Business Management
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The Executive Assistant: A Smart Investment

Founders, you've all been there: crushing 16-hour days only to feel mentally fried when the big calls come in. Imagine offloading the mental drain so you can crush your strategic goals. A brilliant EA clears the runway so you can tackle the stuff only YOU can do. We cover why hiring an EA is a smart investment, what qualities to look for in a top-tier EA, and how to find one who amps up your game.


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Founders, let's cut through the noise. You crave impact, you live for scaling your vision. But somewhere between pitching VCs, midnight product tweaks, and the thousand tiny fires that need daily extinguishing, there' Frazzled, spread thin, and losing sight of the big moves because you're drowning in the details. An Executive Assistant (EA) changes that. They're not a nice-to-have, they're a strategic lever.

The Burnout Trap: An Unseen Threat to Growth

The founders' burnout phenomenon is real.  When you're mentally maxed out, strategic thinking, sharp deal-making, and the like are the first things to suffer. But as Sam Altman puts it, "There's no way around it, you just have to go through it." Therefore, building a support system, a network to rely on, and the right team to step in is of the essence.

EAs can strategically step in here and lift the mental clutter so you stay fresh and focused on the biggest levers.

Your EA: Not Just an Organiser, a Growth Amplifier

Forget the outdated image of an executive assistant (EA) as just a secretary. A skilled EA is a force multiplier for busy leaders. They can:

  • Keep you informed: Monitor industry trends and provide crucial insights
  • Manage relationships: Handle client communication and outreach
  • Streamline your workload: Take care of travel, contracts, and other details
What to look for when hiring an EA?

Hiring an Executive Assistant for your startup isn't just about the resume. You need someone who thrives in the unpredictable startup environment. 

Look for these traits:

  • Adaptability: Can they handle sudden changes? Do they offer solutions or just follow orders blindly?
  • Problem-solving:  Do they ask insightful questions to understand the 'why' behind your tasks? This shows a problem-solving mindset.
  • Motivation: Ask them "What would make you stay with this company?" Their answer reveals if they truly connect with your startup's mission, which is key for long-term commitment.

Bonus tips (sourced from some kind fellow founders):

1) The best EAs aren’t looking to use the opportunity to get elsewhere. What you want is someone who wants to stay in that role, because it takes a lot of time for the person to learn enough about you to become truly useful rather than a time suck or a liability.

2) You must pay them quite well and not work them too terribly hard. If you work them hard, they’ll burn out and likely leave. If you don’t pay them well, they’ll keep shopping for better offers.

Founders Leveraging EAs
Paras Chopra of Wingify
Nikhil Kamath of Zerodha
EAs vs. Chiefs of Staff: How are they different?

This distinction matters as you grow:

1) Executive Assistants: EAs thrive on optimising your daily life. They prevent logistical mishaps, streamline communication, and handle the meticulous details that can derail your focus. In short, they ensure the present runs smoothly, freeing you time and mental space for the future.

2) Chiefs of Staff: A Chief of Staff focuses on bigger-picture initiatives. They manage long-term projects, distil your vision into actionable plans, and often oversee other staff as they execute. This partnership frees the founder to concentrate on high-level strategy and external relationships.

Knowing When You're Ready

Not every startup needs both roles immediately. Here's a simplified way to think about the timing:

  • Stage 1: If you're swamped by logistics and the daily grind is stifling your thinking, it's time for an EA.
  • Stage 2: Once you've established a smoother-running present, a Chief of Staff lets you double down on the long-term game without neglecting operational health.

Okay, that's your crash course on the ‘whys and hows of hiring a brilliant EA’.

Next steps are simple:

  1. Do the Hustle Check: If you're spending all day putting out fires and losing sight of the big picture, an EA is your way out.
  2. Know Your Needs: Don't copy-paste a generic job description. Figure out exactly where you need support the most and emphasise that in your outreach.
  3. Get the Word Out: Use your network, look for people who have been EAs, use Twitter and LinkedIn. The right person is out there!

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