iiinova — where your digital self keeps evolving

Ryan McKeen @ryanmckeen.bsky.social · 1h

Technology isn't neutral. It takes on the character of the people who build it, buy it and use it. A firm with careless habits will use AI carelessly. Fix the habits first.

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Ryan McKeen @ryanmckeen.bsky.social · 4h

Don't ask "Which AI tool?" first. Ask "Which problems do our clients actually have?" Then ask what, if anything, a tool adds. Tools follow purpose.

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Ryan McKeen @ryanmckeen.bsky.social · 6h

Law firms are about to learn what hospitals learned from checklists. Simple, boring rules, written down, followed every time. That's how you stay safe around powerful tools.

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Ryan McKeen @ryanmckeen.bsky.social · 8h

The whole point is dehumanization and normalizing live streaming the state killing of people. I pray 🙏 our political leaders choose a different path.

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Ryan McKeen @ryanmckeen.bsky.social · 8h

You don't need an AI strategy deck. You need a Tuesday meeting. One question. "What did AI help with this week, and what did it get wrong?"

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Ryan McKeen @ryanmckeen.bsky.social · 19h

Lawyers love certainty. AI doesn't offer any. The firms that learn to work well without a final answer will beat the ones waiting for one.

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Ryan McKeen @ryanmckeen.bsky.social · 21h

Referrals aren't luck. They're relationships you tended before anyone needed you. Start tending.

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Ryan McKeen @ryanmckeen.bsky.social · 23h

Another day, another court win, and one step closer to justice. Praise the Lord. civilinquiry.jud.ct.gov/DocumentInqu...

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Ryan McKeen @ryanmckeen.bsky.social · 23h

Pope Leo XIV flags two traps in personal AI use: how easy the results are, and how objective they seem. Both can weaken judgment. Lawyers, easy and objective-sounding is exactly when to slow down.

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Ryan McKeen @ryanmckeen.bsky.social · 08/10/2026

The most useful thing a firm leader can say right now is "We're figuring it out." Then set a weekly meeting where everyone does.

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Ryan McKeen @ryanmckeen.bsky.social · 08/10/2026

Every firm needs someone who owns this question. Not the IT person. Not the intern. A lawyer with authority, curiosity and patience. Messy middles need a captain.

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Ryan McKeen @ryanmckeen.bsky.social · 08/10/2026

A simple test for any AI use in your firm. Could you explain it to the client? To the judge? To your own mother? If not, stop.

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Ryan McKeen @ryanmckeen.bsky.social · 08/10/2026

Lawyers, the speed AI gives you is a loan. You pay it back in checking. Skip the checking and the interest is brutal.

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Ryan McKeen @ryanmckeen.bsky.social · 08/10/2026

Pope Leo XIV offers a test for any new technology. Does it help people become more humane and fraternal? Ask your firm's version before every AI purchase. Does it help us serve clients better and treat each other better?

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Ryan McKeen @ryanmckeen.bsky.social · 07/10/2026

Credibility is currency for lawyers. And unlike money, once you spend it, you can't earn it back at the same rate.

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Ryan McKeen @ryanmckeen.bsky.social · 07/10/2026

A tool rollout isn't a training program. A login isn't a skill. Teaching people when to trust the output and when to doubt it is the actual job.

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Ryan McKeen @ryanmckeen.bsky.social · 07/10/2026

Most of what's hard about AI at a firm is conversation. Partners and associates. Lawyers and staff. Hallway arguments about what's okay. Have those conversations on purpose.

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Ryan McKeen @ryanmckeen.bsky.social · 07/10/2026

Lawyers keep asking, "Will AI replace us?" Better question: "What are we choosing to hand over?" Replacement is a choice before it's an event.

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Ryan McKeen @ryanmckeen.bsky.social · 07/10/2026

AI belongs in the draft. It doesn't belong in the decision. Draft fast. Decide slow. That one rule gets a firm through most of this.

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Ryan McKeen @ryanmckeen.bsky.social · 07/10/2026

Lawyers, sort every task in your firm into three piles. AI can do it. AI can help. Only a human should. The third pile is your firm's soul. Protect it.

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Ryan McKeen @ryanmckeen.bsky.social · 07/10/2026

Lawyers, spend the first hour of your day on one person, not your inbox. Call a client. Thank a staffer. Teach an associate. The inbox will still be there.

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Ryan McKeen @ryanmckeen.bsky.social · 07/10/2026

Pope Leo XIV notes that today's AI systems are more "cultivated" than "built." Developers create a framework, and the system grows inside it. For a law firm, that means test before you trust. Every time.

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Ryan McKeen @ryanmckeen.bsky.social · 06/10/2026

Lawyers, a task list beats a tool list. Write down what your firm actually does all day. Then sort it. Machine. Human. Both. That page is worth more than any demo.

