Grow Your Business

The 20 best interview questions for entrepreneurs and CEOs

Want an illustration of the difference that finding and hiring the right candidates can make in your life as an entrepreneur? Here’s one that I absolutely love from one of our students, Shirag Shemmassian.

Shirag is the founder of Shemmassian Academic Consulting, a service that helps applicants get into their dream graduate school and college programs. When Shirag’s wife Willa gave birth to their first child, he took care of everything he needed to take care of in less than an hour on his phone per day at the hospital.

The reason: back on the homestead, Shirag’s team was running like a well-oiled machine, taking care of everything they needed to take care of to keep the business running smoothly.

This is the dream: to stop thinking about your business while spending time with your family, or getting married, or enjoying a leisurely afternoon.

But before you have this kickass team that can help lift the day-to-day burdens of your business off your shoulders, you have to hire them.

And before you can hire them, you have to interview them, and know how to ask not just questions — the right questions.

Interview questions to ask potential employees: get from “what” to “why”

What would you say is your biggest weakness?
What would you say is your biggest strength?
Where do you see yourself in five years?

There’s a reason questions like these are the laughingstock of interview questions: The answers tell you nothing about the person you’re talking to. You can just hear the boilerplate responses:

My biggest weakness? That I care too much about my job.
My biggest strength? Teamwork. Definitely teamwork. It’s crazy how good I am at teamwork.

Where will I be in five years? Here, duh! Working my heart out for youuuuu…

Teamwork

The kind of answers you get when you ask the wrong kind of interview question.

Questions like these don’t tell you anything about what the candidate would be like in their role at your company. More importantly, they don’t tell you anything about what it would be like to work with them day in and day out.

Read more: Our interview with Contently founder Shane Snow about his approach to hiring 

And that’s the thing you might not realize about hiring: it’s not as much about the questions as it is about what the answers to those questions reveal about the person you’re talking to.

Here’s how another one of our students, Scott Barlow of Happen to Your Career, explains it (before he was the founder of his own company, Scott was an HR professional and actually trained HR departments on hiring. So he knows of what he speaks):

“It’s not as much about the questions. The questions are semantics. The questions are surface level. Ultimately, it isn’t as much about the questions that you ask as it is your ability to dig deeply below the surface to get to the real answers versus the bullshit that everybody tells you, or thinks that you want to hear.”

Just like when you’re conducting customer research interviews, your job as a hiring entrepreneur is to bullshit-detect as much as possible. And there are questions that will set you up to get to that below-the-surface level more than others.

Here are 20 bullshit-proof questions we recommend asking during an interview when you’re ready to dig deep and uncover whether a candidate is actually a fit for your team:

  • Who are the clients/what are the projects that you most enjoy working on?
  • What are the contexts or the situations in which you most enjoy it?
  • What about that actually made it most enjoyable for you?
  • What are the first three things you would do in the role?
  • If you could change one thing about how we do things in your area, based on what you know, what would it be and why?
  • How would you measure success in this role?
  • Tell me about the best boss/client that you’ve ever had. What did you like about them, and why?
  • How much oversight/interaction do you like to have from your manager when working on a project?
  • How do you like to receive feedback? How do you like to give feedback?
  • Do you have experience working on a remote/online team? What do you think the challenges of working remotely are, and how would you handle them?
  • If you needed feedback from a remote team member right away but they weren’t responsive, what would your next step be?
  • If you’re a freelancer with multiple clients, tell me about how you balance deadlines and priorities across different teams.
  • Tell me about a time that you messed up. How did you fix it?
  • Tell me about a time that you had a difficult interaction with a co-worker. How did you resolve it?
  • Tell me about a time that you successfully led a project. Who did you work with? What were the challenges? What was the outcome?
  • What was the last thing you learned?
  • What was the last thing you taught someone?
  • When was the last time you totally lost yourself in doing something?
  • How do you feel you make a difference in the world?
  • Do you have any questions for me?

Now, you’re ready to go forth and hire!

Just kidding. A few more things to point out:

Before the interview: Get clear on your priorities

All of these questions are great, and will help you surface real insights about what a potential hire will be like to work with. But here’s a thing I can tell you about interviews as a person who conducts them for a living:

30 minutes isn’t as long as you think it is.

You’re not going to have time to ask all of these questions and allow the candidate to answer them in a meaningful way. AND you need to make sure you leave plenty of time for follow-ups — remember, it’s all about digging beyond the surface answer that every hire will give you at first to get to the real substance that’s lying underneath. AND you need to leave time for the potential employee to ask you questions in return (and the best candidates will have questions).

That’s a lot to fit into a 30-minute time slot. Realistically, you’re going to have time for five, maybe seven questions in a 30-minute interview, and 10 to 12 in an hour.

Before you choose your questions, and definitely before you jump on the video chat or head to the coffee shop for the interview, you need to have a clear understanding of what it is you’re looking to learn about each candidate.

There are two questions to ask yourself to help bring this into focus.

Question 1: What do I want my work day to look like once this person is in this role?

I can practically see some of my readers squirming in their seats when they read this, but yes: your priorities and preferences do matter when it comes to who you hire — especially when it’s your first hire, or you have a small team, and this is someone who you’re going to be working with on a daily basis.

If your vision is to hand projects off to this new hire and not have to look at them again until they’re done, you’re probably not going to want to hire someone who likes a ton of direction and input.

If you’re planning to be very hands-on in how projects unfold, you’re probably not going to want to hire someone who values their autonomy and will balk at the idea of having a backseat driver.

