Recent articles
Our contracts are too complicated for AI, right?
Paul Lacey
A personal piece: AI made my juniors as fast as my seniors but..
Martin Lukac
How the best legal teams supervise agents (incl. practical tips)
Laura Morris
Just throw (artificial) intelligence at it, right?
Khaled Baroudi
The agent rollout mistake GCs keep making
Taariq Ismail
A personal piece: figuring out what AI can't do for me
Lorna Khemraz
Archive
2026
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Paul Lacey
Our contracts are too complicated for AI, right?
GCs are half right. Complex drafting is two problems, reading the deal and assembling the document. Insights from an enterprise deployment.
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Martin Lukac
A personal piece: AI made my juniors as fast as my seniors but..
A personal piece on managing a team the agents flattened.
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Laura Morris
How the best legal teams supervise agents (incl. practical tips)
We all know how to supervise people. Supervising agents can’t be that much harder, right?
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Khaled Baroudi
Just throw (artificial) intelligence at it, right?
A brief reflection on the commoditisation of intelligence in legal work.
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Taariq Ismail
The agent rollout mistake GCs keep making
Why the requirements document is the wrong starting point.
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Lorna Khemraz
A personal piece: figuring out what AI can't do for me
On being a misfit, shedding the expert label, and the one part of the job I won't hand over.
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Jake Jones
Can you trust your system of record?
Keeping a contract record honest is a full-time job that nobody has.
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Lorna Khemraz
The AI budget line that decides your ROI
For GCs and legal ops leaders deciding where the AI budget goes next.
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Khaled Baroudi
Are you about to automate the wrong thing?
Sort the pile by what you're doing, not what the document is called, and the right first workflow shows up.
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Taariq Ismail
The agentic contract repository GCs are talking about
The cheapest task in legal never gets done, and it's quietly the most expensive one to skip.
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Martin Lukac
Should every contract get the same review?
The trap is checking everything at the same price, whatever the risk.
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Paul Lacey
Why your AI spend hasn't cut costs
and how it could.
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Jake Jones
Are we just accepting that legal is a bottleneck?
How to move the work and resolve the bottleneck.
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Lorna Khemraz
Why your lawyers re-read the agent's work
What a lawyer needs before putting their name behind an agent's work.
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Khaled Baroudi
Sort your AI worries into two piles
..and what a Roman emperor knew about it.
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Taariq Ismail
What your first month with a legal agent looks like
And why the first thing an agent does is hold up a mirror, and why that's the point.
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Martin Lukac
How the best teams buy legal AI
Stop judging legal AI by the demo. Judge it by an ordinary Tuesday.
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Paul Lacey
Which legal work should you automate first?
Choosing the first use case is a strategic bet, not a scoping exercise.
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Lorna Khemraz
When your AI vendor's model gets pulled
The model your vendor runs is a risk you can close with the paper already in front of you.
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Flank
Legal engineering pioneer Alistair Maiden joins Flank
Flank doubles down on its agents-as-a-service model, bringing in one of the most influential operators in the field.
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Jake Jones
How the best legal teams handle intake
What separates the teams that fixed intake from the ones still drowning in it.
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Jake Jones
The Front Door Your Legal Team Already Has
In-house intake processes are messy. This is especially true at the enterprise level. Vendors rarely understand quite how chaotic intake and triage is, and they sell elegant solutions that would be a perfect fit, if only the way the…
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Lorna Khemraz
How to contract around AI model dependency
Most of your AI vendors are running on a model they do not own, and your contract with them almost certainly does not say what happens when that model changes. That gap is one of the most underpriced risks in software procurement right…
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Taariq Ismail
What legal teams get wrong about drafting vs review
Two product categories. One actual job. Here's why that matters.
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Taariq Ismail
Contract drafting and review were never separate jobs
The market sells drafting and review as separate capabilities. The work was never divided that way, and the contract workflows being deployed now make the split impossible to maintain.
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Jake Jones
The headless worker
Today's legal AI gives your team a better place to do the work. I think the next stage does the work for them and hands back the outcome. To make that case I have to talk, briefly, about Flank.
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Jake Jones
Is this the next stage of legal AI?
Today's tools make your lawyers faster. The next stage takes the work off their desk entirely.
