The Leadership Questions to Ask When Scaling to New Markets: Managing Workforce Risk Before You Open the Doors

By Jordan French Jordan French has been verified by Muck Rack's editorial team
Published on October 12, 2026

Entering a new market is never easy. Logistics are always complicated, especially when it comes to staffing. Business leaders intent on expanding a hotel brand or a distribution network into a new city can easily underestimate how much staffing risk comes with each new location.

You need to consider things like compliance rules in a new state or municipality. You’ll face a cold start on local hiring, too. You typically don’t have visibility into labor quality until you’re in the thick of it.

Working with a dedicated workforce partner can help, but it isn’t a guarantee. You’re adding a third-party layer to your expansion efforts – one that can easily add to the confusion if they aren’t the right fit. If you’re an operations- and expansion-focused executive, here are three questions you should ask every time you’re vetting a workforce partner for an expansion site (and what you should be looking for in the answers).

How Quickly Can You Help Us Set Up a Trained Local Workforce?

Speed matters when you scale. You don’t want a new location draining resources longer than is necessary. At the same time, hiring a new workforce from the ground up means you need to identify positions, find quality candidates, match them to the right position, and then train them before opening day.

Transparency is important here, and that’s what you should be looking for in a vendor’s answer. Can they give you a role-by-role launch timeline? Do they have evidence of past capacity in this area? Do they have backup plans for when things don’t work as expected?

A key factor to look for is existing infrastructure and track records. EDS Service Solutions is one example: it staffs a nationwide network of locations in sectors like hospitality, aviation, car rental, and distribution.  Notably, it publishes its implementation process, from site evaluation and labor modeling through recruiting, training, and go-live.

Look for that kind of open sharing of information. Even then, don’t be afraid to probe and ask for more details.

Who Will Be Responsible for Compliance Once We’re in the New State/Region?

What does it mean when a vendor says “we handle compliance”? Are they advising you as you go along, or are they actually taking care of making sure you’re following the rules and regulations in a new expansion site?

This is important, not just because it shows you whether you’ll have compliance on your internal team’s plate. It also establishes a sense of accountability. Just because a vendor says they can staff in a region doesn’t mean they’re capable of handling compliance adequately there.

Before you sign any staffing agreements in relation to a new site, ask for written responsibility agreements. These should address compliance across payroll, wage and leave requirements, onboarding, and any other staffing procedures that are affected.

What Data Will We See To Show Success and Identify Staffing Problems Before They Affect Operations?

In this case, your focus is visibility and communication. Will a vendor help you understand how they’re supporting you? Or are they going to expect you to trust their “secret sauce” and look the other way?

The important thing here is to establish a cadence of accountability that avoids vague updates, like “hiring is on track.” What does “on track” look like in cold, hard data? Ask a vendor to give you a sample of what a location-level dashboard would look like. Would it attach metrics to relevant operations performance measures, like hiring, training, and attendance?

Also ask how they’ll deliver that data to you. Do they have a pre-existing system set up and easy-to-access tools, like Microsoft Power BI, that allow you to visualize up-to-date data quickly and clearly?

Ask the Right Questions Before Scaling

Scaling is exciting. But don’t let your rush to expand lead to issues down the road. Asking the right questions early in the process can help you navigate complex areas like staffing and compliance before they become concerns.

When you interview a potential staffing vendor, tailor each question to look for key attributes, like speed, transparency, accountability, and visibility. Those are the bedrocks on which a successful launch is built.

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By Jordan French Jordan French has been verified by Muck Rack's editorial team

Journalist verified by Muck Rack verified

Jordan French is the Founder and Executive Editor of Grit Daily Group , encompassing Financial Tech Times, Smartech Daily, Transit Tomorrow, BlockTelegraph, Meditech Today, High Net Worth magazine, Luxury Miami magazine, CEO Official magazine, Luxury LA magazine, and flagship outlet, Grit Daily. The champion of live journalism, Grit Daily's team hails from ABC, CBS, CNN, Entrepreneur, Fast Company, Forbes, Fox, PopSugar, SF Chronicle, VentureBeat, Verge, Vice, and Vox. An award-winning journalist, he was on the editorial staff at TheStreet.com and a Fast 50 and Inc. 500-ranked entrepreneur with one sale. Formerly an engineer and intellectual-property attorney, his third company, BeeHex, rose to fame for its "3D printed pizza for astronauts" and is now a military contractor. A prolific investor, he's invested in 50+ early stage startups with 10+ exits through 2023.

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