktops, so it was easily done.

Junior management hated it, though. They couldn’t tell what their staff were doing when not in the office and assumed the worst.

In the end, senior management made sweeping redundancies and so even hot desking was no longer required, let alone any kind of remote working. As soon as this happened, the junior management stopped people working from home, only allowing staff that they trusted to do it – fellow managers.


For the last three years I’ve been working for a fully remote company – that’s one with no offices – everyone works at home (or wherever else you can perch a laptop). Before that I spent almost 30 years in the most dyed-in-the-wool, traditional office environment that you can imagine. It was all wooden cubicles and strict rules that few people remembered what they were for. Here’s a picture of what it was like in the 1990s:

Photo courtesy of Sally White

And during that time I spent 4 years working for a well known IT company. When it comes to old-fashioned, traditional IT companies, which name comes to mind?

That’s right, IBM.

The contrast was extreme but it means that I’ve seen how it works from both sides: managing people in the office and managing remote workers.

What’s the different between working from home and remote working?

You’ll find I use this pretty interchangably but it’s important to know the difference. Remote working is the ability to work from anywhere, where as working from home is doing so from that one location.

For some (like me), they’re both the same – I can work anywhere but choose to work from home. If a company talks about “working from home”, it’s always worth checking if they really mean “remote working”.

Remote working requires changes to how you manage people. And it can benefit everyone.

First of all, let’s get one thing straight – you cannot manage people who are working from home in the same way that you manage people sat in the office. But – and this is the good bit – techniques for managing remote staff can often also be applied to office staff and will bring benefits to both environments.

So, if COVID-19 has forced you to suddenly start managing your staff remotely, changes now can be continued once the pandemic has subsided and you’re all breathing air-conditioned air once more.

But don’t take my word for it…

[remote working] requires a specific mindset and a completely different management structure and workflow.

Mario Peshev, CEO of DevriX

But, office working, well, works?

Does it?

Do you know how much time the average office worker in the US spends actually working during a typical eight-hour day? It’s just under three hours. Stop laughing at the back, UK workers, because for us it’s half an hour less.

The rest of the time is spent having breaks, going to the toilet, getting coffee, chatting to colleagues about The X-Factor, etc. And, yet, there’s a perception that remote workers are the ones who slack off. Another study found that remote workers were 13% more productive, took fewer days off and were more likely to work their full shift every day.

Yet companies such as Yahoo and IBM have tried home working and abandoned it. Why?

Most of the time, management consists of seeing people are sat in front of their keyboard and doing something vaguely work-like. So, when remote working is introduced and someone is working from home, how do you know what they’re doing? Well, you can’t. And two things then tend to happen:

  1. Your staff take advantage of this
Photo by Courtney Cook on Unsplash
  1. You become paranoid. Maybe for good reason, maybe not
paranoid rami malek GIF

Measure Output

Both of these things would be eliminated if you actually knew what your staff were doing. Let’s look at what happened at Bloomberg…

Employees took advantage of the perk. One was unavailable for hours at a time. Another wouldn’t communicate with co-workers all day.
Ten months in, we scrapped the benefit and now require all employees to come into the office every day.

Richard Laermer on Bloomberg

I think it’s interesting that it’s referred to as a “perk” and a “benefit”, as if it’s something beneficial only to the employees. That mindset there tells you a lot.

What Bloomberg were doing, as Yahoo and IBM before them, was that they were trying to manage their staff as if they’re still working in an office.

There’s also the fact that the immediate communication you can get in an office – walking up to someone and asking them a question – now doesn’t work. They may have gone to the toilet or to fetch a coffee – you ring or message them and they don’t reply, raising your suspicions. So there has to be a change of mindset too.

What’s the solution? Simply put it’s better tracking of what people are doing at a meaningful level. Does it matter if somebody is watching something on Netflix or chatting about the beer-filled evening they just had, if they actually deliver what you need them to?

Make sure you understand what people should actually be doing, how long it will take and follow that up. Have grown-up conversations about expectations and work on all of this together.

As the author Scott Berkun says…

Shouldn’t the quality of work be the primary measure of worker performance?

