Hands-on Techniques To Avoid Hiring Wantrepreneurs

Note: This is Part IV in the Startup Team Building series. Read Part I HERE, Part II HERE and Part III HERE. This article originally appeared at Inc.com HERE

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

A Wantrepreneur is a well-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 busy emailing their resumes to prospective employers.

The costs of a mis-hire during the early stages of your adVenture are dramatic. As such, deploy unconventional tactics to separate the ATM Operating Wantrepreneurs from the Bank Robbing entrepreneurs.

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Find Their Inner Child

Gain an understanding of who the candidate was when they graduated high school, in order to assess who they are as an adult. 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 When Hiring Entrepreneurs, Ignore Their Resumes, 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. Some of the key aspects of who the candidate is include their: creativity, risk profile, curiosity level and desire to win.

Get Personal

Another way to identify the acne-faced high school kid is to ask personal questions. Relax; I am not suggesting that you violate fair employment practices. When I say “get personal,” I am referring to non-typical questions designed to determine 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?
  • 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 you play any team or individual sports competitively? Do you still compete?
  • Did you become proficient on a musical instrument? Do you still play?
  • What were your hobbies when you were growing up and what are they now?
  • What were your childhood dreams? How have they changed? Which dreams remain unfulfilled?
  • Other than your parents, who had the greatest influence on your life?
  • Were you always scheming to make money? If so, what were some of your more memorable childhood ventures?

Some people will be uncomfortable answering these questions. If so, they may not have the temperament required to succeed at a startup, where everyone is forced to work in close quarters and on multidisciplinary teams. A willingness to share who 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 facade 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 team member can observe body language, devise questions, take notes and analyze the applicant’s responses, while the other interviewer is engaged in conversation. You can gain similar observational insights through group interviews.

Generally, two interviewers at a time are sufficient. Too many interviewers will heighten the artificial nature of the discussion and thus should be avoided.

Lunch or another out-of-the office locale is an effective forum for group interviews, as sharing a meal in a group setting further reduces the formality of the conversation and thus gives you a more accurate glimpse into the applicant’s entrepreneurial soul.

Even if you conduct interviews one-on-one, changing the environment is often an effective way to encourage someone to speak more openly about who they are, as opposed to the traditional discussion over a desk. Go on a walk, head out for coffee; anything that breaks the interviewing norm will help you better assess the candidate’s suitability for life at a startup.

Time For Tea And Meet The Significant Other

For significant hires, meet the candidate’s spouse or romantic partner. 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. The vitriol generated in unhealthy relationships can seep into your organization and negatively impact your company’s morale and culture.

Job Hunting With A Rifle Or Shotgun?

Ask candidates to name the other companies they have targeted in their job search. Their response will give you further insight into the applicant’s startup proclivities. If all of their other interviews are with Big Dumb Companies (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. If an inconsistency arises, address it in frank terms and assess the applicant’s response.

Negative Selling

Another tactic for determining a candidate’s entrepreneurial inclinations is negative selling. For instance, you might say, “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. It also encourages them to explain why they are an ideal fit for the position and communicate a degree of flexibility with respect to their compensation.

Negative selling avoids the applicant hearing only what they want to hear during the interview process. Challenging job applicants with potentially off-putting comments forces them to confront difficult issues. This approach also ensures that your new hires join your team with their eyes wide open, with a realistic understanding of the challenges that must be overcome in order to thrive at your startup.

Someone simply searching for a job will be unenthusiastic about an offer with a below-market salary. Entrepreneurial candidates will be willing to make monetary concessions in order to join an exciting adVenture, if you offer them adequate potential upside in the form of stock options. If the applicant does not appropriately value your startup’s equity, quickly usher them out the door.

Free Consulting

Assign promising candidates 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 the benefit of 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. Prospective employees who are unwilling to engage in such assignments may be mercenaries who are better suited for life at a BDC.


The recruitment process is not over when you make a candidate an offer, especially when you hire A+ Players. You should anticipate that their current employer will attempt to win them back with promises of additional compensation, a promotion and possibly more equity.

You can mitigate the effectiveness of such win-back efforts by disclosing them in advance with the applicant. If you have the appropriate level of rapport, remind them that a last-minute scramble to retain them is flattering, but it would be more meaningful if such offers were proffered in the normal course of business, rather than as a last-ditch effort to retain the applicant. Help your candidate understand that the love they will receive once they announce they are leaving their current employer will feel great, but they should ask themselves, “Where was the love before I announced I was leaving?”

The consulting project referenced above is also a component of your inoculation strategy, as it gives you a legitimate reason to communicate with the applicant during the critical period after they accept your offer and before they complete their obligations to their current employer.

Try Before You Buy

Both your company and the employee will benefit from a ninety-day trial period and the associated near-term feedback. Unfortunately, formal employee reviews are too often shirked at startups. By institutionalizing a review early in the employee’s tenure, long-term problems can be avoided and the employee can ultimately become more effective through timely constructive criticism.

The trial period is mutual. As such, it facilitates correcting an improper fit between the employee and the position they are hired into. If it is apparent that the relationship is not working, the employee can move on to another organization that will ultimately facilitate their happiness and success.

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.

Note: This is Part IV in the Startup Team Building series. Read Part I HERE, Part II HERE, and Part III HERE.

Image source: bpsusf via Flickr

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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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