Redlines might be part and parcel of your day job, but let’s face it – not all mark-ups are created equal.

We’ve all been on the receiving end of a PDF with unintelligible edits, or an inbox full of ‘one last change’ emails long after we thought the deal was done. Redlining might seem like a purely technical exercise, but it’s often where your professionalism, commerciality and empathy really shine through. Get it right, and you’ll make life easier for everyone involved. Get it wrong, and you risk slowing the deal, souring relationships, and setting off a painful chain of back-and-forths.

So here’s our take on the redlining rules every in-house lawyer should know – but that no one really talks about.

1. Don’t send redlines as PDFs

We’ll start with the obvious (but still somehow necessary): don’t send mark-ups in PDF format. It’s the legal equivalent of speaking to someone with a mouthful of marshmallows – clunky, unclear and frustrating. Redlines are meant to be collaborative. If you freeze your comments in a PDF, you’re putting all the onus on the other side to decipher, recreate and respond.

Stick to track changes in Word – and use them well. That means clear comments, consistent formatting, and a version history that doesn’t make anyone weep.

2. Don’t drip-feed your changes

You’ve reviewed the contract, you’ve shared your comments – and then… a second batch. And a third. Maybe even a few “just spotted this” stragglers on Friday at 5pm. Sound familiar?

The more you drip-feed, the more friction you create. It’s inefficient, confusing, and risks eroding trust – especially if the other side starts to feel like there’s no clear end in sight. It also opens the door to version control chaos.

Take the time to consolidate your review internally before hitting send. If others need to weigh in, wait until all input is collated so you can share a single, cohesive mark-up. It’s a small act that makes a big difference.

3. Don’t reopen agreed points without good reason

Redlines aren’t a free-for-all. If something’s already been discussed, agreed and closed out, treat it as sacred ground – unless there’s a genuine commercial or legal reason to reopen. Rehashing previously settled points not only undermines goodwill, but also signals disorganisation or internal misalignment.

Of course, sometimes a new risk comes to light. But if you do need to revisit something, flag it explicitly, explain why, and take ownership of the late-stage change. It’s all about how you handle it.

4. Don’t redline for the sake of it

Tempting though it is to tweak that comma or reword that clause to sound more like “your style”, ask yourself: does it actually matter?

There’s a time and place for house style, but mark-ups should be meaningful. Unnecessary changes slow down the deal and make it harder for the other side to spot what really matters to you. Pick your battles – and let the rest go.

5. Don’t forget the human on the other side

It’s easy to fall into transactional mode when redlining – but there’s always a human at the other end. A well-drafted mark-up can build trust, show your commercial nous, and set the tone for a collaborative relationship. A clunky, pedantic or aggressive one? Not so much.

So be clear. Be fair. Be human. And don’t forget to include a short cover note when sending the redline, outlining key themes or potential sticking points – it’s a small touch that builds massive goodwill.

6. Do agree a process up front

One way to avoid most redlining headaches? Agree how you’ll handle edits from the outset. That might mean:

• aligning on who’s leading the mark-up
• setting expectations around response times
• agreeing a clean way to resolve points of principle

It doesn’t need to be formal – but a quick conversation can prevent weeks of pain down the line.

Let’s raise the bar on redlining

As in-house lawyers, we know redlines are more than just technical edits – they’re how we show up in a negotiation. They’re a window into our thinking, our priorities, and our approach to collaboration.

So next time you’re tempted to fire off a PDF or lob in a few last-minute tweaks, pause. A little redline etiquette goes a long way – and your counterpart (and future self) will thank you for it.