How I would set up agents to do real leadership work in a product organization: what triggers them, what they may do alone, where a human decides, and how you know they are working.
I advise leadership teams on running AI as part of their operating model. The shift I see most teams miss: using AI is not the same as running agents. Using AI means a person pastes a prompt into a chat. Running agents means software that is triggered by events, works with defined tools and permissions, hands off to other agents, and escalates to a named human at set checkpoints. That second model needs the same management discipline as a team of people. This repo is what that discipline looks like in practice.
| Agent | Triggered when | Hands off to | |
|---|---|---|---|
| Decide | Decision memo agent | A thread passes 20 messages or 7 days with no decision | Decision owner, then the decision log |
| Red-team agent | A plan is marked as a one-way door | The plan's owner | |
| Plan | Roadmap coherence agent | A planning cycle opens, or a roadmap changes | CPO |
| Market landscape agent | A new product idea is logged | Discovery agent, product lead | |
| Govern | Board pre-read agent | 14 days before a board meeting | CEO or CPO |
| Due diligence agent | A partnership, acquisition or board conversation is scheduled | The executive taking the meeting | |
| Learn | Discovery agent | Interview notes are added | Product lead |
idea logged ──> Market landscape ──> Discovery ─────────────┐
v
thread stalls ──> Decision memo ──> owner decides ──> DECISION LOG
│ │
one-way door ──> Red-team ──> owner decides ───────────┘ │
v
planning cycle ──> Roadmap coherence ──> CPO Board pre-read
(reads the log)
The decision log is the spine. Every agent that informs a decision writes to it, and the board pre-read agent reads from it. That is how you can see, over time, whether agents are making the organization decide better. (Log format: product-operating-system.)
Each agent file follows the same agent spec:
- Trigger: the event that starts it. Agents that wait to be asked are just chat.
- Inputs and tools: what it can read, and with which systems.
- Permissions: what it may do alone, what needs approval, and what it may never do.
- Hand-off and human checkpoint: who receives the output, and where a person decides.
- Escalation: when it stops and asks instead of continuing.
- Metrics: how you will know it is working.
- Where it goes wrong: its predictable failure modes, designed for in advance.
These are the rules I recommend to leadership teams, and apply to my own work.
- Every agent has a named human owner. Not a team. A person who answers for its output.
- Permissions are set before it runs. Research, drafting and analysis can be autonomous. Sending, publishing, committing budget or speaking for the company never is.
- Confidential data only goes into approved tools. Board materials, financials and customer data stay inside systems the company has cleared for them.
- Agents are reviewed like direct reports. Quarterly, against a scorecard: is its work accepted, what does it catch, how often does it need rework, and is it making decisions faster? Agents that do not earn their place get retired.
- Design for failure, do not discover it. Every agent here has its failure modes written down before it runs.
- Measure decisions, not hours. Hours saved is the wrong return on AI. Decisions made better and sooner is the right one.
- Agents that reassure. Models tend to agree with whoever set them up. Every agent here is instructed to state the case against.
- Too many tools in one agent. I once automated a daily research brief that combined live web search with structured output. It broke every other day. The simpler version held up. Every extra tool is another way to fail.
- Letting summaries replace sources. The human at the checkpoint reads the original for anything that matters.
- Agents without an owner. They drift, nobody notices, and their output quietly stops being trusted.
engine-diagnostic: an AI maturity diagnostic for leadership teams, built on my ENGINE frameworkproduct-operating-system: the templates, decision log and agent role card these agents work with- More about me on my profile