Casey Flaherty on Messaging Overload

Messaging overload is not just about the total number of messages. It's also that so many messages are of such low quality.

Casey Flaherty on Messaging Overload

Summary: Messaging overload is not just about the total number of messages. It's also that so many messages are of such low quality.

Casey Flaherty is Co-Founder & Chief Strategy Officer at LexFusion. (LinkedIn)

We were kindly introduced to him by

  • Javier Pablos Sánchez, Director of IT Service Delivery (EMEA) @ Baker & McKenzie. (LinkedIn)
  • Chris Kitterman, Associate Director @ Baker & McKenzie. (LinkedIn)

Recently, Casey took the time to give us his thoughts on the problems of messaging overload, and some suggestions for how we could approach these problems.


1) High-level professionals are inundated with emails and messages. This is a cognitive tax.

2) The way to adapt to the environment of information overload is to carefully make professional connections that a) provide value and b) don't waste time.

3) Buffering access to professionals by charging a fee per message is an interesting approach.

4) But: Professionals really don't want to add friction to their important clients, or people who are potentially important clients. Suggestion: Think about whitelists / blacklists / reputation scores.

5) Many professionals would be embarrassed to make money from charging for their time. Suggestion: Allow them to auto-donate their earnings to a charity.

6) Messaging overload is not just about the total number of messages. It's also that so many messages are of such low quality.

7) The problem of email / messaging is the same as its primary advantage: It's frictionless. The lack of friction leads to overconsumption of the resource.‌‌‌‌

Image generated at Model = Imagine V4, Prompt = "A man in an office, with many screens, looking at many emails and notifications."

Casey Flaherty is very familiar with the problems of operating in a world of information overload.

He has written an informative article, Preview of the LexFusion Second Annual Legal Market in Review, which looks at the problem of runaway legal complexity that affects most of the world's large companies. (Entertainingly, he labels each section with a relevant quote from Game of Thrones.)

Two excerpts from the article:

What is true, underappreciated, and unquestionably annoying is that even businesses that have entered cost-cutting mode may experience a net increase in legal needs because the complexity of the external operating environment continues to explode.
In a rapidly globalizing world, every unit of economic growth carries with it an ever larger burden of legal complexity. Thus, over time, assessing the benefits and protections of law becomes correspondingly more expensive.

A one-sentence description of LexFusion:

  • LexFusion evaluates the congested legal innovation marketplace and selects solutions geared toward helping legal professionals optimize their money, time, and resources.

An interesting excerpt from an interview with Casey in which he explains the value proposition of LexFusion:

I asked Flaherty why an inhouse counsel would want to work through LexFusion rather than directly with the individual companies. He said that a key aspect of LexFusion’s value is in helping its clients begin to navigate the ever-more crowded landscape of legal tech companies.‌‌‌‌

“It’s figuring out which companies you need to talk to in the first instance,” he said. “So many inhouse counsel have done a good job of identifying their problem, but need to find a problem-solution fit, and they’re not entirely clear on what solutions are out there. To whom should they speak first?”

Source: Casey Flaherty Leaves Baker McKenzie To Join Legal Tech Collective LexFusion

The rest of this article contains my notes from our conversation.

Casey recently talked to the CIO of a large global legal firm.

  • Question: "How many unsolicited emails do you receive per day from people asking you for things?"
  • Answer: "Numbers don't go high enough. It's infinite."

The idea of a "gating function" for incoming communication is interesting.

Casey's business is trust. He never wastes someone's time, ever. This means that people can trust his advice and suggestions. "I have a business because everyone is operating in information overload."

The way to adapt to the environment of information overload is to intentionally make professional connections that a) provide value and b) don't waste time.

"Almost anyone in a buying position in a very significant law firm (~1000 of these in the USA) is receiving approximately 100-500 unsolicited emails per day."

-> "There is no spam filter good enough to deal with this."

Suggestion for Tela: Track everyone's response rate. Then you can see at a glance if the person that you're writing to is likely to respond, or not.

Issue: What about people that I trust ? Should they really have to pay to contact me ? I.e. a whitelist or "safe list".

-> What about people who work for an organisation that I trust ? E.g. their emails are sent from the Baker McKenzie domain ? Perhaps a listed of trusted identities / domains / companies ?

-> What about people who are publicly notable ? If the CEO of a large firm wants to contact me, I don't want to make that difficult for him.

Top professionals: Their inboxes are inundated, and it drives them crazy. If there was a spam filter for this, people would pay just for that.

With Tela, the filtering is manual, which takes effort, but if it's paid, then it's true that there's an incentive to make the effort.

"What are the prices for sending someone a message on Tela ? How much will these prices vary ?"

Fundamental issue: "I don't want to add friction to the people who matter."

Problem: How to determine who matters, and more specifically, who matters to you personally ?

The problem with email is the same as its primary advantage: It's frictionless. So the lack of friction leads to overconsumption / overuse.

Nicholas Piano: The message fee buffers access to attention. It's not just a way of making money.

Casey: I see. Hm. A lot of people I know would be embarrassed to make any income from this... What about auto-donating to a charity ? E.g. Many legal firms work with pro-bono charities that tackle societal problems.

Legal firms try very hard to remove any friction between themselves and a client (or a potential client). "What about a blacklist, instead of a whitelist ?"

Another interesting question: What level of budget do sales companies really have for contacting prospects ? If it's low, and they had to pay for sending messages, perhaps they'd move to sending email only to very specific people, rather than contacting everyone in the organization.

By adding friction, the total volume of email traffic could be reduced...

Demographics other than lawyers will have different incentives. For example, serious hobbyists might be perfectly happy to publicly charge for responding to messages - this would fund their hobby.

Suggestion for Tela: Use an LLM that studies my previous answers to suggest responses. "Then I can use that as my starting point for answering a new question."

Casey notes that every new company raising money at the moment has to provide their AI strategy.

However, a caveat: "The unauthorized practice of law". An LLM cannot legally provide legal advice - only a licensed lawyer can do this. This is a sensitive area at the moment.

Obviously, this whole issue isn't just an email overload problem. It's a general issue - we keep adding more and more platforms and communication tools, and each new system makes the overload worse.

Every message is a cognitive tax. This tax keeps getting higher.

The problem is not just the number of messages. It's that the sender often puts little effort into the message - so most of the messages are low-quality.