Outlook tips

How do I track changes in an Outlook email?

May 7, 2024


Daniel Yim

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Why track changes in draft emails?

Before looking at how to track changes in draft emails, it’s worth clarifying what we’re trying to achieve.

The most common reason lawyers want to track changes in draft emails is for internal feedback and learning purposes.

Think about the typical email drafting workflow in a law firm. Somebody will prepare a first draft, and then send it to a more senior team member for review. That reviewer will probably want to make some changes, but they will also want to make sure the original drafter understands and learns why those changes are being made. After all, the legal profession is all about mentorship and developing your lawyers so they can be more effective going forward. In fact where there’s a large team working on a matter, it’s not uncommon for important emails to be reviewed and edited by 4 or 5 different team members before being sent out. Each of those points of review is a learning opportunity.

If all that mattered was getting the work done, it wouldn’t be important to track changes on draft emails. But that’s not the case. Mentorship matters. Learning matters.

Manually formatting your edits

Many people will know the manual method of tracking changes on draft emails. This involves manually selecting whatever text you have just edited, and then styling it to make it highlighted, underlined, blue, strike-through or whatever else so it’s apparent to others what you’ve changed.

While this method is familiar, it’s incredibly tedious. Yet people still do it, because they care enough about developing their team that they’re willing to spend their own time painfully formatting each change.

Other problems with the manual process include:

  • it doesn’t align with the normal way people edit emails, which is not to make changes from start to finish like a robot, but rather play around with the wording and re-edit and revise their own changes;
  • it’s not suitable if the person making the edits wants to send the email out themselves (and therefore it has to be in clean), rather than back to the original drafter;
  • the original drafter needs to tidy up all the formatting before sending the email out, so there’s a risk they will miss something and make the firm look unprofessional; and
  • if you are editing on your phone, it’s simply not feasible.

Work on the email in Word, and then copy and paste into Outlook once finalised

MS Word obviously has a track changes feature built in, so it’s certainly possible to prepare draft emails in Word and have people markup their changes there rather than in Outlook. Once the text of the email is finalised, it can be copied and pasted into Outlook.

While this workflow might sound ok in theory, it’s difficult to make work in practice. This is because:

  • it adds more things for lawyers to do. They now need to open another window, save the edited Word document, and attach it to a reply email;
  • if there’s anything in the email chain that’s important, that probably won’t be visible in the Word document;
  • it’s unworkable if people are reviewing and editing draft emails on their phones; and
  • people want to know how their email will look to the ultimate recipient, not how it will look if it was sent as a Word document.

Print the email, and get out the red pen

Printing a draft email and marking it up by hand is the tried and tested method of many old school practitioners. If this works for you, that’s absolutely fine. And there is some merit in the idea that making people copy type the corrections themselves aids in the learning process.

Given increasing numbers of lawyers now prefer making edits by typing rather than handwriting however, this method is dying out. It’s also difficult when:

  • you’re not in the office and don’t have access to a printer; or
  • your team members are not in the same physical location - you’ll then need to scan the hand markup and email it, adding more steps to the process.

On top of that, this workflow produces another physical document to clutter your desk, you have to worry about making sure the printout is securely destroyed, and it’s not nice to trees.

Use Sideline

The easiest way to track changes in draft emails is by using the Sideline Outlook Add-in. Sideline allows lawyers to make their edits in clean, and then choose whether they:

  • send the email as is (with the edits in clean) back to the original drafter or out somebody else. When the original drafter receives the edited email (either as the direct recipient or cc’ed in), they can click one button in Sideline to automatically see a redline; or
  • select the edited paragraphs and click one button in Sideline to automatically style the text as tracked changes (blue/underline and red/strike-through). When the original drafter receives the edited email, they can use the accept and reject features in Sideline to finalise the email.

Sideline doesn’t require anyone to change their workflow. You don’t need to open a new window, you don’t need a new username or password, and you don’t even need to sign-in (well, technically you do, but it’s all taken care of in the background through SSO).

Best of all, busy senior practitioners don’t need to press any extra buttons. They can simply make their changes in clean and send. If they’re used to manually formatting each of their edits, they no longer need to do that. If this sounds good, please get in touch today.

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