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Dennis Kennedy

@denniskennedy.bsky.social
495 followers 245 following 36 posts

Consulting innovator, citizen of creator economy, Director of MSU Center for Law, Technology & Innovation

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Dennis Kennedy @denniskennedy.bsky.social · 13/08/2026
August Personal Strategy Compass newsletter is out: “The Night Watchman.” You create white space, and your analytical mind uses it to keep worries illuminated. That’s when strategic reflection turns into night-watchman duty. And that's not a good thing. dennis538.substack.com/personal-str...
dennis538.substack.com
Personal Strategy Compass | August 2026
The Night Watchman: Converting Solitary Anxiety into Strategic Leverage
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Dennis Kennedy @denniskennedy.bsky.social · 23/04/2026
New newsletter. Bruce Springsteen cleared the stage on the Tunnel of Love tour. Fewer things. More signal. Turns out that's a planning methodology. open.substack.com/pub/dennis53...
open.substack.com
Personal Strategy Compass - April 2026
Navigating your success your way, one quarter at a time
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Dennis Kennedy @denniskennedy.bsky.social · 16/02/2026
What would you actually think about if your to-do list disappeared for a weekend? I tried it. The answer surprised me. New on DennisKennedy.Blog: www.denniskennedy.com/blog/2026/02...
denniskennedy.com
What Disappears When You Stop Carrying It?
I ran an experiment at the beginning of February. I closed my planning system and didn't look at any of it for 48 hours. No peeking. No referencing. I
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Dennis Kennedy @denniskennedy.bsky.social · 15/01/2026
My Personal Strategy Compass Substack newsletter is now free for everyone. This month: using Oblique Strategies to break strategic loops during your personal quarterly planning. Your expertise creates invisible patterns. These cryptic prompts force you to see around them. dennis538.substack.com
dennis538.substack.com
Personal Strategy Compass | Dennis Kennedy | Substack
"Navigating your success your way, one quarter at a time" with Dennis Kennedy's newsletter on Personal Quarterly Offsites. Click to read Personal Strategy Compass, by Dennis Kennedy, a Substack public...
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Dennis Kennedy @denniskennedy.bsky.social · 18/12/2025
Sherlock Holmes didn't solve cases by working more hours; he solved them by protecting his mental RAM. Most professionals are entering December with high anxiety and low vitality. Don't be one of them. Read the diagnostic: dennis538.substack.com/p/personal-s...
dennis538.substack.com
PERSONAL STRATEGY COMPASS - December 2025 Issue (Limited Free Version)
Stop Hiring Your Anxiety to Work for You
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Dennis Kennedy @denniskennedy.bsky.social · 18/11/2025
The "Cult of the Final Billable Hour" is a trap. We must reframe deep rest as a Strategic Input. Your Q1 success depends on defending a "Crucible Zone" of non-work time to process complex Q4 data. My solution is in the new Personal Strategy Compass issue at dennis538.substack.com/p/personal-s...
dennis538.substack.com
Personal Strategy Compass Issue #12: November 2025 (Free Preview)
The Strategic Imperative: Disengaging for Deeper Insight
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Dennis Kennedy @denniskennedy.bsky.social · 21/10/2025
Don't wait for a mythical "Hell Yes!" That's a trap. The real danger is the "Risk of Rusting." Start running "Strategic Probes"—small experiments to get a "Return on Information." The new"Open House" edition of my newsletter all about this. www.denniskennedy.com/blog/2025/10...
denniskennedy.com
Personal Strategy Compass Newsletter #11: The Strategic Probe
For ambitious professionals, saying "no" is a celebrated strategic act. We use the "Strategic No" to reclaim our time, prune our commitments, and simplify
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Dennis Kennedy @denniskennedy.bsky.social · 15/09/2025
Overwhelmed? New issue of my Personal Strategy Compass newsletter on The Strategic 'No' helps you cut clutter & reclaim focus. Learn my 4-gate Commitment Audit & "Spectrum of No" scripts. Your autonomy depends on it! www.denniskennedy.com/blog/2025/09...
denniskennedy.com
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Dennis Kennedy @denniskennedy.bsky.social · 21/08/2025
What if your biggest productivity win this week isn't starting something new, but finally finishing something old? My latest Personal Strategy Compass newsletter explores the massive mental clarity you reclaim by strategically closing open loops. www.denniskennedy.com/blog/2025/08...
