Podcast Ep #13: Taming Email Overwhelm

And be sure to listen all the way through to the end because I’m giving you a downloadable template for creating your own communication policy and it’s prefilled with the recommendations from this episode. Ready to become a more agile attorney? Let’s go.

Welcome to The Agile Attorney podcast powered by Agile Attorney Consulting. I’m John Grant and I’ve spent the last decade helping lawyers and legal teams harness the tools of modern entrepreneurship to build practices that are profitable, scalable, and sustainable for themselves and their communities. Each episode I offer principles, practices, and other ideas to help legal professionals of all kinds be more agile in your legal practice.

Hello. Welcome back to The Agile Attorney podcast and welcome if this is your first time. So in today’s episode I’m going to try to tie together some elements from my last episode with Alex Devendra, talking about design and intentional design in your legal practice. And also the set of episodes that I did before that had to do with quality standards and policies as ways of improving things in your law firm. And specifically today I want to talk about how to design a better communication policy for your law firm in the form of an email policy or maybe a broader communications policy.

Now, I will admit, the number of podcasts, articles, LinkedIn stories, whatever, that have to do with writing better email could probably wrap around the globe a couple of 100 times if you stacked them end to end. It is a hot, hot topic. And yet it’s one that continues to plague people and maybe that’s why it’s such an evergreen topic, because it’s an evergreen problem. Email and communication in general is overwhelming in modern society And it’s probably overwhelming, at least in parts, of your law practice.

So I’m going to give you some of my tips and tricks that have been useful for me. And also things that have worked with a lot of my clients in terms of getting a better handle on email communication specifically. And the place I want to start is with the notion that the goal of communication design from my standpoint is to design more effective communication, which often leads to less overall communication. We want to actually reduce the volume of email that is coming through your systems by having better emails.

Now, I’m mostly going to be talking about email, but a lot of what I’m going to say here can apply to Slack, Teams, whatever other real time messaging you might be using within your team. And I’m going to say I’m not a huge fan of some of those tools. I know people really like them, and I understand why. But I also think that even more than email, Slack and Teams have the ability to create a lot of distraction.

And we think they’re solving a problem, and they are. They’re solving one problem really well, which is this problem with email where it forks into these multiple reply threads. when multiple people reply at different times and on different timelines and it becomes this really big challenge to follow the thread or find the thread in a complex email chain. And Slack and Teams solve for that by creating a sort of single threaded message. But in doing that, they can exacerbate the interruptive nature of emails unless you’re really good about using do not disturb or sort of other tools like that.

And part of why they’re so good at grabbing your attention is that your communications with other people are this this paradox. It’s absolutely necessary for getting things done in a multi person or multi team situation. But because we’re social creatures and we’re wired to crave communication, it’s got this inherent ability to hijack our attention, like practically nothing else on the planet.

The ding of your email system or the flash of a new Slack message really sort of wires into the central nervous system to pull us out of whatever we’re doing and get us to pay attention to this new thing in a way that often isn’t productive. So the question is, how do we design better communications?

Or using the language of my episodes before the design episode. How do we create policies that will help us be more consistent with better communication in an intentional way? So that we can use those policies when we’re busy or stressed or otherwise in the heat of the moment, where we’re tempted to succumb to our own sort of lesser instincts.

The other thing in terms of background and the purpose of designing your communication overall. Is that your communications policy should be squarely within the vein of trying to improve the flow of work through your practice, through your workflows and your systems. The reason we’re communicating to begin with, when we ping someone else with a question or a request, it isn’t that there’s some inherent good when we get an answer. The value comes from the answer being able to help us make progress on a project or a matter and help get it moving forward in the workflow.

Or if you’re using a Kanban board, moving from left to right across the board, getting those deliverables done. And the problem with poorly crafted communications, emails or whatever is that they can be a significant source of administrative overhead in your work and in your team’s work. And administrative overhead that isn’t actually helping move a thing forward. It’s what the lean community would refer to as waste. Anything that requires an investment of your time or energy or resources, that doesn’t yield a clear or direct benefit.

