Product Exercise: Making a better email experience


A few years ago while attending a professional development meeting for emerging company attorneys, one of my colleagues shared an interesting pain point about the legal practice. As a senior partner for an emerging companies practice, one of his primary roles is to coordinate the efforts of other attorneys in order to support the client. This routinely consists of sending and receiving numerous emails (hundreds a day) to both internal and external audiences. Having only limited experience in a law firm, I suggested some of the tools I used with my team for software development (Trello, Google Docs, Slack, etc.). The attorney told me that they had tried several of these tools but they did not integrate well with their workflow. ‌

I recently took the opportunity to investigate this issue a little more and try to imagine a potential solution. The following is the process I followed to ultimately design a first iteration of a new way to interact with email. ‌


Market Research

To start, I wanted to learn more about the legal market and how legal participants (clients and lawyers) use email. I had previously come across the Clio Legal Trends Reports and found them very insightful when learning more about broader trends in the legal market. Thankfully, the 2019 report focused heavily on attorney-client communication statistics. Anyone remotely interested in legal trends should definitely read the full report for themselves but here is some interesting data I pulled from the report. ‌

  • 82% of surveyed clients indicated that lawyer timelines were important to them
    • 81% want a response to each question they ask
    • 80% say it is important to have a clear understanding of how to proceed
    • 76% want a clear sense of how much their legal issue could cost
    • 74% want to know what the full process of their case will look like
  • Ways that clients say lost their business
    • 65% didn’t get any indication of what to do next
    • 64% didn’t get a sense of how much the matter would cost
    • 62% didn’t get enough information they could understand
    • 52% said the lawyer they spoke with wasn’t likable or friendly enough
  • 76% of lawyers say they are overworked and 68% say they are under appreciated

Next, I started to do a high-level survey of software tools specifically marketed to lawyers to help improve their client communication practices. While I was able to find several live chat tools marketed to professional service firms, I wasn’t having much luck finding email management tools. After asking around a little I was referred to two products for the legal market. ‌

  • Workstorm – Enterprise collaboration platform with a suite of services (messaging, video conferencing, email integrations, document management, etc.)
    • Utilizing typical SaaS pricing (per user per month)
    • The primary insight is to move all services into one integrated platform without sacrificing functionality.
  • Dashboard Legal – Lawyer founded/designed tool to integrate several work processes into one client-centered dashboard.
    • Seems to be relatively early in the development process
    • A few people in my NYC legal tech network have met founder Mat Rotenberg and gave positive feedback
    • Not sure what pricing structure they will be utilizing

I also wanted to do a review of some of the other email-based collaboration tools that are in the market. ‌

  • Gmelius – YC backed company offering features that allow teams to run projects, customer support, and sales all out of their email service provider.
    • Per user per month pricing
    • Marketed more to non-professional service companies/teams (no Outlook integration yet)
    • A wealth of content and support
  • Front – Communication collaboration out of email inbox
    • Per user per month pricing
    • Specifically are targeting travel management, rental management, logistics, and client service as segments
    • Seem to have some features around visualizing emails, attaching notes, chat, and sharing conversations
  • Hiver – Using email as an integrated customer service/help desk tool
    • Per user per month pricing
    • Shared email management tool
    • More of a light-weight way to manage support and other shared emails through Gmail
    • Provides CRM and automation services

The legal market strategy for better communication and collaboration tools appears to be a platform model looking to centralize processes within one tool while in the broader market the strategy is to derive more functionality within the email service provider. All the tools understandably utilize a per user per month pricing structure.

User Interviews

While I was doing broader market research, I also began to do some outreach to talk to more people within the legal industry to learn more about their experience with email. ‌I started my user interview process by talking to several lawyers I personally know. Most of these attorneys have experience in transactional matters like negotiating company financings and corporate mergers. These types of legal matters involve several attorneys on each side of the deal that often involve highly complex legal matters. Before I began speaking to these attorneys though I created a user interview guide. Creating an interview guide before having any sort of conversations has become standard practice for me to make sure I organize my questions, assumptions, and takeaways from each conversation.

