What YOU say about highlighting text in emails

What’s the best way to highlight text in emails? That’s the question I posed in a poll. I took away three main lessons from your responses. Thank you very much, respondents, for answering and generously sharing your email tips!

How to highlight text in emails

Lesson 1. Bold wins for highlightingPoll results for email highlighting

Use bold to emphasize text in your emails. That was by far the most popular answer to my poll asking, “What technique do you use for emphasizing text—for example, an appointment date—in an email?” This squares with my instinct to bold for emphasis, as in the example below:

May I call you on Mon., Feb. 16, at 2 p.m. Eastern?

However, with 45.71% selecting bold, it failed to win a majority. The next most popular answer, at 28.57%, was “More than one of these techniques.” I sometimes use bold plus larger font size or capital letters. You suggested other options, including some that are mainly useful in plain-text emails.

Lesson 2. Text-only email limits your highlighting options

Your poll responses provided a valuable reminder to me. Unlike me, some people force incoming emails into a plain-text format. This strips out fancy formatting—such as bold, italics, and colors—that relies on HTML code. People do this for reasons such as reducing the risk of computer viruses or cutting the email’s size once it’s stored on their computer.

Take note if you have an important correspondent who only reads emails in plain text. You’ll need to adapt your formatting for them.

How can you learn about your correspondent’s email-reading capabilities? If their emails to you look as if they were created on a typewriter, they’re plain text. Also, often when you reply to their emails, you’re not able to apply fancy formatting using HTML.

Some experts suggest that you send emails in both HTML and plain-text formats. But who has the time?

If you send plain-text emails, my poll respondents suggest using asterisks, underscores, or capital letters to highlight text. Here are some of their comments:

  • Unless I know for certain the recipient can read HTML e-mail I’ll use *asterisks* to set off the text. If the recipient is getting the mail in HTML.
  • Most of my email accounts don’t allow for [HTML]. The only thing I can do to bullet something important to place it between asterisks.

I particularly like the idea of using capital letters because they’ll seem less strange and old-fashioned if some of the readers of a group email use HTML.

Lesson 3. Remember other highlighting techniques

I agree with the respondent who said, “I think the more important point is to make sure writers are getting to the point quickly in their email messages. They need to keep the reader’s needs for information in mind and get every message off to a fast start.”

Your comments reminded me of other techniques for highlighting content in your emails, including

  • Strong subject lines, summaries at the top of your emails, and headings, an approach that I emphasize in my presentations on “Writing Effective Emails“—as one respondent said, “I place important information first in the subject line, then there’s no need to emphasize it in the email.”
  • White space to set off important information—as one respondent said, “I often isolate the information on its own line, surrounded by an empty line above and below (this is called using ‘white space’).” Indenting the information can be part of this technique.
  • Good writing techniques in general—as one respondent said, “It may be an old-fashioned notion these days, but I thought that formatting doesn’t always work in email, so I have always tried to use my writing to draw attention. I use very brief sentences, bullets, one line standing alone with a piece of important information, repeat major point again at the end – things like that. Some people use the email’s subject line, i.e., Deadline is tomorrow! I also adhere to the short and sweet method of writing, because people tend to read emails on their phone. So I’ll jump right to point – hey, my deadline is tomorrow.”

A funny HTML story

Here’s a reminder from a respondent that what you see in your email program isn’t always what appears on the recipient’s screen:

I use a Mac and one of my editors uses a PC. She kept putting what looked like little J’s after sentences in her mails to me. I finally asked what those were – turns out, that’s how her smiley emoticons were being interpreted by Mac Mail. (Not sure what she saw with my Mac smileys – I think something weird, too.) I know this isn’t about emphasizing text per se, but it does show some cross-platform problems still exist within email. 🙂

What will YOU do differently now when you write emails?

After reading your poll responses, I may use capital letters more often for emphasis since they appear the same in both HTML and plain-text emails. Is there something you’ll do differently after reading my poll results?


Note: This post was updated on Oct. 31, 2022, to reflect the fact that Constant Contact no longer automatically generates plain text versions of your newsletters.

Propel email conversations forward

Email matters. As communication channels proliferate, email endures. As a result, the better you manage your email conversations, the more smoothly your work and personal lives are likely to proceed.

