Robert W. Dempsey
@robertdempsey.bsky.social
Author of The AI Decision Advantage (Feb 9).
Moving leaders from "Chief Troubleshooting Officer" to Strategic Architect.
Get Chapter 1 free 👇
https://aidecisionadvantage.com/bsky
Moving leaders from "Chief Troubleshooting Officer" to Strategic Architect.
Get Chapter 1 free 👇
https://aidecisionadvantage.com/bsky
Stop paying the "Time Tax" on AI. ⏳
If your AI strategy requires you to be more "on call" today than yesterday, you've just automated friction.
How to evaluate "free" tools: https://aidecisionadvantage.com/cost-of-free-ai-time-tax?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
If your AI strategy requires you to be more "on call" today than yesterday, you've just automated friction.
How to evaluate "free" tools: https://aidecisionadvantage.com/cost-of-free-ai-time-tax?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
January 20, 2026 at 3:01 PM
Stop paying the "Time Tax" on AI. ⏳
If your AI strategy requires you to be more "on call" today than yesterday, you've just automated friction.
How to evaluate "free" tools: https://aidecisionadvantage.com/cost-of-free-ai-time-tax?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
If your AI strategy requires you to be more "on call" today than yesterday, you've just automated friction.
How to evaluate "free" tools: https://aidecisionadvantage.com/cost-of-free-ai-time-tax?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
You can delegate a task, but never the accountability. AI agents don’t just talk; they act.
The mistake? Deploying them without a "Decision Ceiling"—the point where AI must stop for human judgment.
In 2026, the win isn't having the most agents; it's having the best delegation architecture.
The mistake? Deploying them without a "Decision Ceiling"—the point where AI must stop for human judgment.
In 2026, the win isn't having the most agents; it's having the best delegation architecture.
January 19, 2026 at 3:01 PM
You can delegate a task, but never the accountability. AI agents don’t just talk; they act.
The mistake? Deploying them without a "Decision Ceiling"—the point where AI must stop for human judgment.
In 2026, the win isn't having the most agents; it's having the best delegation architecture.
The mistake? Deploying them without a "Decision Ceiling"—the point where AI must stop for human judgment.
In 2026, the win isn't having the most agents; it's having the best delegation architecture.
Sunday is for orientation. Look at your calendar for the week ahead.
How much of it is spent "Troubleshooting" fires, and how much is spent "Architecting" systems?
Use today to reclaim your role as the Designer, not just the firewarden.
How much of it is spent "Troubleshooting" fires, and how much is spent "Architecting" systems?
Use today to reclaim your role as the Designer, not just the firewarden.
January 18, 2026 at 3:01 PM
Sunday is for orientation. Look at your calendar for the week ahead.
How much of it is spent "Troubleshooting" fires, and how much is spent "Architecting" systems?
Use today to reclaim your role as the Designer, not just the firewarden.
How much of it is spent "Troubleshooting" fires, and how much is spent "Architecting" systems?
Use today to reclaim your role as the Designer, not just the firewarden.
Even as we approach AGI, the responsibility for the consequences remains 100% human.
Technology provides the data, but the Architect provides the accountability.
Don't outsource your integrity to an algorithm.
Technology provides the data, but the Architect provides the accountability.
Don't outsource your integrity to an algorithm.
January 17, 2026 at 3:01 PM
Even as we approach AGI, the responsibility for the consequences remains 100% human.
Technology provides the data, but the Architect provides the accountability.
Don't outsource your integrity to an algorithm.
Technology provides the data, but the Architect provides the accountability.
Don't outsource your integrity to an algorithm.
In an age of infinite automation, "No" is your best strategic tool. An Architect knows that doing everything is a recipe for doing nothing well.
Strategic Restraint isn't about moving slowly; it's about precision.
If you can't say No to the wrong AI, your Yes means nothing.
Strategic Restraint isn't about moving slowly; it's about precision.
If you can't say No to the wrong AI, your Yes means nothing.
