r/ChiefsOfStaff

genuine question bc I feel like i’ve tried everything. between investors, leadership, key partners etc, i’m constantly trying to recall not just who someone is but where we left things - open threads, what they care about, when I last actually followed up
spreadsheet worked for like a month then just became a graveyard of stale info nobody updated.
tried a CRM too, way too much overhead for what’s basically internal relationship tracking, not sales
I ended up cobbling together my own system in notion for this - mostly bc i was tired of the mental load - and it’s actually held up well for me. context, next touch reminders, all in one spot I actually check
curious what other COS’s are doing here though, feels like this should have a better answer than “ I built my own thing”

Former Chief of Staff for 16 months, straight out of a top hospitality school + entrepreneurial experience at 27. Been looking for a similar role or even a strategic projects management role regardless the title ever since as I love being in the epicentre of things while managing my family office in the same field (~20 applications). Landed a handful of interviews/calls, went really well. Unfortunately did not get the final call. Need guidance on what may be going wrong?

Would appreciate any help. Two years of keeping mental health in check is starting to take a toll.

Hey all! I’m a new CoS (since Jan 2026) in a small org (<15) with a flat structure. I have a great leader who values work-life balance, etc. However, I’m finding it tough to respect my own leave. Part of this is because of emergent issues that need my attention, staff issues or questions since our leader is mostly external facing, and also part of this is on me and not having good boundaries since starting this role (my work boundaries were really solid - working 9-5p. Now it’s 9-8:30p and working during my PTO)

How have others navigated this? I have a leadership coach and my leader wants me to break, but the reality of the job is often different.

(AI assisted draft)
I’m trying to understand how others would classify my role based on what I actually do rather than my title.
My official title is Referent der Geschäftsführung in German (Officer to the Management Word by Word) at a large university institute, which is very difficult to translate. Also, my guess is that I am actually doing a lot more than this title implies. Within the salary System of German public administration, I am ranked as an expert (Master degree) with 8years of relevant experience.

While we’re in academia, we’re highly business-facing: executive education is a major part of what we do, we work closely with companies and senior executives, and our organizational language and mindset borrow quite a bit from the corporate world. I work directly with Ministers, CEOs and Supervisory Board Members but also all the way down to our Student Assistants: I am basically working with everybody in every project we have, unless it’s Daily Business which is not my Turf.

Our hierarchy is roughly:
Director → Managing Directors → Team Leads → Teams
I primarily work with the Director and one of the Managing Directors, but I sit somewhat outside this formal hierarchy.
My background is in project/program management rather than administration. Before joining, I managed publicly funded projects involving budgets, implementation and complex stakeholder networks across government, business and civil society. Earlier in my career, I was also a military officer.

My current role has three main components:
Leadership support & strategy: I prepare the Director for speeches, panels and important meetings, draft briefings and decision papers, work on governance and strategic issues, and coordinate with senior internal and external stakeholders.
I am often connected with other executive Assistants, CoS, personal Assistants, executive Advisors and so on.

Cross-functional execution: I take ownership of ad-hoc or smaller projects that don’t have a natural owner, coordinate across teams and help unblock important or time-sensitive issues.

External relationships & programs: I follow up with relevant people we meet at events and try to turn those contacts into partnerships, speakers or contributors to our projects. I also manage a fair amount of events and programs – though in our case, education is essentially our product, so this often combines logistics, content, stakeholder management and strategic positioning.

There is a separate secretary responsible for the Director’s calendar and traditional administrative support, so calendar management, travel booking etc. are generally not my job.

What I find most challenging is my position within the leadership structure.
The Managing Directors naturally don’t want an additional layer between themselves and the Director. At the same time, Team Leads increasingly come to me when something important gets stuck or they need additional support. I try to help without becoming a shadow manager or interfering with their ownership. My perspective is supposed to remain cross-functional and focused on the institute’s overall development.
So I have influence without much formal authority.

I don’t manage teams, own the Director’s entire agenda or have a blanket mandate to act on her behalf. But I increasingly seem to function as additional leadership capacity: connecting people and topics, filling ownership gaps, unblocking issues, preparing the Director and translating external opportunities into internal action.
I do realize that without the directors and managing directors backing, my work gets more difficult because I lack „hierarchical authority”. This is one of the reasons I’d like to change my title to chief of staff. Same goes for external stakeholder relations.

Would you consider this a Chief of Staff-type role, an Executive Advisor role, or something else?
And for actual CoS: what is the key responsibility or authority that separates a Chief of Staff from someone doing what I’m doing?

Thanks !