So if you send a single email with all of the things that you need and then you get all of those things back in return on time when you need them, then yeah, there’s administrative overhead. But the investment in that communication is well worth it because the email has actually helped move the matter or the project forward. But as soon as you have to ping someone multiple times or answer a follow-up question or otherwise keep engaging in that back and forth around the topic, that is so easy to happen in email or Slack or Teams.

Now you’re squarely into that waste territory where the administrative overhead is just adding to the cost, but it’s not really adding to the benefit. A few episodes ago, I had another word for this and it was failure demand. Remember, that is anything that causes demand on your finite capacity, your time and attention, that is a result of some other failure in the process. And maybe the failure started with you, maybe you were unclear in your request or you didn’t give it the right context.

Maybe you asked things in a way that were hard to follow, and so the person that you were sending that email to lost part of the thread. Or, of course, the failure could have been on the other person’s end where they were maybe hurried when they wrote a response or didn’t think things all the way through when they answered. There’s a whole art to crafting good email responses too, that I’m not going to get into today.

The one thing I will say is when you’re the originator of an email. There are things you can do to increase the likelihood that you’re going to get the answers and information you’re looking for in the timeframe you need it, even if the person on the other end of the communication isn’t giving it their 100% effort.

So in the rest of this podcast, I’m going to give you some ideas for maybe a personal policy or a firm wide policy around email communication design. And I’m here talking specifically about email, but this can be helpful in other contexts as well. And these are things that have worked pretty well for me and for many of my clients when crafting a policy like this. And like any policy I create, I want to start with a purpose statement.

So the purpose of this communication policy is, number one, to reduce the total number of communications we need to process so that we can spend more time working on the actual deliverables, the work product.

Number two, I want to eliminate as much of the back and forth as possible, the stuff that causes administrative toll and delay in finalizing a communication or a piece of work that you need to communicate about.

And in doing so, number three, I want to accelerate the flow of information that we need to do the actual work and especially client work so that we can accelerate the delivery of the work itself. The whole point of these lean and agile and Kanban methods is to get work to flow more smoothly.

So my first concrete suggestion is that your emails should be longer. I think a good email should read more like a memo than what we traditionally think of as an email message. And I’ll admit, this is going to take a little bit more time upfront and a little bit more care to produce. But we’re doing so in the vein that your upfront investment is going to make it much more likely that you’ll get a good result or a good answer on the return side.

One of the things that I’ve been adopting lately that’s going really well for me is, I’m adding section headings to my emails. If there’s an email that has more than one topic, I’ll add a line, I’ll give it a topic sentence. I’ll often bold or change the size of that topic sentence. And actually sort of organize things a lot more like I would organize a memo. It doesn’t have to be quite as formal, but giving some direction can be really helpful.

Underneath those headings, I try to be really careful about writing things in bullet points whenever possible and creating some white space so that the individual items are easy for people to unpack. And it’s not just walls and walls of text that might have parts that are easy for someone else to miss.

Once I finish drafting an email, I usually try to go back and use a technique called the BLUF, the B-L-U-F, which is a military acronym for bottom line up front. It’s the executive summary, the header, here are the things I’m about to talk about part. And oftentimes I will put a clear question at the end of that BLUF. I want something that says “As a result of this email, I need these three things from you or I’d like an answer to this specific question.” It’s a TLDR in internet speak, but giving people that context even before they go and read the details can be really helpful.

And whenever there’s a question or an action item or a response needed, I put a header around that. It’ll say action item, colon, and then describe the thing that needs to be done or a response needed colon and then ask the question. And I’ll put that action item response needed in bold or highlight it.

I’m really trying to give sort of a visual roadmap so that if someone is going to invest only a little bit of energy into this thing, I want to make sure that it’s really easy for their eyes to catch the important parts so that I can get back the things that I really need in order to move something forward. And I’m going to acknowledge again, it takes a lot more work to do this upfront than to just shoot your thoughts out into the ether.

But I have experienced this in my own practice and my clients, and others that have felt this way as well. It’s that ounce of prevention that results in the pound of cure. And doing that investment of time upfront pays dividends. It yields benefit in the form of faster response times, more complete responses, more accurate responses and a lot less back and forth.