January 16, 2026 at 3:01 PM
In an age of infinite automation, "No" is your best strategic tool. An Architect knows that doing everything is a recipe for doing nothing well.
Strategic Restraint isn't about moving slowly; it's about precision.
If you can't say No to the wrong AI, your Yes means nothing.
Strategic Restraint isn't about moving slowly; it's about precision.
If you can't say No to the wrong AI, your Yes means nothing.
The "gap" between problem and action isn't a delay—it's a calibration tool.
In The AI Decision Advantage, John learns:
Speed hides blurred responsibilities.
- Alignment > Velocity.
- Slowing down = Leverage.
- The gap is where judgment lives.
Join now:
In The AI Decision Advantage, John learns:
Speed hides blurred responsibilities.
- Alignment > Velocity.
- Slowing down = Leverage.
- The gap is where judgment lives.
Join now:
The AI Decision Advantage | Book Waitlist | Robert W. Dempsey - The AI Decision Advantage
Stop chasing the AI hype. Join the waitlist for Robert W. Dempsey’s story-driven guide for SMB leaders. Get Chapter One and the AI Decision Readiness Brief immediately. Launching Feb 9, 2026.
aidecisionadvantage.com
January 15, 2026 at 3:02 PM
The "gap" between problem and action isn't a delay—it's a calibration tool.
In The AI Decision Advantage, John learns:
Speed hides blurred responsibilities.
- Alignment > Velocity.
- Slowing down = Leverage.
- The gap is where judgment lives.
Join now:
In The AI Decision Advantage, John learns:
Speed hides blurred responsibilities.
- Alignment > Velocity.
- Slowing down = Leverage.
- The gap is where judgment lives.
Join now:
Leadership fails in the gap between Information and Action. To close it, I developed the Decision Lens. It’s a framework to protect human judgment and ensure technology serves strategy.
Don't fall for the "Urgency Trap." Explore the methodology:
Don't fall for the "Urgency Trap." Explore the methodology:
The Decision Lens Manifesto | Strategic AI Leadership for Leaders
Stop being the "Chief Troubleshooting Officer." Download The Decision Lens Manifesto to move from reactive AI troubleshooting to strategic architecture and intentional leadership.
aidecisionadvantage.com
January 14, 2026 at 3:02 PM
Leadership fails in the gap between Information and Action. To close it, I developed the Decision Lens. It’s a framework to protect human judgment and ensure technology serves strategy.
Don't fall for the "Urgency Trap." Explore the methodology:
Don't fall for the "Urgency Trap." Explore the methodology:
AI isn't a bypass for messy processes. Deploying an agent into chaos creates automated chaos.
Use the Discovery Lens before you spend a cent.
Read the brief: https://aidecisionadvantage.com/discovery-lens-vetting-ai?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
Use the Discovery Lens before you spend a cent.
Read the brief: https://aidecisionadvantage.com/discovery-lens-vetting-ai?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
January 13, 2026 at 3:02 PM
AI isn't a bypass for messy processes. Deploying an agent into chaos creates automated chaos.
Use the Discovery Lens before you spend a cent.
Read the brief: https://aidecisionadvantage.com/discovery-lens-vetting-ai?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
Use the Discovery Lens before you spend a cent.
Read the brief: https://aidecisionadvantage.com/discovery-lens-vetting-ai?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
On a personal note, it's a good thing I have a standing desk, as this little rascal - Clover - or our other cat, Zephyr, love my office chair!
Anyone else with pets who steal their seat?!
Anyone else with pets who steal their seat?!
January 12, 2026 at 6:54 PM
On a personal note, it's a good thing I have a standing desk, as this little rascal - Clover - or our other cat, Zephyr, love my office chair!
Anyone else with pets who steal their seat?!
Anyone else with pets who steal their seat?!
AI doesn’t solve a bad strategy; it just makes it happen faster. Technology is a propellant. If you are headed in the wrong direction, AI gets you to the failure point in record time.
