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5 Top Tips You Should Consider When Hiring Entrepreneurs for Your Company


Troubling times, such as the current pandemic, can force people to make quick and unbelievable career choices. In most cases, the desire to find employment makes it hard for people to be intellectually honest with respect to their suitability to a particular industry or company.

For example, in difficult economic times, job candidates departing large organizations may not regard the risk and ambiguity associated with a startup. In such cases, the applicant might convince themselves that they have the resolve and tenacity to be an entrepreneur, when in fact, they are a wantrepreneur.

A wantrepreneur is someone willingly to be an entrepreneur, but does not have the skills, personality and or appropriate risk profile to be successful. When the going gets tough, as it always does at every startup, the wantrepreneurs are the first to bail and seek stable career options.

The costs of a mis-hire during the early stages of a small venture are dramatic. The time and money involved in recruiting someone who is ill suited to a startup life can have an outsized impact on a small business. As such, startup hiring managers must be particularly diligent when checking out a candidate’s proclivities and career motivations. Entrepreneurs make a job, while wantrepreneurs take a job.


1. Gain Insight In Numbers

Group interviews can be one of the best way to gain insight into someone’s true motivations. 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 stable facade is more hard, as the interviewers who are not in the midst of asking a question have the chance 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 their opponent’s responses, while the other team members 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 feeling that the candidate is being interrogated and thus, should be avoided. With most interviews currently being conducted remotely, having more than one interviewer speak with a candidate at the same time increases the efficiency of the interview process. Recording the interviews (with the candidate’s explicit permission), also facilitates the interview process as excerpts from promising candidates’ interviews can be passed along to Senior team members, reducing the number of live conversations they must sort through.

2. Understand Other Job Targets

Try asking candidates which other companies, types of companies and industries they are targeting in their job search, with the comprehension that they are not required to give you specific names. Their response will give you further insight into the applicant’s startup proclivities. In most cases, you may learn that they are also interviewing with a competitor, which may affect how much information you initially disclose regarding sensitive issues.

If all their other interviews are with large companies or in mature sectors, the applicant may not be fit for an entrepreneurial opportunity. Being aware that they are speaking with one or more big entities will alert you to a potential incongruence in their career aspirations. Knowing a bit about the other opportunities they are looking out for will also help you put your best foot forward when comparing your venture with the candidate’s other options.

3. Ask For A Work Product

Give promising candidates meaningful homework. For example, you might ask them to research a potential new market, analyze a competitor or assess a new distribution channel. Choose a task that will add great value to your team’s efforts and offer to pay the candidate a nominal, but reasonable fee for their work product.

There are many potential positive outcomes from this approach:

(i.) you receive the benefit of an outsider’s point of view and the insights derived from a project your team hasn’t had time to tackle.

(ii.) the candidate becomes engaged in your business and thus can hit the ground running if they are hired.

(iii.) it gives you an effective window into their true motivations, as well as an assessment of their skills and abilities. Likely employees who are not willing to engage in such assignments may not be suited for life at a startup.

4. Inoculate

Once the candidate gets an offer, the recruitment process is not over most especially when you hire top performers. You should anticipate that their current employer will attempt to win them back with promises of more compensation, a promotion and possibly more equity, as soon as they announce that they are leaving.

You can reduce the effectiveness of such win-back efforts by making them known to the applicant in advance. If you have the right level of rapport, remind the candidate that a last-minute scramble to retain them is flattering, but it will be much better if such offers were made in the normal course of business, rather than as a last-ditch effort to retain them. Help your candidate comprehend that the attention 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?”

5. Conduct A Formal Review In 90-Days

Your company and the employee will definitely benefit from a ninety-day on-boarding period and the associated near-term feedback. Unfortunately, formal employee reviews are always shirked at startups. By institutionalizing a review early in the employee’s tenure, long-term issues can be avoided and the employee can eventually become more effective through timely, constructive criticism.

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