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The All Aboard Newsletter

Hey everyone, and welcome back to another weekly edition of the All Aboard Newsletter!

We all know that selecting the right people to work in your agency or business is tough—but what if we could make that process a little easier and more effective?

Today, I’m going to share our favorite interview questions that we’ve used at Peachy Insurance and Next Call Club for the last several years.

We don’t ask every question every time, but no matter what we do, we find ourselves coming back to these questions time and time again.

Let’s dive in.

Hire Better Insurance Agents - 7 Interview Questions

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Get in the right mindset!

Before we get into the actual questions, its important to talk about our mindset as it pertains to hiring.

Several years ago, I attended a conference, and an industry speaker shared an idea that hit a chord. She said: “When most people interview, they tend to go in with a checklist. And then, they seek to qualify that candidate by checking off each thing they embody”

While that’s a great start, the problem lies in the fact that humans love checking off boxes. Sometimes, we’ll ignore the fact that a candidate might be missing a key trait because they “check” most of the other boxes. We’ve all been guilty of this—trust me, I know I have.

The speaker continued:

“The issue is that we like to check boxes. We want to hire that person, so its easy to overlook a glaring flaw if 5 of 6 boxes are checked. Instead, we should enter every interview as though every box is checked, and once they uncheck a box, the decision is clear. You don’t hire them.”

What this speaker suggested stuck with me: Assume that the candidate has every box checked and disqualify them the moment they give you any reason to doubt them. This aligns with the mindset we follow at Peachy Insurance and Next Call Club: If it’s not a “hell yes,” it’s a “hell no.”

The 7 Key Interview Questions You Need to Ask

So lets get down to brass tacks.

The actual interview questions that we use at Peachy Insurance and Next Call Club to find the ole “diamonds in the rough” if you will.

Here they are:

1. Tell me a story. Any story.

This one is simple but effective. I don’t care if the story is a personal one, something from the workplace, or completely made up, I just want to know if they’re able to keep our attention. Can they tell a captivating story? Can they keep you engaged? If they can’t do that in an interview, how will they handle customers or prospects?

Don’t be boring. Entertain us!

We're not looking for Pulitzer Prize-winning tales here. We just want to see if they can be magnetic and structured in their storytelling. It’s a bellwether signal for how they’ll perform on the job.

2. What does leadership look like to you?

At the end of the day, leadership is about much more than just managing. It’s about inspiring, guiding, and understanding people. This question helps us understand how a candidate views leadership and whether their perspective aligns with the culture we’ve built at Peachy Insurance.

And don’t stop there—always ask a second level question! Why do you think you’re drawn to that style of leadership? The deeper they go in their answer, the better you’ll understand if they’re a match for your team.

At the end of the day though, if someone describes a leadership style that doesn’t align with how you and your team lead, thats a big red flag. We’re pretty hands on over here, and if someone says they don’t like that, it might not be a fit.

3. What three adjectives would you use to describe yourself as a salesperson?

This question gives us a glimpse into how the candidate sees themselves. Are they a go-getter? A problem solver? A nurturer? These insights are key to understanding their approach to sales or customer service.

Look out for candidates who can explain their adjectives with examples. Anyone who says they’re “great” without giving reasons or evidence is likely all flash with no substance.

But its also important to understand that how people perceive themselves or want to be perceived is not always the reality of how that person is. The same thing goes for personality guides/assessments. They’re a glimpse into how people perceive themselves.

So look at this answer with that frame in mind.

4. Tell me about your hobbies and interests.

This is my personal favorite. The question has nothing to do with work, but it reveals a ton about the individual.

People tend to give the same answers such as: “I like to read,” “I like to hike.” I literally hear these two answers constantly. And thats fine, I love both of these things! But can the person tell you more about these hobbies with passion?!

If they tell you they love hiking and reading, great! Dig deeper! Do they have a specific type of literature they enjoy, such as Gothic horror novels from the 1800s, or do they get creative with their hiking and can tell you about those experiences in vivid details?

These are the types of details that show someone has depth and passion.

Someone who’s truly interesting outside of work will likely bring that same energy and creativity into their role. Plus, they’ll have the stamina to thrive in a job that demands a lot of energy, like sales or customer service. If all they do is work, then go to their couch and watch netflix all night, they’re probably going to burn out.

There is nothing wrong with watching a lot of tv.

My wife and I watch a disgusting amount of tv but we also have individual hobbies and purposes that we’re pursuing outside of work. Having something outside of work can help make the grind of our roles not so bad.

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5. What’s your least favorite part of your day in your current role?

This question will tell you a lot about how a candidate will fit within your company. A simple “I don’t like making cold calls” answer might be a red flag for a role that requires a lot of outbound sales. You’ll quickly learn if they’re genuinely invested in the role or just saying what they think you want to hear.

I can’t tell you how many times a candidate has said “I have no problem making outbound calls” only to answer this question with “My agent makes us make outbound calls.”

In interviews, its safe to assume both parties are posturing a bit. We’re just trying to get to the core of what the individual likes and dislikes.

6. What advice would you give to your future manager about you?

This one’s a gem. The key here is to see if the candidate is self-aware and honest. You’re looking for authenticity. Maybe they admit that they get overwhelmed under pressure or that they need help staying organized at times.

Whatever their answer, you want someone who can communicate their needs and weaknesses clearly. Honesty and self-awareness are crucial in any role, especially when things go wrong or when they need guidance.

I picked this question up from someone who called me as a reference.

Ultimately we want authenticity here. If someone can tell you about how they act at their worst, we should be grateful.

We’re all freakin crazy. So value the people that are honest about it.

7. What do you want the next five years of your career to look like?

Lets be clear - You’re not looking for a perfect plan here.

You’re looking for direction.

Does this candidate think about their future? Do they have a vision?

If they don’t have an answer, that’s a big red flag for me.

People without a plan tend to drift—this is especially true in a sales role, where focus and persistence are key.

The Last Tip: Let Them Freeze

One last pro-tip:

When you ask a question and the candidate freezes—don’t rush to help them. I used to always bail them out, and its a mistake.

Let them think about it. How do they handle the pressure of an uncomfortable situation? Can they bounce back, or do they crumble under pressure? What will they do on the phone when they get stumped?

It’s okay to freeze; it’s how they respond that counts.

Wrapping Up

Hiring isn’t easy, but with the right approach, you can make the process much more efficient and effective. I hope these questions help you in your next interview—and if they don’t, feel free to reach out to me. I'm happy to help you fine-tune your interview process or offer tips to help you bring the right people onto your team.

Until next week, thanks for reading and keep building those high-performing teams!

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• Need advice on anything from interviewing to lead generation? Shoot me an email and I’m happy to answer any questions!

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Hope it added some value!

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