denniskennedy.com
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Dennis Kennedy @denniskennedy.bsky.social · 15/07/2025
What if your best career insights are buried under layers of overthinking? This month’s Personal Strategy Compass newsletter provides a toolkit to excavate them with the "Lightning Round" technique. www.denniskennedy.com/blog/2025/07... #personalstrategy #newsletter #lightninground #pqo
denniskennedy.com
Bypass Analysis Paralysis with the 20-Minute Lightning Round
If you are a high-achieving professional, you live with a fundamental tension. You know that deep, strategic thinking is the engine of your success, yet
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Reposted by Dennis Kennedy
Legal Talk Network @legaltalknet.bsky.social · 14/07/2025
🚨 Hourly billing isn’t broken—but it might be breaking you. Matthew Kerbis runs his firm on subscription and shares how AI makes alternative pricing models more viable. @denniskennedy.bsky.social 🎧 Apple: apple.co/3XjzW1C 🎧 Spotify: spoti.fi/3XgLWyA
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Dennis Kennedy @denniskennedy.bsky.social · 18/06/2025
It's halftime for 2025. Don't just keep running. The new Personal Strategy Compass issue guides you through a "Halftime Personal Quarterly Offsite" to review your first half and create a winning game plan for the second. Check it out: www.denniskennedy.com/blog/2025/06...
denniskennedy.com
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Dennis Kennedy @denniskennedy.bsky.social · 31/05/2025
Are you a legal professional planning your next chapter? My new newsletter, "Personal Strategy Compass," delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
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Dennis Kennedy @denniskennedy.bsky.social · 14/05/2025
Are you a legal professional planning your next chapter? My new newsletter, "Personal Strategy Compass," delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. Issue #6 published today. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
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Dennis Kennedy @denniskennedy.bsky.social · 08/05/2025
Are you a legal professional planning your next chapter? My new newsletter, "Personal Strategy Compass," delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
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Reposted by Dennis Kennedy
Tom Martin aka @lawdroid @lawdroid.bsky.social · 21/04/2025
𝗘𝘃𝗲𝗿 𝘄𝗼𝗻𝗱𝗲𝗿 𝘄𝗵𝗮𝘁 𝗵𝗮𝗽𝗽𝗲𝗻𝘀 𝘄𝗵𝗲𝗻 𝘆𝗼𝘂 𝗰𝗼𝗺𝗯𝗶𝗻𝗲 𝘀𝗺𝗮𝗹𝗹-𝘁𝗼𝘄𝗻 𝗿𝗼𝗼𝘁𝘀, 𝗽𝘂𝗻𝗸 𝗿𝗼𝗰𝗸, 𝗮𝗻𝗱 𝗮 𝘃𝗶𝘀𝗶𝗼𝗻𝗮𝗿𝘆 𝗮𝗽𝗽𝗿𝗼𝗮𝗰𝗵 𝘁𝗼 𝗹𝗲𝗴𝗮𝗹 𝘁𝗲𝗰𝗵? Then, don't miss my conversation with @denniskennedy.bsky.social www.lawdroidmanifesto.com/p/the-digita...
lawdroidmanifesto.com
The Digital Disruptor: Dennis Kennedy
Where I interview Dennis Kennedy, a true legal tech pioneer, who has been innovating at the intersection of law and technology since the early internet days
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Dennis Kennedy @denniskennedy.bsky.social · 17/04/2025
New issue of my Personal Strategy Compass Substack newsletter on Personal Quarterly Offsites is live! Declaring Your Major—choose one focus for next quarter. • Why “one thing” beats many • My story of “Strategic Simplification” • Free Major‑Finder Toolkit www.denniskennedy.com/blog/2025/04...
denniskennedy.com
Declaring Your Major: One Decision That Can Turbo‑Charge Your Next Quarter
Issue 5 of my Personal Strategy Compass Substack email newsletter (premium) has been published and sent. It has some new insights and some practical
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Reposted by Dennis Kennedy
Legalverse Media @legalversemedia.com · 11/04/2025
Is AI’s Real Impact in the Messy Middle of Legal Work? AI isn’t just about efficiency. Its true power may lie in handling complex, customized legal tasks — and clients are already using it. Read @denniskennedy.bsky.social' take: legalversemedia.com/beyond-effic... #AI #Innovation #LegalProfession
legalversemedia.com
Beyond Efficiency: Is AI's Sweet Spot in the Messy Middle of Legal Work? - Legalverse Media
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Dennis Kennedy @denniskennedy.bsky.social · 05/04/2025
Lawyers: Overwhelmed? Try a Personal Quarterly Offsite (PQO)! My new newsletter issue guides you step-by-step. Get clarity, focus, & results. Premium subscribers get exclusive tools! #PQO #PersonalProductivity dennis538.substack.com/p/personal-s...