Reading John Kim’s “Sadly, 20 email tips,” I was struck by his suggestion that email writers should “move the conversation forward.” When I’ve written about email in earlier posts, I didn’t  think about ongoing conversations. Instead, I thought of only one email being sent to one recipient in an exchange that ended after the initial email or one response from the recipient. However, email is often more complex than that, as Kim’s post reminded me. Emails sometimes embroil many recipients in long email threads.

To keep the email conversation moving, try the following tips.

1. Make it clear what you want and from whom

Do you want one or more recipients of your email to do something? Make it clear what you want each person to do and give them a time frame in which to do it.

When you’re writing to only one person, you can put the gist of your request in your subject line. For example, “Please review and reply by AUGUST 1.”

Things become more complicated when you have more than one task and more than one recipient. This is where a summary statement at the top of your email—something that I recommend in most emails—is particularly useful.

For example, you might list the tasks in the order in which they must be done, followed by the names of the people responsible. If multiple tasks are to be done simultaneously by different people, list the people, followed by their responsibilities.

Kim says that he uses the phrase “no action required” for everyone who does not need to act on an email. However, consider whether you can omit those people from the email. I understand that sometimes you need to inform people from whom your email does not require a response.

Moreover, if the mix of people and tasks is complex, consider breaking your message into multiple emails to avoid confusing people. When readers see that large chunks of an email are irrelevant, they tend to stop reading.

2. Help people make decisions

What if you want your email recipients to decide something as a group? Naturally, you can highlight that fact at the top of your email. It also helps to organize the pros and cons, or other considerations in your email. Consider using headings to make your email easy to scan. You might use the headings “Pros” and “Cons.” However, if there are many points to consider, a series of “Pro #1,” “Pro #2,” etc. may work better. On the other hand, a long discussion may belong in a Microsoft Word attachment so you can control its formatting.

3. Rein in diversions

If an email thread is spinning out of control, rein it in. You might ask one person to move a question into a separate email. Or, you might request that the group wait until later to address a specific topic.

Kim says, “If an email thread is ‘spinning’; take the time to super-summarize the situation like meeting minutes with background, situation, decisions needed. This will become a ‘stake in the ground’ that all the people will refer to and prevent more ‘pinging’ of emails back/forth.”

Also, consider picking up the phone to save time, as Kim suggests. I think this can also be easier on participants’ egos when you’re trying to rein them in. Sometimes you should avoid email conversations.

4. Write well, and then edit

Every email will benefit from being written well. Take the time to edit and proofread before you send. Bad writing and typos prevent readers from grasping your message. They also undermine your credibility.

For more on writing good emails, see:

Thanks, Eric, for your help with email conversations!

By the way, I must thank my friend, the writer Eric Menn, for introducing me to John Kim’s blog posts about writing. Eric has been a source of ideas and encouragement since we first met years ago. By the way, he also recommends Kim’s Minto’s Pyramid Principle, which he calls “a great thought piece for writers of all stripes and media! (Except novelists and poets, maybe….)”

Can chronology improve your email?

Bryan Garner’s HBR Guide to Better Business Writing has a great chapter on “Use chronology when giving a factual account.” Bryan Garner: HBR Guide to Better Business Writing

You and your readers benefit whenever you organize your emails using easy-to-follow logic. Chronology is one of the easiest organizational schemes for writers and readers.

Garner suggests “creating a chronology of relevant events before you write, then string the events together in your draft. But avoid the rote recitation of unnecessary dates.” That’s good advice.

Here is an example of such an email that does not go overboard with using dates. I think Garner would like that I use one out-of-chronological-sequence sentence at the beginning to get to the point quickly.

Re: Set next appointment?

Let’s set an appointment next month to discuss your year-end tax planning. Please click here to access my calendar.

At our last appointment we discussed your overall financial planning, including the benefits of year and tax planning. Selling some funds and buying others can help to reduce your taxes while keeping your portfolio appropriately invested across different kinds of Investments.

At our next appointment, we’ll go into the details of your year-end tax planning. We’ll also discuss other timely Issues.

I look forward to seeing you.

