Interview Questions for an Executive Candidate 7

In my years of being interviewed for leadership roles at tech startups as well as in interviewing leadership candidates, I have found that more often than not, the interview questions don’t seem structured nor derived from a list of questions consistently asked of all candidates. However, there are many experts that have generally accepted values they believe are vital for an effective leader.

Interview Questions – Inaccurate Judgments

Daniel Kahneman, Dan Lovalli and Oliver Sobony comment on inaccurate judgement in interviews in their paper “A Structured Approach to Strategic Decisions – Reducing errors in judgment requires a disciplined process.“

“The body of research on the job interview, the most common tool for employee selection, contains a wealth of information about the accuracy of evaluative judgments. Most companies still use traditional (unstructured) interviews to make a global evaluation. The interviewer starts with an open mind, accumulates information about the candidate, and then reaches a conclusion.

Unfortunately, a vast amount of evidence indicates that unstructured interviews lead to biased evaluations that have very little predictive value. That’s because the interviewer forms a mental model (colloquially known as an “impression”) of a candidate, a process that psychologists have shown has three specific limitations:

1. Excessive coherence.

Mental models are usually simpler and more coherent than the reality they aim to assess. As interviewers, if we assume, for in- stance, that a particular candidate is an extrovert, we tend to ask questions that confirm this hypothesis.

2. A “quick and sticky” quality.

We form our mental models rapidly, often on the basis of limited evidence at the start of the process, and we alter our models slowly as new facts emerge. That explains why, as common sense would suggest (and research has confirmed), first impressions have a disproportionate effect on the assessments we make of people in general and on the outcome of job interviews.

3. Biased weighting.

Our mental models often don’t give each pertinent fact the weight it deserves. We may discount important bits of information or, in contrast, give great weight to factors that should be entirely irrelevant. For example, an interviewer may wrongly perceive that a male candidate has great leadership qualities just because he is tall and has a deep voice.“

Structured interviews are both rare and important, and it seems interviews at higher-level are often the most unstructured. In structuring your interview question, I provide some thoughts on questions from various respected leaders below.

Interview questions derived from various respected leaders

Below are a few lists of interview questions for an executive candidate at a tech startup that would assess the values put forth by the experts listed below. Note, the questions do not come from the individuals but are derived from values they have spoken to and/or written about:

Interview Questions for a Startup Exec

Amy Edmondson: 

  1. How do you create a psychologically safe environment for your team?
  2. What is an example of a time when you had to deal with a mistake or failure? How did you handle it, and what lessons did you learn?
  3. How do you encourage your team members to speak up and share their ideas, even if they are different from your own?

Angela Duckworth: 

  1. How do you stay motivated when faced with challenges?
  2. How do you help your team members to persevere in the face of setbacks?
  3. How do you create a culture of grit and resilience in your team?

Brené Brown: 

  1. How do you build trust and vulnerability with your team?
  2. How do you create a culture of courage and authenticity in the workplace?
  3. How do you help your team members to feel a sense of belonging and connection?

    These questions are designed to assess the candidate’s understanding of Brown’s work on vulnerability, courage, and belonging, and how they would apply these principles to their leadership role in a tech startup.

    Here are some follow-up questions that you could ask:
  4. Can you give me an example of a time when you demonstrated vulnerability with your team?
  5. How do you create a psychologically safe environment for your team members to take risks and learn?
  6. What are some specific things that you do to promote diversity and inclusion on your team?

Carol Dweck: 

  1. How do you foster a growth mindset in your team?
  2. How do you help your team members develop their skills and talents?
  3. How do you create a culture where people are comfortable taking risks and learning from their mistakes?

    These questions are designed to assess the candidate’s understanding of growth mindset and their commitment to creating a workplace where people can thrive.

    Here are some additional questions you could ask:
  4. Can you tell me about a time when you had to overcome a challenge? How did you use your growth mindset to help you succeed?
  5. How do you praise and give feedback to your team members in a way that encourages growth and development?
  6. What are some specific things you do to create a psychologically safe environment for your team?