Scott Berkun, The Year Without Pants

Since the pandemic, there’s been a rise in employers forcing monitoring software onto their staff’s computers and phones. This software can take regular snapshots of what’s on their screen, some even maintain always-on webcams, as well as reporting on websites you’ve been to and applications you’ve opened. This kind of reporting is an incredibly blunt tool and, again, tells you nothing about their actual output – starting up Word for 30 minutes tells you nothing about the content that was then put into it. But, again, this allows managers to get away with not knowing what people are actually producing.

Until recently Zoom had a feature that would tell you if somebody in a meeting wasn’t paying attention during a screen share. It was removed as part of changes to privacy and security. For me, the issue is less about privacy but more of just how irrelevant this information actually is – in the end it distracts you from bothering to understand the “if” and “why” of the situation.

I work in support, and that’s an easy one to measure. Kind of. The obvious one, is how many customer tickets I get through. In fact, we also measure documentation changes, internal posts I make and all sorts of communication. That’s then measured monthly against any vacation time that I had. That also needs comparison against everyone else, so a natural lull in customer queries would be seen across everyone in the same time zone. There’s also a recognition that we’re not robots and it’s going to fluctuate. We’ll have bad weeks and good weeks.

So, during the day I can move away from my desk, maybe have a plumber over to fix a leaky tap or I could mow the lawn. I know there’s a clear expectation for me to get work done. This translates into reviews twice a year, where my progress is correlated with expectations – the reviews are not uni-dimensional and there’s no number that tells the whole story. Instead, we look at the outcome of the background projects that I’m contributing to as well as a wealth of data around my primary work – customer interactions. I work together with my lead on creating this review, which gives me an incentive to keep track of my own performance and achievements throughout the year.

As a result of all this, if I was sitting at home not doing any work, it would be clear to my manager, without needing to go over the top with their monitoring, that work wasn’t happening.

But this is a two way process. As Scott, again, says…

If you don’t make your work visible it’s invisible

Scott Berkun, Distributed Podcast

So, there equally has to be some over-sharing sometimes of your work and also of your conversations. Automation can help here – to vocalise, audit and track things that you may be doing.

And measuring output isn’t something that only works for somebody who’s working from home – it can bring immediate benefits to managing anyone. Even if you don’t want to do remote working, moving to a similar solution will give you a better view of what those who report to you are doing. And in a split working environment, you can use the same methodology for everyone.

Make home working flexible

When you’re at home and there are things around you that need doing, the temptation is to do them. Why not build that in? Make the working day as flexible as possible, rather than putting up artificial barriers that are so often prevalent in working situations.

I used to work with a developer who was incredibly talented and a real asset to the company. However, he wasn’t a morning person. He would often wander in around 11am at the earliest, but he’d do many more hours than he was contracted to do, often being in the office until the late evening and even working at the weekend. Because of “rules” he was told he had to be in the office by 10am. Now, there are some people where stricter rules on hours worked are important, except that wasn’t the case here. It was a regimented, single rule that applied to everyone, not taking into account individuality. He soon left.

Again, to quote Scott Berkun:

We faithfully follow practices we can’t explain rationally. Why is it that work has to start at 9am and end at 5pm? We have little evidence these habits produce better work. They become so familiar we’ve forgotten they are merely inventions.

Scott Berkun, The Year Without Pants

By introducing autonomy, along with the aforementioned tracking of work, people can be free to benefit from the flexibility that remote working provides, whilst allowing them to work at times when they will be most productive – as a result you gain the best from people.


Not that you should be expected to work from home. Remote working doesn’t mean home working and, you’ll get a bigger variety of people interested in it if you provide flexibility to go wherever they want. Sitting alone at home isn’t for everyone. Once the current pandemic is over and people can move about, you’ll find that more extroverted people will often shun home working as they need the company of others. What about provisions for people to use co-working spaces?

You’re probably thinking now that a co-working space is only applicable if you don’t have an office – you wouldn’t want to pay for them to be in an another office when you already have one. In fact, all of those benefits of remote working are generated precisely because they’re not in your company office. An ad-hoc co-working space is ideal for those where working from home isn’t going to work. They still benefit from a reduced commute, fewer distractions and you don’t need to have such a big office.