Could this chronological approach work for you? My sample may explain too much for some of your clients. I imagine that you can get by with one paragraph for some clients. However, the sample gives you an idea of how the chronological approach works.


Disclosure: If you click on the Amazon link in this post and then buy something, I will receive a small commission. I link only to books in which I find some value for my blog’s readers.


The image in the upper left is courtesy of OpenClipart-Vectors on Pixabay.

Out-of-office auto-reply: vacation necessity?

It’s summertime. Vacations abound, so you’d think that out-of-office auto-reply emails would be just as numerous. Think again. It seems as if they’re on the decline, just like the length of time that we see the sun now that we’ve passed the summer solstice. That’s frustrating for people like me. We could adjust our plans if the vacationers let us know that they’re away. Instead, we’re in limbo.

I’m not alone in my perception that out-of-office messages are less common. My LinkedIn status update on this topic attracted many likes and people saying that they’ve noticed this phenomenon. It also scored more than 2,500 views, which is huge for me.

What’s behind the out-of-office auto-reply’s decline?

I blame the decline of out-of-office messages on the rise of the smartphone. Now that people carry their email everywhere, they think they’ll reply from vacation. They may not plan to reply to every email, but at least to important ones. However, desire seems to collide with vacation-induced inertia—or the judgment that emails like mine aren’t important.

The smartphone may not be the only culprit. One respondent to my LinkedIn update said that some people lack the ability to set up auto-reply messages. Financial technology expert Blane Warrene says,

If someone is anchored to mobile only, it can be tricky handling out-of-office messages. Some accounts do not allow for the Automatic Replies feature in Outlook on mobile, for example, when they are not powered by an Exchange server. A little how-to prep can fix this, though. Even simple POP and IMAP accounts (for example, if you have a GoDaddy domain that also anchors your email accounts in a small business) offer web access to the setting that enables out-of-office responses.

In general, though, most mobile apps do allow for setting up mobile out-of-office settings. This includes iCloud, Gmail (free and professional), as well as the aforementioned browser access.

If this discussion of servers and domains confuses you, you’re not alone. There are people who struggle to follow instructions to set up auto-reply messages. I have one friend who relies on a helper to set up auto-reply messages. Some people may avoid setting up auto-replies because they don’t know how to create them.

Another potential culprit: the explosion of spam. Graphic designer Karen Coleman said in response to my LinkedIn update, “I don’t like auto-responders going from my email account. I don’t want it going to spam bots so they know the email is active.” She’s afraid she would receive even more junk emails if she used auto-reply messages.

Self-employed people are especially likely to worry that an out-of-office message alerts thieves to their absence. No one wants to advertise, “Hey, come break in!”

When do you need an out-of-office auto-reply strategy?

I don’t believe that you need to turn on your out-of-office message when you’re out of the office for only one day. But if you’re out for an entire week, it’s polite—and good for business—to let people know that you won’t be reading or responding to email.

Warrene agrees, saying, “I have found through years of both corporate work and starting and operating businesses, that the out-of-office message is woefully underused.”

Put some thought into your message. Sue Hershkowitz-Coore, author of Power Sales Writing, says:

With the expectation of an immediate reply, an out-of-office auto-reply can be quite helpful. The challenge is the message needs to be more than “Thanks for your message, I’m not here.” Beyond explaining when to expect a reply and an alternate contact, if available, it must also be on-brand. This is key to engagement.

A good out-of-office message will improve the quality of your time away from your email. Warrene says, “The out-of-office message can be used artfully (with well written and useful directions for correspondents) so blocked time can be used efficiently when on the road for business or pleasure.”

If you can’t or won’t respond to email from vacation, then set up a workaround. For example, you could ask a colleague to monitor your email. If you’re a solopreneur, you hire a virtual assistant to check email for you, as Coleman suggested in her LinkedIn reply to me. This gets around the concern that an out-of-office message will alert thieves that their homes are ready to be robbed.


Writing an email help request that gets results

“I NEED HELP!” This line will get your email recipient’s attention. But email help requests that sound this desperate won’t get the results you seek. Nor will requests that are too subtle. Strike a balance to achieve the best results.