Ginni Rometty: 

  1. How do you use data to make decisions?
  2. How do you create a culture of innovation and risk-taking?
  3. How do you build a diverse and inclusive team?

    These questions are designed to assess Rometty’s values of data-driven decision making, innovation, and diversity and inclusion. All of these values are essential for success in today’s tech startups.

    Here are some follow-up questions you could ask to get a better understanding of the candidate’s answers:
  4. Can you give me an example of a time when you used data to make a difficult decision?
  5. What are some specific things you have done to create a culture of innovation and risk-taking at your previous companies?
  6. How have you built diverse and inclusive teams in the past?
  7. How do you make decisions in a data-driven way?

Indra Nooyi:

  1. How do you build a diverse and inclusive team?
    • Nooyi was a strong advocate for diversity and inclusion at PepsiCo. She believed that diverse teams are more innovative and successful.
  2. How do you create a culture of high performance and accountability?
    • Nooyi was known for her high standards and her expectation of excellence from her team. She also believed in the importance of accountability.
  3. How do you balance short-term and long-term goals?
    • Nooyi was a long-term thinker. She was willing to make short-term sacrifices in order to achieve long-term success.

Liz Wiseman: 

  1. How do you develop your team members and make them smarter?
  2. How do you create a culture where people feel safe to take risks and learn from their mistakes?
  3. How do you build a team of impact players who are motivated and engaged in their work?

    These questions are designed to assess the candidate’s understanding of Wiseman’s values, such as the importance of developing people, creating a safe environment for learning, and building high-performing teams.

    Here are some follow-up questions that you could ask:
  4. Can you give me an example of a time when you successfully developed a team member?
  5. How do you create a culture of psychological safety on your team?
  6. What are some of the things you do to motivate and engage your team members?

Marissa Mayer:

  1. How do you create a culture of innovation and risk-taking?
  2. What is your experience with building and managing high-performing teams?
  3. How do you create a culture of innovation and risk-taking?

Meg Whitman:

  1. How would you describe your approach to customer focus, and what are some specific examples of how you have put this into practice in your previous roles?
  2. How do you create a culture that fosters these values, and how do you balance the need to innovate with the need to execute on existing plans?
  3. How would you build a diverse and inclusive team at your company, and how would you create a culture where everyone feels welcome and valued?

Stacey Abrams: 

  1. How do you build and empower a diverse and inclusive team?
  2. How do you lead with courage and authenticity, even in the face of adversity?
  3. How do you use your platform to amplify the voices of others and make a positive impact on the world?

Susan Wojcicki: 

  1. How do you build a culture of innovation and risk-taking in your team?
  2. How do you develop and empower your team members?
  3. How do you make decisions in a way that is both data-driven and user-centric?

Interview questions derived from another set of respected leaders

Interview Questions for a Tech Startup Exec

Adam Grant:

  1. How do you create a culture of generosity and giving within your team?
  2. How do you help your team members to think for themselves and to challenge the status quo?
  3. How do you foster a culture of learning and experimentation within your team?

    These questions are designed to assess the candidate’s commitment to Grant’s values of generosity, challenge, and learning.
  4. Generosity: Grant believes that generosity is essential for success in the workplace. He argues that when people are generous with their time, knowledge, and resources, they create a more positive and productive work environment.
  5. Challenge: Grant believes that it is important to challenge the status quo and to think for oneself. He argues that the best ideas often come from people who are not afraid to question the way things are currently done.
  6. Learning: Grant believes that learning is essential for success in the workplace. He argues that the best teams are those that are constantly learning and growing.

Ben Horowitz: 

  1. What are the most important things you have learned about building a successful company culture?
  2. How do you balance the need for short-term results with the need for long-term growth?
  3. How do you create a decision-making process that is both fast and informed?

