If you’re anything like us, you’re constantly sending attachments to co-workers and clients — sometimes tons of ‘em. Sometimes tons of ‘em in a single email!

Let’s say you’re an account executive. You might be attaching important marketing collateral like product intro decks and case studies; if you’re in advertising, you might be attaching important campaign information and ad performance data; if you’re an operations leader, maybe you’re attaching important documents to resolve cultural challenges. All these functions are critically important to business continuity and organizational success, but you’re never going to get there if you’re stuck hunting for files and sending them all piecemeal.

Luckily, sending multiple attachments at one time isn’t rocket science. Gmail — an industry-standard platform for business email — makes sending attachments a relatively straightforward exercise:

  • Click “Compose”
  • At the bottom of the pop-up message box, click the paper clip “Attach files” icon
  • Select the files you’d like to attach
  • Click “Open”

Don’t want to click through folder after folder to find the attachments you need, though? Don’t worry — we’ve got you. Teamstand offers a better way by providing the files you need in a collapsible side panel within Gmail. Also, Teamstand lets you send multiple email attachments faster with multi-select to attach them all at once. For example, if you have four or five files you typically send to a lead at a certain point in your sales cycle, you can easily find and attach all those files at once, instead of having to pick them one by one and without having to download and upload them.

But what if you mess up? Hey, it happens. Using either Gmail’s file picker or Teamstand, if you attach the wrong file or decide that you don’t want to send an attachment, clicking the “x” at the end of the file name will remove it from your email.

And what if you're sending sensitive information? Gmail also allows you to send attachments with its more secure confidential mode. Keep in mind, though, this option is only available on work and school accounts, and it must be switched on by an admin. To use confidential mode, attach all your files and then:

  • Click “Turn on confidential mode,” located at the bottom-right of the pop-up message window
  • Enter an expiration date and passcode
  • If you select “No SMS passcode,” those using the Gmail app can directly open the email
  • If you select “SMS passcode,” a passcode will get texted to the phone number that you enter
  • Click “Save”

Avoid Looking Suspicious When Sending Multiple Email Attachments

Oftentimes email attachments are associated with phishing and other types of scams. If you’re emailing a teammate, you probably don’t have to worry about looking like a scammer. However, if you’re cold-emailing someone, you should take steps to make your email look more trustworthy.

If at all possible, you should try to avoid sending attachments with cold emails. In addition to triggering the Spidey Sense of some prospects, you’re also being a bit presumptuous. Cold emails are about starting a conversation, not closing a sale. Start by dipping a toe in the water with a friendly text-only email.

If you get a warmer response to your cold email, go ahead and hit them with that one-pager. In situations where you absolutely need to send an attachment with a cold email, try to sound as natural as possible in the body of your email. It’s also a good idea to describe any attachments you're sending so your recipient knows what they’re getting.

Best Practices for Sending Multiple Attachments in One Email

You might not consider the unwritten rules governing emails and attachments, but if you don’t know these socially agreed upon guidelines, you run the risk of annoying your recipients or even embarrassing yourself professionally. Don’t know if you’re stepping on anyone's digital toes? Not to worry — we’re here to help. 

Be sure to review the file you are going to attach before attaching them. If you’re working with multiple versions of a file, it's very easy to pass along the wrong version, possibly one that contains information you don't want your receiver to see. Also, make sure your file is in a common format that works for Windows, Mac, Android, and iOS.

For larger email attachments, check to make sure they don't exceed the size limit for your platform, which is 25 MB in Gmail. If your file is too big, you could send it as a link to a file stored in Google Drive.

This next tip should probably go without saying, but we're going to say it anyway: make sure you attach your file first before writing the body of your message. Admit it, you’ve sent multiple emails without their attachments and it's a bit embarrassing to have to send that second, sheepish follow-up email. Save yourself the face-palming and attach the file first.

It's also a good idea to mention the attachment in the body of your email to let your recipient know to look for it and to signal that your email is legit and not a phishing attempt.

Use Email More Effectively With Teamstand

You probably spend a ton of time composing emails and hunting down the files that need to be attached to them, right? Why not simplify the process by using Teamstand? 

Available as a Chrome extension, Teamstand automates the organization of files in Gmail, Google Drive and Slack to make it easier to find key files. Our app presents your important files in a collapsible panel within Gmail, bringing critical assets to where you’re already working. And like all the best apps, it’s intuitive and simple. Contact us today to get free access to Teamstand’s automated digital filing finding cabinet.

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