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Paul Lacey
The middle of the job is disappearing
A few weeks ago our product designer came to me and told me he was having a crisis. Not a vague one. He sat down and said, fairly directly, that it felt like his role had changed underneath him and he was not sure what was left of it.
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Paul Lacey
What legal work does Claude do well?
AI doesn't replace roles evenly - it hollows them from the middle.
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Lorna Khemraz
Looks great from a distance
A few weeks ago I ran one of the AI automations I use to speed up a chunk of my own work. It started generating immediately. The output was structured, the tone was close, the length was right. For the first forty seconds I thought: this…
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Lorna Khemraz
How to go from AI pilot to business results
The sequencing, measurement, and expertise that separate pilots from outcomes.
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Martin Lukac
What GCs should evaluate in legal AI
Every vendor's demo looks sharp. The difference shows up at week six.
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Martin Lukac
Anyone can build the harness now
A few weeks ago I watched a general counsel run a clause past Claude over breakfast. She had a redline from a counterparty, an indemnity carve-out that did not sit right, and forty-five minutes before her first call. She pasted the clause…
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Taariq Ismail
The Quiet Conversations GCs have about AI
Notes from The Lawyer's GC Summit in Alicante, May 2026
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Lorna Khemraz
How to turn AI FOMO into a plan
Why the only thing that resolves the AI FOMO is a plan that is yours.
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Paul Lacey
We built the product at her desk
Why faster AI makes being in the room more valuable, not less.
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Martin Lukac
The build vs. buy answer every GC needs right now
What coding agents changed about the build vs. buy decision, and why the answer is still buy.
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Taariq Ismail
Your team reviews every NDA twice
52% of legal teams use AI. 7% have moved the spend number. The architecture explains the difference.
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Jake Jones
The eight principles of a highly effective legal team
What an enterprise legal function should look like when headcount stops being the constraint.
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Lorna Khemraz
The end of the billable hour
Output is no longer scarce. The question is what the lawyer's hour was always for.
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Paul Lacey
What your legal ops dashboard is actually measuring
The data is there. The surface to make it useful isn't.
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Taariq Ismail
The one question to ask every legal tech vendor in 2026
Most legal ops leaders aren't asking it yet. In two years, it's the only one that will matter.
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Lorna Khemraz
Claude reviewed the contract. Legal didn't.
AI knows contract law. It doesn't know your company.
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Lorna Khemraz
Your juniors aren't learning
Legal training worked through proximity, observation, and correction. All three are breaking.
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Paul Lacey
We watched a GC fix his own playbook
The playbook had a gap. The agent found it.
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Jake Jones
The Weakest Square (pt. 2)
The erosion of human endeavour by agentic automation.
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Taariq Ismail
"Faster NDA review" is the wrong job
Why most legal AI pilots solve an activity, not a need.
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Martin Lukac
Try something worth breaking
Why the absence of failure in legal AI is itself a failure of ambition.
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Paul Lacey
Legal AI doesn't scale without a front door
The front door is how legal AI stops being a pilot and starts being a production system.
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Taariq Ismail
Your AI rollout has a people problem
Change management is the variable nobody budgets for.
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Lorna Khemraz
Most legal agent failures are not actually agent failures
Why the deployments that 'failed' were never built to succeed.
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Martin Lukac
Legal AI has an infrastructure problem
Why 52% of legal teams adopted AI but almost none reduced costs.
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Jake Jones
The Weakest Square (pt. 1)
A nine-year-old beats six boys with a four-move algorithm. Decades later, machines prove that even intuition is computable.
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Taariq Ismail
Just pick one thing
Why most legal AI pilots fail to move out of pilot stage.
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Paul Lacey
Why your AI rollout will stumble and why that's the plan
The real risk profile of scaling AI agents: the jagged edge is structural, not temporary, but recovery is measured in minutes.
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Jake Jones
Your external legal spend is the budget for agents
The services line item that enterprise legal teams are starting to reallocate.
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Taariq Ismail
These legal tech investments will still matter in three years
The same capability that makes legal software better eventually makes it unnecessary. The question is which layer you're buying.
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Martin Lukac
Same engine, different machine
Why better AI doesn't mean a better model.