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Ryan McKeen @ryanmckeen.bsky.social · 06/10/2026

Spent 2 days in work with an amazing law firm and outside of signs that say Roma, this is my favorite sign of all.

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Ryan McKeen @ryanmckeen.bsky.social · 06/10/2026

Nobody gets this right on the first try. Firms will struggle, argue and backtrack. Good. The struggle is the training. Skip it and you've skipped the learning.

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Ryan McKeen @ryanmckeen.bsky.social · 06/10/2026

Lawyers, think of AI as a new associate who read everything and has never met a client. Brilliant. Fast. No judgment about people. Supervise accordingly.

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Ryan McKeen @ryanmckeen.bsky.social · 06/10/2026

The firms that win this decade won't have the best AI. They'll have the clearest answer to what AI is for, and what it isn't for.

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Ryan McKeen @ryanmckeen.bsky.social · 06/10/2026

Nobody fully understands how these systems work. Not the vendors. Not the lawyers. That isn't a reason to avoid AI. It's a reason to test it, write down what you learn and stay humble.

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Ryan McKeen @ryanmckeen.bsky.social · 06/10/2026

Lawyers, stop going to conferences to collect business cards. Go to have one real conversation. One is enough. It can change your whole career.

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Ryan McKeen @ryanmckeen.bsky.social · 06/10/2026

Lawyers, "What should AI do here?" is a business question. "What should AI never do here?" is a character question. Firms need both answers.

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Ryan McKeen @ryanmckeen.bsky.social · 06/10/2026

A firm without an AI policy still has an AI policy. It's whatever each lawyer decided alone at 11 p.m. Write it down.

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Ryan McKeen @ryanmckeen.bsky.social · 05/10/2026

The messy middle of AI in law is a list of unglamorous questions. What matters here? What's important? What should the machine do? What should it never do? Answer them in writing.

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Ryan McKeen @ryanmckeen.bsky.social · 05/10/2026

Law firm owners, buying the tool is the easy part. Deciding what it's for is the work. Tools have no point of view. Your firm has to.

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Ryan McKeen @ryanmckeen.bsky.social · 05/10/2026

Every firm is asking the same question. What should AI do here? Start with the better one. What must stay human? Work backward from there.

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Ryan McKeen @ryanmckeen.bsky.social · 05/10/2026

Lawyers who aren't jerks get better results.

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Ryan McKeen @ryanmckeen.bsky.social · 05/10/2026

Pope Leo XIV writes that everyone, including the people who design AI, understands only part of how it works, and that anything said about AI risks going stale fast. If the builders are humble, lawyers can be too. Start where you are.

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Ryan McKeen @ryanmckeen.bsky.social · 05/10/2026

Nobody has the answer for AI in law firms. That's not a reason to wait. It's the reason to start working it out together.

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Ryan McKeen @ryanmckeen.bsky.social · 05/10/2026

Lawyers, the hard part of AI isn't the technology. It's the messy middle. What matters. What AI should do. What it should never touch. Someone has to decide. That someone is us.

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Ryan McKeen @ryanmckeen.bsky.social · 04/10/2026

Lord, make me an instrument of your peace: where there is hatred, let me sow love; where there is injury, pardon; where there is doubt, faith; where there is despair, hope; where there is darkness, light; where there is sadness, joy. -St. Francis

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Ryan McKeen @ryanmckeen.bsky.social · 04/10/2026

AI is rapidly reshaping the legal profession. Jobs that exist today won’t exist in the near future. Here’s the good, the bad, and the better of that…. lnkd.in/p/gp__SRpz

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Ryan McKeen @ryanmckeen.bsky.social · 02/10/2026

In the world’s smallest FU to Peter Thiel - I bought 40 copies of Pope Leo’s Encyclical Letter on AI “Magnifica Humanitas” for my church. Team Leo.

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Ryan McKeen @ryanmckeen.bsky.social · 30/09/2026

My favorite prayer. Wishing all who celebrate a Michaelmas. St. Michael is my confirmation saint. Total baller.

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Ryan McKeen @ryanmckeen.bsky.social · 30/09/2026

If you’re an employer and you pressure women employees to do drugs - you’re a Cornell frat boy with a degree on their wall.

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Ryan McKeen @ryanmckeen.bsky.social · 30/09/2026

When someone turns away from God the result is chaos.

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Ryan McKeen @ryanmckeen.bsky.social · 29/09/2026

Fuck every aspect of society that protects abusers. Ban NDAs and arb clauses in employment law. Name names. And fuck those who are complicit through silence.

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Ryan McKeen @ryanmckeen.bsky.social · 29/09/2026

And the story is so often the same. Men pressuring women to do drugs so they can rape them.

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Ryan McKeen @ryanmckeen.bsky.social · 29/09/2026

And professionals, if you’re someone’s boss and you try and sleep with them - you are a Cornell frat boy in a corner office.

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