The other thing that I will say is that this is a place that AI can be really helpful. So I’ve been using cluade.ai. I’ve done the same sorts of things with ChatGPT. I’ll give it a command that says, “Without changing the specific language of this email, please organize it into sections. And please let me know what the list item of deliverables are or action items are.” And that can often do a pretty good job as a first pass of giving me an organization format. It won’t be perfect. I still need to edit it and massage it, but it really helps get things into a more structured format that I can then copy paste back into my email message.

My second recommendation, and this is something that I’m going to talk more about in this episode that I still haven’t done yet, and I keep teasing around client homework. But the same thing is true for any sort of communication with email, and that is, give people a clear deadline for responding and ideally give them a short one. My default time duration for getting a response from someone else is three days. And I know that can feel really short and a lot of lawyers are in the habit of giving clients weeks if not longer to come back with things.

But there’s a few reasons why I think a short deadline is a better one. Number one is that people have a lot clearer sense of what’s going on in their life over the next three days than they do over the next three weeks. People can hold sort of a mental model of what their next few days looks like. So if you ask them a question, “Is it realistic for you to respond to me by the end of the day Friday?” Then they’ll be able to give you a pretty good answer to that pretty quickly.

Another reason for that three day deadline is that the information you’re trying to give them and their motivation around dealing with whatever their matter is or the question is, it sometimes has sort of a half-life. So especially if you’ve just engaged with someone over the phone or in a meeting, and then you follow up with an email around something. And if you email them with further requests and ask them to turn it around quickly, it’s going to be more likely that they are remembering all the things and all the context if you give them a relatively short deadline.

If you give people a two week deadline, they’re going to mostly wait until just before that deadline to do it and by then there’s a good chance that some of the details have dropped out of their head. And of course, from a flow perspective, I want to keep things moving and flowing forward as much as possible. And starting with a short deadline is a really effective way to do that and I’m not draconian about it.

In fact, I even suggested in my phrasing a second ago. When I give people a deadline, it’s never an absolute assignment or rarely an absolute assignment. I usually will say something to the effect of, “I would love to have this back by the end of the day Friday. Is that realistic?” And I give them the ability to have an out. And if it isn’t realistic then what I’ll often say is, “If that’s not doable, please let me know how soon you can get it back to me.” And that’s a key question too.

I don’t say, “When can you get it back to me”, because that’s open-ended. And that starts to leak people further and further into the future. I like the question, how soon can you get it back to me? Because it communicates a sense of urgency and importance around keeping things moving.

My third recommendation is one that I’ve actually been using for probably decades now. I actually learned it back when I was in the corporate world before I even went to law school. And that’s, whenever possible ask people a question that has a binary answer, a yes/no question or a true/false question. And this is something that really reduces the cognitive load for the person that you’re trying to get a response from.

If I ask someone, “Hey, when do you have time to meet?” That is a surprisingly complicated inquiry. It forces people to ask themselves any number of sub questions around, do I even want to meet with this guy? When will I be ready to meet? Will I be prepared? Do I have an available slot on my calendar? Things like that. This notion of, when do you have time? It just puts a ton of pressure and work on the person that has to answer the question.

And when they see that question come in that requires a lot of thinking, there is a likelihood that they’re not going to respond or not going to respond quickly. But if you phrase it a different way, if you say, “Hey, do you have time to meet at 3:00pm on Thursday the 15th in order to discuss edits to the TPS report?” Now it takes a lot more work for me to craft the question, but it actually makes it way easier on the other person’s brain. It’s a much lighter lift. They can give a really clear yes or no answer pretty quickly.

And then the likelihood that you’re going to get that answer and keep things moving forward, we’re looking for flow, is going to be a lot higher. I will sometimes take it a step even further, and specifically if it’s a question around scheduling a meeting, I will basically say in my email, “Hey, I’m going to schedule this. I hope Thursday the 15th at 3:00pm works for you. I’m going to send you a meeting invite right now. If that time doesn’t work, feel free to reject the invite.”

Or if you’re in one of those tools that has the ability to request alternatives or propose alternatives, then they can do that too. But the reason I like that is it reduces one more set of back and forth if it’s a yes answer. If I ask the question, “Do you have time?” And then they say yes. And then I’ve got to go back and schedule it. That’s a whole thing that puts more work on me. But if I do the request and the scheduling back-to-back, give them permission to reject it, but then their answer is, “Yeah, I can meet then”, then we’re done.

