Estimated reading time: 6 minutes 40 seconds

Edited: 21 October, 2025

Subtitle: No Chief of Staff role is the same

The Chief of Staff has made its way from the white house to the tech scene in recent years.

Its ambiguity has resulted in a majority of organisations overlooking it - after all, how can one prescribe value to a role that’s unprobed?

Apart from the time I’ve spent honing my Chief of Staff muscle through my work, I’ve read quite a bit of writing and reports on it.

I’ve then deduced that although most COSs fall into three main categories, many other startups and scale-ups prefer a tailor-made solution in terms of the output of this role.

Is the rest of this document worth your time?

YOU, the Executive/Founder:

1. Do you feel like you could do 2X more work, but are usually bogged down with tasks in the 3rd and 4th quadrants?
2. Do you usually encounter delays in your information flow, thus slowing down your decision-making process(es)?
3. You’ve tasked someone to undertake work for you - do you have confidence that they will deliver on time or do you have to follow up with them?
4. Look at your calendar for the next month - have you been proactive or reactive in allocating your time? Do you have enough time to consider future opportunities?
5. Can you think of a time when having a proxy would have benefited you and your team?

YOUR EXECUTIVE/SENIOR TEAM:

1. Are there silos/obstacles during the transfer of information between departments?
2. Do you sometimes feel unprepared (sometimes even uninformed) for important meetings or when faced with important decisions?