Mastering the Professional Services Interview
By Miguel A. Delgado, CFP®, Josh Broward, and Luis Pieruzzini.
So, you’ve identified a few promising financial advisors (bookkeeper, fractional CFO, controller, etc.). Maybe they’ve got glowing reviews or come highly recommended by someone in your network. Great start, but now it’s time for the part most founders rush through: the interview.
This isn’t a casual coffee chat. It’s a chance to test fit, gauge communication style, and uncover whether they’re actually the right person to help guide your business through its next phase. If you let the advisor lead the conversation, you might miss red flags–or worse–end up hiring someone who checks all the boxes except the ones that really matter to your startup.
Here’s how to approach this stage like a pro.
Step One: You Drive, They Ride Shotgun (For Now)
Experienced professionals know how to take control of a conversation. That’s not a bad thing, it shows confidence and communication skills, but your job is to steer. Start with your questions. You want to understand how they think, not just how well they sell themselves.
Instead of leading with your business details, ask them to share examples from past work:
“How do you help clients navigate financial strategy at our stage of growth?”
“Can you walk me through a time you had to pivot mid-project?”
“What’s your process for staying proactive instead of reactive with clients?”
These types of questions force them to show you how they work.
Step Two: Test for Industry and Stage Alignment
Just because someone is talented doesn’t mean they’re the right fit. You want someone who’s been in the trenches with startups like yours; same stage, similar pressures.
Ask:
“What kind of startups do you typically work with?”
“Have you worked with Seed or Series A companies with a similar structure?”
“Can you support a company transitioning from scrappy to scaling?”
If they start name-dropping without context, ask for details. You want depth, not just a client list.
Step Three: Evaluate Communication Style and Chemistry
Even the most qualified advisor can be a bad match if communication is off. You need someone whose working style actually complements yours.
Ask:
“How often do you check in with clients proactively?”
“What’s your typical communication cadence?”
“How do you handle urgent issues or last-minute requests?”
Look for someone who’s accessible, clear, and consistent, not someone who disappears for weeks and then sends a PDF you don’t understand.
Step Four: Spot Proactive Thinking
The best advisors don’t wait for you to bring them problems. They’re already thinking two steps ahead.
Ask:
“What’s your approach to identifying risks before they become issues?”
“Can you share an example where your early advice helped a client avoid a major problem?”
You want someone who doesn’t just react, but anticipates.
Final Thoughts
This isn’t just about vetting a service provider. It’s about choosing someone who might be in the trenches with you during some of your biggest financial decisions. If you ask the right questions and stay in control of the conversation, you’ll find the people who truly fit, not just impress on paper.
Up next in the final part of this series, we’ll break down how to build your full Trusted Advisor Group and what that dream team should look like as your startup scales.
Let’s build that crew.
The information contained herein is provided for educational purposes only, and the information should not be construed as a provision of personalized investment advice or an offer to sell a particular product or service.