Welcome to a little reboot of The Engineering Manager. I’m going to be trying out a few new things. 

Firstly, I’m going to get back into writing on a more regular cadence. It turns out that doing two books almost back to back is fairly time consuming. Who’d have thought?

Secondly, I’ve migrated my mailing list to Substack, because this will give you, the reader, way more flexibility in how you can read the website. I’ll be posting on The Engineering Manager blog as per usual, but I’ll also be publishing those articles on the Substack mailing list as it gives an alternative reading experience through your inbox.

Make sure to subscribe if that’s up your street.

I thought I’d kick things off by answering a series of questions, since I’ve realised that lots of people ask me for all sorts of advice, and being able to record the answers in one place might be useful to a wider audience.

Q: How do I get better at writing?

That’s a good question. I get asked this all of the time. I think that my answer won’t be entirely straightforward, because fundamentally I can’t teach you how to get better at writing. However, maybe I can explore your motivations for asking the question, and point you towards some avenues in which you can begin to hone your craft.

Let’s begin with your motivation. It’s important to understand where this motivation comes from before you can decide on how to get better. This is because if you don’t have a genuine desire to get better at writing, you probably won’t. Some self-reflection is required first.

Why is it that you actually want to get better at writing? Are you wishing that you were able to communicate better with your colleagues each day at work? Do you currently struggle when it comes to putting together design documents or proposals? Do you find your email and chat conversations are frustrating because you can never quite get your point across? Do you wish that you could find more joy in pressing the keys on your keyboard?

These are all genuine, practical desires that you can work towards with intention.

If you want to get better at writing because you would love to write a book, or want to have a high traffic blog and some internet fame, or because you think it would be cool to be seen as a writer or author, then these desires may be doomed to fail, and it’s likely that they will lead to frustration before you actually become a good writer.

Why?

The reason is that writing shares many similarities with programming. It is a lifelong craft, and you can always improve, right up until the end. Those that succeed at becoming excellent programmers are the ones that fall in love with the ability to express themselves and to solve problems elegantly, rather than those that have a sole aim to become wealthy or notable in some way.

Those that write well have gotten to that state by spending hundreds, if not thousands, or hours writing. Most of which either yielded nothing of value or were simply the act of taking the opportunity that presents itself in every email, chat message or document to strive for something just a little bit better than they had done before, purely for the love of the craft.

Anything that you genuinely want to become world class at cannot only be a means to an end, because the practice becomes shallow and won’t yield the same results. If you asked any writer how they became great—and I certainly don’t think that I am great, by any means—they would probably tell you that they have no prescription for you to follow in order to follow in their footsteps. 

Everybody’s journey is different. You have to take that journey yourself in order to experience the act of doing, and learn what the path to mastery looks like for you.

I find that I produce my best writing when I am just following along with my fingers, tapping out the stream of conversation that is coming out of my brain. I don’t even know how to do it. This cannot be strictly taught or followed: it’s a state. And the quality of that state comes with intentionality, practice and reflection.

The way to get better at writing is to write. And those that are able to access that flow state and produce text with the ability to self critique will improve. It’s an exercise to the reader to understand how you can find those seconds, minutes and hours each day in order to sink into this state and just write.

Writing has become more important than ever in our careers. It is a key skill to progress to senior levels where the most impactful ideas and conversations are expressed in writing, because that is the only medium where they can be expressed fully and distributed widely.

Those that can write well find that their days are more focussed, efficient, and asynchronous. They may also find that there is a significant increase in the visibility that their work is getting.

Conversely, those that find writing challenging may find that they are unable to express themselves properly. Their documents may make them look like messy thinkers, even if they’re not. Their messages and emails create confusion rather than clarity, and calls are often needed to clear up the details. This is often a bug, not a feature.

I’ve found that the reason that people struggle with writing often stems from a few common bugs. 

Let’s have a look at some of them. The good news is that correction only requires small mindset shifts that have a proportionally outsized positive result.

Bug #1: Writing to think is not writing to communicate

The biggest issue that I see when people write bad longer form text such as design documents and proposals is that writing well is a two-phase process. 

This is explained brilliantly by Larry McEnerney, Director of the University of Chicago’s Writing Program. I’ve reproduced the diagram that he draws on the blackboard in the video below.

