Being a Chief of Staff: an excuse to be curious
“A Chief of Staff who can't speak for their boss is no use at all."
This sentence is from Gavin Barwell’s book Chief of Staff (he was COS to the UK Prime Minister from 2017 to 2019), and it distils so much of the Chief of Staff role in just a few words.
It doesn’t matter whether you do or don’t speak for your boss – some principals don’t want that from their COS. But you still have to know what they think. You need to be able to steer others, triage problems and filter out noise for them. You are, in many ways, their interpreter and amplifier. And to do that well, you need to know their mind as well as (sometimes better than) they do.
You also have to do it fast. There’s no time to sit quietly absorbing information, waiting for a lightbulb moment. You need to model what I call structured curiosity.
So what does that look like?
1. Do your homework – and recruit AI
If you have time before starting a new COS role, prepare. Watch interviews. Read op-eds. Study their public statements. Mine their LinkedIn profile and company press releases. Find their patterns – how they talk, the words they repeat, the causes they champion, the positions they don’t explain.
And if you’re already in role, you can still do this. You’re probably just too busy to think of it as "homework".
This is also where AI can help. Use your preferred assistant to:
Pull together a timeline of public statements on a key topic (for example, “What has [Person X] or [Company Y] said publicly about AI regulation since 2021?”)
Summarise their last three public interviews
Be alive to the fact that public statements rarely show the full picture. Your boss may have strong views they choose not to air, or may say what’s politically expedient rather than what they really believe. But this gives you a solid base. A starting point. And over time, you’ll add your own context and nuance.
2. Notice everything (within reason)
COS work is often referred to as “chief noticing officer”, and for good reason. You’ll need to hone your observation, perception and synthesis skills. You’re not just collecting information; you’re making sense of it. Reading the room, clocking tone shifts, facial expressions, timing, omissions. Connecting the dots.
Highly sensitive people (HSPs) are naturally great at this. But it’s a skill anyone can learn. You just have to practice. Try this:
On a video call, pick one person and spend 30 seconds noting how they speak, where they look, how they respond to others.
After a meeting, jot down two things no one said, but you sensed.
Watch how your boss starts and ends meetings – who do they defer to, where do they subtly signal impatience, who do they light up around?
Do this enough, and it becomes second nature. You’ll develop a kind of sixth sense for where things are going. And that’s invaluable – not just in meetings, but in spotting risks and opportunities before they crystallise.
3. Ask deliberate questions (and listen closely)
The best COSs ask second-order questions. These are questions that give you more than one insight at a time. For example:
“What’s your biggest worry about that deal?” gives you insight into both the deal and their risk appetite.
“If we had to pull that report tomorrow, who would be best placed to do it?” tells you how they see their team’s strengths.
You’re not just getting answers – you’re building a map of how they think, what matters most to them, and how they make decisions.
And once you’ve asked a good question, listen like it’s your job. Because it is.
You’ll hear things between the lines – words they repeat, topics they downplay, decisions they make instinctively. Note these things down (securely and appropriately – cybersecurity matters), and use them to build a picture over time.
Tempting as it is to rely on memory, don’t. You’ll be across too many things. Have a system – a password-protected OneNote, a secure spreadsheet, or a coded notebook. Make sure it’s one you’ll use and update. Think of it as your COS knowledge base.
If all else fails, ask their EA
The Executive Assistant is a powerful team member. They often know more about how the boss thinks, works and reacts than anyone else. They are masters of structured curiosity, because they’ve had to be. They notice mood shifts, strategic signals, what’s not being said – and they do it with no fanfare.
Be useful to them. Share context. Ask their take on a tricky interaction or a knotty meeting prep. They’ll almost always have an insight you missed.
Why this all matters
Knowing your principal’s mind – really knowing it – means you can:
Speak with authority when representing them
Protect their time and attention by filtering noise effectively
Pre-empt problems, because you see things coming before they do
Coach their team, in line with what the boss actually wants (not just what they say)
And, over time, it gives your boss confidence that you “get it”. That you’re in sync. That you’re someone they can trust with the unspoken things.
Which, in a COS role, is everything.
Final thought
Structured curiosity isn’t a job requirement you’ll see in the job ad. But it’s one of the defining traits of excellent Chiefs of Staff. It’s what separates the reactive from the proactive, the helpful from the indispensable.
So if you’re in the role – or heading towards it – start now. Practice curiosity. Notice more. Ask better questions. Use the tools available. Be interested, and interesting.
And if you ever get stuck, ask the EA.
They always know.
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