I like technology. I like good engineering. I even like some legal tech products. What I do not like is most legal tech marketing.
Not because it fails to generate clicks or demos. It clearly does that. I dislike it because it is often fundamentally misaligned with how lawyers actually build trust, assess risk, and decide what they are willing to put their name on. It signals the wrong things, to the wrong people, in the wrong way, and then acts surprised when lawyers remain unconvinced.
Here are ten recurring failures.
- You Do Not Understand How Peer Recommendation Actually Works
Lawyers do not adopt tools because they saw a compelling demo. They adopt tools because another competent lawyer they respect quietly said “we’re using this and it’s fine”. That is how goodwill moves in the profession. It is slow, informal, and deeply human.
You cannot shortcut that with testimonials written by marketing teams. You cannot replace it with logos on a slide. Lawyers trust other lawyers because reputational risk is shared. If your marketing strategy does not centre peer usage and renewal, you are optimising for attention, not adoption.
- Your Comparison Pages Are Unprofessional
Comparison pages are not just ineffective. They are actively off-putting.
Lawyers are trained not to disparage the profession. We might gossip like a knitting circle behind closed doors, but publicly we speak about our “friends” with “the greatest of respect” (hint: those phrases typically mean the opposite). Marketing pages that implicitly mock competitors signal poor judgment.
They read as insecure and juvenile. They are not the “done” thing.
If your product is genuinely better, lawyers will work that out for themselves. If it is not, a comparison table will not save you.
- You Think Awards Matter
They do not – for you. The only awards lawyers care about are the ones that tell them where they sit in the ecosystem. If Doyle’s Guide ranks them, that matters. If your product wins a “Legal AI Innovator of the Year” award handed out by a conference sponsor, it does not. Random, paid-for industry awards look naff. They impress investors. They do not move lawyers. But if your product gets listed in Doyles Guide as a leading lawyer in its field, sure put that down.
- Your Sales Copy Reads Like AIDA Fan Fiction
Attention. Interest. Decision. Action.
This might work for selling gym memberships. It does not work for selling tools lawyers will rely on in professional work. “Transformative”, “game-changing”, and “unlocking value” are not persuasive. They are red flags.
Coffee is for closers works in Glengarry Glen Ross. Law is not sales theatre. Inflated language signals imprecision, and imprecision is poison in a profession where words have consequences.
- You Were Not Founded by Lawyers and It Shows
This is not an argument that only lawyers should build legal tech. It is an argument against pretending to understand legal workflows when you do not. Microsoft was founded by non-lawyers and it is the greatest legal tech company – but they don’t pretend to be lawyers.
Lawyers immediately notice when someone does not grasp version control anxiety, precedent gravity, or the asymmetric cost of getting something wrong. Marketing that glosses over those realities tells us the product probably does too.
- Your Thought Leadership Is AI-Generated and We Can Tell
Lawyers argue for a living. We can hear when a piece of writing has no stake in what it is saying.
AI-generated articles that avoid positions, avoid specificity, and avoid the possibility of being wrong are not thought leadership. They are content padding. They do not build trust. They erode it.
- You Comment “Try X” Under Every LinkedIn Post
Who thinks this works? This is not networking. It is spam. And it is almost always the behaviour of a non-lawyer founder who has not spent time watching how professionals actually interact.
All it does is train lawyers to associate your brand with annoyance.
- You Ask for a Coffee Instead of Sending the Details
Lawyers are busy. If you want to pitch, send the information. Let us read it. Let us decide.
The ritualised coffee request signals that the pitch cannot stand on its own merits. That is rarely a good sign.
- You Hide Your Pricing
Lawyers have statutory and ethical obligations to give cost disclosures and estimates. We operate in a world where pricing is difficult, nuanced, and heavily regulated.
When a legal tech company pretends pricing is impossibly complex and must be hidden behind a sales call, it looks unserious. Choosing a number between one and a thousand and adding “per user per month” is much easier than the disclosure regimes lawyers have to abide by. So if we can manage to give our fee estimates, you can give us a number too. Price is an important part of an “invitation to treat” – if those words mean something besides Halloween to you.
- You Sell Software When Lawyers Want You to Hold Their Hand
This is a core failure. Lawyers do not want another plugin. They want outcomes. They want someone to set the system up, tune it, explain it, and stand behind it. Their time is more valuable than yours or your team’s. If your business model assumes self-serve adoption and hides support behind a helpdesk, you have misunderstood the market.
We do not need your software. We need you to make it work. And yes, showing lawyers how to use your product may feel like helping your ageing grandfather set up his phone. It can be slow, repetitive, and occasionally frustrating. But if you do not absorb that pain, the lawyers have to. And at that point the economics become very clear very quickly, because guess who has the higher hourly charge-out rate.
The Punchline
After doing all this wrong, many legal tech companies complain that lawyers are dinosaurs, resistant to change, or afraid of AI. They are not. What lawyers resist is being talked down to by people who do not understand their profession, their risks, or their incentives. This is not a failure of lawyers to adapt. It is a failure of legal tech marketing to understand the industry it is trying to sell to.
The irony is that many of these products are better than their marketing suggests. But lawyers do not buy potential. They buy credibility, earned slowly, through behaviour, not slogans.
If you want lawyers to use your product, stop trying to impress them and start trying to understand them.