Excerpt of the Interview Guide

I started by having five conversations over the course of two weeks. Here are some of the insights I gathered from those conversations. ‌

  • Email is the preferred way to communicate because it is episodic and not rapid like Slack or other chat tools.
  • The manual nature of being able to add and remove recipients is an important function of managing the progression of a legal matter.
    • Controlling and auditing the contact list is more important than I imagined.
  • Depending on how you are approaching the deal as an attorney, it can be hard to quickly get context on the matter’s progress.
    • Specialists (like tax attorneys) particularly run into this problem.
  • Firm knowledge management wants lawyers to document and file their emails
    • This is not really done with any consistency
    • Sometimes lawyers actually make a conscious choice not to document their emails
    • Most of the firm’s knowledge lives within their attorneys’ emails.
  • There are several practices for naming emails and whether the message should be a thread or a new email subject line
  • It is not always easy for an attorney to understand if they should just follow the conversation or if they are supposed to be an active participant
  • Context switching between the agreement and the email conversation is a time suck and frustrating

With the insights I gathered from these conversations, I started to imagine a new way that lawyers could manage their email conversations. ‌

Design Process

I am not a seasoned visual designer. However, I am a firm believer that most people can use simple sketches to start to paint a picture and communicate how a piece of software could function.

Initial sketch

I started with just a very rough sketch in my notepad. Since the beginning of this exercise, I have been considering if a visual approach to email would be valuable. Initially, it seems that rather than creating a new platform, an email extension may be a better approach. This way, the barriers to adoption would be lower since it is an additional service on a product the attorney uses every day.

My concept was creating swim lanes that would separate messages based upon sender groups (law firm, opposing counsel, third parties, etc.). Additionally, I thought incorporating a chat function and message note features could be an interesting way to declutter messages and help provide additional context for the users. I added a right rail as a way to visually designate portions of the conversation with iconography to quickly communicate things to the user like if something was time-sensitive or to flag it for the user’s review.

Second sketch

In the spirit of my first attempt, I also made my second drawing in my notebook. This time I wanted to see how the experience could look with drafting the email and incorporating the email feed directly into the experience. Additionally, I added the folder management system in the drawing as an expandable left-rail feature to mimic many email service providers. I also thought about including different types of email classifications to help the attorney focus on the highest priority emails. This second attempt was definitely getting more fleshed out but still felt a little functionally lacking.

Third sketch

For my third version, I got a little fancy with graph paper (I can’t draw straight lines) and tried to see how color adds to the visual experience. This version was a more polished version of the second drawing. However, I reviewed my interview notes again and decided to add a little more functionality to the right rail. Specifically, I used the top portion to be a designated area to indicate role-specific information to the user (time-sensitive and flagged for their review). The middle portion of the right rail I imagined space to link-out to other app features like a contact list audit, file attachment audit, and performance data. In the bottom section of the right rail I decided to leave space for possible future integrations like document management systems and other collaboration tools. ‌

At this point, I was ready to move these drawings into a digital format to do a final design for this exercise. ‌


Digital mock-up

In my final mock-up, I used Vectr to start to turn some of my pen and paper drawings into a digital representation. This final drawing got rid of the email classification structure. It seemed a little superfluous at this stage so I decided to remove it. ‌

Using the version above, here is a summarization of my design choices:

  • This way to visualize emails is imagined as an Outlook email extension. Lawyers predominately use Outlook and to ease the adoption curve it makes sense to iterate on top of Outlook rather than build a new platform.
  • This is a more visual approach to getting context from a written communication feed. By using visual elements (layout, color, and iconography) my hypothesis is that more information can be quickly and easily gathered from an email.
  • Built into this design is the idea to connect to other important services that the attorney uses. In this way, the product doesn’t have to compete across a portfolio of features but can be a valuable integration point within the email inbox to other services.
  • Providing lawyers more data on the conversations they are having gives an opportunity for an additional value offering to help firms improve their communication practices (helping their bottom line).
  • Being able to attach notes to the visualized conversation rather than as an additional internal email help to quickly exchange context. This is a feature that I used in Intercom for team collaboration that I found a lot of value from.


So, what do you think? ‌

This was a fun little exercise I undertook to primarily see if I could come up with a concept for myself that could help solve some of the lawyer email communication pain points. I am interested to see what some of the initial responses are to this approach and if it makes sense to continue to iterate on this idea. If it gets a warm enough response, I might continue my user research process to improve the design into more built-out wireframes. Either way, this was a fun project that gave me an excuse to walk through the early product development steps to start to validate assumptions and my hypotheses.

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