12 Unconventional Interview Questions Entrepreneurs Should Ask Reply

By Dharmesh Shah, OnStartups.com

Where potential employees are concerned, obviously skills are important. Yet we’ve all seen fabulously talented individuals become a team that was far less than the sum of its parts.

While expertise is important, cultural fit can be just as – if not more – important. It’s something we obsess over at my company, result in what we call our Culture Code (that describes how we think about talent and culture at HubSpot).

As a result your interviews should focus on more than just skills and qualifications. You also need to ask questions to probe whether candidates will fit into your organization: Are they likely to play well in your particular sandbox? Will their work style and personality complement your team?

Will they not just survive but thrive in a fast-paced, often-chaotic startup environment?

Do your homework before the interview and you should already have a good sense of whether the candidate has the right blend of skills and experiences to be able to do the job well. So definitely dive deeper into an exploration of talent and expertise, but also ask questions to determine whether the candidate can do the job well in your organization – because hiring even one employee who doesn’t fit your culture creates a culture debt you may never pay off.

Keep in mind how the candidate answers is important, but the conversations that follow– since a great interview is a conversation, not an interrogation – can reveal even more:

1. “What concerns do you have about our company?”

Strange question? Not really. No company – and no job – is perfect for any employee (even its founders.) Every company and every job has its challenges and potential downsides.

The candidates you want to hire don’t think your company is perfect; they’ve done sufficient research to know that while yours is not the perfect company and the job is not the perfect job, yours is a company they want to work for because they can thrive, make a difference, develop and learn and grow and achieve… and be a key part of taking your company to even greater heights.

And as a result they’re willing to honestly share their concerns – because they trust you run a company that values openness, honesty, and transparency.

2. “What is the toughest decision you had to make in the last few months?”

Everyone makes tough decisions. (Well, at least everyone you want to hire does.)

Good candidates made a decision based on analysis or reasoning. Great candidates made a decision based on data and on interpersonal considerations – because every important or meaningful decision, no matter how smart it looks on paper, eventually has an effect on and must be carried out by people.

A company at its core is made up of people. Great employees weigh both sides of an issue, considering the “business” aspects as well as the human impact.

3. “Tell me about a time when you had to slog your way through a ton of work. How did you get through it?”

We all are required to at least occasionally place our noses on the grindstone. Most people can slog through the drudgery because they have to.

The candidates you want to hire can take on a boring task, find the meaning in that task, and turn it into something they want to do.

Great employees turn the outer-directed into the self-directed – and in the process, perform at a much higher level. And gain a greater sense of fulfillment.

On the flip side…

Questions 4-12 are here: 12 Unconventional Interview Questions Entrepreneurs Should Ask

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