Writing: A Manager's Superpower

Article Summary

• Why should you read this?  Written communication has always been important for managers, but it’s only got more valuable with the rise of remote work. As team members have seen each other less in person, they have shared less information. This can slow decision-making and damage inclusivity and trust. Consciously moving some communication into writing (e.g. memos, documentation, briefing notes) can help fill this gap. This article fleshes out these issues, and as writing has become an increasingly valuable skill, also includes a manager’s guide to writing if you would like some tips.
  

• The benefits of writing more: at it’s best, written communication is inclusive (it can reach everyone on your team in the same way, no matter their timezone, availability or language); it scales beyond the confines of a meeting; it creates a transparent record which enhances trust and accountability; it enables people to focus by reducing the number of meetings they have to attend; and it can lead to more considered discussions. Increasingly, if you have something worthwhile to say, we think you should write it down.
  

• Where to start: ask yourself 1) are you in any meetings which could be replaced with written communication; and 2) could any of your written output be improved.  In particular, meetings which exist to ‘bring people up to speed’  likely just communicate information which could be written instead.
  

• A manager’s guide to writing: changing habits is difficult, particularly when it involves practicing a skill which can take time to improve, like writing. This article includes a quick manager’s guide to writing, which we’d encourage you to read in full. However, we have tried to summarise below in three sections.
  

• Before you start: much of what leads to bad writing occurs before you’ve even picked up your metaphorical pen. You need to understand the impact you want to have, the audience you’re addressing, the format you’ll use and any context you’ll need to provide.
  

• Whilst writing: bad structure and style can blur the clearest arguments. Your reader is likely busy and doesn’t have the time to figure out what you’re trying to say. On structure: address the most important points first; use headings to signal key issues; only address one idea per paragraph/sentence; make it more digestible with graphics/bullets/images/video; and use summaries to provide direction. On style: avoid jargon and cliché; use less words; use the active rather than passive voice; but through all that try and retain your own unique style which will appeal to the reader.
  

• After you finish: always edit (checking for tone, structure and meaning) and proof (checking for errors) your work. Don’t be shy to ask others for help/guidance. Don’t forget to use spell check, and other tools like Grammarly and Hemmingway if you find them useful.

• A reflection on you: Your writing reflects your personality. Rather than being worried about what others might think, try and see it as an opportunity. Good writing is a chance to impress and influence people and organisations on an incredible scale. As a manager, take that chance wherever you can.

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It’s become almost worthless to say that communication is important for managers.  Of course it is.  If you needed us to tell you that, you might be in the wrong job.  The much greater challenge is what to do about it.  

There are so many different ways to communicate in a modern organisation that it can be hard to know what is most effective when.  So we wanted to speak about just one.  A skill which is becoming increasingly important with the rise of remote work. 

In terms of which one, well the 2020 Google trends report found that the world’s top question around communication last year was ‘how do lobsters communicate’.  

Whilst a deep dive on that would be interesting (and a little gross - apparently they pee at each other), instead we’re going to look at the power of writing. 

Specifically we want to look at long-form writing of memos, status updates, documentation etc.   ‍

The Rise of Business Writing

Written communication has always been an important part of being a manager.  But in the last twelve months it has become even more vital, possibly without you even noticing it. 

As the world shut down its offices and relegated everyone to kitchen table desks, interruptions from kids and zoom office parties (potentially the worst of the three), the ability to share information also changed.  

Meetings which people hated (yay a weekly sales update), but which were at least saved by the promise of spending time seeing people you liked, now just became dreary zoomathons for colleagues with limited attention spans.  Not only that, they were exclusionary dreary zoomathons as various remote colleagues missed meetings due to personal commitments, like childcare, or living in Australia.  

In an office context that would be annoying, but informal communication around the water cooler would often fill in enough gaps for the whole system to inefficiently totter along.  Not anymore. 

Cumulatively this has meant that as we have moved more remote, a lot of information which would usually circulate through teams, improve decision-making and make them more efficient, now doesn’t.  

Fortunately writing’s here to help. 

‘Speaking only helps who’s in the room, writing helps everyone.’ - Basecamp

Why you Should put more in Writing

To generalise, we bet that most teams would benefit from writing and documenting more.  So this doesn’t just apply to managers.  But frequently managers are those with pertinent information which needs to reach a wider audience.  It is in these situations where writing can prove a phenomenal communication tool, particularly when it’s alternative is a meeting.

