r/ChiefsOfStaff

I'm working on a research report - State of Executive Workflows 2026 - and I'd really value perspectives from people actually doing this job.

Quick on the why: there's a lot of LinkedIn-flavored content about how AI is "transforming" the role, but most of it sounds like marketing copy.
I want to understand what's actually changed in daily work, what tools matter, and what hasn't moved at all, including the parts no tool touches (judgment calls, soft follow-ups, the context you carry that nobody documents).

What it is:
- 25-minute conversation
- You'll see the findings before they go public
- You can be named in the report or stay anonymous, your call
- Once the report is done, I'll share a summary back with this sub

Looking for 12 Chiefs of Staff who work closely with senior leaders.
DM me or comment here if you're open to it.

Disclosure: I'm building a product in this space (AI tool for executive teams) but this research isn't a sales pitch, I want the honest picture, including what tools don't help.
Happy to answer any questions about that upfront.

Hey folks! I joined an early stage tech company as “VP of strat and ops” but I’m effectively chief of staff. Some people refer to me as such internally.

Some background: I have worked with this company as a contractor while employed elsewhere but parted ways due to high volatility. I have a commercial and product mgt background so I can help across several areas of the business. My biggest challenges are:

1. Getting the CEO to use systems/get info out of his brain and into places where others can see it.
2. Lack of role clarity. I expected role ambiguity and that’s fine, but with a COO and other highly autonomous hires (like our VP of product, head of GTM) and random other people the CEO will hire or bring on as contractors without notice, I’m struggling with how to carve a role out for myself here.

I have taken charge of some systems things on the product development side, customer acquisition (process, CRM hygiene, etc), onboarding/HR, but every time I produce something someone else creates their own version of it or redoes it. And it’s actually not personal…everyone seems to do it to one another.

Has anyone dealt with this kind of ambiguity and mess at a very early stage company? What did you do to create more clarity for yourself?