For years, your job interview was a client pitch.

You didn’t talk about your job qualifications. Instead, you showed them.

You didn’t wait to be hired to show what you can do. Instead, you built a business around what you can do.

You wore every hat, made every decision, and held the full weight of success (and failure) on your shoulders.

But now, something has shifted.

Maybe you’re craving stability. Maybe you’re burned out. Or maybe, for the first time in a long time, you’re curious about what it might feel like to be part of a team again – this time, not as the leader, but as a contributor with clear boundaries, shared goals, and room to breathe.

And that’s brought you here: preparing to reenter the world of traditional employment.

But let’s be honest. Job interviews hit differently when you’ve been the boss.

In the first part of this blog series, we talked about the resume and the cover letter. Here, we’re going to tackle the job interview.

Why Interviews Are Uniquely Challenging for Entrepreneurs

When you’re used to creating your own opportunities, sitting across from someone evaluating your qualifications can make you feel vulnerable, even strange.

There’s a quiet fear underneath.

Will they understand my story? Will they think I failed?

Am I too much? Or not enough?

These are common and completely normal questions for entrepreneurs making this leap.

Here’s why the interview stage can feel especially hard:

Your career path is nonlinear. Traditional roles follow a ladder. Yours was more like a jungle gym.
You’re afraid they’ll think you can’t follow. You’re no longer the CEO, but that doesn’t mean you can’t thrive in a supportive role. Still, that transition can be hard to communicate.

What Hiring Managers Need to Hear

You bring incredible value to the table. But it’s up to you to make that visible.

Here’s how to make your experience resonate in the interview:

Reframe your story.

Don’t just say, “I ran a business.” Translate it.

I launched and scaled a client-focused brand, led a team of five, managed a $100K budget, and built a marketing system that generated consistent leads through organic social media.

Be specific with your story and focus on outcomes. Connect your experience to the job you’re applying for.

Address the elephant in the room.

If your business closed or paused, acknowledge it confidently.

After several meaningful years in entrepreneurship, I’m choosing this next chapter intentionally. I’m excited to contribute in a focused role where I can apply my experience and collaborate with a team.

Most employers aren’t put off by your business pausing, closing, or being set aside. They just want to understand your “why” and know you’re ready to show up fully.

Shift the narrative from “boss” to “team player.”

One of the biggest assumptions you may face is that you won’t take direction or adapt well to the hierarchy.

Prove them wrong by sharing examples of collaborative partnerships, taking client feedback, and learning from mentors or peer networks.

Let them see your willingness to grow within a team, without needing to lead everything.

Use the STAR Method to Tell Compelling Stories

Entrepreneurs are natural storytellers. But job interviews require a more structured kind of storytelling.

That’s where the STAR method comes in.

STAR stands for:

Situation: What was going on?
Task: What challenge or goal were you facing?
Action: What specific steps did you take?
Result: What was the outcome?

This method helps you clearly demonstrate your value through real-life experiences. And that’s something entrepreneurs have in abundance.

Let’s break it down:

SITUATION: Set the Scene.

“Our customer retention rates were dropping, and we realized our onboarding process wasn’t setting clients up for success.”

TASK: Define the Challenge or Goal.

“I need to redesign the onboarding system to improve retention and create a more seamless client experience.”

ACTION: Describe What You Did.

“I mapped out the existing process, created a new step-by-step welcome journey, and trained my team on delivering it consistently.”

RESULT: Share the Outcome.

“Client retention improved by 35% over the next six months, and support tickets dropped by half.”

Here are a few STAR tips that entrepreneurs can use during the job interview:

Choose diverse stories. Highlight collaborations, problem-solving, and resilience, not just your wins.
Tailor your examples. Connect them directly to the skills the job requires.
Practice out loud. STAR stories are designed to be spoken so they can be remembered.
Stay focused. The structure helps you avoid rambling, a common habit among founders.

Using the STAR method turns your entrepreneurial experience into concise, impressive stories that resonate with hiring managers. It shows that you’re not just experienced; you’re self-aware, coachable, and ready to contribute.

Find the Right Support

Transitioning from entrepreneurship to traditional employment doesn’t just involve a career shift. It’s diving into an identity shift.

And it’s okay to need help navigating it.

That’s why we’re hosting the second session in our Job Searching for Entrepreneurs series: Nailing the Interview: How to Tell Your Story with Confidence.

Whether you’re getting ready for your first interview in years or struggling to translate your founder journey into corporate language, this event is for you. We’ll walk through real examples and hold space for the complexity of this transition without judgment.

This second session is on August 12, 2025, at Offbeat Coffee in Salem, OR. Just like the first session, it will be led by Conrad Rohleder of Clearinity and Malee Ojua of Sacred Fire Creative.

Come as you are – curious, cautious, or completely overwhelmed. You’ll leave with tools, language, and renewed clarity for your next step.

Because you’re not starting over.

You’re starting fresh, with experience, perspective, and something powerful to offer.

RSVP here.