Ambiguity is not a problem

Hi {{first_name|there}},

Spring is in full swing, and so is our community. This week brings a packed calendar of CoS gatherings across three continents; from leadership workshops in multiple cities to hands-on AI sessions that'll help you build practical tools for your role.

Most people treat ambiguity as a problem to solve; something to get through on the way to clarity. The best Chiefs of Staff treat it differently. Ambiguity is the job. It's where the highest-leverage work lives, precisely because no one else has claimed it yet.

That reframe shows up clearly in venture capital, where the CoS role looks almost nothing like its startup counterpart. There are no departments to bridge, no headcount to manage, no product roadmap to align around. Instead, the work is infrastructural in the deepest sense: building the fundraising systems, the LP relationships, the operational backbone that lets a small team of investors do what they're actually there to do — find and back exceptional founders. The CoS at a VC isn't connecting the dots between teams. They're often the one deciding which dots need to exist.

Stefania Greco, Chief of Staff at Bicycle Capital, describes it as sitting in a "tower of power" — a vantage point from which you can see what's missing before anyone else does. Not reacting to problems, but anticipating the friction that will matter six months from now. That's a different cognitive mode than most operational roles require.

Her most useful habit is deceptively simple: she regularly asks her executive, what are you working on right now? The status update isn’t important, what is critical is to find the gap between where their attention is going and where the organization actually needs it. That gap is usually where her best work starts.

The question she leaves open — and it's worth sitting with — is how you tell the difference between solving the right problem and just staying productively busy. Because ambiguity creates cover for both.

THE FRONTIER is here. On June 4, Austin becomes the gathering point for Chiefs of Staff operating inside the companies at the cutting edge of innovation — from space and defense to energy and advanced manufacturing.

If you're operating at the frontier, grab your spot. And if you know a Chief of Staff who should be there, send this their way. The right people in the room make all the difference.

Check out the full agenda below and get ready.

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best,
Scott  
Founder, Chief of Staff Network & BizOps Network