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Lorna Khemraz
Knowing what to automate is the easy part
Legal teams can name what to automate instantly. The hard part is building the reliability and scalability infrastructure around it.
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Paul Lacey
We gave an agent our hardest problem
Why enterprise contract complexity is no longer a ceiling for AI agents.
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Lorna Khemraz
What “it depends” is hiding
How operational chaos masquerades as legal complexity, and what happens when you separate the two.
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Martin Lukac
Same engine, different machine
Every legal AI product runs on the same handful of LLMs. The staggering difference in output quality is entirely a product problem.
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Paul Lacey
The complexity ceiling is higher than you think
Enterprise contract complexity is no longer a ceiling for AI agents. The boundary is moving fast.
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Jake Jones
The ChatGPT Moment for Legal Agents
The week legal AI stopped being theoretical
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Jake Jones
Three economic models, one technology
The legal services market is three markets with different economic engines. Agents will hit law firms, ALSPs, and in-house teams very differently.
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Jake Jones
The Throughput Problem
The throughput problem nobody is measuring
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Sam Oliver
Beyond hype: why ROI will define Legal AI in 2026
For the past few years, the legal industry has been in a phase of exploration. We have seen firms and in-house teams adopting Generative AI tools largely for the novelty factor – testing the waters to see what is possible.
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Sam Oliver
Eating mashed potato: why AI will save lawyers from boredom, not their jobs
There is a pervasive fear that autonomous AI replaces the need for legal expertise. The reality is the opposite: it clarifies the value of true expertise by stripping away the drudgery.
2025
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Sam Oliver
How to scale legal operations without hiring a single lawyer in 2026
For decades, the economic model of the in-house legal team has been broken. It was a linear equation, but not any more.
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Sam Oliver
Silence in the inbox: the rise of 'invisible' autonomous agents
The ultimate measure of success for a legal AI deployment in 2026 is not how many lawyers are logging into a tool. It is whether the business users even know the tool exists.
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Sam Oliver
Why reasoning models are the missing link for transforming legal
For the last two years, lawyers have been told that AI is "almost there". Yet, in private, the reality has been different.
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Lilian Breidenbach
The Great Decoupling: how 2025 changed the legal AI paradigm
If 2024 was the “Year of the Pilot”, a time of cautious experimentation, proof-of-concept projects, and learning what works, then 2025 marked the beginning of the shift.
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Sam Oliver
Introducing Flank: agentic legal AI that resolves legal requests autonomously
Flank is the first enterprise-ready agentic system built for legal work. Instead of assisting lawyers; it handles the work itself: reviewing, drafting, redlining, triaging, and filing across the systems your team already uses such as Outlook, Teams, Jira, and Salesforce.
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Lorna Khemraz
Legal AI Alignment: Why Judgment, Not Just Automation, Matters
This post explores how to build aligned legal AI agents that reflect context, escalation paths, and layered decision-making - not just outputs. That's because useful legal AI isn’t just about automation. It’s about understanding how lawyers think.
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Lilian Breidenbach
Flank Raises $10M to Scale Autonomous Legal Agents — Embedded, Invisible, and Built for the Enterprise
Trusted by DeepL, Bolt, SumUp, TravelPerk, Axel Springer and more.
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Lorna Khemraz
Legal Ops Was Never About Control
What if legal ops wasn’t just about efficiency, but about changing how legal teams think and lead? In this conversation, Yesenia Santiago Egner shares why the future of legal ops is about mindset, not just mechanics.
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Lorna Khemraz
What is Agentic AI and What Does it Mean for Legal?