The crux of the problem is that in order to think about the world, you have to write. In technology we work in a complex domain on problems that require a lot of thinking, so the process of initially creating a proposal or a design document is to enable that thinking process to happen.

We rarely have everything figured out in our head before we write it down: instead, we have to write in order to uncover all of the details. This is because the act of writing forces us to explore the problem space. The issue here is that the text that you produce in order to think about the world and come up with a solution to the problem is rarely the best text to portray your view to the reader. Therein lies the problem.

You still need to write in order to derive a solution, or to form an argument. But it needs additional work and rework in order to make it something that’s best for your audience. Without your audience using your writing to further their own thought, you simply haven’t written for anyone but yourself.

Bug #2: An inability to imagine yourself as the reader

This leads into the second bug in bad writing, which is when a writer is unable to imagine themselves as the reader of their work. This involves mentally stepping back, being able to read something with fresh eyes and zero context, and seeing whether what was written actually portrays the writer’s intended worldview. 

If it doesn’t, then it requires further editing to make sure that it becomes apparent on the first pass. It needs to be pitched with the right level of knowledge so that it makes sense effortlessly to the reader: you have to know your audience.

When you read emails, messages or documents that really don’t make much sense, or are written incredibly badly, do you reckon that the writer has truly read it back in order to make sure that it represents the best possible version of their idea or of themselves? Did they really have you in mind?

Probably not. The impedance mismatch between the true impact of what the writer has written and what they think it reads like in their head—where all of the context already exists—is the gap that needs filling by reworking in order to make it better.

Experienced writers are able to immediately switch their brain into “reader mode” at any given point in the writing process and then offer themselves critique, then switch back into “writer mode” and implement the changes. You have to act as your own editor, and being able to train the muscle of self-editing comes through exposure to writing that is far better than your own, so you can feed its characteristics into that self-critique model during future use.

It’s worth mentioning that in a work context, “better” writing often means “clearer and easier” rather than “impressive”. You are not being read as a novelist or poet in your work, so leave the grammatical trick-shots for your spare time. Again, know your audience. The reader of your text needs to immediately understand what you mean and what you want them to do as a result.

Bug #3: A lack of clear actions and next steps

Which moves us neatly on to our next point. If writing at work is to spread your ideas and to allow you to exert your influence, then you need to remember that those that you wish to influence the most are often those with the least time. 

You need to write in such a way that captures their attention, makes it explicit what you want them to do (read, comment, decide, or ignore), then make it as easy as possible for them to do it.

A good tip is to prefix any long form text that takes more than a minute to read with a bullet point summary of the main points and the required actions. I receive a lot of update emails at work of which I don’t always have the time to read in detail, but the summaries of the key points mean that I can safely choose to move on if I am time-pressed.

Saving your readers time by being explicit in what you want is one of the biggest gifts that you can give. We’ve all read books that could have just been a blog post, and we’ve all read long documents that seemingly go nowhere or are unfinished. This causes friction for the reader and it reduces the trust between them and the writer for future interactions.

If you’re looking for a decision, be explicit. If you’re sharing your thoughts in case they’re interested, then say so, since if they are not they can choose to skip. If there are clear actions that need to be taken as a result of what you’ve written, make sure that it is impossible to miss them. 

Again, this requires iteratively switching into “reader mode” and giving yourself that self-critique. It’s a muscle that needs to be trained.

Bug #4: Just not enough time in the gym

You can’t expect to become a good writer overnight. It takes lots of practice, often in secret, often producing hot garbage that may never see the light of day. I’ve probably deleted far more sentences than I’ve published over my lifetime.

As I said earlier, the best way to become better at writing is to write. I missed a critical word from that sentence, however: improvement comes through writing intentionally.

The good news is that there are countless opportunities to be intentional. Every email, every document, every chat message, every SMS, and every note to yourself during your working day is a chance to sharpen the sword.

These opportunities aren’t particularly glamorous and they will often be unseen. This is why I opened this piece of writing by discussing motivation: if you truly want to get better at writing then all of the opportunities that you need to do so are right there underneath your nose. But they won’t make you a famous writer. That may or may not come in the future as a side effect of the level you reach in your craft.

So, there’s no prescription, just practice. And by the time you’re good at it, you won’t even care whether you’re good any more. You’ll just write, because you have to.