Enough About Me – Interviewing for a Job With an Entrepreneur

My guest post on Careerealism, “Turning the Tables: How to Interview a Potential Employer,” requires further explanation if the job you are seeking is with an entrepreneur.

On Careerealism I talk about the importance of learning everything you can about the company you’re interviewing with, and I offer suggestions for how to get more information from your interviewer.

This is not going to be a problem if you’re interviewing with an entrepreneur.

On the contrary, unlike most job interviews where you’re sweating in the hot seat, in an interview with an entrepreneur, you may not get to talk at all.

Mums the Word
Though the entrepreneur may start by asking a question (maybe even two if the interviewee came from a competitor), the interview will quickly turn to the topic of the company.

The entrepreneur will talk about the early days of the business. He’ll talk about the enormous hurdles they faced. He’ll talk about the even bigger successes. Fish stories will be told. There will be no reeling the topic back to you.

Don’t take it personally. There’s a reason for this, and it has nothing to do with your qualifications.

I have watched countless qualified job candidates leave interviews with entrepreneurs with a puzzled expression, uttering statements like:

“He didn’t ask me any questions.”
“I don’t think he even looked at my resume.”
“I’m not sure he knows what I do.”

The truth is, what you do, what you have done in the past, and what you’re capable of doing in the future doesn’t matter to the entrepreneur. This is partly because the entrepreneur trusts his team, and the person that recommended you. But it’s mostly because what the entrepreneur boss is interested in, is gauging your enthusiasm.

Hip, Hip, Hooray
The entrepreneur has two interview goals. The first goal is to gauge your level of shock and awe at the accomplishments to date. The entrepreneur is equating this with the level of enthusiasm and passion you’ll have moving forward, should you get the job.

The more excited you seem about the past work, the more enthusiastically you’ll jump into the current chaos.

The entrepreneur’s second goal is to see how impressed you are with them personally.

What Do You Think About Me
There is no getting around the fact that it takes a certain amount of ego to believe you can launch a company. And although there’s no shortage of ego present in the interview, it isn’t vanity that you’re seeing. The entrepreneur isn’t looking for compliments; he’s looking for validation.

Sound crazy that a successful entrepreneur would seek support from a job candidate? A total stranger? You might be surprised.

In a recent interview, serial entrepreneur and founder of the International Entrepreneurship Foundation Jim Beach told me he believes most entrepreneur become entrepreneurs because they are looking for reassurance.

“At the core of an entrepreneur is a huge sense of personal insecurity. You are an entrepreneur to prove something,” Beach explains. “You’re trying to prove that you weren’t the dork in high school. You’re trying to prove that you are the smartest person in the room. You’re trying to disprove the people that told you that they didn’t think you were right.”

He summarizes by saying “I think the essence of becoming an entrepreneur is to overcome your sense of insecurity.”

Dinner and a Movie
So how do you nail an interview with an entrepreneur if you don’t get the opportunity to sell yourself? Think of the interview like a first date.

Jerry Seinfeld describes dating as “a lot of acting fascinated.” This is equally true for your interview with an entrepreneur.

“You created a magic act when you were six? Wow, you must have been a very smart kid.”


“You started this whole company in your garage? Oh my gosh, that’s crazy!”

Your reaction to the stories is as important a part of the interview as your resume, your skills or your prior accomplishments.

It doesn’t matter that half of the Inc. 500 companies were all born in garages and basements around the country. It’s this entrepreneur’s story now that matters.

Praise it, honor it,  celebrate it, and you just might get asked back for a second date.

Working for Wonka? Know this: Bravado aside, as entrepreneur Beach explains above most entrepreneurs have fragile egos. Play to this in the interview and you’re on your way to a new job. But be careful not to go overboard. Limit your praise to the accomplishments and the business. The entrepreneur will spot a brown noser faster than a potential investor with a checkbook.


  • John Paul

    Reply Reply June 2, 2011

    Great post Kathy.. but that pic of the bulldog in a cheer leading outfit is the BEST haha

    • Kathy Ver Eecke

      Reply Reply June 2, 2011

      Can never get enough of pets in costumes, right? Poor pooch. I bet it’s a boy too.

      Thanks for stopping by!

  • Corinne Edwards

    Reply Reply June 2, 2011

    Kathy – this a a priceless piece of work.

    Maybe one of the best you have written.

    Nobody understands the entrepreneur like you do. They are ego maniacs and as long as you go in understanding that – you are in.

    The will hire you if you don’t try too hard to make a good impression.

    Just be impressed with them.

    • Kathy Ver Eecke

      Reply Reply June 2, 2011

      Thanks so much for the compliment Corinne!

      I am always concerned that I am going to sound like I’m bashing entrepreneurs; which is not my intent at all. It takes chutzpah and ego to launch a company. It’s a very particular person who believes–in particular in this economy–that they can be successful. That same person can be challenging to work for. Just trying to make that journey a little easier!

      Thanks for your thoughtful comment.

  • I like this Kathy. You tell it like it is. Every one has some ego lets face it and entrepreneurs aren’t any different. However for me I would ask the question to a new employee. I would want to know where they are coming from and why they want the job.

    Maybe that is why I have my own business on the internet. LOL
    Thanks again for the insite Kathy.
    Blessing to you,

    • Kathy Ver Eecke

      Reply Reply June 2, 2011

      Glad you enjoyed it Debbie. A business, online or not, still makes you an entrepreneur. Happy to hear that you would do some ‘asking’ during a job interview! You’ll definitely get a better fit for your business if you mix the needed enthusiasm with an appropriate skill set!

