BY DANIEL BLACK

It’s a controversial topic, but in the world of the Send Later feature in Outlook, I’m against it.

Send Later allows you to delay sending your email messages until a date and time you choose (other platforms, such as Gmail and Slack, offer similar delayed send options). In a LinkedIn poll we conducted recently, we found that use of the Send Later feature varied:

More than 80 people responded to our poll. I’ve also received numerous texts and emails and had several lively discussions on the subject. Reactions to the Send Later feature vary widely. I’ll admit it myself: the first time I was offered the option to delay sending an email, I panicked. “Send later?” No? Yes? Maybe? Definitely no. I wrote the email now, I’d like it sent now.

But… what if now isn’t a good time for my recipient? I can think of reasons why they don’t want or need to receive my email now: they’re asleep; or awake but not working; or awake and already dealing with a work crisis. You get the idea. 

I can also think of reasons why delayed send is useful in helping the sender keep up with work without burdening colleagues with their off-hours pings: the sender may be a parent juggling kids and work; they may work a nontraditional schedule; they may be a busy professional who is catching up on work but doesn’t want to set a precedent for late-night work; they may be on a business trip in a different time zone; and the list goes on. These are all compelling reasons. Sort of.

Protecting the Recipient or Punishing the Sender?

When it comes to using delayed send, I’m generally against it. It’s not that I want everyone to work 24/7. In fact, it’s just the opposite. I recognize, now more than ever, that people are optimizing their work–life balance.

Case in point: I’m finishing this blog post late on a Sunday night because Monday morning I’ll be at my daughter’s school for a program on social emotional learning. If there’s a world where I can both engage with my kids and be dedicated to my work, count me in. The pandemic redefined how, where, when, and even why we work. How can we say we’re acknowledging different work schedules but then confine our email communications to outdated work hours?

Two close friends of mine—both highly accomplished professionals and parents—use delayed send because they work “odd hours.” Exactly. Why are we making them feel like they’re the ones doing it incorrectly? Their hard work is commendable. Their colleagues may notice their “gaps” during traditional work hours, but shouldn’t their colleagues also see their “catch-up” hours? Both friends are moms, and their “odd hours” refrain is common among working women. If they’re working on Saturday morning and that’s part of their gig, and a colleague sent an email on Friday night, wouldn’t that help them be productive? (For the record, neither of them was complaining—I’m the one upset by it.)

When in Doubt, Just Hit Send

Most see delayed send as a helpful tool to manage work–life balance. They’re not wrong. For instance, workaholics can be intimidating or overwhelming, and if they’re in a leadership role, sending emails at night or on the weekend can set a work ethic precedent that isn’t for everyone. Or perhaps the sender is emailing a new contact; maybe they shouldn’t send the message at 10 p.m., and instead should send it during traditional work hours. Some also see delayed send as a way to avoid sending a message they’ll regret: sometimes some of the best emails are the ones we don’t send—or we send after walking away and then coming back to edit further.

As a communications professional, with some of these nuances aside, I see it differently: we’re thinking too much. What are we doing when we schedule the email to be sent later? We’re thinking for our recipient. And that’s bad. Only my recipient can be responsible for setting healthy, productive work–life boundaries. We can’t, and shouldn’t, babysit one another, nor do we know what our recipients’ schedules look like.

Stop (Over)Thinking for Your Audiences

The issue of thinking for our email recipients doesn’t just apply to how we communicate with other people. It also applies to the world of marketing and how brands communicate with their audiences.

Stop me if you’ve heard this one before: “Do you think our prospect will want to go straight from the email to the live demo with our sales rep, or to a case study highlighting our success with a similar organization?” And the debate ensues. 

It’s not our job—in fact, it would be an impossible job—to predict how every person wants to interact with a business. It’s different for everyone. It is our job to give as many touch points, routes, and options as feasible. Offer up the case study and the live demo, and a few other choices as well. Sure, some marketers worry that “we’ll overwhelm them with too many choices.” Perhaps. But we might be shooting ourselves in the foot if we give one option and it’s the wrong one. Call me crazy, but I think people are smart enough to know what they want.

This logic applies to so many, perhaps all, areas of marketing. Email. Social media. Content. Websites. The answer isn’t one option or the other, it’s both. It’s the “yes, and …” approach. How many emails should we send? Which call to action will be most effective? Should we post on Tuesday and Thursday or Monday and Wednesday? Which blog topic do we think is most interesting?

For sure, there’s some strategy to the timing and frequency of marketing touch points. But don’t overthink it. Here’s some advice:

• Adopt a more-is-better mindset to content, materials, and engagement.

• Communicate early and often; repeat and repost.

• Encourage audiences to indicate when, where, how, why, and on what platform they want to engage with your brand.

• Offer multiple on-ramps to connect with your business.

• Let your audiences customize how they interact and do business with your company.

• And as we’ve stressed before, if you’re not sure (and let’s be honest, we’re often not sure), then be sure to test, test, and test until you are.

Think of your audiences as traveling from point A to point B. Are they flying or driving? Taking the scenic route or prioritizing speed? How they get there should be up to them. It is your job to show them the route and provide the necessary support and infrastructure along the way.

The next time you’re about to make an important decision, think to yourself: Do I know what is going on in the lives of my target audiences? Can I accurately predict what they’re thinking and doing and what they want from my company? If not, and that’s likely the case, pick a path that optimizes for options. Give your audiences the flexibility to engage in whatever way they want.