How is agentic AI transforming legal work? Unlike traditional AI, agentic AI can set goals, take action, and iterate with minimal human input. From automating contract reviews to drafting arguments, it's reshaping legal workflows. But how…
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Lorna Khemraz
Rethinking the Legal Career Path with Henry Nelson-Case, aka @ThatCorporateLawyer
The legal career path is evolving, and Henry Nelson-Case—aka @ThatCorporateLawyer—is proof. From viral content to TEDx talks, he’s challenging outdated industry norms, pushing for mental health awareness, and redefining what it means to be…
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Lorna Khemraz
The Hard Truth About Legal AI Adoption with Peter Duffy
AI is here, but legal adoption is just beginning. How are forward-thinking legal teams moving beyond the hype, embedding AI into workflows, and unlocking its potential to transform legal work, making it faster, smarter, and more strategic?…
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Lorna Khemraz
AI, Automation & Agile Innovation: Andrew Krug on Legal Ops at Twitch
How do you bring an engineering mindset to legal ops? Andrew Krug, Head of Legal Ops at Twitch, shares how AI, automation, and agile thinking are transforming how legal teams work - helping them prioritise smarter, move faster, and stay…
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Lorna Khemraz
Stop Pretending: Leila El Gharbi on Authenticity, AI, and Transforming the Legal World
Yes, AI is taking legal work, especially the grunt kind. In this episode of Mind At Work, Leila El Gharbi unpacks how AI is transforming in-house legal from reactive to proactive, why resistance to legal tech is really a trust issue, and…
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Lorna Khemraz
Legal Ops Conferences 2025: The Best Events for GCs & Legal Ops Leaders (+ Full Calendar)
If you’re serious about legal innovation, the best insights won’t come from another whitepaper—they’ll come from the right conversations. That’s why we’ve put together a 2025 calendar of must-attend legal innovation events to help you…
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Lorna Khemraz
How Human Skills and AI Are Shaping the Future of Law
AI is reshaping legal, but human skills—resilience, creativity, and empathy—remain irreplaceable. In our latest episode, Claire Sanders shares how embracing a "squiggly career" and leveraging AI can unlock human potential rather than…
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Lorna Khemraz
AI: More Than Just Hype, It’s History in the Making
AI is revolutionising innovation as we know it. At Flank’s Hungry Counsel AI Summit, Oliver Yonchev unpacked its transformative power—from sparking creative breakthroughs to reshaping the way we work. His message was loud and clear: AI…
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Lorna Khemraz
From Bottlenecks to Breakthroughs: GWI's Legal Ops Transformation with AI
Managing thousands of queries with a small legal team was a constant challenge for GWI—until they discovered the power of automation. Here’s how they used AI to cut response times from weeks to seconds, freeing up their team to focus on…
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Lorna Khemraz
Effie Dower on How to Lead with Connection and Innovation In-House
Discover how strategic innovation can transform your legal operations and position your team at the forefront of technological advancement.
2024
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Lorna Khemraz
How AI is Redefining Law, Creativity, and Contracts
Imagine a world where legal professionals spend less time buried in paperwork and more time driving strategic decisions. AI isn’t just streamlining routine tasks—it’s reshaping the very nature of how we approach creativity, contracts, and…
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Lilian Breidenbach
The Human Element in AI: Redefining Legal Roles, Scaling in Enterprises, and Leading in 2025
Jake Jones and Richard Mabey delve into the future of legal work, balancing AI automation with human nuance, overcoming enterprise adoption challenges, and shaping the next generation of in-house legal teams.
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Lilian Breidenbach
Building Agents, Tackling RAG, and Finding Early Adopters
Jake Jones and Richard Mabey unpack the challenges of building autonomous legal agents, the limitations of current technologies, and the mindset shifts driving innovation in this masterclass on product thinking.
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Lilian Breidenbach
The Evolution of Legal Tech and AI Agents
Discover the origins of Flank and the shift to legal automation that changed the game. Jake Jones and Richard Mabey explore co-pilots, autopilots, and the human quality of legal services in this deep dive.
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Lilian Breidenbach
The Power of New Technologies: What History Has Taught Us So Far
What do lawyers and horses have in common?
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Lorna Khemraz
AI Is Changing the Law Faster Than You Think
How to develop a unique advantage when the legal industry is being completely transformed by AI?
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Lorna Khemraz
Forget Cost Centre, Legal is a Strategic Powerhouse and Here’s How
Legal departments have suffered from a bad rep for a long time, but this perception can be completely transformed. Here's how.
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Lorna Khemraz
Understanding AI: A Simple Glossary
Want to know more about AI but don’t have much time to spend learning all the lingo? Read this instead.