Let me illustrate what works—and what doesn’t—with a before-and-after example of a financial professional’s email request for help. Imagine that you’re a financial blogger asking respected experts to contribute to an article, and you need their responses by a specific date. How would you tackle it? The writer of “Email help request 1” makes mistakes.

Email help request 1

Here’s “Email help request 1”

Re: article on my blog

Hi Charlie,

I am writing the latest article for my blog, which I update weekly. I think it would be great if you could contribute something to my blog. My readers are interested in saving for retirement and you write a lot of articles about retirement. Your good name could help me get better known in this space. Could you send me your opinions on what works in terms of rolling over a traditional IRA into a Roth IRA? It would be great if you could reply by the second week in March.

Compared with “Email help request 1,” the author of the next email writes in a way that’s easier for the recipient to understand.

Email help request 2

Re: Answer Roth IRA question by March 6?

Hi Charlie,

Our mutual friend, Janet Brown suggested, I contact you because she thinks you would be a great expert to contribute to my blog. Also, she experienced a boost in her e-newsletter subscribers after contributing to my blog last month.

By Tuesday, March 7, could you briefly answer my question about Roth IRAs, so I can incorporate your answer into a blog post? Here’s my question: How does an individual’s number of years until expected retirement affect the attractiveness of rolling a traditional IRA into a Roth IRA? After I compile my blog post, I will check to make sure that I’ve presented your views accurately.

My blog receives 5,000 views monthly, and my target audience of dog-owners in their 50s and 60s for my financial planning business seems to overlap with your target as a consultant. I’d be happy to link to your website and feature your photo in my blog.

Please let me know if you have any questions. I’ll call you next week if I don’t hear from you.

What makes an email help request effective?

I believe the second email request will be more effective than the first.

Why will the second email work better?

  1. The subject line clearly identifies the reason for the email.
  2. The first paragraph establishes a relationship between the writer and the recipient, by referring to their mutual friend.
  3. The second paragraph says exactly what the writer is seeking, including the deadline for a reply.
  4. The third paragraph (and the end of the first paragraph) suggests how the recipient may benefit from responding to the writer’s request. This contrasts with the first email that is mostly about the sender
  5. Breaking the email into paragraphs makes it easier for the recipient to absorb the information.
  6. The promise—threat?—of a follow-up may spur the recipient to reply, even if it’s just to say “No, thanks.”

The first email is too self-centered and makes the reader work too hard to figure out what the writer wants.


If you enjoyed this post, you may also enjoy “Top four email mistakes to avoid when you have a referral.”

Image courtesy of Keerati at FreeDigitalPhotos.net.

Personalized subject lines can backfire in emails

A good personalized subject line can boost your results. But mess up the personalization, and you’ll lose.

Characteristics of good personalized subject lines

It’s great to tweak your email subject line to appeal to a specific recipient. For example, if you know the recipient’s hot button, include it in the subject line.

Another approach is to name the person or their organization in your subject line. There’s some data to support this approach. For example, “Including the recipient’s name in the email subject line increased open rates–some by as much as 42%,” according to Experian data cited in “How Pairing Personalization & Automation Can Skyrocket Email Conversions” on the Kissmetrics blog. I assume there’s a similar effect when you personalize other information in the subject line.

But you need to proofread carefully so you don’t personalize for the wrong recipient. A bad subject line (and email body) can send your email to spam. A badly personalized subject line can doom your email to head into your target readers’ spam folders. That’s true even if your email is relevant to the recipients.

Example of badly personalized subject line

Today’s blog post is inspired by an email that was sent to me in my role as the editor of the NAPFA Advisor magazine. I found it when reviewing my spam folder. The subject line read “Idea for timely content/article for ZZZ Magazine.” The subject line said “ZZZ Magazine” where it should have said “NAPFA Advisor.” I don’t know if that’s why the message went into spam. But the wrong name in the subject line didn’t inspire me to click through on the email.

Putting the wrong name in the subject line puts you on the quick path to an email trash folder.

How to avoid mistakes in your personalized subject line

Proofread, proofread, proofread. That’s the best way to avoid mistakes in your personalized subject line.

Another possibility is to automate the inclusion of personalized information in your subject line. Some email programs allow you to do that in a twist on the mail merges you may know from word processing.