    These questions assess Horowitz’s values of:
  4. Culture: Horowitz believes that company culture is essential to success. He has written extensively about the importance of creating a culture that is values-driven, transparent, and supportive.
  5. Long-term thinking: Horowitz is a long-term investor and believes that companies should focus on building sustainable value over time. He is not interested in short-term gains that come at the expense of long-term growth.
  6. Speed and decisiveness: Horowitz believes that companies need to be able to make decisions quickly in order to be successful. However, he also believes that it is important to make informed decisions based on data and analysis.

Bill Campbell:

  1. How do you build trust with your team members?
  2. How do you create a culture of feedback and continuous learning?
  3. How do you help your team members to develop and grow?

    These questions are all related to Bill Campbell’s core values of trust, continuous learning, and development. He believed that the best leaders are those who are able to build strong relationships with their team members, create an environment where everyone feels comfortable giving and receiving feedback, and invest in the development of their people.

    Here are some additional questions that you could ask to assess the candidate’s alignment with Bill Campbell’s values:
  4. How do you handle conflict within a team?
  5. How do you make decisions?
  6. How do you celebrate success?
  7. How do you deal with failure?
  8. How do you give feedback?
  9. How do you receive feedback?

Daniel Goleman

  1. How do you use emotional intelligence to lead your team?
  2. How do you create a psychologically safe work environment where people feel comfortable sharing their ideas and taking risks?
  3. How do you motivate and engage your team members to achieve their best work?

Dan Pink

  1. How do you create an environment where people are motivated to do their best work?
  2. How do you foster a culture of innovation and creativity?
  3. How do you balance the need to achieve results with the need to create a meaningful and fulfilling work experience for your team?

Eric Ries

  1. How do you use customer feedback to inform your product development process?
  2. How do you create a culture of experimentation and learning within your team?
  3. How do you balance the need to move quickly with the need to build a high-quality product?

    These questions are designed to assess the candidate’s understanding of and commitment to the following values:
  4. Customer focus: Ries believes that the customer should be the center of everything a startup does. He advocates for a process of continuous validation and learning, where startups build and test products with real customers early and often.
  5. Experimentation: Ries believes that startups should be constantly experimenting with new ideas and approaches. He argues that this is the best way to find what works and what doesn’t, and to build a product that customers love.
  6. Speed: Ries believes that startups need to be able to move quickly in order to stay ahead of the competition. However, he also emphasizes the importance of building a high-quality product. He argues that startups can achieve this balance by focusing on customer feedback and experimentation.

Jim Collins

  1. How do you ensure that your company has a clear vision and mission?
  2. How do you create a culture of discipline and innovation?
  3. How do you build a team of A-players?

    These questions are designed to assess the candidate’s understanding of Collins’s core principles, which include:
  4. Vision and mission: Collins argues that great companies have a clear vision and mission that inspires their employees and customers. He also believes that companies should be able to articulate their vision and mission in a concise and memorable way.
  5. Discipline and innovation: Collins believes that great companies are both disciplined and innovative. They are disciplined in their execution of their vision and mission, but they are also willing to experiment and take risks.
  6. A-players: Collins argues that great companies are built on a foundation of A-players. He defines A-players as people who are smart, talented, and have a strong work ethic.
  1. How would you define extreme ownership, and how have you demonstrated it in your previous roles?

    This question assesses the candidate’s understanding of Willink’s core value of extreme ownership, which is the principle that leaders are responsible for everything in their domain, including the successes and failures of their team members.
  2. How do you build and maintain a culture of discipline and excellence in your team?

    This question assesses the candidate’s ability to create a high-performing team environment where everyone is committed to achieving their goals.
  3. How do you handle adversity and setbacks?

    This question assesses the candidate’s resilience and ability to lead their team through difficult times.

Simon Sinek

  1. What is your company’s “why”?
  2. How do you communicate your company’s “why” to your team and customers?
  3. How do you create a culture of inspiration and engagement at your company?