Providing a working environment for everyone is critical but not a “one-size-fits-all” solution – accept that different people want to work in different ways. 

Make sure that everybody is properly equipped

At most companies you’ll be expected to work from home with a small screen laptop and nothing else. Now, working from a laptop on your coffee table is fine for short bursts of time, but isn’t a healthy working environment longer term.

So, consideration has to be made for a home office setup – an external monitor, keyboard and mouse, and even a desk and chair.

And, just how old is the equipment that you’re using?

Where I used to work, they replaced laptops every 5 years, although it was usually 7 by the time they got around to it. Even new they were often pretty underpowered – after 5 years, they were awful to use.

As part of my role, I was on call. And this was a retailer and, at certain times of the year, I could be the only thing keeping their stores trading. And, yet, in an emergency, it was not unusual after lifting the lid on my laptop for it not to be usable for 20 minutes, as a result of how slow it was.

Good quality equipment is just as important for home workers as it is for those in the office.

As a side note to the above story, they only allowed access to their network via VPN, which required a hardware security device to log in. For a combination of security and cost reasons, they limited the number of these in circulation. When the pandemic hit, the majority of their staff, although equipped with laptops, couldn’t work from home due to a lack of the devices. Their own IT limitations had impacted their ability for people, en masse, to work.

At Automattic, your laptop is replaced every 18 months and the most you generally have to wait for any other kind of equipment replacement, even a desk, is 5 years. And you get to select your laptop specification, so you can choose something suitable for your own requirements.

Document… everything!

Remote working brings discipline in a number of ways, many of which can be beneficial to the company at large – documentation is the prime example.

For effective communication, you can’t just lean over and ask somebody sat next to you. And if you’re working flexibly, the person you want may not be around. So timely and accurate documentation is critical. Yet, it should be in an office anyway but is often forgotten. How many times have you spent trying to solve something when it turns out somebody has already done it in the past? How easy is it for new joiners to your company to learn the requirements of their job?

The requirement of remote working ensures that documentation becomes a priority.

And, for much the same reason, it becomes a lot harder to have a “do this thing now” mentality, as the chances are the people and resources you need won’t be available. It’s easy in an office to walk up to someone and distract them from what they’re doing to make them do something there and then, which could have waited.

As mentioned in a recent Economist article, “good writing demands clear thinking and discipline”, which is why remote companies favour wordsmiths.


And, if it’s not apparent already, communication is critical. Or, as we say, in the Automattic Creed…

I will communicate as much as possible, because it’s the oxygen of a distributed company

The Automattic Creed

Put the tools and resources in place to allow good communication to occur. Don’t rely on email and an old instant messenger client that came bundled with your office software. And you need different tools for different jobs too.

When instant communication isn’t always possible you need ways to reach out to groups of people easily. 

In fact, it can drastically improve how you communicate. By writing things down in longform and publishing them and giving people a chance to get back to you on their own schedule, you end up with much deeper, fairer and just generally better discussions. So many things that once may have been a meeting are written down and people respond over a number of days, in their own time, and those conversations are much richer.

At Automattic we use Slack for instant communication, Zoom for video calls, we use forum-like WordPress blogs for longer-form and less urgent communication. We have documentation, both internal and client-facing, that anybody who works for the company can add and update. And on top of that we use other tools such as Trello for specific situations. Email is hardly used.

Poor communication is at the root of most disagreements, conflict, and poorly managed projects.

When people understand each other, difficulties melt away.

The Automattic Creed

The reference to oxygen in the Automattic creed is not accidental: too much oxygen can be fatal as well.It’s important to invest time making sure that the right information isn’t just published, but it’s heard and understood by those who need to. This, again, comes back to having the right tools for the right job.

Anyway, enough of this talk about communicating remotely all the time. If remote working is going to work you need to sometimes be social.

In-person meetups are still important.

In the VIP team we have a yearly company retreat – there’s about 100 of us – and we also have 1 or 2 team meetings every year as well. As well as discussing work topics, we also do things like playing board games, karaoke or going on a city tour. These help us learn more about each other and our families—it’s knowledge we wouldn’t have gained in a normal week. We eat together, work together and have fun together too.

