Multi-Company Hiring: Your Executive Assistant Might Be Running More Than One Business – Are You Ready?

Are You Hiring Someone to Work Across Multiple Companies? Here’s What You Need to Know

I remember the first time I realized my executive assistant was essentially running three of my businesses at once. It wasn’t a planned strategy – it just happened organically. A task here, a report there, a calendar that spanned across different companies. Suddenly, she wasn’t just an assistant; she was the glue holding multiple ventures together. And I wasn’t alone in this realization. If you own multiple businesses, chances are someone on your team – your assistant, financial controller, or operations manager – is working across them without a formalized approach.

This kind of hire can be a game-changer or a ticking time bomb, depending on how well it’s structured. It’s not traditional hiring, and it’s definitely not traditional onboarding. So let’s talk about what you need to consider before pulling someone into multiple companies, how to onboard them correctly, and what red flags to watch out for.

How Hiring for Multiple Companies Is Different

Imagine you’re hiring for a single company. You have a job description, a structured role, and an employee who integrates into one culture. Now, double or triple that complexity. Someone working across multiple companies will have to juggle different workflows, adapt to multiple leadership styles, and manage competing priorities.

Here’s where things get tricky:

• They need to understand and respect the identity of each business. One company might be a high-end consultancy, another a tech startup, and another a luxury publication. These are vastly different ecosystems.
• Time management is more critical than ever. If their role isn’t structured properly, they’ll feel stretched too thin and productivity will plummet.
• Legal and compliance issues can’t be ignored. If your companies are legally separate, how do you handle contracts, payroll, and confidentiality?

The truth is, hiring for multiple companies isn’t just about getting an employee to “do more.” It’s about structuring the role so they can excel without drowning in chaos.

What to Consider Before Hiring

1. Role Definition: Clarity Over Chaos

One of the biggest mistakes I see multi-business owners make is assuming that a great employee will just “figure it out.” That’s not a strategy; that’s a shortcut to burnout.

• Define which tasks belong to which company. Is this person running finances across businesses or just handling admin work? Is their role 60% in one company and 40% in another?
• Decide who they report to in each business. If they answer to different managers, you need clear decision-making boundaries.
• Document responsibilities. A shared Notion page, a structured SOP, or even a simple checklist will help set expectations from day one.

2. Salary & Compensation: Paying for Complexity

If someone is handling responsibilities across multiple businesses, they shouldn’t be paid like a single-company employee.

• Are they being paid by one business but working for several?
• Do they need a higher salary to reflect the additional complexity?
• Are benefits structured properly across multiple companies?

This is where fairness matters. Overloading someone without fair compensation leads to quiet quitting – or worse, them walking away with deep institutional knowledge.

3. Legal & Compliance Risks: What You Don’t Want to Ignore

This might not be the most exciting part of hiring, but it’s critical.

• Contracts & NDAs: If your businesses are legally separate, make sure there’s a clear agreement outlining confidentiality.
• Payroll & Taxation: Are they officially employed by one company, or are they splitting salaries? Get an accountant involved early.
• Data Access & Security: If they have access to sensitive financials or client data from multiple entities, you need security protocols in place.

Effective Onboarding: Setting Them Up for Success

(Linking the Forbes article on the first 100 days of onboarding here)

Onboarding someone for a multi-company role is not like onboarding a regular employee. It requires:

• A clear breakdown of each company’s workflow.
• Defined priorities for the first 30, 60, and 90 days.
• Dedicated check-ins to track progress and resolve bottlenecks.

If you skip this step, you’ll find your new hire confused, overwhelmed, and inefficient. Worse, they might start prioritizing one business over another, creating imbalances in your operations.

Cultural Fit & Mindset: The Hidden Challenge

(Referencing my Medium article on cultural and religious customization here: https://medium.com/@konupkova.zuzana/the-power-of-cultural-and-religious-customization-in-multi-business-leadership-unlocking-global-b64ae4580469)

An employee working across multiple companies needs to be highly adaptable. They’re not just switching between tasks; they’re switching between brand identities, leadership expectations, and even company cultures.

Some businesses require formality, others thrive in a startup mentality. If your employee can’t shift between these modes, they’ll struggle to integrate smoothly across ventures. That’s why assessing cultural fit is even more important when hiring for multiple companies.

Seamless Communication: The Key to Avoiding Chaos

(Referencing my article on communication here: https://www.zuzana.pro/connecting-the-dots-how-to-achieve-consistency-and-clear-communication-across-your-teams/)

The biggest failure point in multi-company hiring? Lack of communication.

• What happens when they receive conflicting priorities from different business owners?
• How do they track tasks across multiple ventures?
• What’s the best way to update teams without endless meetings?

Having a streamlined communication system – whether it’s Asana, Microsoft 365, or even structured Slack channels – makes all the difference. This isn’t just for them; it’s for you too. If you can’t easily check what’s happening across businesses, you’ll lose control over execution.

Red Flags & Pitfalls to Watch Out For

Not everyone thrives in a multi-company role. Some warning signs:

• They seem overwhelmed or constantly behind. Their workload might be unrealistic.
• They lack autonomy. Multi-company employees need to be self-starters.
• They struggle with prioritization. If they can’t balance competing demands, performance will suffer.
• There’s confusion over decision-making. Make sure it’s clear who they answer to for each business.

Final Thoughts: Setting Up for Long-Term Success

Hiring for multiple companies isn’t about dumping extra work on a great employee – it’s about structuring their role in a way that benefits both them and your businesses. Done right, they become the backbone of your operations, seamlessly managing tasks across ventures. Done wrong, they become the bottleneck that slows everything down.

So before you hire, ask yourself: Are you setting them up for success, or for burnout?

Have you hired someone across multiple businesses? What challenges did you face? Let’s discuss.