Whether it's resumes or reports, budgets or broadsides, I'm pretty regularly sent working documents from a wide range of people, and over the years I've noticed some consistent patterns that lead those documents to be less effective than they should be. Even very smart, capable communicators routinely send important documents that distract from, or even undermine, their goals.

This isn't too surprising; we almost never actually teach people how to use the ordinary tools of business communication in more effective ways. So, I'm gathering some advice that I regularly share with people, in hopes that this helps you get your messages across more effectively. All of this is advice that should apply regardless of whether you're using tools like Google Docs (uh... Workspace?), Microsoft Office (or 365 or something?) or whatever else.

Know your audience and your goals

The most common, and most serious, problem people have in creating documents is that they don't consider who they're speaking to and what they're trying to accomplish. This can manifest in many ways, but most often the result is an end result that is technically not wrong (things like grammar and spelling may be correct, or the facts and figures may be accurate) but that is completely ineffective in achieving its goals. Ask yourself a few questions:

• Who are you addressing with your document?
• What is their day like, and what other distractions, concerns or priorities might they have?
• What's the most likely goal they are going to have, or answer they are trying to get, by looking at your work?
• What understanding do they have about your initial context and your own goals and needs?
• What historical context are you assuming about the audience and how they'll see your message?
• Is the framing and narrative that you're using relevant and culturally appropriate to its intended audience?
• If you are asking for something, is it absolutely crystal clear that you are asking for something, and if there are options to choose from, are the options (along with their pros and cons) explictly laid out?
• If there's a decision involved, can you articulate which other parties may have a stake in that decision, and whether they've been consulted or not? Can you clearly articulate the counter-arguments to any answers you're proposing? Are those objections valid and legitimate?
• If the document requires a response or a decision, have you identified a timeframe or a deadline for that decision, and explained why that timeline is relevant — both to you and to the intended audience?

There are more questions in this vein, but what you'll find as a unifying thread amongst all these questions is starting from a standpoint of asking about empathy and perspective. If you don't do this, your output is a failure before it's even shared, but if you get most of these right, any gaps or shortcomings are likely to be addressed in a collaborative way, because the thought and care behind the work will be evident.

The most common failure cases I see in these kinds of situations is people starting from deep within their own heads, either because they've been fully immersed in a particular project, or because they're reacting to their own fears or concerns. (Even if those are legitimate!) I can't tell you how many times I've seen an important document, like a cover letter for a job, or a pitch for fundraising, that essentially starts with a lengthy, off-putting, deeply insular recitation of a list of things that are basically a litany of the author's insecurities. Don't do this!

Start from common ground, identify the shared goal that you and your audience have, name the ways in which you're already on the path together, highlight what remains to be done, and then close by asking for their help (in whatever form) for you all to keep progressing on your collective goal.

Stop formatting everything to death

This classic from Joey Cherdarchuk at Dark Horse Analytics has been kicking around for a full decade, and I still end up sending it to someone about once a week.

If I had one bit of advice that I'd build into these tools, it would be this: Stop overusing formatting! Look at the formatting bar, and ignore almost all of the buttons. You can use bold, sparingly. You can use italics, rarely. Just... never use underlines. Underlining basically only exists now to confuse people into thinking something is a link that they can click on.

The same goes for colors and fonts. Pick one, or maybe two. For the entirety of your document or presentation. (Yes, including any charts and graphs.) You can use shades of one of the colors, if you absolutely have to. But you don't! Do less. Be intentional about where you're applying any formatting, for any reason.

And finally: Don't use more than one of your formatting tools! Bold means something is important. Italics means something is emphasized. Color means something is distinct. Something that is bold, italicized, underlined, and brightly colored means you don't know what's important or what message you're trying to get across — it only communicates distraction. And it's hard to read.

Oh, and don't put borders on anything. If you can, remove and minimize the default borders that your tools put on things. "But then how will I separate stuff?!", you ask? This brings us to our next section...

White space

You know how all your designer friends are always talking about white space? You basically can't have too much of it. Almost every time you want something to stand out, one of the best ways to do that is not through lots of formatting, but through a smart use of white space. Done properly, the point you're making will stand out on its own. Maybe you can just use a bit of minimal formatting to make it really pop, but it shouldn't take much.

