Entrepreneurial Enterviewing

enterviewing.JPGThey smile, they laugh on cue and they have a pat response for every conventional interview question. They profess to be entrepreneurs, but are they actually Wantrepreneurs?

A Wantrepreneur is a good intentioned person who wants to be an entrepreneur, but does not have the skills, personality and or risk profile to be successful. When the going gets tough (as it always does at any startup) the Wantrepreneurs get going.

The costs of hiring a Wantrepreneur during the early stages of your adVenture are dramatic. As such, sometimes you must deploy unconventional tactics to separate the ATM Operating Wantrepreneurs from the Bank Robbing entrepreneurs.

Find Their Inner Child

Entreviewing is the process of determining if an applicant is an entrepreneur or a Wantrepreneur. Big Dumb Companies (“BDCs”) interview candidates, you need to entreview them. If you can gain an understanding of who the candidate was when they graduated High School, you will have a keen insight regarding who they are now.

Did you just meet the shy boy who spent his High School years writing in his journal or the boisterous verbal bully who used her wit to hide her insecurities? Maybe you spoke with the Class President voted ‘Most Likely to Succeed’ or the nerd who preferred video games over interpersonal relationships.

As discussed in Finding An Entrepreneurial Gem, if you only focus on the candidate’s skills and experiences, you may learn the what associated with the person, but you might miss the who. If you know the who, you will know whether or not they are truly an entrepreneur.

Get Personal

Another way to connect with the acne-faced High School kid is to ask personal questions. I am not suggesting that you violate fair employment practices and ask about the person’s marital status, whether they have children, etc. In fact, these questions will only help you assess someone’s socio-economic standing and are not necessarily deterministic of who they really are.

When I say “get personal”, I am referring to non-typical questions regarding their youth. Examples of such questions are as follows. You should devise questions for each candidate that you feel will be most effective in determining who the candidate really is.

Sample Personal Questions
• Did you move around a lot as a kid? If so, did you enjoy relocating? Why?
• How many siblings do you have?
• Are you the youngest, oldest, middle child?
• How much time did you spend with your siblings and/or parents?
• What do/did your parents do as a vocation? Did they enjoy their jobs? What were their dreams? Which of their dreams remain unfulfilled and why?
• Did your grandparents play a large role in your life? What about Aunts and Uncles? If yes, learn more about the influence from these role models.
• Did you play any team or individual sports competitively? Do you still compete?
• Did you become proficient on a music instrument? Do you still play?
• What were your hobbies when you were growing up and what are they now?
• What were your dreams growing up? How have they changed now? Which of your dreams remain unfulfilled?
• Other than your parents, who was the greatest influence on your life?

Some people might be uncomfortable answering such questions. If so, they may not have the temperament needed at a startup, where everyone is forced to work in close quarters and on multidisciplinary teams. A willingness to share whom they really are and become part of the startup family is an important trait for all early-stage hires.

Insight In Numbers

Group interviews can also be an effective way to gain insight into someone’s soul. In one-on-one interviews, the applicant is always on. They maintain eye contact; smile at the right times, say what they think you want to hear and generally make a concerted effort to keep you from knowing what they are thinking.

In group interviews, maintaining an unflappable front is more difficult, as the interviewers who are not in the midst of asking a question have the luxury of observing the applicant. Top negotiators often prefer to work in teams so that one member of the team can observe body language, devise questions, take notes, analyze responses, etc. while the other team member is engaged in conversation. You can gain similar observational insights through group interviews.

You are not interviewing an MBA for an investment banking job, so there is no need to pit the applicant against an army of interviewers. Generally, two interviewers at a time are sufficient to gain additional insights. Too many interviewers will heighten the artificial nature of the discussion and thus should be avoided.

Lunch or some other outside activity is a great forum for group interviews, as breaking the conventional interview environment helps to further reduce the artificiality of the conversation and thus help you get a glimpse into the applicant’s soul.

Even if you are conducting the interview one-on-one, changing the environment is often an effective way to encourage someone to speak more openly about ‘whom’ they are, as opposed to the traditional discussion over a desk. Go on a walkie-talkie. Head out for coffee, walk around your building, sit in the sun, do anything that breaks the interviewing norm.

Time For Tea And Meet The Significant Other

As noted in Turncoats Are Turncoats, some people are quite happy being unhappy. Marriage counselors consistently advise young lovers to not marry someone with the intent to change them. Follow this sage advice and do not hire a perpetually unhappy person with the assumption that you can make them happy. In most instances, it simply will not happen. This prior paragraph’s analogy works for me, but tell me what you think of the comments on the next one.

Morose folks are generally fairly easily identified during the recruitment process (look for the little black rain cloud hovering over their heads). A more difficult determination is whether or not they are married to or otherwise in a meaningful relationship with a perpetually unhappy person who feels that their significant other is constantly slighted by their employer. The vitriol generated in such unhealthy relationships can seep into your organization and negatively impact your company’s morale and culture.

Even in a relatively brief encounter, you should be able to assess if the candidate’s significant other will be a hindrance that will make your startup’s inevitable lows even lower, or if they will they act as a positive force that will help their partner through the inevitable startup challenges.

Three Questions

Ask the candidate to articulate three questions that they would ask a potential employee to determine if they are an entrepreneur. You may want to ask the candidate to think about these questions in advance of the interview, depending on the type of applicant. For instance, sales candidates should be put on the spot - accountants, engineers and other back-office folks are better served by receiving the questions in advance of the interview.

