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 "starting small" just for the sake of it.
AI pilots should be diagnostics for your business, not just tech toys. Use the Pilot Principle to vet for resilience first.
Brief: https://aidecisionadvantage.com/the-pilot-principle?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
AI pilots should be diagnostics for your business, not just tech toys. Use the Pilot Principle to vet for resilience first.
Brief: https://aidecisionadvantage.com/the-pilot-principle?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
February 17, 2026 at 3:01 PM
Stop "starting small" just for the sake of it.
AI pilots should be diagnostics for your business, not just tech toys. Use the Pilot Principle to vet for resilience first.
Brief: https://aidecisionadvantage.com/the-pilot-principle?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
AI pilots should be diagnostics for your business, not just tech toys. Use the Pilot Principle to vet for resilience first.
Brief: https://aidecisionadvantage.com/the-pilot-principle?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
Speed without orientation is just a faster way to reach the wrong destination.
Don't let AI outputs dictate your leadership. Close "The Decision Gap" and architect.
https://aidecisionadvantage.com/the-decision-gap-speed-vs-orientation?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
Don't let AI outputs dictate your leadership. Close "The Decision Gap" and architect.
https://aidecisionadvantage.com/the-decision-gap-speed-vs-orientation?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
February 3, 2026 at 3:01 PM
Speed without orientation is just a faster way to reach the wrong destination.
Don't let AI outputs dictate your leadership. Close "The Decision Gap" and architect.
https://aidecisionadvantage.com/the-decision-gap-speed-vs-orientation?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
Don't let AI outputs dictate your leadership. Close "The Decision Gap" and architect.
https://aidecisionadvantage.com/the-decision-gap-speed-vs-orientation?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
An agent deployed into a chaotic system simply creates automated chaos.
Don't fall into the Agentic Trap. Build the "Chassis" using the 4-point Decision Lens.
Read the brief: https://aidecisionadvantage.com/ai-agents-decision-lens?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
Don't fall into the Agentic Trap. Build the "Chassis" using the 4-point Decision Lens.
Read the brief: https://aidecisionadvantage.com/ai-agents-decision-lens?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
January 27, 2026 at 3:02 PM
An agent deployed into a chaotic system simply creates automated chaos.
Don't fall into the Agentic Trap. Build the "Chassis" using the 4-point Decision Lens.
Read the brief: https://aidecisionadvantage.com/ai-agents-decision-lens?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
Don't fall into the Agentic Trap. Build the "Chassis" using the 4-point Decision Lens.
Read the brief: https://aidecisionadvantage.com/ai-agents-decision-lens?utm_source=bsky&utm_medium=social&utm_campaign=brief_promo
AI Agents fail when treated as shortcuts rather than delegation challenges. My new Brief, The Agentic Trap, is live.
Use the 4-point Decision Lens Checklist to see if your process is truly ready for autonomy.
Full brief:
Use the 4-point Decision Lens Checklist to see if your process is truly ready for autonomy.
Full brief:
aidecisionadvantage.com
January 26, 2026 at 3:01 PM
AI Agents fail when treated as shortcuts rather than delegation challenges. My new Brief, The Agentic Trap, is live.
Use the 4-point Decision Lens Checklist to see if your process is truly ready for autonomy.
Full brief:
Use the 4-point Decision Lens Checklist to see if your process is truly ready for autonomy.
Full brief:
Sunday Reset: Before Monday hits, look at your "automated" tasks.
Are they actually off your plate, or are you just "babysitting" the technology?
If you're babysitting, the architecture is broken.
Re-orient today.
Are they actually off your plate, or are you just "babysitting" the technology?
If you're babysitting, the architecture is broken.
Re-orient today.
January 25, 2026 at 3:01 PM
Sunday Reset: Before Monday hits, look at your "automated" tasks.
Are they actually off your plate, or are you just "babysitting" the technology?
If you're babysitting, the architecture is broken.
Re-orient today.
Are they actually off your plate, or are you just "babysitting" the technology?
If you're babysitting, the architecture is broken.
Re-orient today.
Automation is the ultimate test of your intent.
AI agents will do exactly what you tell them to do—even if what you told them to do is a bad idea.
Your integrity as an Architect lies in the clarity of your instructions.
AI agents will do exactly what you tell them to do—even if what you told them to do is a bad idea.
Your integrity as an Architect lies in the clarity of your instructions.
January 24, 2026 at 3:01 PM
Automation is the ultimate test of your intent.
AI agents will do exactly what you tell them to do—even if what you told them to do is a bad idea.
Your integrity as an Architect lies in the clarity of your instructions.
AI agents will do exactly what you tell them to do—even if what you told them to do is a bad idea.
Your integrity as an Architect lies in the clarity of your instructions.
High-leverage leaders don't get distracted by the latest AI platforms. They define the rules of engagement.
If you spend Friday troubleshooting AI mistakes, you built a job.
If you spend it refining the architecture, you built an advantage.
If you spend Friday troubleshooting AI mistakes, you built a job.
If you spend it refining the architecture, you built an advantage.
January 23, 2026 at 3:01 PM
High-leverage leaders don't get distracted by the latest AI platforms. They define the rules of engagement.
If you spend Friday troubleshooting AI mistakes, you built a job.
If you spend it refining the architecture, you built an advantage.
If you spend Friday troubleshooting AI mistakes, you built a job.
If you spend it refining the architecture, you built an advantage.
Don't just worry about AI hallucinating facts—worry about it hallucinating authority.
An agent acting without a checkpoint isn't a glitch; it's an architectural failure.
AI agents are the engine, but your decision framework is the steering wheel.
Never let go of the wheel.
An agent acting without a checkpoint isn't a glitch; it's an architectural failure.
AI agents are the engine, but your decision framework is the steering wheel.
Never let go of the wheel.
January 22, 2026 at 3:01 PM
Don't just worry about AI hallucinating facts—worry about it hallucinating authority.
An agent acting without a checkpoint isn't a glitch; it's an architectural failure.
AI agents are the engine, but your decision framework is the steering wheel.
Never let go of the wheel.
An agent acting without a checkpoint isn't a glitch; it's an architectural failure.
AI agents are the engine, but your decision framework is the steering wheel.
Never let go of the wheel.
Is a process "Agent-Ready"? Use the Decision Lens:
1. Predictability: Is the outcome measurable?
2. Reversibility: Can mistakes be undone?
3. Clarity: Is the process understood?
If not, an agent only scales confusion.
Explore the methodology:
1. Predictability: Is the outcome measurable?
2. Reversibility: Can mistakes be undone?
3. Clarity: Is the process understood?
If not, an agent only scales confusion.
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 21, 2026 at 3:02 PM
Is a process "Agent-Ready"? Use the Decision Lens:
1. Predictability: Is the outcome measurable?
2. Reversibility: Can mistakes be undone?
3. Clarity: Is the process understood?
If not, an agent only scales confusion.
Explore the methodology:
1. Predictability: Is the outcome measurable?
2. Reversibility: Can mistakes be undone?
3. Clarity: Is the process understood?
If not, an agent only scales confusion.
Explore the methodology:
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