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Lorna Khemraz
Charlotte's Story: From a Serendipitous Childhood Ski Trip to Co-Founding Flank
A chance meeting on a ski trip sparked a lifelong friendship and a revolutionary AI venture. Dive into Charlotte Kufus' story and what led to Flank’s cutting-edge success.
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Lilian Breidenbach
How to Deploy AI for In-House Legal
Find out how to unlock the power of AI in your organisation with these practical tips on how to deploy GenAI for legal and other expert teams.
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Jake Jones
Navigating Automation in Enterprise: Challenges, Opportunities, and Best Practices
Discover how enterprises can effectively implement automation and AI by retrofitting capabilities into existing workflows for seamless integration and high adoption rates.
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Lorna Khemraz
How AI Will Transform Organisation Dynamics And Why We'll Still Need Lawyers, With Gett's Eleanor Luker
"I can't see [lawyers] being redundant any time soon...Until AI can understand the politics of a fraught meeting including various stakeholders, their own political agenda and how lawyers deftly navigate this, I think they can rest easy."
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Lorna Khemraz
Why Tolerating Friction is Self-Destructive
There's a hidden message in everyday noise. If you pay attention, you can grab the smallest opportunities to make a big difference in your day-to-day. Here's how.
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Lorna Khemraz
Customer Success: TravelPerk's Enterprise-Wide Empowerment Through AI Integration
The team at TravelPerk have been on the cutting edge of innovation, experimenting steadily and leading the way when it comes to re-imagining in-house legal. Read about their success in this article.
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Lilian Breidenbach
Why we need to move on from RAG
RAG is great but not enough on its own. Here's what you actually need.
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Lorna Khemraz
Rethinking Law and AI: The Transformative Vision of QA’s General Counsel
"A GC who knows AI, knows the tech, and who can relate to stakeholders, from the position of trust and confidence, are the individuals who will thrive...". Read on to find out about Phil Young's innovative take on the role of a General…
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Lilian Breidenbach
A new model every day: Demystifying the evolution of foundation models
Flank's Jake Jones and Marcel Marais discuss the latest foundation model releases and their impact on AI product development.
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Lilian Breidenbach
Free strategy advice for law firms with Andy Cooke – Part Two
Confronting radical uncertainty, quitting the grind, fostering customer delight.
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Lilian Breidenbach
Flip the Script: Disruptive Strategies in Legal Ops
Imagine a world where legal operations not only support but drive strategic business decisions. A world where the implementation of generative AI is not just an option but a necessity to stay competitive. Welcome to the future of legal…
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Lorna Khemraz
Customer Success: How Leading Business Intelligence Firm Lusha Streamlined Their Legal Processes with Flank AI
Read on to find out how Lusha, the business intelligence organisation, leveraged Flank AI agents to allow its business departments to self-serve on expert support.
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Lilian Breidenbach
Same Same But Different – Unblocking Commercial Teams with AI Agents
Unlock the full potential of your commercial teams with AI agents. This solution, adopted by many expert teams, handles repetitive tasks to unblock commercial teams. It frees up business departments to focus on strategic growth initiatives.
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Lorna Khemraz
Navigating AI Policy: Key Insights and Practical Tips for Enterprises
AI Policy in enterprise: the key considerations to bear in mind and some guidance as to where to start.
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Lorna Khemraz
How Lusha Deployed AI Agents
This is how a B2B tech company optimised for GenAI and successfully rolled it out.
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Lilian Breidenbach
Are AI Assistants Safe to Use?
What the risks with AI assistants are and how to mitigate against them.
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Lilian Breidenbach
Legal OS becomes Flank
May 21st, 2024 – Legal OS has rebranded as Flank and unveiled its mission to eliminate drag in commercial workflows. Twelve months ago, Legal OS introduced the first steerable legal assistant for commercial teams. Since launch, Legal OS…
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Lilian Breidenbach
How to boost your career as a legal counsel in a fast-growing company
Are you a legal counsel in a fast-growing tech company? This is how to secure your role, boost your career, and elevate your team's impact on the companies' growth. Become the AI champion in your organisation and get recognised for it –…
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Lorna Khemraz
AI Regulation and Governance made simple (yes, that's possible!) with Emma Haywood
Read on for the key principles of AI Regulation and Governance and an understanding of how different jurisdictions around the world are balancing the risks and opportunities of AI.
