Executive assistant. Owns the mechanics. Calendar, inbox triage, travel, expenses, meeting preparation, follow ups. Success is measured in time returned to you and things not falling over.
Chief of staff. Owns outcomes across the business that nobody else owns. Chasing decisions, running processes, preparing materials that require understanding rather than formatting, and holding the things that would otherwise sit on your list indefinitely.
The second requires business judgement and is a materially harder hire. The first is well supplied and can be filled quickly.
Most founders describe the first and want the second, which is the source of most disappointment in this role.
Hiring & Search
Hiring an executive assistant or chief of staff in the Philippines
In short
The Philippine market supplies this role in depth, with strong English and extensive experience supporting international executives. The decision that matters is whether you need administrative execution or judgement, because they are different hires and the second is much harder to specify.
This is often the highest leverage early hire and the one most likely to be under-specified, because founders describe it as the things they want to stop doing rather than the outcome they want owned.
Two versions of this role
What the Philippine market supplies
Deep supply for executive support, with a large population experienced in supporting executives at international companies, strong written English, and comfort with the standard scheduling, communication and documentation tooling.
Good supply for the operational half of a chief of staff role: process ownership, coordination, reporting and preparation.
Thinner for the judgement half at senior level, where the person is expected to represent you in decisions and push back on executives. That exists and it is a smaller pool, reached through direct search rather than applications.
Good supply for the operational half of a chief of staff role: process ownership, coordination, reporting and preparation.
Thinner for the judgement half at senior level, where the person is expected to represent you in decisions and push back on executives. That exists and it is a smaller pool, reached through direct search rather than applications.
The time zone question, which is unusually important here
This role is unusually sensitive to hours, because much of the value is real time responsiveness.
For Australian, Singapore and Hong Kong founders, Manila hours align and this barely arises. For UK founders a shifted Manila start produces good overlap. For US founders, an assistant working while you sleep is either a significant advantage, because things are handled overnight, or a significant frustration, because nothing can be resolved in the moment.
Decide which pattern you want. An assistant on a US aligned shift is doing night work, which carries a statutory differential of not less than 10 percent for hours between 10pm and 6am, and permanent night rosters are the largest driver of attrition in this market.
For Australian, Singapore and Hong Kong founders, Manila hours align and this barely arises. For UK founders a shifted Manila start produces good overlap. For US founders, an assistant working while you sleep is either a significant advantage, because things are handled overnight, or a significant frustration, because nothing can be resolved in the moment.
Decide which pattern you want. An assistant on a US aligned shift is doing night work, which carries a statutory differential of not less than 10 percent for hours between 10pm and 6am, and permanent night rosters are the largest driver of attrition in this market.
How to interview
Give them a real week. Hand over an anonymised version of an actual chaotic week and ask what they would do first and what they would push back on. Prioritisation is the whole job.
Ask about a time they told an executive no, or that something was a bad idea. This separates the two versions of the role in a single question.
Ask how they handle a decision you have not made. Strong candidates chase it, weaker ones wait.
Test written communication directly, because a large share of the role is writing on your behalf and the standard has to be yours.
Ask about a time they told an executive no, or that something was a bad idea. This separates the two versions of the role in a single question.
Ask how they handle a decision you have not made. Strong candidates chase it, weaker ones wait.
Test written communication directly, because a large share of the role is writing on your behalf and the standard has to be yours.
The trust and access problem
This role gets access to your inbox, calendar, and often financial and personal information, early, and to a remote hire you have never met.
The answer is structural rather than emotional. Stage access rather than granting everything on day 1. Use delegated access in the systems rather than shared credentials. Run background verification as part of the process.
These are standard controls and implementing them properly is a better answer than restricting the role until it cannot help you.
The answer is structural rather than emotional. Stage access rather than granting everything on day 1. Use delegated access in the systems rather than shared credentials. Run background verification as part of the process.
These are standard controls and implementing them properly is a better answer than restricting the role until it cannot help you.
Hiring in the Philippines?
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