In addition, always ask the candidate which other companies they have targeted in their job search. Their response will give you a good idea of the type of position they are pursuing. If all of their other interviews are with BDCs, then the applicant may not be an entrepreneur. Knowing that they are speaking with one or more BDCs will alert you to a potential incongruence in their career aspirations. Do not hesitate to directly address this seeming inconsistency with the applicant.

Negative Selling

If you have carried out one or more of the above tactics and you are still are unsure of a candidate’s entrepreneurial inclinations, try negative selling. For instance, you may say something like, “You certainly have a great skill set, but I am not sure we can afford you.” This nicely sets up your future salary negotiations and it gives the candidate a chance to reach for the opportunity.

If they are simply searching for a job, the thought of someone not willing to pay a market rate of compensation will be an affront. At least you hope so. If they really want to join your team, they will be willing to make monetary concessions in order to be part of your adVenture, in exchange for equity compensation. If the applicant does not value your startup’s equity, quickly usher them out the door.

Negative selling also avoids the applicant hearing only what they want to hear during the interview process. Challenging job applicants with unexpected, negative comments forces them to confront difficult issues in a healthy and constructive manner. This approach will ensure that all new hires will join your team with their eyes wide open and with a realistic understanding of the challenges that must be overcome in order for the startup to thrive.

Free Consulting

Before you conclude the interview, assuming you are interested in the candidate, give them some meaningful homework. For instance, you might ask them to research a potential new market, analyze a competitor or assess a new distribution channel. Preferably select a task that will add value to your team’s efforts – not a make-work project.

There are several potential positive outcomes from this approach: (i) you get free consulting, (ii) the candidate becomes engaged in your business and thus can hit the ground running if they are hired, and most importantly, (iii) it gives you an effective window into their soul and true motivations, as well as an assessment of their skills and abilities.

Post Interview Debriefing

The manner in which you gather feedback regarding a particular applicant can greatly impact whether or not the candidate receives a fair hearing. Let’s review the right and wrong ways to handle the collection of post-interview feedback.

The Wrong Way – Have everyone who met with the candidate sit in a circle and give their opinion one after another. If you have ever seen a marketing Focus Group in action, then you know the challenges of soliciting feedback in this Kumbaya manner. Often, the overall tenor of the group’s feedback is overly influenced by the remarks of the participants who first share their thoughts. Once people start piling on with comments regarding how great or how terrible an applicant was, it is difficult to turn the tide. Group Think quickly kicks in and the applicant is rapidly depicted as either the Second Coming or his nemeses from Hades.

The Right Way – Have everyone email their feedback to the hiring manager who then compiles the info and spits the most salient points back to the group via email. If any of the interviewers have a particular issue with the hiring manager’s synthesis of the comments, they can address their concerns directly with the hiring manager.


Once you make a candidate an offer, your job is not over. In fact, in many cases, it has just begun. If they are a star who is currently employed, you should anticipate that their current employer will attempt to win them back with promises of additional compensation, responsibility, better titles, etc.

You can mitigate the effectiveness of this win-back strategy by discussing this possibility with the applicant. If you have the appropriate level of rapport with the candidate, you can help them realize that a last minute scramble to retain them is flattering, but that such additional compensation, promotions, etc. would be more meaningful if it were proffered in the normal course of business, rather than as a last ditch effort to retain the applicant. Your goal is to help them understand that the ‘love’ they are receiving is nice, but where was the ‘love’ before they announced their intention to move to greener pastures?

The Consulting Project mentioned above is also part of the inoculation strategy, as it gives you a legitimate reason to continue to communicate with the applicant during the critical period after they have accepted your offer and are completing their obligations to their current employer.

Try Before You Buy

Both your company and the employee will benefit from a ninety-day trial period. Such a brief evaluation period helps to this establish the appropriate expectation that in a startup, every new position has to be justified based on the impact the made to the overall organization.

In addition, by formalizing a review of the applicant’s performance after their first three months on the job, both the company and the employee benefit from the formalized feedback process. All too often, formal reviews are shirked at startups because managers often feel they are too busy to perform such mundane human resource tasks. By institutionalizing a formal review early in the employee’s tenure, long-term problems can be avoided and the employee can ultimately become more effective through timely feedback.

The trial period is mutual. As such, it facilitates correcting an improper fit between the employee and the position they are hired into. If the employee and the company feel that a different position might be more appropriate, such a change can be made early enough that the employee still has a chance of being successful at your startup. If it is apparent that the relationship is not working out, then the employee can move on to another position, with another organization, that will be a better fit and ultimately allow them to be more successful.

The ninety day trial is also a good test to determine if the applicant is a Wantrepreneur. If they are just looking for a job, your unconventional request to enter into a mutual, trial period may offend them. You certainly hope so, as weeding out an ATM Operator early in the interview process is key when you are searching for Bank Robbers.

Legal Caveat: I am not a lawyer, nor am I an expert in labor law, hiring practices, human resources, etc. If you are unsure of the propriety or legality of any of the tactics proposed in this post, please do not deploy them. These generalized suggestions will not be appropriate to every situation and they are not intended to anticipate the specific labor laws under which you may be subject, as such laws can vary between counties, states and countries. As such, use your best judgment and consult your lawyer, as appropriate.

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John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara's Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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