We don’t have to have another round of emails or communications that either one of us have got to deal with. And that’s what I’m going for. I want to reduce that total administrative burden on both of us so that we can keep things moving. I’m going to give you two more sort of smaller tips and this isn’t an exhaustive list. These are the things that are top of mind for me as I record this podcast, but I do think these are things that are useful.

So my fourth recommendation is if the subject changes, if in the course of you communicating with somebody else, start a new thread. There’s this funny thing that people do, and I get why. They go to the last email thread that involves some or most of the people that you want to ask a new question of, and they do a reply all to that previous thread. It’s really easy to do, but it makes it so much harder for people to follow the conversation and understand what’s needed now.

So I say, resist the urge to do that, the thing that’s quick and easy, maybe a bit lazy, I don’t know, that’s okay, but start up a new thread and especially start a new thread when you start a new topic. And I would say when in doubt, start a new thread because the threaded email and the ability for these forks and these different multi threads to sort of emerge like gremlins really is one of the biggest problems of email based systems.

My fifth recommendation is, only copy people on your email messages if they’re absolutely necessary in the thread. And especially for folks that are on your internal team, I try to resist the urge to copy people as an FYI. There’s better ways to do it. And a lot of lawyers are doing this already, if you’re using a plug-in or another tool that will automatically route emails into your law practice management tool or your document management system, let your team members go look for it there.

Don’t force it into their inbox where it’s yet another distraction. We’re trying to reduce the number of emails overall. And making sure that people are only necessary is a great way to do that. Another place to do this and this is something that Cal Newport actually talks about in one of his older books, A World Without Email. If you’re using a Kanban system to manage projects or task sets. Then one of the best things you can do is make sure that you’re copying the card on the email. The thread can show up.

There’s a lot of these Kanban systems, and the ones that I use both do this. They’ve got this little mini Slack channel inside of the card or a little mini Teams thread inside of the card. And that is a far more effective place to put these communications than to have them scattered across different systems in different places, so that’s it.

So my homework for you or my call to action for this episode is, sit down and give some thought around how you might craft, again either a personal policy or a team or a firm wide policy around your communications and your email communications. And I’m going to make your homework a little bit easier because I’m going to put on my website a version of a policy document that actually incorporates a lot of suggestions that I’ve made in this podcast episode.

It’s also going to articulate some of the reasons for having a communication policy. And also some metrics you might consider for how to measure the effectiveness of the policy, because I think all of those are really important components of a well-crafted policy. And as a bonus, you’ll be able to then use that template for other policies you might want to draft for your law firm as well. And I keep promising future episodes, but I am going to do another one on this idea of sort of a policy about policies. And I’ll put that template in a few places. It’ll be in the show notes for this episode.

But I also want to let you know that I have created a new page on my website, it is agileattorney.com/start. And that’s where I’m trying to build out sort of a clearinghouse for a lot of my more popular recommendations and tools. So you can go to that page, you can see all of the various resources that I’ve put out into the world. And get information about how you can get access to them and use them. And almost all of them are free or at least partly free. There are some software recommendations and other things that obviously you eventually have to pay for.

So hopefully you’ll do that and find it useful. Take some time and think about these things. Maybe there’s some of the suggestions I’ve made, maybe it’s some other stuff that you already do, but you haven’t documented, one of those unspoken policies I talked about a few episodes ago. Maybe it’s suggestions that other people have made but you just haven’t quite formally incorporated them into your workflow.

The key is, think about how you can create a policy that is going to help you protect yourself and create the conditions for your team to be more successful, for your quality output to become higher and ultimately for your work to flow more smoothly in your practice. Thanks for listening and I will see you next time.

Thanks for listening to The Agile Attorney podcast. I’m your host, John Grant. If you found today’s episode interesting or useful, please share it with someone who you think would benefit from a more agile approach to their legal practice. If you have any questions, feedback or maybe a topic you’d like to hear me cover, you can reach me at john.grant@agileattorney.com.

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