Exhibit A: Can the instant-messaging app Slack worm its way into the legal world?

Just as email replaced letter writing, Slack, an instant-messaging app for the workplace, is threatening to wipe out email. The proof is in the numbers. The three-year-old startup is valued at $3.8 billion — as of this April — and boasts nearly three million users. It’s one of the tech world’s prize pigs. But what’s most impressive is that Slack is moving into traditionally tech-resistant territory: law.

“We get so many emails every day,” says Andrew Cooley, an associate at SkyLaw in Toronto, a boutique corporate firm that uses Slack. “For quick internal updates and questions, it’s faster to send each other messages over Slack.”

The firm has also Slackembraced one of Slack’s most popular features: group chats organized by topic, called “channels.” Rather than relying on long email threads, the firm sorts internal chatter into its own unique channels. Popular ones include #blogideas, #lunchplans and #economistwisdom, where they share interesting tidbits they read in the Economist.

But channels can be for more than just chit-chat. At Momentum Law, a boutique business firm in Ottawa, lawyers place entire agreements and resolutions into channels, to solicit feedback from colleagues. “Different people can chime in simultaneously,” says Megan Cornell, the founder of the firm. “And while writing and sending emails takes time, Slack is an informal, ongoing conversation, so it speeds things up.”

Slack is useless, however, without buy-in from the whole team. “If only the most junior lawyers use Slack, it might become a place for griping about the office,” says Cornell. “But if senior lawyers join, it becomes a great tool.”

Getting that buy-in can be tough. Just ask James Brink, a partner at Ormston List Frawley LLP, a small corporate firm in Toronto. When he suggested using Slack, about a year ago, nearly half of the firm’s 12 lawyers agreed to give it a try. Now it’s just him and a junior associate. “It comes down to inertia,” says Brink. “People are used to email and it requires a real mental shift to jump to something else.”

There’s another reason some lawyers are wary: privacy concerns. Slack offers free and paid subscriptions, but none of them include protection in the event of a data breach. The company may offer more security features down the line, but when asked to comment for this story, a Slack spokesperson would only say, in an email, “We are committed to constantly improving our features to make sure teams of all sizes can collaborate.”

Though Brink is a fan of Slack, he dislikes the self-help style of customer service that relies on FAQs. Having a live customer-service rep on the phone, he says, is helpful “so you have someone to yell at when the partner is yelling at you because he can’t find his document.”

This story is from our Winter 2016 issue.




Illustration by Alina Skyson

Trial & Error: How to write the perfect email

In my last column, I tackled a subject lawyers are all too familiar with: email, and when to use it instead of in-person meetings or talking on the phone. Sometimes, I concluded, email is the best choice. And for those times, here are six tips for drafting the “perfect” email. (Shout out to Bindu Cudjoe, the deputy general counsel and chief administrative officer at BMO Financial Group, who helped develop this list.)

1. Be careful about who is in the “to” and “copy” address lines

Most people receive hundreds of emails every day. So try not to unnecessarily load up someone’s inbox. Also, to ensure everyone receives the email, make sure there is no “auto-fill” error.

2. Cater your salutations to the recipient of each email

I use email for all kinds of matters, so I use salutations to convey the level of formality in the communication. I start my informal emails with “Hi” and I sign off with my name or, simply, “Cheers.” For formal emails, to clients and co-workers, I address recipients by their name only. I address them by their first name if I’ve met them before, and “Mr./Ms.” followed by their last name for everyone else. I sign off formal emails with “Regards” or “Best.”

3. Always include your contact information in your e-mail

Quite often, when you send an email, the recipient will want to phone you. Make your phone number east to find. Not doing so is one of Bindu’s pet peeves — and it likely is for several of your clients and co-workers, too.

4. Have a clear, detailed subject line

I typically send and receive a couple hundred emails a day, so clear subject lines help me locate the emails I want when dashing between meetings. In each subject line, I include the name of the matter or file, followed by the specific item or task under discussion. If appropriate, I add what our next step should be. For example, in a transactional context, a good subject would look like: “Acme Inc. Deal – Prospectus – MT Comments.” In litigation, a good subject line would be: “Jane ats Joe – Discoveries – Please Hold Jan 1, 2015.”

5. Put new thoughts in a new e-mail

All good e-mail threads must come to an end and new thoughts require a new thread. This is important for many reasons: it makes it easier to forward emails without the baggage of old threads, and for the litigators in the audience, creating a clean motion record.

6. Make your email easy to read

Consider that most people read emails on mobile devices. Bold, highlight, and underline key passages or phrases to draw the reader to your most salient points.

Do you have any other suggestions for e-mail? If so, please share with me on Twitter at @atrishalewis.

Atrisha Lewis is a third-year associate in McCarthy Tétrault’s litigation group. Follow her on Twitter: @atrishalewisAnd also check out all of her past columns.

Trial & Error: Email etiquette for lawyers

Every day, I send and receive at least a couple hundred emails. Yet we, as a profession, rarely step back and consider how we use email — and how we can use it better. And so, I’ve put together what I call “The Lawyer’s Code of Conduct for Email” — drawing on my working experiences and those of Bindu Cudjoe, the deputy general counsel and chief administrative officer at BMO Financial Group. What follows is the first half of my two-part guide, which offers three tips on how to maintain proper email decorum.

1. Use email for scheduling, not decision-making

There are basically three ways to communicate with someone: in-person, on the phone and via email. When I spoke to Bindu, she said email is best used as a scheduling tool — to set up meetings and longer calls — rather than for detailed discussions or making substantial decisions. You can use email to record those decisions and suggest next steps, but when you want to go in-depth, hop on the phone.

2. Respond to clients promptly, even if you can’t answer their questions

Clients demand timeliness. So when they email me, I respond in a couple of hours, or within 12 hours if they email outside of business hours. If I need more time to consider the request, my response might be as simple as “Will do” or “Will get back to you.” And if I know I’ll be away from my email, I always set up an out-of-office alert that tells the sender when to expect a response. The point is: clients should never be kept out of the loop, wondering when you will get back to them.

3. Stop sending emails at 4 a.m.

Okay, I’m as guilty as anyone of sending emails whenever the impulse strikes. But, when working late, unless the recipient needs the information right away, wait until the next day to hit “send.” In Microsoft Office, use the “delay send” feature so the email arrives at more appropriate time — say, 9 a.m. the next morning. I often schedule emails to arrive when I know the recipient starts his or her workday (that’s 7:30 a.m. for known early-risers). That way, my messages are less likely to sink to the bottom of their inboxes.

Atrisha Lewis is a second-year associate in McCarthy Tétrault’s litigation group. Follow her on Twitter: @atrishalewisAnd also check out all of her past columns.