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Lilian Breidenbach
What is GenAI? How does it differ from traditional AI? Why does it matter?
GenAI VS AI - what's the difference? Read on to find out.
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Lorna Khemraz
What On Earth Is A GenAI Use Case?
Read on for an easy-to-follow guide to finding a GenAI use case.
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Lilian Breidenbach
Removing Friction: Using Gen AI to Find, Hone and Generate Data
What are the quick wins with GenAI? How can you leverage data to optimize for GenAI deployment? How can you use data to hone processes and create efficiencies?
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Lorna Khemraz
Legal tech is SO 2020. Here's why.
For tech to be truly impactful and effective, it needs to be solving for an organisation, not nurturing siloes. Why is legal specific tech an outdated notion? What should tech companies be focusing on instead? Where is the real power of AI?
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Lilian Breidenbach
“Doing more with less” - the most overused euphemism for drowning legal teams
"Doing less with less" - for legal teams who want to empower their business functions to receive legal expertise on demand, reduce workload, manage risk, and work smarter. How to put this into practice is illustrated using the example of…
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Lorna Khemraz
The Biggest Red Flags in Legal Ops and How to Navigate Them
Tips for Legal Ops success. How to choose the best solution and the secrets for successful implementation.
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Jake Jones
How to Get Great Responses from RAG Tools: Content Curation
The success of a RAG system is deeply intertwined with the quality and curation of the data it's fed. By embracing the ethos of meticulous content curation, businesses can unlock the full potential of retrieval augmented generation tools
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Lorna Khemraz
The Anatomy of Success: Key Insights from AI-Driven In-House Teams
What are the best practices for deploying AI? What are the key challenges in AI deployment and how to avoid them? How to pick a good AI use case? How to successfully leverage GenAI in organisations?
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Lilian Breidenbach
Free strategy advice for law firms with Andy Cooke
How will the emergence of AI impact the law firm model? Why are law firms not the center of innovation they could be?
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Lorna Khemraz
A Not-At-All-Intimidating Guide to Large Language Models (LLMs)
What are LLMs? How do LLMs learn? What is RAG? What are some real word applications for LLMs? What are the challenges for LLMs? Can you really boost sales using AI?
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Lilian Breidenbach
Deploying legal AI assistants in health tech.
Deploying legal AI assistants in health tech. An interview with Zeno Capucci, GC @ Docplanner
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Lilian Breidenbach
Generative AI Use Cases for Tech GCs with Damian Olthoff
A conversation with Damian Olthoff, GC at PROS.
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Lilian Breidenbach
Andy Cooke on the Future of In-house in the Age of AI
Andrew Cooke (Andy) is the General Counsel at TravelPerk, the world’s leading B2B travel management platform. Andy delves into the pivotal trends driving the success of AI for internal teams, recounts TravelPerk's experience in rolling out…
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Lilian Breidenbach
10 Best AI Chatbots of Legal Teams
Explore the top 10 leading AI chatbots for in-house legal teams. What are AI chatbots? What is the best AI chatbot for lawyers?
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Lilian Breidenbach
Rolling out Legal AI Assistants at Scale. A discussion with Tom Rice.
Tom Rice is the director of Legal at TravelPerk, one of Legal OS' first customers. He joined our co-founder and CPO, Jake Jones, in our first webinar of 2024 to discuss the opportunities and challenges of rolling out AI at scale.
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Lilian Breidenbach
On family, community, and the origins of Crafty Counsel. Taking a walk with Ben White.
Ben White is the founder of Crafty Counsel, a community for in-house legal professionals. Crafty Counsel provides high-quality creative content, intimate community meetups, and larger events, as well as access to resources for in-house…
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Lilian Breidenbach
Deploying an AI Privacy Assistant
This is the story of how TravelPerk leverages generative AI to empower their sales and deal desk teams, demystify legal, and bring joy to the teams they support across the business.
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Lilian Breidenbach
Unicorn Legal Teams rolling out Generative AI at scale
Legal OS, a Berlin-based startup backed by Google, announces the public launch of its generative AI platform. The new platform, targeted at in-house legal teams, provides business teams, such as sales and marketing, with a legal assistant…
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