So, consideration has to be given to this aspect as well.

Even in a mixed working environment you need to get your staff all together throughout the year and not in a way that’s all meetings and business. Because that social interaction is something that you need to put back.

Obviously, cost is a big consideration for doing something like this. Keep in mind, though, that a typical remote team saves money by not having to pay for an office (or paying for a much smaller one than you’d normally have to have if you’re a partially remote team). Invest the money you save on office-related expenses into these meetups because of the invaluable team-building these experiences provide. 

It’s not cheap, but what’s even more expensive is having a remote team that doesn’t work well together.

Consider specific hiring for remote workers.

Who’s ever been hired where they had a probationary period?

Now, these are really interesting because in most countries they exist and there is nothing in law. The companies may say that there’s something special about in your contract, except contracts can’t override country laws and usually labour laws prevent you from, say, getting rid of someone after a month because you don’t like the look of them.

Yet, companies will often make out as if they can do exactly this.

Why do probationary periods exist in the first place?

A probation period allows you to assess whether an employee is right for you. You can take the time to evaluate if your new employee is showing that same potential that you identified in them during the application process and at interview.

Breathe HR

Put simply, the hiring process was not sufficient to tell if somebody was a good fit or not. In fact, this quote, they make mention of an application and an interview, which is often all that hiring consists of. How do you assess somebody’s technical capabilities, let alone whether they’re a fit for the working environment, with an interview?

So, at Automattic, we don’t have probationary periods. Instead, we have trials. Where we take a prospective hire on as a paid contractor for a number of weeks. We give them projects to do during this time and carefully monitor their progress, including how they fit in with the team. We also ask specific questions during the initial interviews around remote working and we carefully watch this during the trial. People can do the trial at the same time as maintaining a current job, as you fit it into your own time.

Before someone even gets to the trial stage they will often have 1 or 2 technical exercises to do, often quite complex and demanding. Even if this is an office hire, you can do this, with them performing this work at home and sending it in.

And some people who do hiring don’t like this. “They could get help.” “They could look up answers.” Isn’t this what people, when they’re working, do in real life, anyway?

I went for a job interview many years ago to be a PHP developer. After the more traditional face-to-face interview, I was sent into a room. Now, this was before smartphones were a thing, and all I had was a PC, disconnected from the internet. On it, was a test that I was expected to complete.

It was questions such as this…

“What is the 4th parameter of the str_replace PHP command and provide an example of where you would use it?”

Who memorises all the parameters of PHP? What everybody does is look them up, when they need to know.

I answered about 2 out of 20 questions, instead leaving a long complaint at the end of the test about how unrealistic it was. I didn’t get the job.

And I was right. This was an unrealistic test. It isn’t how people work in reality.

Even if this is an office hire, why not do the same trial method yourself? Unless doing the job requires you to be physically in an office, you can test the capabilities of a potential hire. If you’re then allowing some staff to work from home, then you can add in checking to see if they’re a good fit for this.

The important thing is not to give them the answers in the actual question. So, make them open-ended. For example, you could ask questions such as…

  • What would your week look like?
  • Have you worked remotely before? What were the biggest benefits and challenges?”

These are questions that we ask at VIP.

As well as being very targeted on the questions and general expectations, we’re thorough. As a result, just 2.3% of Support Engineer applications make it through to the trial stage, with less than 54% of those being hired.

That doesn’t mean we have a large number of resources to achieve this – a lot of the time it’s me. Instead, it’s done remotely and is all prepared and documented. We use scripts for interviews and tools to manage applicants.

Have a process that hires the right people

So…

  • Ask open-ended questions about remote working
  • Trial people, if you can
  • Don’t have probationary periods

Nothing in this article is revolutionary. Many of the practices and techniques for managing home workers shouldn’t be difficult for a business to implement, yet are likely to lead to happy and more content staff.

If you have any questions about any of this, please do comment below or reach out to me on Twitter or LinkedIn.

This is an expanded version of an article originally published on The Big Tech Question.


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