A related technique is to spray them with bullets. Bullet points are a super powerful way to make content more skimmable for an audience, and perform a useful forcing function in making you edit your points down to be concise and roughly consistent. One less-obvious benefit of using bullet points is that it can often reveal to you as an author whether the information that you're providing is all in the same category. In prose, it can be easy to sometimes drift off-topic into unrelated topics, but with bullets, if you've got a list that has items which are very evidently out of place, it can be more evident.

Conversely, only use images and illustrations with purpose. Clip art almost never adds value. The same stock photos that came with your template are also meaningless. It is far better to have white space on the screen for your audience than to fill up that space with a graphic that has no meaning, especially if it's not specific to your context or message. Visual noise has a huge cost in its impact on people being able to absorb and understand your message, and it's extraordinary how common it is for people to have a slide that is 1/3 really carefully-crafted points that took a long time to devise and 2/3 an image that has zero purpose and was added at the last minute. Don't undermine your work with an unnecessary compulsion to fill up space just because a template suggests that you should.

Learn your tools

You should master the formatting tools (especially in written documents and slideshow presentations) that let you control spacing and margins around your content. You can assign consistent styles (like headers in a document) to always have a lot of breathing room at the top, and then just consistently apply that style across your document.

A really common anti-pattern that I often see is needless inconsistencies. For example, people will vary the size, color or emphasis of titles across different slides in a presentation. Sometimes, this is an artifact of their creation — slides with this font came from this team that was working together, but slides with this other font were copied from some older presentation. But to the audience, the immediate message that they'll take away from a difference in formatting on the title of a slide is, "There must be a reason this changed, let me understand its significance." Suddenly, your audience is trying to deduce the semantic meaning of a change that you didn't even make on purpose.

The reason we start by saying to stop formatting everything to death is that this then makes it much easier to catch the inevitable inconsistencies and errors in formatting that will arise when you tell a complex story. Audiences are sophisticated, and used to seeing highly-produced media, and are very skilled at the innate human habit of identifying changes in pattern and shape. So they will assume that any change in formatting over the course of a document has some purpose and intent behind it. If you don't anticipate this reality, you end up with the worst of both worlds — you've captured their attention with something that's not relevant, and emphasized your own lack of preparation.

Learning your tools and using them well will make it easier to hide the seams between the different people and processes that created the work that you're sharing. And sweat the details here — if you're bringing over assets (like images, charts or embedded content) from other sources, make sure to use your tools to do another formatting pass and make it consistent with the rest of your document.

Pay attention to sequencing and order

Just as many documents begin by exposing the insecurities of their authors, many times the order of information in a document reveals the relative difficulty of creating different kinds of content, rather than its actual importance. But people assume the first thing in a list is the most important! And they're being rational when they do so!

Especially in a world when some of the people attending your event, or participating in your meeting, will not have had time to review the whole thing in advance, assume that you have to front-load your key points at the beginning of the document. And within a particular page or slide, assume that you have to put the most pertinent info at the top, with supporting points below. If you're not ordering things by importance (because you want to set up a chronological flow, or because you're organizing by some historical categorization you've inherited) make that explicit in the text that your audience sees. Otherwise half your audience will be lost right at the top, wondering in their minds why these items are in an inexplicable order.

It's not a murder mystery

Similar to the importance of sequencing and order, you almost always want to start by clearly and simply stating your conclusion, or declaring your request or question. Very often, people feel a lot of anxiety about the need to preface their big dramatic point with lots of build-up. But you almost never want to be building dramatic tension in a professional context; this isn't a thriller where you're trying to surprise them with twists and turns.

It's perfectly fine to open with a key question or conclusion, step back to walk through the logic and context that leads to that point, and then restate at the end to drive towards your goal. But more often than not, if you don't set the stakes and make your point clear up top, you'll exhaust your audience, or leave them distracted trying to guess where you're headed all along the way.