My current job is technical but after some leadership change I proposed to our new exec of the dept if he’d consider me playing the CoS role for him — which he’s agreed to.

He provided me a list of initiatives he’s prioritizing before EOY and the ask from me is to ensure things are progressing along with these initiatives by the team. I don’t want to just play the role of doing progress checks with the team and “reporting” back to him. How can I start moving away from doing that and be more hands on with this role?

Some background: I’m new to being a CoS so I’m not really sure what to even expect. I’m still doing my technical work that’s part of my job

Thanks in advance!

Been a Chief of Staff/EA to the founder at a small investment firm (hedge fund) for about 4 months. $100k base, remote, so obviously there are reasons I don't want to just walk away. But I'm starting to wonder if this is completely insane - and if I am valid in feeling like I am losing my pride and my backbone.

I'm required to sit on Zoom from 8-7 every day with my camera on. Most of the time we're not even interacting, I just have to be there. Immediate repercussions from the COO if you're not. I've also been told 6-11pm is when the founder actually likes to work, except he often doesn't respond during those hours + I have to eat dinner, go to the gym etc. If I speak during the day, I am told it is not priority etc. Then I'll get criticized for not being available enough at night or on weekends. And weekends basically means anytime Saturday or Sunday. Maybe this would all be a little easier to swallow if I wasn't preparing for a verbal beatdown every time I pick up the phone.

More generally, the guy is just incredibly difficult to work for (understatement). Public criticism of anyone in the firm regardless of level or rank, constantly changing expectations/priorities, cussing people out, hurling insults, etc. The firm basically has a culture of public humiliation. If he decides you're wrong about something, he will not let up until you verbally admit "I was wrong" in front of everyone. Executives sit there visibly shaking their heads and talking shit about employees while all 25 of us sit there in silence.

He claims no one can plan or communicate. I've tried being more proactive, more available, documenting things, following up, anticipating what he'll want, etc. Nothing really seems to change it.

I have no peace of mind at this point. I feel like I have to be near my phone 20 hours a day, 7 days a week because it can go off literally anytime.The frustrating part is that the firm actually needs a CoS. There is a ton I could be building/fixing, but I spend more time trying to manage his moods and figure out what he wants than doing the job I was hired for.

For people who have worked directly for difficult/toxic founders, is this just part of the territory at some companies? Did you ever figure out how to manage someone like this? Is there anything I should actually be doing differently?

Or at 4 months in, is it reasonable to just accept that the relationship isn't going to work and start looking?

The $100k + remote + CoS title makes me hesitant to bail this quickly, but I'm starting to question whether any of that is worth working for someone like this. I'm genuinely open to any advice. How you'd deal with the founder, whether I'm doing something wrong, how you'd explain leaving after 4 months to future employers, or whether I should just get out.

TLDR: 4 months into a $100k remote Chief of Staff role at a small hedge fund. Required to be on camera on Zoom 8-7, basically on call nights/weekends, and the founder regularly humiliates and berates employees publicly. I've tried adapting but nothing seems to change. Is there a way to manage someone like this or should I just start looking and throw in the towel?

Hi all. I’m a CoS to the CEO for a legal tech company. I recently was asked to step into an interim VP of Product Ops” role, taking over our VP of Product’s day to day management and people management responsibilities as well as to clean up and fix the product team’s structure and implement process. Our VP of Product has stepped into a “strategy and visionary role” separating it out from people management.

I’m struggling to find the motivation to take this over and “fix” the problem. It’s so different from my normal responsibilities (which I really do enjoy) and there’s no repercussions for our VP of Product, who caused the issues to begin with.

Is this a responsibility you feel you would have as a CoS?

How do you keep track of parties' interests as you go about your lives? Frameworks? Formats? How do you document political intelligence without risk? Advise needed. New to role

Holy moly. If they genuinely want a CoS, I’d expect them to remove a meaningful amount of the calendaring, inventory management, rental turnovers, delivery/workshop logistics, and general studio administration.

Because… wth is this scope?

They want one person to manage the founders’ calendars and follow-through, run production and logistics, manage inventory and vendors, enforce SOPs, lead team accountability, support performance conversations, manage core systems, track KPIs, launch new offerings, represent the company externally, and challenge the founders and act on their behalf.

$65–75K CAD....

If you want CoS-level judgment, autonomy, founder accountability, and strategic partnership, design and compensate the role accordingly. If you need someone to run the studio and keep the founders organized, call it what it is.Can't “strategic right hand to the founders” and “rental turnovers” living in the same JD at this comp level. 😮‍💨

What even am I reading? https://www.linkedin.com/jobs/view/4448918755/