Yet another way in which a COS role is different
Enquiring minds wish to know…
By the time you've landed a CXO role, tentativeness has – rightly – been trained out of you.
You've made it. You know how to move fast, trust your instincts, and project confidence. Hesitating too long is a liability. Being decisive is the whole point.
Unless it's a Chief of Staff role. Then, as usual, things are different.
The usual rules don't apply neatly here for a few reasons:
In most senior roles, you come in with a mandate. The scope is (broadly) defined. The function has a history. You can look at what your predecessor did, talk to your team, and get oriented relatively quickly. You develop your own view and then you act on it.
A Chief of Staff role doesn't quite work that way. There's no inherited playbook. The remit is defined in large part by the person you report to – and that person is different every time. Understanding them isn't a nice-to-have.
That's why the most important habit to develop – early, deliberately, and consistently – is sense-checking.
Sense-check all the time, especially at the beginning.
Time in a Chief of Staff role tends to be limited. Three years is a long tenure. Two is common. One isn't unusual. You can't afford to spend six months passively absorbing your principal's priorities, preferences, and perspective. You need to actively seek them out.
The good news is that sense-checking isn't aimless. You can structure it. There are three categories worth keeping in mind, and they all start with P, as it happens!
Priorities. In any given situation, what governs the decision? Is it growth? Ethics? Transformation? Safety? Reputation? Your principal probably hasn't written this down, and they might not even be able to articulate it in the abstract. But watch how they respond when two things come into conflict, and ask about it directly when the moment is right.
Perspective. How does your principal see the world? Is every stranger just a friend they haven't met yet, or do they keep their inner circle purposefully small? Are they instinctively optimistic or do they need convincing? Do they see problems as threats or as puzzles? This shapes everything from how you brief them to how you manage upwards on their behalf. Importantly, it also shapes what you can and can't say to them, and how. A principal who sees constructive challenge as disloyalty is a very different proposition to one who actively wants to be pushed. Figure this out early.
Preferences. This is the practical layer on top of everything, and it’s not to be skipped. How does your principal communicate best? Email? Phone calls? A quick text? Voice notes? Do they want bullet points or flowing prose? Do they want the headline first, or do they need the context before the conclusion lands? Do they have introvert tendencies – preferring time to think before they respond – or are they energised by talking things through in real time? Get this wrong, and even the best insights and recommendations get ignored. Get it right, and you become indispensable faster.
If you're still interviewing
Ask these questions early; before you accept the role, if you can.
Some candidates hesitate to ask questions that feel "too personal" or too detailed at interview stage. Personally, I wouldn’t shy away from them. A principal who is taken aback by questions about how they like to work, what they prioritise, and how they see the world is giving you very useful information – and it could be a bit of a red flag. You want a principal who welcomes that conversation and who has clearly thought about it. Who answers with some self-awareness and specificity.
Make sure, too, that the principal appreciates what sense-checking actually is. It isn't a sign of being too junior. It isn't hand-holding. The job of a Chief of Staff is, in part, to enquire, validate, and discern. If that isn't already understood going in, the relationship will be harder than it needs to be. More on that below.
If you're already in the role
Ask yourself: do you actually know the answers to the three Ps above?
If you do – great. But remember they change. Priorities shift as the organisation moves through different phases. Perspectives evolve, sometimes because of things that have nothing to do with work. Preferences change too, often gradually and without announcement.
Build regular sense-checking into the cadence of your relationship with your principal. It doesn't need to be a formal exercise – it can be as simple as checking your assumptions at the start of a new project, or asking one deliberate question at the end of your weekly 1:1.
If you don't know the answers – start now. The three categories above are a useful framework. Structure your questions around them. And remember what your principal tells you and, just as importantly, what they show you.
A quick word for principals
If you're a principal who’s found this, here's something worth considering:
The sense-checking your Chief of Staff is doing is not evidence that they don't know how to do the job. In fact, the opposite is true. A Chief of Staff who isn't doing this – who assumes they already know, who stops questioning, who operates on autopilot – is one who will eventually get it wrong. Probably at an inconvenient moment.
So the fourth P, if you're on that side of the relationship, is patience.
Your Chief of Staff is asking questions because that's what the best ones do. They're probing, checking, recalibrating. They're trying to represent you well, and to make calls that you would make. That requires understanding you deeply and continuously – and the only way to do that is to keep asking.
The best thing you can do in return is answer well. Be specific. Be honest. If your priorities have shifted, say so. If you're in a different headspace than usual, acknowledge it. The more you invest in helping your Chief of Staff understand you, the more they can do for you. It really is that direct a relationship.
Sense-checking isn't tentativeness. In any other CXO role, it might look that way. In a Chief of Staff role, it's a clear sign that someone understands what they're there to do.
If you're an aspiring or current Chief of Staff and would like to work on how you build and navigate the COS-principal relationship, I'd love to chat. You can book a free consultation at chieflycos.com.