The goal for 2026 isn't AI; it’s Durable Architecture. Build the chassis before you floor the gas.
The goal for 2026 isn't AI; it’s Durable Architecture. Build the chassis before you floor the gas.
January 12, 2026 at 3:01 PM
AI doesn’t solve a bad strategy; it just makes it happen faster. Technology is a propellant. If you are headed in the wrong direction, AI gets you to the failure point in record time.
The goal for 2026 isn't AI; it’s Durable Architecture. Build the chassis before you floor the gas.
The goal for 2026 isn't AI; it’s Durable Architecture. Build the chassis before you floor the gas.
Clarity is a choice. Before tomorrow’s "urgency" hits, reset your Decision Lens. Don’t react to tremors—maintain the architecture.
January 11, 2026 at 3:01 PM
Clarity is a choice. Before tomorrow’s "urgency" hits, reset your Decision Lens. Don’t react to tremors—maintain the architecture.
Automation is execution, not strategy. Tech can’t "decide" for you—it processes your parameters. If you're misaligned, you're architecting a catastrophe.
January 10, 2026 at 3:01 PM
Automation is execution, not strategy. Tech can’t "decide" for you—it processes your parameters. If you're misaligned, you're architecting a catastrophe.
AI budgets prioritize speed over judgment. But if your decision process is broken, AI just helps you fail faster. The real advantage in 2026 is intentionality, not just adoption.
January 9, 2026 at 3:01 PM
AI budgets prioritize speed over judgment. But if your decision process is broken, AI just helps you fail faster. The real advantage in 2026 is intentionality, not just adoption.
Are you an Architect or a Troubleshooter? Troubleshooters react to AI fires; Architects design the guardrails that prevent them.
If you’re stuck in "reactive mode," it's time to re-orient.
Read Chapter 1 of The AI Decision Advantage:
If you’re stuck in "reactive mode," it's time to re-orient.
Read Chapter 1 of The AI Decision Advantage:
The AI Decision Advantage | Book Waitlist | Robert W. Dempsey - The AI Decision Advantage
Stop chasing the AI hype. Join the waitlist for Robert W. Dempsey’s story-driven guide for SMB leaders. Get Chapter One and the AI Decision Readiness Brief immediately. Launching Feb 9, 2026.
aidecisionadvantage.com
January 8, 2026 at 3:02 PM
Are you an Architect or a Troubleshooter? Troubleshooters react to AI fires; Architects design the guardrails that prevent them.
If you’re stuck in "reactive mode," it's time to re-orient.
Read Chapter 1 of The AI Decision Advantage:
If you’re stuck in "reactive mode," it's time to re-orient.
Read Chapter 1 of The AI Decision Advantage:
"Decision Architecture" builds clarity before you choose a solution. Use the "Decision Lens" to ensure technology amplifies your systems rather than breaking them.
Don't just implement. Architect.
Join the weekly orientation:
Don't just implement. Architect.
Join the weekly orientation:
The Briefs | Leadership Orientation for the AI Era
An archive of strategic insights for leaders. Learn to identify friction, set human boundaries, and find your "Quiet Win" in an age of technical noise.
aidecisionadvantage.com
January 7, 2026 at 3:02 PM
"Decision Architecture" builds clarity before you choose a solution. Use the "Decision Lens" to ensure technology amplifies your systems rather than breaking them.
Don't just implement. Architect.
Join the weekly orientation:
Don't just implement. Architect.
Join the weekly orientation:
Stop being a troubleshooter for your tech.
If your AI strategy makes you more "on call" today than you were yesterday, you've automated your stress.
Use the GC model.
New Brief: https://aidecisionadvantage.com/general-contractor-model?utm_source=social&utm_medium=bsky&utm_campaign=brief_promo
If your AI strategy makes you more "on call" today than you were yesterday, you've automated your stress.
Use the GC model.
