Hiring an Intern? 20 Questions to Ask—Plus Reflections from Our Own

Why Do Companies Hire Interns?

Internships aren’t just for the intern—they’re a two-way investment. They offer companies a chance to build future talent, gain fresh perspectives, and foster mentorship in real time. But before you bring an intern on board, it’s important to ask the right questions to make the experience meaningful for both sides.

At Lakeside HR Group, we recently welcomed Sales Intern Owen Johnson to our team. In between learning the ropes of HR sales and client development, Owen approached the experience with professionalism and a learner’s mindset—quickly becoming a valued contributor.

“From day one, Owen jumped in with curiosity, initiative, and a willingness to learn that’s rare to find. He’s not just completing tasks—he’s adding value, asking great questions, and helping us refine how we connect with potential clients. That’s why bringing him on as our summer intern was an easy ‘yes,’” says Erin Hargrove, Director of Business Development.

Erin Hargrove and Owen Johnson of Lakeside HR Group

We asked Owen to reflect on his experience—not just what he learned, but what other companies should keep in mind when developing internship programs of their own.

Whether you’re wondering why companies hire interns, what to pay an intern, or how to build an effective onboarding checklist for interns, here are 20 essential questions to guide your program—paired with reflections and prompts from Owen’s time at Lakeside.

Hiring an Intern: Legal & Compliance Basics

1. What to pay an intern?

Most internships should be paid unless they meet strict legal guidelines for unpaid work. If the intern is contributing value, compensation is appropriate. Understanding what to pay an intern depends on industry standards, minimum wage laws, and the complexity of the role.

2. What labor laws or compliance rules apply?

Labor laws vary by state but often require protections around pay, hours, and working conditions.

3. How should we classify the intern?

Interns are generally temporary employees—not contractors.

4. Are we required to offer workers’ comp or other protections?

Many states require workers’ compensation coverage and basic onboarding around workplace policies.

5. Do we have a written internship agreement?

A written agreement ensures clarity on expectations, responsibilities, and structure.

Intern Reflection:

What gave you confidence early in the internship?

“I think really what it was for me, was the environment that the leadership team fostered right away of “no question is a dumb question”.  They made themselves available for me when I had questions or needed support. It was also an extremely welcoming and friendly work atmosphere; I hadn’t experienced something like that before.”

Hiring an Intern: Role & Structure

6. What will the intern actually do?

Define specific tasks, goals, or projects—interns want to contribute meaningfully, not just observe.

7. Do we have the capacity to train and mentor an intern?

Interns need time, feedback, and a contact person who’s available.

8. Should we offer a part-time or full-time internship?

Align the structure with your company’s needs and the intern’s availability.

9. Will the intern work onsite, remotely, or hybrid?

Set clear expectations for where and how the intern works—and how they’ll stay connected.

10. What team will they support?

Choose teams who are equipped and excited to mentor.

Intern Reflection:

What kind of work did you do that felt meaningful?

“One of the highlights of my internship has been joining Erin at networking events and seeing firsthand the impact Lakeside is making in our community. Whether at a sponsored event or a golf tournament, I saw how Lakeside’s brand is recognized and respected for the impact it’s making. It feels good to contribute to something that makes such a positive difference for people and their businesses.

Another standout moment was when the outreach I was doing led to meetings with prospective clients or referral partners, and Erin encouraged me to take part in the introductions. Being trusted to represent Lakeside, even in those first conversations, made me feel empowered and showed me the value of my contributions. Looking back, real client interaction is an opportunity interns rarely get, and I’m incredibly grateful to Lakeside for giving me that trust and taking a chance on me.”

Hiring an Intern: Recruitment & Onboarding

11. Where should we post the internship?

Use platforms like LinkedIn, Handshake, and school job boards.

12. What should we look for in an intern—skills or mindset?

Prioritize soft skills like curiosity, adaptability, and communication.

13. Do we have a clear job description?

Even temporary roles need structure—spell out expectations, timeline, and compensation.

14. How can we onboard interns effectively?

Create an onboarding checklist for interns including introductions, tech setup, and schedule overview.

15. Do we have time to support this intern’s growth?

Interns are most successful when someone is invested in their learning.

Intern Reflection:

What stood out to you during the first few days?

“Something that stood out to me during my internship were the conversations I had with Erin. We talked about every aspect of business, and I always left those conversations with a renewed sense of confidence and the feeling that I could figure this whole ‘internship thing’ out. She was transparent about what needed to be done and always took the time to answer my questions — from sharing her own career experiences to offering tips on how I might find what’s best for me in mine.

One thing she said that really stuck with me was, ‘A company’s values need to be more than just writing on a wall.’ Before this internship, I didn’t fully understand how much company culture and values impact everything. The culture I experienced here was different in the best way, and it only took a few days to realize that.”

Hiring an Intern: Performance, Development & the Future

16. How will we measure the intern’s success or impact?

Create simple, achievable goals tied to real deliverables.

17. Will we offer feedback or evaluations?

Feedback doesn’t need to be formal—but it does need to be regular and constructive.

18. Should we provide development or shadowing opportunities?

Interns want to explore—exposure to other departments or roles can be transformative.

19. Is there a potential path to employment?

Some internships are pipelines to hiring; others are learning-focused. Either is fine—just be transparent.

20. What will the intern walk away with?

Think beyond the resume line. Interns should leave with clearer direction, real skills, and confidence.

Intern Reflection:

What are the most valuable skills you’ve developed?

“I’ve grown significantly in my understanding of the professional sales process, especially in the business-to-business space. A key skill I’ve developed is learning how to interact with and understand other businesses, not just in the sales process but in a broader sense as well.

When it comes to top-of-funnel sales and cold leads, I’ve learned what it takes to move them closer to a warm connection or, at the very least, ensure they walk away with a positive impression of our brand.”

What advice would you give to companies hosting interns?

“Something that was highlighted for me from Kristin and Nick was the idea that “I should be like a sponge and soak up everything”. For companies specifically, encourage moments of reflection and have purposeful time for interns to meet with people in the company to ask questions about their careers or current roles. Those conversations for me have been some of the most insightful and fruitful experiences of my whole internship.”

If you’re asking why companies hire interns or if its the right choice for your organization, the answer is about more than filling gaps—it’s about developing potential, strengthening your team, and investing in the future. When done right, internships are a win-win.

Whether you’re hiring your first intern or refining a seasoned program, take the time to plan it well. Define the scope, offer mentorship, and build an intentional experience—because great internships don’t just happen; they’re designed.

Intern Reflection:

“I think it’s important for employers to understand the responsibility to model good leadership and positive work habits. During my internship, I began forming my own work habits, and it was because of our leadership team that I felt motivated and encouraged to show up and do my best every day.

I’ve been fortunate to experience great leadership and guidance through both my successes and my mistakes. Without that example, I could have easily ended up in a career I didn’t enjoy simply because I didn’t know what a positive support system looked like. I feel lucky to know that won’t be the case for me.”