dennis538.substack.com
Personal Strategy Compass - Issue 4: March 2025
Navigating your success your way, one quarter at a time
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Dennis Kennedy @denniskennedy.bsky.social · 13/03/2025
Are you a legal professional planning your next chapter? My new newsletter, "Personal Strategy Compass," delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
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Dennis Kennedy @denniskennedy.bsky.social · 27/02/2025
Are you a legal professional planning your next chapter? My new newsletter, "Personal Strategy Compass," delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
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Dennis Kennedy @denniskennedy.bsky.social · 13/02/2025
Fresh issue of my Personal Strategy Compass newsletter is live! Learn about the "Grace Period" Personal Quarterly Offsite for catching up on your goals, plus how to create a focused PQO ritual anywhere. For #legalinnovation folks especially: dennis538.substack.com/p/personal-s...
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Dennis Kennedy @denniskennedy.bsky.social · 06/02/2025
Are you a legal professional planning your next chapter? My new newsletter, "Personal Strategy Compass," delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
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Dennis Kennedy @denniskennedy.bsky.social · 20/01/2025
Are you a legal professional planning your next chapter? My newsletter "Personal Strategy Compass" delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. In this issue: Minimum Viable PQOs dennis538.substack.com/p/personal-s...
dennis538.substack.com
Personal Strategy Compass - Issue #2
Your Minimum Viable PQO: Get Started in Under an Hour
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Dennis Kennedy @denniskennedy.bsky.social · 02/01/2025
Are you a legal professional planning your next chapter? My new newsletter, "Personal Strategy Compass," delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
010
Dennis Kennedy @denniskennedy.bsky.social · 27/12/2024
Are you a legal professional planning your next chapter? My new newsletter, "Personal Strategy Compass," delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. Just wrapped up my last PQO of 2024. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
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Dennis Kennedy @denniskennedy.bsky.social · 24/12/2024
For legal leaders planning their next chapter: get monthly guidance on Personal Quarterly Offsites - my proven framework for navigating transitions with clarity. My new Substack newsletter - Personal Strategy Compass. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
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Dennis Kennedy @denniskennedy.bsky.social · 16/12/2024
Are you a legal professional planning your next chapter? My new newsletter, "Personal Strategy Compass," delivers monthly mini-masterclasses on Personal Quarterly Offsites - my proven framework for clarity in transitions. www.denniskennedy.com/blog/2024/12...
denniskennedy.com
Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites
I'm excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly
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Dennis Kennedy @denniskennedy.bsky.social · 01/12/2024
Other than perhaps AI, the hottest topic in #legaltech today! Make #Collaboration your superpower! The Lawyer's Guide to #Collaboration Tools and Technologies, Work from Home Edition, by @denniskennedy and @TomMighell -- Grab it from Amazon now! "Smart ways to work together"
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Dennis Kennedy @denniskennedy.bsky.social · 22/12/2023
New post on denniskennedy.blog is called "Year-end Gifts from DennisKennedy,Blog" and shares some content gifts for the end of 2023 from me. denniskennedy.com/blog/2023/12... #legaltechnology #personalquarterlyoffsites #generativeai #lawdepartmentinnovation
denniskennedy.com
Year-end Gifts from DennisKennedy.Blog
The end of the year is a time of sharing at DennisKennedy.Blog. I have a special set of gifts for readers of the blog to celebrate the end of 2023. Help
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Dennis Kennedy @denniskennedy.bsky.social · 04/10/2023
My latest post on DennisKennedy.Blog is called "Slides from My Recent AI Presentation" and shares a PDF of my slides from my recent presentation to State Bar of Michigan providing introduction to AI for not-overly-technical lawyers and link to my white paper on guided advisory layers for #genAI.
denniskennedy.com
Slides from my Recent AI Presentation
I recently presented to a great audience at the State Bar of Michigan Information Technology Law Section's Annual conference about AI. I described my
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Reposted by Dennis Kennedy
Dennis Kennedy @denniskennedy.bsky.social · 10/09/2023
My new post on DennisKennedy.Blog is my new white paper called "Adding a 'Group Advisory Layer' to Your Use of Generative AI Tools Through Structured Prompting: The G-A-L Method" It sums up results from one of my big #genAI experiments over the summer. www.denniskennedy.com/blog/2023/09...
denniskennedy.com
Adding a 'Group Advisory Layer' to Your Use of Generative AI Tools Through Structured Prompting: The...
