Management Assistance Program

Generational Changes in Communication Styles

By Jim Calloway

Technology advances have led to many changes in society. Between text messages, emails and social media, today most of us transmit many digital messages each day and we purchase fewer postage stamps for our personal use.

There are noteworthy generational changes in many areas. We differentiate the various generations with words (e.g., Baby Boomers) and letters (X, Y and Z), and as certain as the sun will rise in the east, many in older generations will complain about the emerging new generation.

“The children now love luxury; they have bad manners, contempt for authority; they show disrespect for elders and love chatter in place of exercise. Children are now tyrants, not the servants of their households. They no longer rise when elders enter the room. They contradict their parents … and tyrannize their teachers,” said Socrates by Plato. Although, like many a good story, this has been challenging to historically verify.

A headline in Forbes caught my attention – “Millennials Hate Phone Calls, And They Have A Point.” I’m an official member of the “no longer a young lawyer club” and a parent of a millennial, so I have often said, “Can’t we just talk by phone and not text?”

I recommend you read the article because it makes several valuable points, at least where law firms and most businesses are concerned.

While millennials are often accused of not wanting to use email, for many that reflects their attitudes about their personal lives rather than work lives.

According to the article, “[this is the millennial work email standard: 1) If it can be said in an email, send an email; 2) always send an email, if sending an email is possible; and 3) the only reason an email should not be sent to communicate basic information is if the conclusions, objectives or answers are not yet decided upon, and multiple people should be present to weigh in on them.”

Millennials hate leaving a 45-minute meeting and thinking “that should have been an email,” and they are not the only ones. Meetings may often be required but they should be no longer than necessary.

The writer also makes the point that email threads are better for organization. A well-run meeting without minutes or with incomplete or poor minutes may result in a weaker outcome than a disjointed email thread that culminates with a positive final solution which all stakeholders approve. The documentation may not be perfect but at least it exists. Lawyers appreciate the value of good documentation.

We all will not agree on this subject. Personally, I still think there is often a superior personal connection with a voice phone call as opposed to short digital messages. However, law firms do have to recognize that interactions with people who try to avoid phone conversations are going to increase. Demographics is, as the saying goes, destiny. Young people grow older and take over positions of importance.

There are times when digital communication is more efficient. We can all agree that you can reply to eight emails more quickly than you can return eight phone calls when you only have a short amount of time – especially since not all eight phone calls will be answered.

On the other hand, absent a court-authorized wiretap, a two-party voice phone conversation is more “private” than an email which can be forwarded or disclosed via discovery many months into the future. Unencrypted email is not secure, as I have frequently noted.


The CEO of a major computer services vendor serving the legal profession recently asked in an address to a large group of legal professionals, “Don’t you just hate talking on the phone?” Many attendees murmured their agreement. He went on to note new offerings from his company that would allow lawyers to have more digital text communications with clients, reducing the dreaded phone calls. I want to point out what a great potential client his company would be for a law firm. The company has hundreds of employees, has many customers and is extremely well funded, but he hates talking on the phone.

How well would your law firm do in representing this company? Do you have processes in place where he can avoid frequently talking to your lawyers and staff on the phone or would that representation just not really work for your firm?

A common definition of millennial is those born between 1981 and 1996 (or 1997). Individuals born in 1981 turned 38 in 2019. Certainly, some entrepreneurs younger than that are leading businesses today, and the “changing of the guard” means more millennials are assuming corporate leadership roles. When I was in private practice, I represented lots of individuals under the age of 40. I’m sure that’s true for many lawyers today. Plus, these date ranges are not strict demarcations. It’s probable that an individual born in 1980 will have the same attitudes about voice phone calls as one born a year later.

Our profession has focused on returning client phone calls because not returning phone calls promptly was a chronic complaint about the profession’s failure to communicate and could give rise to professional discipline.

Is your firm ready to serve clients who strongly prefer digital communication and certainly don’t want to participate in many voice telephone calls? If not, it’s something to consider.

The successful law firm in the future will both promptly return client’s telephone calls and will also provide communication alternatives for the clients who hate talking on the phone.

One undeniable benefit of digital communications between lawyers and clients is that there will be a precise record of exactly what you said and what the client said in the event there is ever any grievance or question about your legal services. As we know, it is not unheard of that two parties to a voice telephone conversation may have very different interpretations about what was said later.

Another benefit of digital communications is that it is asynchronous communication, meaning the parties involved in the communication don’t have to be available at the same time. That’s one of the best things about email. A client who works the graveyard shift and sleeps during the day may be better served by digital communication tools.

There are many different methods of digital communications available today. Let’s discuss how these work in a law firm setting.


I’ve written and lectured frequently about using client portals for a more secure communications platform than email. Practice management solutions that cater to medium-sized and small law firms generally provide secure online client portals as one of the service’s features. These can be used for communications but are designed more for sharing documents with clients.

There are other providers of secure portals that a firm can utilize, but sharing documents with clients using the same tool as you would to file them in the digital client file is a very efficient process.