New Brief: https://aidecisionadvantage.com/general-contractor-model?utm_source=social&utm_medium=bsky&utm_campaign=brief_promo
January 6, 2026 at 3:02 PM
Stop being a troubleshooter for your tech.
If your AI strategy makes you more "on call" today than you were yesterday, you've automated your stress.
Use the GC model.
New Brief: https://aidecisionadvantage.com/general-contractor-model?utm_source=social&utm_medium=bsky&utm_campaign=brief_promo
If your AI strategy makes you more "on call" today than you were yesterday, you've automated your stress.
Use the GC model.
New Brief: https://aidecisionadvantage.com/general-contractor-model?utm_source=social&utm_medium=bsky&utm_campaign=brief_promo
Leaders are asking: "How fast can we adopt AI?"
In my book, The AI Decision Advantage, John asks a harder question. The noise feels heavy. He needs a map, not just a tool.
I wrote this to help you find clarity.
Read Chapter 1 & Join the waitlist:
In my book, The AI Decision Advantage, John asks a harder question. The noise feels heavy. He needs a map, not just a tool.
I wrote this to help you find clarity.
Read Chapter 1 & Join the waitlist:
The AI Decision Advantage | Book Waitlist | Robert W. Dempsey - The AI Decision Advantage
Stop chasing the AI hype. Join the waitlist for Robert W. Dempsey’s story-driven guide for SMB leaders. Get Chapter One and the AI Decision Readiness Brief immediately. Launching Feb 9, 2026.
aidecisionadvantage.com
January 5, 2026 at 3:03 PM
Leaders are asking: "How fast can we adopt AI?"
In my book, The AI Decision Advantage, John asks a harder question. The noise feels heavy. He needs a map, not just a tool.
I wrote this to help you find clarity.
Read Chapter 1 & Join the waitlist:
In my book, The AI Decision Advantage, John asks a harder question. The noise feels heavy. He needs a map, not just a tool.
I wrote this to help you find clarity.
Read Chapter 1 & Join the waitlist:
Sunday reset: Use this window to check your orientation. If you find yourself troubleshooting more than you’re architecting, it’s time to find your footing again. Sunday is for strategy; Monday is for intent.
Join the orientation here:
Join the orientation here:
The Briefs | Leadership Orientation for the AI Era
An archive of strategic insights for leaders. Learn to identify friction, set human boundaries, and find your "Quiet Win" in an age of technical noise.
aidecisionadvantage.com
January 4, 2026 at 3:02 PM
Sunday reset: Use this window to check your orientation. If you find yourself troubleshooting more than you’re architecting, it’s time to find your footing again. Sunday is for strategy; Monday is for intent.
Join the orientation here:
Join the orientation here:
Observation for the weekend: We spend billions on AI "intelligence" but neglect the human judgment that triggers it. The goal of a Decision Architect isn't to replace the human; it's to ensure the technology amplifies their existing systems rather than breaking them.
January 3, 2026 at 3:02 PM
Observation for the weekend: We spend billions on AI "intelligence" but neglect the human judgment that triggers it. The goal of a Decision Architect isn't to replace the human; it's to ensure the technology amplifies their existing systems rather than breaking them.
The "Implementation Gap" in AI is rarely about the tech. It’s about the decision frameworks behind the tech. High-speed activity without durable architecture is just a faster way to accrue technical debt. Build the chassis before you floor the engine.
January 2, 2026 at 3:02 PM
The "Implementation Gap" in AI is rarely about the tech. It’s about the decision frameworks behind the tech. High-speed activity without durable architecture is just a faster way to accrue technical debt. Build the chassis before you floor the engine.
Day 1 of 2026. Your current decision frameworks determine the technical debt you'll carry by December. Aim to be an Architect of your technology, not a Troubleshooter for it. Start the year with orientation.