Those of you who are already familiar with this debate will know that we are discussing synchronous vs asynchronous forms of communication.  Synchronous communication requires that both parties be engaged in real time to exchange information (e.g. conversations, meetings, and some Slack/Teams/email). Asynchronous, or async, means information can be received and interpreted at any time (e.g. documentation, notes in project management tools, meeting notes, video recordings, some Slack/Teams/email).

Now, for some things, synchronous communication is still useful. For example anything which requires active discussion and participation, is sensitive, or is time-urgent.  But in many other cases, async, of which the long-form writing we’re discussing is part, can have some distinct advantages:

• It’s inclusive: because you don’t have to be in the room to receive it, async writing can reach everyone on your team in the same way, no matter the timezone or their availability.  If you think it’s absurd that calendars should define your comms, you’re right - they don’t have to.  It’s also easier to translate for those who have a different first language.   

• It scales: once your thoughts are written down, they can scale beyond your team to other stakeholders and parties.  Projects have been approved, careers have been boosted and funding has been found all because memos found their ways to influential audiences.
  

• It’s transparent: having a clear written record which can be referred to later helps create trust and transparency around decision-making. 
  

• People can focus: without the interruptions of meetings, your team can choose to read your output when it suits them.  This enables longer productive stretches of focussed work.  
  

• Quality: with written communication, both sender and receiver have time to better consider their approach and response.  This often leads to higher quality communication and debate.
  

Potentially the greatest endorsement of the power of putting more in writing is that many fully-remote companies have built their own software tools just to facilitate better documentation and writing.   Buffer built Threads, Doist built Twist, Automattic built P2, and Gitlab, well they just use Gitlab but you get the idea.

Increasingly, if you have something to say, write it down. 

“Words and software share a wonderful attribute: Write them once and they can benefit an infinite audience at no additional expense.”  CEO of Upstart

Where to Start

So with all that laid out, we wanted to provide managers with some ideas for using written communication better in their teams. 

We’d ask you to think about two things:

1. Are there any meetings which could instead be replaced by written communication? 
2. Is there any of your writing which you could improve to make it even more useful to its audience? 
   

If so, we’re here to help. 

In particular, if there’s one meeting we’d like to kill as a result of this article it’s anything that involves bringing people ‘up to speed’.  From now on when you see or feel like uttering that phrase, run for the hills - or at least to a word processor.  If it’s not a matter that’s time sensitive or requires immediate participant discussion, you’re just communicating information and it can probably be written instead.  

If you think this will be culturally difficult for you in your workplace for an existing meeting, then you can always suggest it to meeting participants beforehand, or run a trial.  They’ll probably thank you for it.  ‘I’d really rather not, because I try and maximise my number of meetings a week’.  Said no-one ever.   

A recent survey of 9000 employees commissioned by Slack, found that those remote employees who received status updates via email reported a higher sense of belonging (+6) compared to those who attended status meetings (-3). 

Remember that the CEO of Shopify, a multi-billion dollar e-commerce giant with thousands of employees, once cancelled every recurring meeting in the company to see if the world would cave in (narrator: it didn’t).  So you’ll be fine. ‍

A Manager’s Guide to Writing

That’s not to pretend that it will be easy.  Writing well is a craft, which takes practice to improve.  In the short term, it can also feel counter-productive.  Gitlab again: 

"Taking the time to document a solution isn't very satisfying in the moment, and is easy to deprioritize when other seemingly urgent tasks seek your attention"

So we wanted to put together a quick manager’s guide to writing to help you improve your existing communication, and maybe start replacing some of those meetings.  Here goes.

(Actually, pause briefly.  We’ve very aware that in writing a guide about writing we are inviting all sorts of criticisms about our own writing.  But if we provide some value to readers and start a discussion, that’s all we’re trying to do.  However we do appreciate feedback, so please send any along). 

Before you Start 

Much of what leads to bad writing occurs before you’ve even picked up your metaphorical pen.  If you don’t briefly plan what you want to say, to who, and how, then you’re shooting yourself in the foot before you’ve even got started.

• Impact: ask yourself what impact do you want your writing to have? Perhaps you’re trying to ensure your team understands a set of positive sales results, or to make sure an internal process is documented and followed, or to lobby for resources for a project.  Each of these will require a different approach, so it’s important to be clear about the impact you want to have.  What do you want people to feel and know when they read your work?  
  

• Audience: who is your audience? You will select this based on the impact you want to have.  Your audience could range across a diversity of roles, seniority, backgrounds and familiarity, each of which will define the approach to your writing.  A senior exec with limited knowledge of your team will want a very different memo from the junior software engineer you work with every day.
  