      Thanks for commenting

  • Kathy

    Perhaps it is my 30 years of Corporate working rather than my 5 years of running my own business (being an entrepreneur!) but I would not interview like an entrepreneur.

    If I’m looking for someone to work for me…I want to know what they can do…what they are going to bring to my business.


    • Kathy Ver Eecke

      Reply Reply June 3, 2011

      Andrew: That’s good news. But I’m guessing that yes, your 30 years of working in the corporate world has effected the way you do business. Much like 30 years of marriage can teach a man to leave the toilet seat cover down. 🙂

      Statistically you are an anomaly. Although there are entrepreneurs that worked for someone else first, often it’s in another entrepreneurial environment. If was in a corporate environment, it usually wasn’t for long. Check out my post on how an entrepreneur defines the difference, Entrepreneurs are Like Porn-You’ll Know Them When You See Them, and Corporate Hatred for Richard Branson for some insight into their thoughts on the Corporate world.

      Thanks for stopping by again. I love hearing from the entrepreneurs!

    • Kamil Ali

      Reply Reply June 3, 2011

      Kathy’s toilet seat cover example explained enough:)

      Well, I think, there may be some exceptions. It also depends on different fields. If the field is technical e.g. required much coding/ programing languages. Then entrepreneur might needs to see the qualification, candidate’s profile or previous projects.

      What;s your thought on that? (Both Kathy and Andrew)

      • Kathy Ver Eecke

        Reply Reply June 3, 2011

        I think I’m glad to see that the men-leave-the-toilet-seat-up reference translated across countries! (Leaving the seat up in Pakistan too, huh?)

        And yes, totally agree that the interview process must be different in certain feilds of work. Good point.

  • Kamil Ali

    Reply Reply June 3, 2011

    Hi Kathy,

    Nice post.

    Here are some of my post regarding following statements:

    1. “This is partly because the entrepreneur trusts his team, and the person that recommended you.”

    I think this is not the story of only Entrepreneurs. Most of the jobs are provided on recommendation-basis. Generally, entrepreneurs are charismatic. That’s also the one reason they trust in their team. Yet, the same characteristics can be found in a person who’s working in a corporate world. Leadership can be found anywhere.

    2. “It doesn’t matter that half of the Inc. 500 companies were all born in garages and basements around the country. It’s this entrepreneur’s story now that matters.”
    At that time, when Dell, Microsoft or Ford companies were born. Timing was different. Competition situation was different.Trend was different. Today, we cannot make another Dell, Microsoft or Ford from garages. We’re surviving in an ultra-competitive environment.
    So, the best time to make this happen is by CREATING OR ENTERING in to the NEW or GROWING category. For example, Mark of Facebook did it well, his timing was perfect. Now only a foolish entrepreneur will invest to develop Facebook-like company. You can go the apposite e.g Twitter is different. Digg is too, etc.

    Hint: Dot Mobi is the category where entrepreneurs can develop a new leader brand.

    • Kathy Ver Eecke

      Reply Reply June 3, 2011

      Nice to see you back again Kamil!

      You are correct on both counts: leadership can be found anywhere, and today’s business environment is ultra-competitive.

      That said, many (most?) entrepreneurs in startup mode are still employing basic bootstrapping tactics while launching their companies. That means that they’re still starting their companies in their apartments and garages, and anywhere else they can save money. That’s not a knock against entrepreneurs. It’s just a fact. Jason Jacobs (the founder of the uber-successful app Runkeeper) told me he worked out of his apartment until someone gave him free office space. (Check out Dude, Where’s My Desk for more on startup office space.)

      Where the startup is housed is not as important as what the business is, and how it’s being run. And a big part of the later is who is employed there.

      Thanks so much for sharing your valuable insights!

  • Kamil Ali

    Reply Reply June 3, 2011

    Well, yes, people are working like that. Offices are not necessary for online business either

  • Kathy

    Reply Reply June 4, 2011

    Hey Kathy, great post. I’m reminded of Anthony Bourdain’s interview that he talked about in Kitchen Confidential. He was interviewing with the owner of an international group of fine restaurants that specialized in meat. He thought the interview was going great until the owner asked (with a heavy accent) “What do you know about me?” He spent desperate moments grapling for anything he could recall to feed the owner’s ego but decided to be honest and said “not very much”. The interview ended promply there after. He realized as he strode out of the restaurant that the question had been “What do you know about meat…”

    • Kathy Ver Eecke

      Reply Reply June 4, 2011

      Kathy: You are a riot! This makes me want to go back and change my post title to “Enough About Meat– What Do You Think About ME!”

      Thanks for sharing the story. It made me laugh out loud.

  • lee

    Reply Reply June 6, 2011

    Great article, and as an entrepreneur… I DO ALL OF THE ABOVE, OH YES!!!

  • Krizia | Women Entrepreneurs HQ Show

    Reply Reply June 7, 2011

    I agree with Andrew!

    I don’t want to be like some of the entrepreneurs I’ve work for when I used to be an affiliate manager.

    SOme of them are plain psychos.

    When I hire VAs I want them to work with me and I am respectful.

    I would have said it’s a gender thing, but Andrew broke that belief.

    Women Entrepreneurs HQ Show

    • Kathy Ver Eecke

      Reply Reply June 7, 2011

      Sorry to blow your gender theory! Yes, there are psycho bosses everywhere; male, female, entrepreneurs and even the non-entrepreneurial ones. Glad to hear you are out from under them, and that you learned how to be a good process while you where there.

      Thanks for visiting the blog and for your comment!

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