In the May 2019 Oklahoma Bar Journal, I wrote a feature story titled “Text Messaging for Lawyers.” In that piece, I covered some do’s and don’ts for lawyers, the security of various text messaging apps and tools to use to send and receive text messages from a computer. I mentioned ZipWhip as a leading tool to use for texting from a computer while retaining copies of all texts sent and received for the client file. The ZipWhip app allows text messaging with a cellphone without disclosing the cellphone number. ZipWhip can provide immediate digital communication. While text messages are less intrusive than a voice phone call, they still interrupt the recipient’s day and are better for brief communications.

A solo practitioner contacted me after that article was published and wanted to know if there were other options. I told him that Apptoto.com was well-regarded by a respected consultant I knew and one OBA member, but I hadn’t tried it personally.

He reported back later that he loved Apptoto. He said:1

Apptoto will integrate with calendar software. That is, if we type an appointment into my calendar and type the client’s cellphone number into the appointment, Apptoto will automatically pick up the meeting and will send a text to the client before the appointment, notifying them of the appointment. My secretary likes this feature because she can type an appointment into the calendar and does not have to take any extra steps. I learned to use Apptoto and then all I had to do was tell the secretary to continue entering appointments into the calendar. I chose Apptoto precisely for this reason [my secretary was concerned she’d have to do additional work and learn to use a new tool]. My secretary was very happy and thanked me for the choice I made.

He detailed how his office uses the software:

I can program Apptoto to send the client a text at a specified time before the meeting. I’ve programmed my account to send each client two texts – one at 6 p.m. the day before the appointment and another text one hour before the appointment. I can also program Apptoto to send a client a different text message based on what I type into the appointment. For example, if I type ‘appt’ into my calendar, Apptoto will send the client a text saying, ‘Appt Reminder: You have an appointment with [my name] today at 4:30 p.m.’ If I type ‘Court Appearance’ into my calendar, Apptoto will send the client a text saying, ‘This is [my name]. You have a court hearing tomorrow on Monday, Nov. 4, at 1:30 p.m.’ The text will also ask the client to press 1 to confirm that they received the message.

Apptoto has set me up with a local number … If the client texts a response, the client’s text response will be emailed to me. If the client calls the number, the call will go to my land line.

Apptoto is very affordable. The plan I have costs $29 per month. For $29 per month, Apptoto will handle 200 appointments per month and will sync with three calendars. The plan I have will also email and give voice calls to clients, but I haven’t used this feature yet. The plan I have is the lowest-cost plan they offer. Other plans will handle more appointments and sync with more calendars.

Most health care providers now text appointment reminders to their patients. Lawyers can use Apptoto or ZipWhip to do the same for clients, but these tools can be used for other text message communications as well.


Microsoft Office 365 now provides great digital communication tools to subscribers. Office 365 Groups and Teams are often compared and contrasted. Some reviewers state the most logical way to look at Groups and Teams is that they are complementary.

At this point, at least based on my anecdotal observations and conversations with others, relatively few law offices have embraced Groups or Teams because the firm had already implemented processes to reach many of these goals.

Probably the simplest and best way to look at these are that they are co-working spaces that highlight different co-working aspects. One thing that seems certain is that as Office 365 completes its takeover of corporate America’s computer systems, we are going to see greater utilization of these tools by businesses. For example, a law firm might build a team that includes members of the law firm, representatives of the client, expert witnesses and others involved in a particular matter. The challenge for lawyers is to use these working groups in a way that promotes efficiency, cooperation and sharing without compromising confidential information or creating some other ethical challenge.

Both Groups and Teams are a part of your Office 365 subscription that you can only access by logging in. As Microsoft’s Ben M. Schorr noted in his January 2019 Law Practice Magazine article “Obtaining the Most from Office 365,” a Group includes a shared email inbox for the Group conversations, a dedicated calendar, a shared document library, a OneNote notebook for the Group, a SharePoint site for the Group and a Microsoft Planner.

Suffice it to say that the above list contains almost any tool one might imagine an online co-working would require. It is hard to say how quickly law firms will start using these tools since they have similar systems in place, but business will increase use of these tools and some lawyers’ first exposure to them will be when a client invites them to join one of these co-working spaces.


Slack is an online group working space that does not require an Office 365 subscription.

Many technically proficient individuals swear by Slack. It is easy to understand how Slack operates because the free version allows up to 10,000 searchable messages plus 10 apps and integrations. It is very affordable. The standard plan is approximately $6 to $8 per user per month. Slack focuses on good digital security and has a significant number of security compliance certifications.

Slack allows message discussions to be organized by different channels. This would be quite a handy feature if you are part of a large Slack group. It does allow for file uploading and integration of apps like Google Drive, Google Calendar or Zapier. I’m relatively new to Slack myself but know others who have used it for quite some time and love it.


While we opened this discussion with an examination of generational differences in communication styles, I hope the broader point is that law firms represent individuals with many different communication preferences. Law firms have to be open to the idea that the ways they have always communicated may not be optimal for certain clients. There are certainly tradeoffs when choosing methods of communication, but lawyers will always have a need to document their client communications, whether it is using digital communication tools or making careful notes during a voice telephone conversation.

Mr. Calloway is OBA Management Assistance director. Need a quick answer to a tech problem or help solving a management dilemma? Contact him at 405-416-7008, 800-522-8065 or jimc@okbar.org. It’s a free member benefit!


  1. I have lightly edited his comments for space constraints.

Originally published in the Oklahoma Bar JournalJanuary, 2020 — Vol. 91, No. 1

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