• Format and Distribution: what’s the best way to present your work to your audience for maximum impact?  Amazon famously uses six page memos to communicate information.  But you may have an internal project management tool.  This may be the first in a regular series of updates rather than a one-off.  You might have a boss who loves long emails.  Or a team which hates them.  Decide in what format you’re going to send and present your work, as that will define how you write.  If you don’t know what people would prefer, ask them.  They’ll appreciate it.
  

• Context: how much does your audience already know about your subject? In order to have the desired impact you will need to give sufficient context that your points can be understood.  Financial literacy is a classic example.  Many a company financial update is sent to employees who have never been taught the importance of EBITDA or gross margins.  Without this context and knowledge, what’s the point.  Generally assume your audience has little to no context, and write as appropriate.
  

This may seem like a lot, but once you’re familiar with it, it can become a two minute planning exercise which ensures you write with purpose, to the right audience, in a way they’ll be receptive to, and with the context they need to understand your work. 

That’s more than half the battle.

Whilst Writing

As for when you’re typing away, we’ll focus on structure and style.  We cannot overstate the importance of both.  Poor structure and style can blur even the clearest arguments. 

Structure

You should assume that your reader is very busy and you’re competing for their attention.  With that in mind:

• Lead with the headline issue: don’t lead up to a big reveal.  Put the most important information up top. 
  

• Use informative headings:  if your piece looks too long, break it up with headings which make it clear what each section is about.  Your reader should just be able to read your headings to get the overall meaning of your piece.
  

• One idea, one paragraph: don’t try and make multiple points in the same paragraph.  
  

• One idea, one sentence: definitely don’t try and make multiple points in the same sentence. 
  

• Use summaries: if you think your reader might not have the time to get through your piece, provide a summary at the top.  Look what this article begins with. 
  

• Avoid walls of text: where possible avoid giant passages of text, which can be hard to digest.  Use images, graphics, embedded video, bullet points etc to present your thoughts in an engaging way.  Why do you think there’s a picture of a koala and a lobster in this piece? 
  

• Size matters: have a rough idea of how long your piece should be for the audience and format.  If you think it’s getting wordy and too long, it probably is. 

Style

If you’re writing with purpose, for the right audience, in the right format, in a good structure, you’ll probably be most of the way there to the right style.  So this section is more about avoiding things which could compromise that.

• Avoid jargon: it can seem like the world of work loves jargon.  Everywhere you look you’ll find examples of synergies disrupting leveraged solutions.  Don’t join the club.  Using jargon makes your work less clear and compromises your style. Write in plain language in your own voice.  
  

• Avoid clichés: in the real world, companies are rarely in the eye of the storm, people don’t think outside the box, and strategies don’t involve low-hanging fruit.   Again, write in plain language in your own voice.  
  

• Don’t use 3 words when one would do: remember, your audience has a short attention span.  
  

• Use the active rather than passive voice: ‘she wrote the article’ is more direct and purposeful than the article was written by her’.  
  

• Specific dates: if you really want your writing to scale and last the test of time, phrases like ‘last week’ aren’t helpful.

For more detail on these style points, check out these writing tips from the CEO of Upstart - we generally agree with all of them.  There are also numerous style guides out there from major publications which you can use for inspiration.‍

After You’ve Finished 

Congratulations.  By this point you’ve hopefully written an update/email/memo/document which will have exactly the desired impact with your audience.  Except maybe you haven’t.

• Editing and Proofing: always edit (checking for tone, structure and meaning) and proof (checking for errors) your work.  Do these things separately.  On occasion get others to edit and proof your work, particularly if you don’t trust your attention to detail and it’s important.  The best writers in the world make mistakes in their first drafts, you will too.  It’s not an issue, it’s just the process, and could save you a lot of embarrassment later on. 
  

• Use tools to help: it’s amazing how many people think highly enough of themselves not to use spelling and grammar tools to check their work for errors.  Use them.  You may also find tools such as Grammarly (writing assistant) and Hemmingway (assesses clarity) useful.  

Now you’re ready to publish. 

And Finally…

As Phil Libin, co-founder and former CEO of Evernote, said:

“Many people can pretend to be something they’re not in person, but very few people can do so in writing.”  

Your writing reflects your personality.  Rather than being worried about what others might think, try and see it as an opportunity. 

Good writing is a chance to impress and influence people and organisations on an incredible scale.  As a manager, take that chance wherever you can. 

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