#Blogfirst Adding a 'Group Advisory Layer' to Your Use of Generative AI Tools Through Structured Prompting: Using Personas for Advisory Boards, Task
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Dennis Kennedy @denniskennedy.bsky.social · 10/09/2023
My new post on DennisKennedy.Blog is my new white paper called "Adding a 'Group Advisory Layer' to Your Use of Generative AI Tools Through Structured Prompting: The G-A-L Method" It sums up results from one of my big #genAI experiments over the summer. www.denniskennedy.com/blog/2023/09...
denniskennedy.com
Adding a 'Group Advisory Layer' to Your Use of Generative AI Tools Through Structured Prompting: The...
#Blogfirst Adding a 'Group Advisory Layer' to Your Use of Generative AI Tools Through Structured Prompting: Using Personas for Advisory Boards, Task
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Reposted by Dennis Kennedy
Melanie Mitchell @melaniemitchell.bsky.social · 06/09/2023
Worth reading: article explaining how prompt-injection attacks work and why they are a big problem for LLMs: www.wired.com/story/genera...
wired.com
Generative AI’s Biggest Security Flaw Is Not Easy to Fix
Chatbots like Open AI’s ChatGPT and Google’s Bard are vulnerable to indirect prompt injection attacks. Security researchers say the holes can be plugged—sort of.
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Dennis Kennedy @denniskennedy.bsky.social · 17/08/2023
New post on DennisKennedy.Blog is called "Displaying and Evidencing Contract Terms in a Post-Visual Era" and summarizes key points, conclusions, and action steps from my article for Michigan State Law Review Forum.
denniskennedy.blog
DennisKennedy.Blog
Lawyer, author, blogger, speaker and podcaster Dennis Kennedy offers insights on the application of technology in the practice of law.
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Dennis Kennedy @denniskennedy.bsky.social · 11/08/2023
In the latest episode of The Kennedy-Mighell Report podcast, "Dennis’ Latest Legal Tech Notions—Thumbs Up or Thumbs Down?" we unveil a new #legaltech gameshow experiment and want your feedback.
legaltalknetwork.com
Dennis’ Latest Legal Tech Notions—Thumbs Up or Thumbs Down? - Legal Talk Network
A new Kennedy-Mighell Report game has begun. The premise? Dennis has a whole lot of ideas, and Tom just loves pointing out their flaws. The guys introduce
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Dennis Kennedy @denniskennedy.bsky.social · 29/07/2023
In new episode of The Kennedy-Mighell Report podcast, Amani Smathers guests on our Fresh Voices on Legal Tech interview series to discuss her unique niche, perspective and insights. legaltalknetwork.com/podcasts/kenne…
legaltalknetwork.com
Fresh Voices on Legal Tech with Amani Smathers - Legal Talk Network
What makes it so difficult for some lawyers to embrace technology? Fear, confusion, and that feeling that they just can’t ever catch up create a wall that
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Dennis Kennedy @denniskennedy.bsky.social · 27/07/2023
In new episode of The Kennedy-Mighell Report podcast, "The Current State of Generative AI in Legal," we take a hard look at ChatGPT's practical capabilities and limitations as of now. legaltalknetwork.com/podcasts/kenne…
legaltalknetwork.com
The Current State of Generative AI in Legal - Legal Talk Network
Despite Tom’s attempted prohibition of ChatGTP on this podcast, it’s weaseled its way in once again. The guys take a hard look at where ChatGPT is really
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Dennis Kennedy @denniskennedy.bsky.social · 05/05/2023
“Our Vanishing Internet: Disappearing Data, Paywalls, and Memory Holes” - new episode of The Kennedy-Mighell Report podcast. legaltalknetwork.com/podcasts/kenne…
legaltalknetwork.com
Our Vanishing Internet: Disappearing Data, Paywalls, and Memory Holes - Legal Talk Network
In light of the recent Internet Archive lawsuit, Dennis has some serious questions about what it and other recent happenings may mean for the future of
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