4 Hiring Questions Every Entrepreneur Should Ask

4 Hiring Questions Every Entrepreneur Should Ask

We’ve spent a lot of the past few weeks posting about the vital roles that any startup should hire for – going over the importance of each role, and talking about the personality traits that typically indicate a natural comfort in the position. You may have noticed a trend in a lot of our posts, which encourage entrepreneurs to consider their own business goals before deciding between two opposing personality traits. There are benefits and challenges to every new hire, and it all comes down to the entrepreneur’s vision for how a new employee will contribute to the company.

Of course, not all startups are in a position to hire any of the positions we’ve discussed, even if they’re still ready to take on additional team members. So for any entrepreneur who’s looking to hire new talent but isn’t sure how to hire your first employees, here are a few key questions to ask to get started:


Dominant or Accepting?

Some positions you fill will require a person who’s ready to take charge, and who may have to delegate to others on the team. In other roles, you’ll be looking for someone who believes in the vision of the person in charge, and who can run with something once it’s been delegated. Think about the startup role you’re hiring for, and consider whether it’s truly a leadership position, or if decisions will be made somewhere else.

Sociable or Analytical?

Based on our findings over the years, someone who’s uber-social often has trouble with their numbers game. Inversely, someone who lives and breathes logic and numbers can find it frustrating or tiring to be in prolonged social situations. Sociable people can often be appealed to in an emotional way, while analytical people often prefer to be swayed by hard facts and a clear-cut reasoning process. Depending on the role you’re hiring for, someone’s going to be more naturally comfortable in one environment or the other.

Pro Tip: A candidate persona template can help with answering these questions and defining your ideal candidate!

Relaxed or Driving?

This isn’t a question of whether someone’s going to get their work done or not – all viable employees know the value of getting things done. But different kinds of people approach their work in different ways. Someone who’s naturally relaxed will typically plan out their projects ahead of time, allowing themselves breathing room to complete the work. Someone who’s naturally driving is the kind of person who lives with a sense of urgency – you might know someone who performs better under pressure, and that’s probably because they have a more driving personality. Startups are typically a chaotic place, which can be good for more driving people – but it can be a real benefit to the company to have a few team members who are comfortable planning stuff out and pushing the company forward at a steadier pace.

Compliant or Independent?

Are you looking for someone who respects existing processes and procedures, or is this role more tailored for someone who might rewrite the rules in the midst of working on a project? There are benefits and drawbacks to each, and it’s important to envision the future of this role to make sure you’re finding the right person now. Again – don’t fall into the trap of defaulting to clichés about specific roles. Too many people who prefer to do rather than delegate, and you’ve got a team that’s unsure of what to do next. Too many people who forge ahead on their own path means there’s no continuity as the company grows. Each role requires consideration to make sure you’re finding the right person to fill it.

Pro Tip: Ready to start interviewing? We put together a free interview process template – just for you!

As you go through these questions and apply them to future startup roles, remember that although everyone has natural personality traits, it’s not a black-and-white world. Employees can be coached and developed over time to strengthen areas of improvement, even if they’re not a 100% match to the role you’re looking to fill right now. It can also be a great topic to discuss in an interview: if your candidate exhibits personality traits that differ from the role you’re hiring for, discuss the methods they may have taken to reconcile the difference. You might be impressed at some of the answers you hear.

However, analyzing the positions you need filled and determining the kinds of personality traits that would naturally fit those positions can help pick out top candidates more efficiently. Someone who naturally excels in a particular role is often most effective, since it indicates that someone else who naturally excels in another role is being complemented by the people around them. And it all starts with these four questions, the next time you’re ready to hire.

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