Making a List, Bolding It Twice

Writing is meant for reading.

Sometimes, the reading doesn’t matter that much. We might dash off a quick text, toss out a laugh line, or send a rote confirmation. Our emoji are leaves on the wind.

Other times though, the reading matters a lot. Occasionally we need to write something that must be understood, absorbed, and acted on. The more important it is that readers understand and act, the more time you should spend refining the writing.

There are a lot of things you can do to make an email, blog post, proposal, or process document clearer. For example you can keep it short, make it engaging, or have a colleague refine it before sending it out. These can all help a lot.

However, if it’s critical to you that your writing is read – especially by busy people – you need to make it skimmable.

There are a few ways you can facilitate this.

You can use short sentences and paragraphs, for example. That helps a lot because folks tend to primarily read the beginning of each paragraph. It’s kind of a hack, but it works.

There is one core approach though, one workhorse of the skimmable document, that is worth mastering: lists. Lists are rightly derided in the era of Buzzfeed, but the same principles that drive engagement on social media also drive engagement in a Google Doc or email. So today, I’d like to share one weird trick to quickly writing a clear and useful list: The Bolding Trick.

The Bolding Trick

1. Draft a bulleted list, whether it’s the key goals for a process, the main principles in a design, or whatever. Rather than trying to make it perfect on the first go, just get it out.
2. Your list should only have 3-8 items on it, with each item 1-3 sentences, which should keep it readable and digestible. Still, unless each item is extremely short, the resulting block of text can still be a slog to read, appearing monotonous and causing your audience’s eyes to glaze over, or – worse – cause them to decide to read it later.
3. For each point in your list, find and bold the key phrase in the paragraph. For example, the key phrase in this point was “bold the key phrase”. This will make the list far more skimmable.
4. If it’s an important list, it’s worth also pulling those bolded phrases up front. Once the core points are bolded, run down the list again and pull the bolded part to the beginning of each item, making it the heading/summary of the item.
5. Your eminently readable and skimmable list is now ready to be absorbed and acted upon, and easily maintained.

A thing I love about this process is that when you pull out the key phrases into headings, it also naturally drives you to edit the prose to be clearer:

The Refined List

1. Make a bulleted list. Hammer out the key goals for a process, the main principles in a design, or your weird trick for making lists.
2. Include 3-8 Items. Make the list clear and focused by keeping it to 3-8 items of 1-3 sentences each.
3. Bold each key phrase. Go through the items you wrote and mark in bold the 1-4 words that matter most. This would be often be a verb phrase in a process document, or an adjective phrase in a list of goals.
4. Make the phrases headings. While you can stop after bolding, it’s often worth also pulling the key phrases into inline headings. Rewriting your list this way also helps you refine and repeat the key points.
5. Share and maintain. The formatting will make your list much easier to read, update, and act on.

I find this approach faster than trying to come up with the headings first, and it has the added bonus of being incremental: after each pass you can stop and you have a useful document.

Once upon a time, when I would try to document a process or a project, I’d approach it like a blog post. I’d spin a narrative, write pages worth of context and detail, and really get to the heart of the matter. Once the resulting tome was complete, it would be read once, and then left to the sands of time. That was fine for battle stories and manifestos, but not so much for process or design documents.

Now, I write short docs consisting mostly of lists and bolded key phrases. They get read and maintained.

It’s a lot better.