Similarly, put the important points on the page! It's absolutely astounding how often people will take the most important conclusion about their work, or the most vital bit of context needed to make a decision, and assume they'll speak to it alongside the presentation of the document or slides. This is a surefire way to ensure that one of your most important stakeholders will be absent or distracted, and completely miss your point, and then go back and look at your document and not see that key fact you were trying to share. Even in many cases when people do include the key point, it's very often buried in some obscure place like the speakers' notes on a slide, or in an appendix that doesn't seem like a central part of the document. Don't demote your central statement to an ancillary channel.

Give people wayfinding

People want to know where they're at in the story. This doesn't have to be fancy, you don't need a full timeline bar like a YouTube video. But a quick outline of progress (and, if you've got a particularly long document, recapping your position in that outline as you go) can help ensure people that they understand their place in the overall conversation.

This is one of those rare places where you may well want to use color. If you've got multiple distinct sections of a document or presentation, assign colors to them (keep your palette limited!) and use them utterly consistently so people know where they are, and that'll help build confidence that your audience knows how far along they are in the story.

Similarly, summarize any data that you present. You can trust people to be smart and to dig into numbers or charts, but start them off on the right foot with a little bit of "here's what these data show" right in the title of your chart or figure or data table, so they're mentally in the right place to absorb the more dense or inaccessible information.

Ask answerable questions

An absolutely vital requirement, especially for documents or presentations that are driving towards a particular goal: Ask questions that are answerable. This sounds like an absurd contraint, but the actual absurdity is how often you'll see a giant headline on a slide that asks something like, "How can we do better?" That's a philosophical debate, not a prompt for an organization to make a choice!

One thing I've learned from being a parent is that constraining choice is a great way to get unstuck; unsurprisingly, the same tactic that works on 3-year-olds is very effective in board meetings. Rather than "what do you want for dinner?" (Inevitable answer, "I don't know, what do you want?") you can ask someone "Do you want spaghetti or chicken nuggets?" and even a 3-year-old will suddenly have a much more constructive answer.

Similarly, you'll want to constrain your requests to your audience to be something they can react to constructively. "Do we want to invest at the higher cost of Option A to move faster, or go with the lower cost of Option B to be more cautious?" That's an answerable question! And it's perfectly fine if it leads to a conversation where a third option is explored — but you never would have gotten there with a prompt that says, "What do we want to do next?"

Close by reiterating your mission and goals

You can never go wrong by restating first principles in the closing of your message. Remind people about alignment on purpose, and ideally alignment on values. This sets up for a constructive conversation, and clarifies the priorities that you all share in having a dialogue in the first place. You'll never go wrong thanking your audience or reminding them about past collaborative successes, either.

If your goal is to persuade, this gives your audience psychological permission to believe that you have their best interests in mind, too. If your goal is to make a tough decision, this gives them courage to go forward knowing that you'll be alongside them in their choice. If your goal is to inform, they'll feel more comfortable asking clarifying questions when you remind them that you're sincere in wanting to share your story.

That's it! Good luck making better documents, and just pretend that the underline button in your apps doesn't even exist anymore.

Bonus Update: Name things right!

(Thanks to Waldo Jaquith for the reminder to add this one!)

One of the most important types of information you can share in a document is the title of the document itself. But so often, names are either just default generated titles, or reflect a lack of thought about context for the file.

Like we said to start, you need to start by thinking about the context of your intended audience. What are the words they'll use to search their email to find the file in the future. For example, you don't want to lead with the name (or the company/organization name) of your intended audience most of the time! If you're talking to someone at another company or organization, they'll try to retrieve a document by searching for the name of you or your organization, so include that in the title. If you're all on the same team, include the context of the project or initiative you're working on, and the specific goal you're working toward.

Similarly, you'll want to briefly include the date and a summary of the topic being covered in the document. This advice even extends to meeting invitations — inviting Sam to a meeting called "Meeting with Sam" is only going to create a useless or confusing entry on their calendar. Think through how they'll be referring to the conversation, and name the meeting after that context. Then name the document after the purpose of the meeting.

Finally, for versioning, sequential numbers are almost never sufficient on their own. (And needless to say, appending _final_final to a document is... not going to produce the results you'd hope for.) Pick a naming convention that includes some kind of version context like dates right in the name, and it'll be much easier for your audience to know if they've got the most recent version.