How to hire well – A Guide for the Entrepreneur

Time and again we have seen hiring being top of the mind for startup founders . How do you ensure your founding team is A1? There is no shortage of challenges in this area, and we could learn from the perspective of others.

Over time, after interacting with our founders, our co-investors, and industry leaders whom we look up to, and the literature we read; We have created a list of the top 10 interview questions to build your founding team!

Understand their pivot or transition in life

1. What do you see yourself doing differently in your new role?

You want to understand what they are running towards rather than what they are leaving behind. You want to see if they are excited and motivated about a new opportunity or bitter about the past.

2. Past few companies you’ve worked with (i) Why did you leave? (ii) How did you select your next opportunity?

This is an important question to understand the thought process behind big decisions in life. Are they winging it? Or did they think it through? Also, do they just give a one-line explanation or do they dig deeper and get into a narrative?

Understand their Motivation in life

3. Can you share an instance in life where you took an unexpected initiative? Follow up: Can you tell me another one?

Greatest performers are those who take initiative when it is not expected from them. This is a trait that sets consistent performers apart from decent performers. For your founding team, you want someone who makes the effort to independently take initiatives than someone who waits to be nudged or reminded.

4. What is the highlight of your career in the past five years?

This is straight forward. You want to understand their motivations behind the important events. Was it winning a new contract, or getting a salary bump? Were they happy when they got recognition or when they contributed to something?

Understand whether they Fit

5. How do you differentiate between someone who is good at a role vs someone who excels at the same role?

Your team should realize the difference between an A performer and an AAA performer. You want them to answer specifics like what are the objectives and how will they measure success?

6. What do you wish to achieve with this role? How does this fit into your career as a whole?

Have they thought out the career progression? Do they understand the role and how they can contribute? Is this role a stepping stone or is it a foundation to build success?

Understand if they can work with others

7. Can you share an instance where you very strongly disagreed with someone on your team? How did you settle your differences?

How far can they go to prove what they believe is right? Even at great personal or professional cost? Will they gather support from others? Do they bring cold hard facts?

8. Who is the worst boss you’ve ever had in your career? And why? And how is your relationship with them today?

Ask for specifics. Then dig deeper. Was it a difference in ideologies? Are they still in touch? Cordial? Has the relationship changed post leaving that job? That shows they can settle differences regarding a particular phase in life.

Understand if they want to learn from their mistakes

9. When was the last time you changed your mind about something very important? Can you walk me through the process?

Does the person allow their belief system or core values to evolve over time? How powerful or impactful did the experience have to be to change their views of the world?

10. Tell me about a time when you really screwed something up. How did you handle and address the mistake?

You test for humility, self-reflection, problem-solving, and communication skills in one go. Mistakes are a part of life. How we handle their correction gives us the perspective in life.

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