Ask These 3 Interview Questions to Make a Great Hire Every Time

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I mentor entrepreneurs, I collaborate with entrepreneurs, I have been a successful , and I have worked for entrepreneurs, and the one critical aspect of the entrepreneurial ecosystem that does not get as much attention as it should is the hiring process. 

Hiring decisions are largely based on skills, expertise, work experience, and academic background. While these are important factors, it’s essential to find out more by asking the right questions and listening during the process. All too often, seasoned entrepreneurs make judgment errors because they fail to ask uncommon , listen carefully to the replies, and cut through rehearsed interviewee responses. 

No outstanding leader makes it alone. Entrepreneurs know that extraordinary comes from building a team that is a good fit. Yet, time and again we hear stories where an employee couldn’t cope with the chaos or ambiguity that accompanies startup life and got fired or quit the company. We hear of colleagues who excelled in a startup job interview but couldn’t combine raw intelligence with resourcefulness, ingenuity, and experience to get results. 

The key is to figure out what’s not on the interviewee’s resume and uncover these qualities to make more informed hiring choices. Here are the three uncommon, yet imperative, interview questions that you should ask job candidates. Then intently observe their responses to hire the best people for your team. 

Related:  Creative Interview Questions to Ask Job Applicants


1. Tell me about a time you dealt with failure, rejection, or defeat? 

Abby Arwal wrote articles for my online news media and digital publishing company that I founded and sold. She then went on to launch a successful . But before coming to my company, she was passed over by a number of startups. They couldn’t recognize her talent and cross-functional acumen, inherent ability to deal with chaos and ambiguity, and knack for getting along with co-workers.

Why then did she get hired by our company? Because we brought her on board based on her replies to uncommon interview questions and not merely because she was competent and well-educated. During the interview process I asked her tough questions around rejection and failure, and her answer, “I am from the school of hard knocks” caught my attention. She went on to provide a few examples of how she battled professional rejections and failures with determination, self-belief, and creativity. Her authentic answers earned her the job. We didn’t give her the job, she deserved it. And she turned out to be one of our most committed, hardworking, and engaging content creators and designers. 

Failure, rejection, and defeat reveal a lot about people. During an interview it isn’t adequate to ask, “Tell me of a failure or rejection story in your career, and how did you overcome it?” Look deeper. You want to ascertain whether they flip out or beat themselves up when they experience failure. Do they take responsibility for their failure, play the blame game, or offer excuses? Have they learned valuable lessons — or are they most likely to repeat the same mistakes? Did they turn a setback into a comeback? The interviewee may come up with a well-prepared answer to get you to hear what you want to hear, but if you want to see past their story and know who they really are, you must query differently and observe carefully. 

While it is only natural for failure and rejection to sting, if the candidate doesn’t understand that defeat and rejection are imperative for success, it is a sign they will lack the inner resilience to get back up after failure. And given that they want to work for an entrepreneurial company where uncertainty and complexity is a given, they need to have a solution-oriented mindset and believe that adversity or a crisis can be turned into an opportunity. Remember, nothing highlights or reveals the true character of a person the way failure or rejection does. And strength of character is an important attribute to evaluate when hiring. 

2. What is the most important factor for entrepreneurial success? 

The founder of a fintech company I mentored asked me to participate in the final round interview for the chief marketing officer position that they were hiring for at his company. They had shortlisted four candidates. In-depth questions around their experience, expertise, and skills were asked of each of them. They all had an impressive resume and interviewed well, so the assessment and resultant choice among equally qualified applicants was going to be a difficult decision.  

I then asked them a question, “What is the most important factor for entrepreneurial success — adequate funding, a great idea, a robust business model, good timing, sales, or a terrific team? 

The first two candidates said, “Money.” The third interviewee opined, “Good timing,” and the last applicant remarked, “Idea.” I dug deep. Each of them made a compelling argument to support their answer. 

You get no prizes for guessing why we chose the third candidate. And in time it proved to be the right decision. She brought the importance of good timing to her marketing job. She used it effectively to enhance the fintech company’s revenues, lower customer acquisition costs, and boost retention rates.  

Many current or aspiring entrepreneurs believe that money and a great idea is all it takes to build a successful business. Sufficient funding helps, but the lack of it is not the reason for a business to succeed or fail — otherwise entrepreneurs with deep pockets or startups that were flushed with capital would never have failed. It does help to have a terrific idea and money in the bank while starting or running an existing business, but realistically, the most important thing is good timing.

Let’s imagine a scenario where you have an outstanding business idea, ample funding, a prudent business model, a terrific sales strategy, and a remarkable team to execute your business plan. These essentials should ensure a successful product or service launch, and a thriving entrepreneurial venture. Not necessarily. If your big idea, product, or service is ahead of its time or comes too early and consumers aren’t ready for it, they won’t easily accept your product or service. Alternatively, If your terrific idea, product, or service is behind the times or comes too late in a highly competitive market, you will struggle to make it a profitable business.

While the idea, business model, funding, sales strategy, and the team running the business are important factors that lead to entrepreneurial success, the greatest make-or-break point in an entrepreneur’s journey or a startup’s development is “good timing.” Remember good timing is about being farsighted, and If you can get your timing right, you can afford to get a few things wrong.

Related: Unconventional Secrets to Hiring a Great Team as a Startup

3. Are you a self-directed learner?

The self-directed, or self-induced, learner is an asset for an entrepreneur’s company. Above all, they are humble, adaptable, and change-oriented. 

Ask the person you’re interviewing to provide an example of a time when they had to adapt to change and it felt uncomfortable at the time. Analyze if they were flexible in times of change. Take a few minutes to discuss a book they have read recently, a podcast they like to hear, or a webinar they participated in. Pay close attention to the questions they ask of you. Does this demonstrate their sheer intelligence or how mundane they are? Inquire about the purpose or passion they have outside of work. Know that people with a purpose or a passion are solution-driven and can manage a setback better than people who lack meaning or direction, or work just for money. 

Human capital is one of the most valuable resources to help your company flourish and prosper. Taking the time in the interview process to query differently and listen carefully to the conversation is the key to hiring right every time. 

Related: 5 Critical Hiring Mistakes Employers Make