Get your Strategic Orientation Score:
Get your Strategic Orientation Score:
AI Strategic Orientation Scorecard | Stop the Sprint Trap
Are you an AI Architect or a Troubleshooter? Take the 2-minute diagnostic to define your Human Boundary and move from the Weight of Knowing to the Quiet Win.
aidecisionadvantage.com
January 1, 2026 at 3:02 PM
Day 1 of 2026. Your current decision frameworks determine the technical debt you'll carry by December. Aim to be an Architect of your technology, not a Troubleshooter for it. Start the year with orientation.
Get your Strategic Orientation Score:
Get your Strategic Orientation Score:
Tomorrow the AI hype cycles reset. My mission for 2026 is to help leaders build "Decision Advantage"—shifting from reactive implementation to intentional architecture. We don't need more AI activity; we need better strategic intent.
Join the orientation:
Join the orientation:
The Briefs | Leadership Orientation for the AI Era
An archive of strategic insights for leaders. Learn to identify friction, set human boundaries, and find your "Quiet Win" in an age of technical noise.
aidecisionadvantage.com
December 31, 2025 at 3:03 PM
Tomorrow the AI hype cycles reset. My mission for 2026 is to help leaders build "Decision Advantage"—shifting from reactive implementation to intentional architecture. We don't need more AI activity; we need better strategic intent.
Join the orientation:
Join the orientation:
The best strategic move for 2026 isn’t a new tool—it’s an audit of 2025's decision failures. Most AI friction is caused by urgency overriding judgment. In 2026, let's prioritize architecture over mere activity.
Start your audit here:
Start your audit here:
AI Strategic Orientation Scorecard | Stop the Sprint Trap
Are you an AI Architect or a Troubleshooter? Take the 2-minute diagnostic to define your Human Boundary and move from the Weight of Knowing to the Quiet Win.
aidecisionadvantage.com
December 30, 2025 at 3:03 PM
The best strategic move for 2026 isn’t a new tool—it’s an audit of 2025's decision failures. Most AI friction is caused by urgency overriding judgment. In 2026, let's prioritize architecture over mere activity.
Start your audit here:
Start your audit here:
People ask how I’ve released 14 guides in a year while working a high-stakes tech job.
The answer is Leverage.
Tomorrow, I’m showing you how to apply that same leverage to your family’s safety with the AI Toolkit.
The answer is Leverage.
Tomorrow, I’m showing you how to apply that same leverage to your family’s safety with the AI Toolkit.
Moving Forward: From Pathfinder Chronicles to AI Decision Advantage
After 14 guides on resilience, I'm refocusing Pathfinder Chronicles on my core expertise: Tech and AI. Join me as I launch the Family AI Safety Toolkit and the AI Strategic Blueprint.
pathfinderchronicles.com
December 30, 2025 at 1:06 AM
People ask how I’ve released 14 guides in a year while working a high-stakes tech job.
The answer is Leverage.
Tomorrow, I’m showing you how to apply that same leverage to your family’s safety with the AI Toolkit.
The answer is Leverage.
Tomorrow, I’m showing you how to apply that same leverage to your family’s safety with the AI Toolkit.
Grief. Anxiety. Old memories come a callin.
The holidays have a way of turning the volume up on everything we’ve *tried* to hold together over the past year.
If the emotions feel big right now, it doesn’t mean you’re breaking, it means you’re human.
Give yourself some space Pathfinder.
The holidays have a way of turning the volume up on everything we’ve *tried* to hold together over the past year.
If the emotions feel big right now, it doesn’t mean you’re breaking, it means you’re human.
Give yourself some space Pathfinder.
December 27, 2025 at 1:27 AM
Grief. Anxiety. Old memories come a callin.
The holidays have a way of turning the volume up on everything we’ve *tried* to hold together over the past year.
If the emotions feel big right now, it doesn’t mean you’re breaking, it means you’re human.
Give yourself some space Pathfinder.
The holidays have a way of turning the volume up on everything we’ve *tried* to hold together over the past year.
If the emotions feel big right now, it doesn’t mean you’re breaking, it means you’re human.
Give yourself some space Pathfinder.