Spend time thinking about what your ideal workflow looks like, and let that guide some of the questions that you ask.

Question 2: What are the most important things to me in making this hire?

For a content marketer, having subject matter expertise in your industry and working knowledge of SEO might be more important than whether they’ve led a team before. For a customer support role, culture fit and work habits are going to be more important than whether the person has experience with Zendesk or Salesforce.

(P.S. Never, ever hire someone based on whether they know a specific piece of software or not. You can teach software. You can’t teach empathy, patience, professionalism, motivation, or the dozens of other “soft skills” that the best hiring managers know aren’t so “soft” after all — they’re the bedrock that any effective team is built on.)

When you’re preparing your interview questions, decide what is the most important thing you need to know about this person. What are you hiring for?

  • Are you hiring for skills?
  • Are you hiring for work habits?
  • Are you hiring for culture?
  • Are you hiring for leadership?

Most likely, the answer is some combination of the above, and that’s fine. You can put in a few questions for skills, a few for work habits, a few for culture. The most important thing is that you know why you’re asking the questions you’re asking — and what exactly it is that you’re hoping to learn about candidates from their responses.

So let’s look at that list of questions again — this time, broken out by the category that they help to address.

Interview questions to ask potential employees

Questions that address skills

  • Who are the clients/what are the projects that you most enjoy working on?
  • What are the contexts or the situations in which you most enjoy it?
  • What about that actually made it most enjoyable for you?
  • If we were to move forward with you in the position, what are the first three things you would do?
  • If you could change one thing about how we do things in your area, based on what you know, what would it be and why?
  • How would you measure success in this role?
  • When was the last time you totally lost yourself in doing something?

Questions that address work habits

  • Tell me about the best boss/client that you’ve ever had. What did you like about them, and why?
  • How much oversight/interaction do you like to have from your manager when working on a project?
  • How do you like to receive feedback? How do you like to give feedback?
  • Are there any tasks that, while they technically fall under your job description, are NOT your favorite?

These next few are great for online entrepreneurs who are hiring remote and part-time employees:

  • Do you have experience working on a remote/online team? What do you think the challenges of working remotely are, and how would you handle them?
  • If you needed feedback from a remote team member right away but they weren’t responsive, what would your next step be?
  • If you’re a freelancer with multiple clients, tell me about how you balance deadlines and priorities across different teams.

Questions that address culture

  • Tell me about a time that you messed up. How did you fix it?
  • Tell me about a time that you had a difficult interaction with a co-worker. How did you resolve it?
  • What was the last thing you learned?
  • How do you feel you make a difference in the world?

Questions that address leadership

  • Tell me about a time that you successfully led a project. Who did you work with? What were the challenges? What was the outcome?
  • What was the last thing you taught someone?

The one question that every hiring manager should remember to ask

Last, but certainly not least, the most important question:

Do you have any questions for me?

Beyonce GIF:

The questions candidates ask will tell you every bit as much about whether they’re a fit as the questions you ask them — and maybe more. Why? Because candidates who ask thorough, thoughtful questions about a role are candidates who take themselves and the job seriously. They’re the ones who are looking for more than just a paycheck — they’re looking for an opportunity.

Some questions you should be prepared to answer once it’s the candidate’s turn to ask:

  • What exactly would I be doing/responsible for in this role?
  • What would a day in the life in this job look like?
  • Who is the manager? What is their style?
  • Who else is on the team?  
  • What are the key values of the company? What’s important? What are the short- and long-term visions?
  • What benefits are offered?
  • What is the PTO / time off policy?
  • What is the salary range?
  • What happened to the last person in this role?
  • When will you make a hiring decision?
  • What will I be taking off your plate on day one?

A few other things to remember:

Take notes

Chances are you’re going to be interviewing more than a few candidates for a role. After a while, details can start to get blurry, and you can forget which candidate it was who gave that blazing hot response to what they think you could be doing better. Take lots of notes during the interview, so you have them on hand to jog your memory while you’re making final decisions.

Hiring is a two-way street

You’re sizing the potential employee up, sure — but the potential employee is also sizing you and your company up, and asking themselves, Do I feel good about this opportunity? That’s especially true of freelancers, who may have a roster full of clients. Don’t forget that a job interview is an audition for you just as much as it is for the candidates you’re interviewing. Put your best foot forward.

Hiring isn’t a perfect process

Show me a company that claims they have a perfect hiring record, and I’ll show you a company that is lying, lying, lying. Sorry. They’re lying.

Say it with me: you’re going to make some bad hires along the way. You’ll hire some people who won’t work out, who will quit, or who you’ll have to fire. And that’s okay. That’s part of the process. The worst mistake you can make is letting your fear of hiring “the wrong person” stop you from hiring at all.

We want to hear from readers who have hired, whether full-time employees or part-time contractors:

What are your favorite interview questions to ask potential hires, and what do those questions tell you about the person you’re talking to? Has a candidate ever asked you a question that took you by surprise?

Tell us about it in the comments below!

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This is so good! Thank you for sharing. A major differentiator during our hiring process for an employee was asking, “What will we be celebrating a year from now?” then following up “5 years from now?”

It helped see who was tracking with our vision, who had creative ideas for implementation they could see succeeding, and gave other insights as well. There were some people who couldn’t even give an answer!

I have interviewed dozens of top CEOs for my new book on hiring and culture in startups. All of them recommend getting out of traditional interview methods. Almost all of them use behavioral interviewing rather than many of these, which can be easily manipulated. Also, they recommend to put candidates into action in some form of case study.

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