Digital Client Communication: Great for Efficiency, Bad for Cases, Careers and Caterers

By Tom Hagy, featuring Peter Norman of Winnieware LLC

The following reversal of fortune was inspired by actual events.

In the crush of a frantic day, and in his excitement to share something big with his colleagues and client, he decides to share it immediately. To speed things up he grabs a prior email that has everyone’s addresses already entered. The efficiency of the “reply all” option allows him to spread his glee with two dozen people. Ah, the 21^st Century. Isn’t it the best? He imagines himself hoisted up on the shoulders of the partners, the client and even the caterer. “It’s just what the case needs!” he thinks. “And it won’t hurt my career any, either.” “Hey, honey, guess who’s the hottest guy around?”

Glee quickly turns to a need to heave when our ambitious young attorney realizes—thanks to an all-caps email from his boss—that opposing counsel was among the recipients of his golden email blast and he just handed them a victory. Cancel the caterer.

The consequences of such missteps range from mere embarrassment or to undermining confidence, from ethics charges to malpractice claims, or from loss of a case to crashing a deal to ending a career. Improper practices also can make an organization’s network more susceptible to hackers or leaks.

The good news is that there are simple measures you can employ immediately to mitigate the risks.

Peter Norman has spent a great deal of time thinking about this, both in terms of practical measures as well as technological ones. He has given it so much thought it’s how he now makes a living. Norman is an attorney, a computer program developer and co-founder of Winnieware LLC, the company that offers the ReplyToSome email app. Prior to becoming an entrepreneur, Norman served as in-house counsel at a renewable energy company, and before that practiced at two large law firms.

“It’s about improving people’s habits,” he said, “but in ways that won’t interfere with their work.” For a large organization, training programs can meet with resistance because hard-working people are reluctant to stop what they are doing for training that they don’t perceive helps them. Norman said, though, that “the best solutions, whether they are training programs or technology applications, provide not only safety but can improve efficiency and quality of work.”

When you have to correct a mistake—in addition to the potentially dire and immediate consequences—it can be a grand waste of everyone’s time. “It can also undermine your credibility in the minds of clients, colleagues and supervisors,” Norman said. “Thoughtful email communications are expected from professionals. Sloppiness can put a crack in your perceived integrity.”

ABA Model Rules of Professional Conduct are intended to address the dangers posed by modern information technology, he explained, adding that they require lawyers to use “reasonable efforts to prevent the inadvertent or unauthorized disclosure or use of, or unauthorized access to” confidential client information.

“The adoption of these rules by nearly half of all state bars (and counting), comes at a time when law firms’ practices with respect to storing and communicating confidential information have come under increased scrutiny,” Norman said.

Cautionary tales include the “Panama Papers” leaks from one law firm, and the recent headline-grabbing breaches at two major U.S. firms. And, of course, there is the brouhaha surrounding former Secretary of State Hillary Clinton’s use of a private email server, whether she inappropriately shared confidential materials, and whether she and her attorneys improperly deleted thousands of emails.

To avoid such calamities, Norman offered some practical ideas for keeping email snafus to a minimum.

For Outside and Inside Counsel

Practice mindfulness. To some, this may sound cosmic, but the approach of paying attention to what you are doing at this very moment has served people well for centuries. Are you hitting send while distracted? Are you simply rushing to get the task off your desk? Take a beat, or a deep breath. [For more on this, read our article, Caution: Read this Before Shaving Your Head—Mindfulness for Attorneys and Executives.]

Double check. Before you hit send, pause and consider who’s receiving the email, what is or is not attached, whether you need to proof your text and subject line, whether the email is confidential and protected, whether you really want to use BCC or a prior email, etc.

Training. For training programs, find the simplest methods of changing behaviors. Use methods that don’t interfere with work. Best practices help. Apps, of course, help too.

It’s not just about avoiding mistakes. For managers considering a training program on best practices and/or technical apps, know that these methods also result in better productivity and better output. 

Second-guess the machine. Keep and eye on auto-fill and auto-correct features. Many email addresses look alike. And so do many words.

Don’t mix business and personal. This should be obvious, but mixing business and personal email can open up sticky privacy and disclosure issues that no lawyer or executive or candidate wants to deal with.

For Outside Counsel

Avoid blind copying your client. “Like the mute button on conference lines, blind copying, or BCC, has a reputation for attracting white-collar thrill-seekers,” Norman said. “It appears that the New York State Bar Association’s Committee on Professional Ethics had this reputation in mind when it issued Ethics Opinion 1076 in December 2015. This opinion does not prohibit the use of BCC, but it does put would-be thrill-seekers on notice. And despite its seemingly limited application, together with recent changes to the American Bar Association’s Model Rules of Professional Conduct and the rules in a number of states, the opinion might open all lawyers’ email practices to ethical scrutiny.”

One size fits some. “Not all clients and cases are alike, and neither are their communications practices or needs for confidentiality, so you will want to tailor your methods to them,” Norman recommends. “For example, a multiparty negotiation will require a different approach, and perhaps different tools, than an internal investigation.” Also, advise your client on proper communications in the context of attorney-client privilege, work-product privilege, ethics rules, and issues around efficiency in communicating, preserving and sharing data.

Inside Counsel

You don’t have the same malpractice issues as outside counsel, but improper disclosures certainly can put your career and your company at risk. Norman says there are steps corporate counsel can take at the beginning of engagements to ensure that they get the confidentiality protections that fit their needs.

Tell external counsel what information is sensitive. “Even the most experienced lawyers might not be aware that a certain piece of information could reveal an important trade secret or piece of corporate strategy. To get the best performance from external counsel, put them on notice from the beginning,” Norman said.

Have a frank discussion about Frank. External lawyers know that in-house counsel want lean, efficient teams working for them, so they might reduce the visibility of all team members by not copying them on emails or by using the BCC option. “Unfortunately,” Norman said, “it is often the lawyers who are peripheral to matters who are the most likely to make mistakes regarding confidential communications. Outside counsel must find ways to keep their colleagues in the loop without either running up the bill or creating opportunities for mistakes.”

Check on preferred safeguards. “Firms increasingly offer a menu of options to secure communications, ranging from conducting messaging through secure data rooms to deploying security add-ins to their existing email software. A simple question from a client about what’s available can ensure that you are getting the full benefit of the firm’s existing resources,” Norman said.

“The new confidentiality rules provide an opportunity for law firms to reassure clients that their information and communications are safe. But the rules ultimately rely on lawyers’ judgment, and for reassurance to be real comfort, corporate counsel should take their own proactive steps to open outside counsel’s judgments to scrutiny,” Norman said.