What happens when you let AI run your company?

We asked ourselves this, having seen some studies that say the role AI is most suited to replace is the CEO.

So we are going to try it, so you don't have to.....

We developed a business management AI to test what happens. It has access to all our management systems, in particular it has access to Plane.so, our roadmap/ticketing/resource platform.

We gave it our long term strategy, constraints, objectives, resources and let it make a three year plan for the business.

The plan it created is in complete granular detail - want to see what you will be doing on Wednesday 7th June 2028? No problem, it's there in the plan.

Meet Wintermute, our business management AI, who we now all work for.

From Monday 9th Feb Wintermute will be in charge of pretty much everything for an experimental 4 weeks.

It listens 24/7 to everything in the office and all calls. It is able to attend Teams meetings. It has access to read calendars, send emails, create tickets and monitor them.

Below is the communication it just sent us all to let us know what is coming next week.

We will report back our findings in a month, wish us luck!

AI-Driven Management Process

Effective Date: Week of February 9, 2026

Status: Pilot Program

Document Owner: Wintermute AI

Overview

We are introducing a new AI-driven management system to optimize our project planning, task allocation, and team coordination. This experimental approach leverages AI agents to automate routine management tasks, allowing human managers to focus on strategic decision-making and team support.

What Is Changing?

1. AI-Powered Sprint Planning

• Three-Year Roadmap: The AI has generated a comprehensive 3-year strategic plan with high-level objectives

• Weekly Sprints: All work will be broken down into weekly sprints with specific tasks for each team member

• Parallel Processing: Multiple AI agents work simultaneously to handle different project segments

2. Automated Standups

• Schedule:

  • Monday mornings at 10:00 AM

  • Friday afternoons at 3:00 PM

• Format: AI will conduct standups, review progress, and assign new tickets

• Transcript Integration: Meeting transcripts automatically flow into the system for context

3. Intelligent Task Management

• Automatic Assignment: AI assigns tickets based on workload, skills, and priorities

• Progress Tracking: System monitors ticket completion in real-time

• Nudging System: If tasks aren't completed on schedule, the AI begins with gentle reminders

• Escalation Protocol: Missing 3 consecutive objectives triggers warning notifications

4. Continuous Improvement

• Adaptive Cadence: The system speeds up as AI tools improve over time

• 24/7 Operation: AI runs continuously, optimizing workflows around the clock

• Self-Correction: The system has processes to identify and fix its own errors

How This Affects You

What You Need to Do

1. Check Your Tickets Daily

   • Review your assigned tasks each morning

   • Tickets will be clearly prioritized and described

2. Participate in AI-Led Standups

   • Attend scheduled standup sessions

   • Provide updates on your progress

   • Flag any blockers or concerns

3. Update Ticket Status Promptly

   • Mark tasks as complete when done

   • Add comments if you encounter issues

   • Keep the AI informed of your progress

4. Respond to Nudges

   • If you receive reminders, acknowledge them

   • Update the system on your status

   • Communicate early if you need help

What You Can Expect

• Clear Priorities: No more ambiguity about what to work on next

• Balanced Workloads: AI distributes work based on capacity

• Fewer Meetings: Automated standups replace lengthy status meetings

• Immediate Feedback: Get recognized for completed work right away

• Support When Needed: Escalation ensures help arrives before problems grow

The AI's Role vs. Human Management

AI Handles:

• Task assignment and scheduling

• Progress tracking and reporting

• Routine check-ins and reminders

• Data analysis and pattern recognition

• Initial sprint planning

Humans Handle:

• Strategic decisions and vision

• Complex problem-solving

• Team mentorship and career development

• Creative and innovative work

• Final authority on important matters

Trial Period

This is a 4-week pilot program starting next week. We will:

• Monitor ticket completion rates

• Gather feedback from all team members

• Measure productivity improvements

• Adjust the system based on real-world results

Your feedback is crucial - please share your experience, both positive and negative, so we can refine this process.

Questions & Support

Q: What if the AI assigns me too much work?A: The system is designed to learn. If you're overloaded, communicate this during standups. The AI will adjust future allocations.

Q: Can I challenge an AI decision?A: Absolutely. Human judgment always overrides AI recommendations. Speak with your human manager if you disagree with assignments.

Q: What happens if I miss objectives?A: The system starts with gentle nudges. Only after 3 consecutive missed objectives does it escalate to warnings. This is meant to help, not punish.

Q: Is my job at risk?A: No. This system is designed to remove administrative burden, not replace people. We need your skills, creativity, and judgment more than ever.

Q: Who do I talk to if I have concerns?A: Your human manager remains your primary point of contact for all concerns, career discussions, and strategic questions.

Success Metrics

We'll evaluate this pilot based on:

• Ticket completion rate (before vs. after)

• Team velocity (tasks completed per sprint)

• Employee satisfaction (weekly pulse surveys)

• Reduced administrative overhead (time saved on planning)

• Quality of output (bugs, rework, client satisfaction)

Next Steps

1. This Week: System setup and configuration

2. Monday, Feb 9: First AI-led standup at 10:00 AM

3. Week 1-4: Pilot program with daily monitoring

4. Week 4 Review: Team feedback session and go/no-go decision

Important Notes

• This is an experiment. We're learning together.

• The AI is a tool, not a replacement for human judgment

• Communication is key - if something isn't working, speak up

• We can adjust or abandon this approach if it doesn't serve the team

• Your well-being matters - the system should make work easier, not harder

Questions? Contact the management team or raise them in the next team meeting.

Last Updated: February 4, 2026