Contrary view on personalized subject lines

Although I argue for personalization in this post, the evidence is mixed on adding the recipient’s first name to your email subject line.

In its FAQ on “How do I personalize the subject line (or content) of my email?“, Benchmark Email says it “does not advocate adding a contact’s first name in the subject line of your emails. Doing so may lead to an increase of spam complaints, as spammers are known for using personal data in the subject line of emails.”

A MailChimp blog post says that subject lines using first names performed worse than those without first names. The blog suggests that names take up space without adding value,  according to “Personalizing Subject Lines – Does It Help Or Hurt Open Rates?” The post appeared in 2008, so it’s possible that things have changed since then.

What’s my take on this debate? Rote personalization—like simply adding the recipient’s name to the subject line—may not work. Personalization that truly appeals to the individual’s interests is powerful. I would have responded differently to an email that correctly named my magazine in its subject line.

Image courtesy of pakorn at FreeDigitalPhotos.net.

Financial Blogging class registration ends Feb. 24, 2017.

Quit sending press releases as attachments!

Is your goal to get your press releases deleted from the recipients’ email inboxes as quickly as possible? Then continue sending press releases as attachments to your emails. Oh, and here’s another helpful tip: don’t hint at the content of your press release in the body of your email. The body of your email should consist simply of “Here’s your press release for this week.”

If you think my first paragraph is sarcastic, you are right. I do not recommend sending press releases as attachments.

Why sending press releases as attachments is wrong

It is annoying to receive press release emails—indeed, any email—that refer you to an attachment for a reason to learn about the sender’s news. When you send press releases only as attachments, you’re making me 1) take an extra step to find the information I need and 2) expose myself to the risk of viruses in the attachment.

My attention span, like that of most email readers, isn’t very long. “Our initial data indicate that, on average, readers are spending 15-20 seconds on each email they open,” said Loren McDonald, EmailLabs VP Marketing in “Alarming Research Results: Average Email Open Time is 15-20 Seconds — Recommendations for Emailers.” That article appeared on MarketingSherpa back in 2005. I imagine that readers’ attention spans have only shrunk since then.

Improve the odds of my reading your press release

If I must click to open your press release sent as an attachment, you’re demanding too much of my time. At a minimum, you should insert some teaser copy in your email that gives me an incentive to click.

However, even better would be to drop the body of your press release into the body of your email.

Concerned that you’ll lose valuable formatting by dropping your text into email? Then use newsletter software such as MailChimp or Constant Contact to increase your control over the appearance of your release.

Email inbox efficiency–can you go too far?

Email productivity is a goal of most people whom I know. We all receive and send too many emails.deep work carl newport book cover

But how far are you willing to go to trim the amount of time you spend on email? It’s the rare person who’ll go as far as Cal Newport recommends in Deep Work: Rules for Focused Success in a Distracted World.

Deep Work rule for email productivity

Newport suggests that you boost your email productivity with the following rule:

Do not reply to an e-mail message if any of the following applies:

  • It’s ambiguous or otherwise makes it hard for you to generate a reasonable response.
  • It’s not a question or proposal that interests you.
  • Nothing really good would happen if you did respond and nothing really bad would happen if you didn’t.

He admits there are exceptions to his rules. For example,  he says you should reply “If an ambiguous message about a project you don’t care about comes from your company’s CEO.”

Could YOU apply this Deep Work email rule?

I can see how Newport’s rule boosts his email efficiency. I could dramatically cut my email volume if I ignored ambiguous emails. But I can’t envision myself applying Newport’s rule often. I need to respond to clients and prospects.

Your ability to apply this rule at work depends on your relative status and role in the company. If you’re a company’s top dog, you have more leeway than a lower-level person who’s serving clients.

Still, perhaps you can alter your behavior on the margin. I like how Newport’s book makes me question my assumptions about my daily work routines.


Disclosure: If you click on the Amazon link in this post and then buy something, I may receive a small commission. I only link to books in which I find some value for my blog’s readers.

Email productivity booster for investment and wealth management

Whether you’re an investment or wealth manager—or a professional or vendor who supports them—you can probably benefit from an email productivity booster. Take advantage of Microsoft Outlook’s “signature” feature to summon up basic email templates at the click of a button. I imagine that other email programs may offer a similar feature.

