Most people use AI the wrong way.
They open a chat window, type a question, get an answer, close the tab. The next time they come back, the AI has no idea who they are, what they're working on, or what they decided last time. Every session starts from zero.
That's not a Chief of Staff. That's a search engine with better grammar.
Here's how to actually use AI as a Chief of Staff — the way that compounds over time and changes how you operate.
Step 1: Give It Permanent Context
The most important thing a Chief of Staff has is context. They know who you are, what you're building, who your key people are, what you care about, and what keeps you up at night. Without that, every answer they give you is generic.
The first thing you need to do with an AI Chief of Staff is brief it — deeply and completely. Not "I'm a business owner." Tell it:
- What your business actually does, its stage, and its biggest constraint right now
- Who your key people are (partners, investors, team members, advisers) and their relationship to you
- What you're working towards in the next 12 months
- Where most of your time goes that it shouldn't
- How you prefer to receive information (bullets vs. prose, headlines vs. full context)
- What you want it to proactively track for you
This context needs to persist across sessions. If you're using a general-purpose chat tool, you're fighting against its statelessness. A purpose-built AI Chief of Staff like Steve stores your intake permanently and injects it into every conversation automatically.
Step 2: Use It Before Every Important Interaction
A good Chief of Staff briefs you before you walk into anything significant. Before a difficult conversation, a negotiation, a board meeting, a sales call — you should already know what you're walking into, what the dynamics are, and what outcome you're aiming for.
Start using AI this way. Before any important meeting or decision, have a five-minute conversation. Ask it to:
- Recap what you last discussed about this topic or person
- Surface the most important things you need to know going in
- Help you think through your position and any potential landmines
- Draft the three questions you most need answered in this meeting
This habit alone — using AI before important interactions, not just for task execution — changes the quality of your decisions.
Step 3: Record Decisions and Open Loops in Real Time
Most executives have more open loops than they can track. Commitments made in passing conversations, decisions deferred until more information arrives, actions delegated to team members without a formal tracking system.
Start treating your AI Chief of Staff as the place you close open loops. After a meeting, spend two minutes telling it what was decided, what was committed to, and by whom. It tracks it. It surfaces it in your daily briefing when something's been quiet too long. It knows the context when you come back to it three weeks later.
This isn't a task manager. You don't need to format anything. You just tell it what happened and what matters, the same way you'd debrief a human CoS.
Step 4: Let It Run the Morning Briefing
The highest-leverage daily habit for any executive is starting the day with clarity rather than noise. Instead of hitting email first and immediately being reactive, you want to arrive at your desk knowing:
- What's genuinely important today
- What's changed overnight that you need to know about
- What decisions are pending
- What one thing should have your full attention
A well-configured AI Chief of Staff delivers this every morning before you open email. It knows your context, your calendar, your open tasks, and your industry. The briefing is personalised to your actual situation — not a generic news digest.
Step 5: Think Out Loud
The underrated use case for an AI Chief of Staff isn't task completion — it's thinking. A good CoS is someone you can think out loud in front of, who will push back, ask the right questions, and help you arrive at a better decision than you would have alone.
Use it that way. When you're stuck on a difficult decision, don't just ask for an answer. Walk through your thinking. Explain what you know, what you're uncertain about, what you're leaning towards and why. Let it probe. Ask it to steelman the opposing view. Ask it what you're missing.
This is where the context investment pays off. Because it knows your business, your history, and your operating style, the pushback is calibrated. It's not generic advice — it's a response to your specific situation.
The Compounding Effect
Here's what most people don't realise: the value of an AI Chief of Staff isn't in any single conversation. It's in the accumulation of context over time.
Three months in, it knows your key relationships, your operating patterns, your biggest recurring problems, and your decision-making style. It can brief a new team member from your institutional knowledge. It can spot patterns in what keeps going wrong. It can remind you of decisions you made six months ago and why.
That's not a productivity tool. That's an operational layer. And it compounds with every conversation you have.
The question isn't whether AI can work as a Chief of Staff. It's whether you're willing to invest in briefing it properly and using it consistently enough to build that layer.
Most people aren't. That's what makes it a competitive advantage for the ones who are.