Writing emails from scratch is a productivity killer

email productivityIf you’re like most of us, you have emails that you send repeatedly, with minimal variations. Maybe it’s a prospecting email. Or a new-client welcome email. Or an email asking if you can update the recipient’s contact information.

You shouldn’t start from scratch every time you write an email. You waste time repeating steps that you’ve already gone through many times before. Sure, you can save templates in your word-processing software, but it’s even more efficient to use one of Microsoft Outlook’s underappreciated features, the signature.

Email productivity booster: Microsoft Outlook’s signature feature

Did you know that you can save an entire model letter in Microsoft Outlook as a so-called “signature”? Most people use Outlook’s signature feature to insert classic signature information, such as your name, contact information, and other promotional information details that go under where you sign off with your name. But, as I learned from organizer Lorena Prime, you can use the Outlook signature for much more.

As you’ll see in the image below, I turned an entire email into an Outlook signature.

Outlook signature for webinar



After loading an email as an Outlook signature, it’s easy to customize and send.

insert signature in Microsoft Outlook to boost email productivity

Go to the Insert tab, then click on Signature to view a drop-down menu of the signatures you’ve previously saved.

I simply go to Outlook’s Insert tab, click on Signature, and then select by title the text that I want to use. After filling in my “To” and “Subject” lines, and adding a greeting, I’m ready to hit “Send.”

This is way faster and easier than writing an email from scratch. It’s even easier than copy-pasting from a Word file because I’d probably forget where I saved the dratted model email.

Here’s what Microsoft says about creating signatures in Outlook 2013, 2016, or 2019.

YOUR email productivity booster ideas?

If you have ideas for boosting email productivity, please share them.

Of course, sometimes the best productivity booster is to keep your email closed and pick up the phone for a quick solution to a pressing problem.

Image courtesy of ddpavumba/FreeDigitalPhotos.net


NOTE: I made some minor editorial tweaks on Dec. 30, 2019.

Email and the mystery of the missing agreement

“Where’s my contract?” A friend’s question about his missing contract inspired this post about the value of structuring your emails properly. The email’s details have been changed in my account. I don’t believe in embarrassing people, especially since I’ve made so many mistakes myself.

Client email problem

emailThe problem started when my friend sent a polite, friendly email with the terms of his agreement with his new client. They’d discussed the terms in a friendly telephone conversation, so he didn’t expect any problems. But a week passed with no follow-up communication from the new client. What went wrong?

I immediately suspected a problem that I’ve encountered in financial advisor emails that I’ve reviewed as part of the research for my presentation on “Writing Effective Emails.” The email was too polite and friendly.

Here’s how I imagine the email might have started:

It was so nice speaking with you today. I look forward to working with you on X, Y, and Z.

It’s a great idea to summarize your conversation with the client in your email. However, email readers tend to focus most on the beginning of an email. My friend’s recipient may never have reached the part of the newsletter where he asked her to reply with an email confirming that she accepted his terms.

In other words, the email didn’t make it easy for the reader to grasp what action was required.

Client email solution

Two changes could have boosted the likelihood that my friend would receive the response he desired.

  1. Put the desired action in the subject line. For example, “OK? Terms for our project.”
  2. Request the desired action at the top of your email. For example, “Please confirm your agreement to the terms by DATE1 so I can begin work by DATE2.”

This kind of email makes it easy for the recipient to understand what you want from him or her. You’re showing respect for the person’s time by clearly specifying the next step.

This kind of action-oriented email may seem cold to you. But it gets results. Also, you can drop the warm and fuzzy content into your email in a less prominent position. You don’t have to come across like a robot when you write action-oriented emails.

My client email confession

I confess that I sometimes put a positive sentiment, such as “Thank you” at the top of my action-oriented emails. I also soften my demands by writing something like “When you get a chance, please confirm receipt of my invoice.”

However, I try to balance that by naming an action in my email subject line.


Whether you’re all business or incorporate some niceness, please write in a way that highlights the next step that your email recipients should take. You’ll make their lives easier and you’ll get more of the results that you desire.

Image courtesy of Stuart Miles/FreeDigitalPhotos.net