    These questions assess the candidate’s understanding of Simon Sinek’s Start With Why framework and their ability to apply it to their own work. They also assess the candidate’s commitment to creating a positive and productive work environment.
  4. Here are some follow-up questions you could ask:
  5. Can you give me an example of a time when you used your company’s “why” to inspire or engage your team?
  6. How do you measure the success of your company’s culture?
  7. What are some of the challenges you’ve faced in creating a culture of inspiration and engagement, and how have you overcome them?

Steve Blank

  1. What is your process for customer development?
  2. What are your thoughts on the importance of failing fast and learning from your mistakes?
  3. How do you build a culture of innovation and experimentation in your team?

    These questions assess the candidate’s understanding of and commitment to the following values that are important to Steve Blank:
  4. Customer development: Blank believes that customer development is essential for startups to build successful products and services. He emphasizes the importance of getting out of the building and talking to customers early and often.
  5. Fail fast, learn fast: Blank believes that startups should embrace failure as a learning experience. He encourages startups to experiment with different ideas and to learn from their mistakes quickly.
  6. Innovation and experimentation: Blank believes that innovation is essential for startups to stay ahead of the competition. He encourages startups to create a culture where innovation and experimentation are valued.

Steven Covey

  1. How do you ensure that your team is working towards the right goals? (This question assesses the candidate’s understanding of Covey’s habit 2: Begin with the end in mind.)
  2. How do you create a culture of accountability and responsibility on your team? (This question assesses the candidate’s understanding of Covey’s habit 3: Put first things first.)
  3. How do you build trust and rapport with your team members? (This question assesses the candidate’s understanding of Covey’s habit 5: Seek first to understand, then to be understood.)
Interview Questions Great Leaders might ask

Recognized, Great Leaders and Interview Questions they’d ask

Andy Grove

Here are three interview questions for an executive candidate at a tech startup that would assess the values put forth by Andy Grove:

  1. How do you create a culture of innovation and risk-taking?
  2. How do you make decisions in a data-driven way?
  3. How do you develop your team members and make them smarter?

These questions are based on the following values that were important to Andy Grove:

  • Innovation: Grove believed that innovation was essential for companies to stay ahead of the competition. He encouraged his employees to take risks and experiment with new ideas.
  • Data-driven decision-making: Grove was a strong advocate for data-driven decision-making. He believed that it was important to have a good understanding of the data before making any decisions.
  • People development: Grove believed that people were the most important asset of any company. He invested heavily in training and development programs for his employees.
  • By asking these questions, you can get a sense of the candidate’s understanding of Grove’s values and how they would apply them in the role of executive at a tech startup.

Bill Campbell

Here is a list of three interview questions for an executive candidate at a tech startup that would assess the values put forth by Bill Campbell:

  1. How do you foster a culture of trust and respect within your team?
  2. How do you develop and empower your team members?
  3. How do you make decisions in a timely and decisive manner?

These questions are designed to assess the candidate’s understanding of Campbell’s core values of trust, respect, development, and empowerment. Campbell was a strong believer in building high-performing teams, and he believed that the best leaders are those who trust and respect their team members, develop their potential, and empower them to make decisions.

Here are some follow-up questions that you could ask to get a better understanding of the candidate’s answers:

  1. Can you give me an example of a time when you fostered a culture of trust and respect within your team?
  2. How do you measure the effectiveness of your team members’ development?
  3. How do you balance the need to make quick decisions with the need to gather all of the relevant information?

Jeff Bezos

Here is a list of three interview questions for an executive candidate at a tech startup that would assess the values put forth by Jeff Bezos:

  1. How do you create a customer-centric culture?
  2. How do you make decisions based on data and evidence?
  3. How do you foster a culture of innovation and risk-taking?

These three questions assess Bezos’s core values of customer obsession, data-driven decision making, and innovation.

Here are some additional questions that you could ask:

  1. How do you balance short-term and long-term thinking?
  2. How do you build and develop high-performing teams?
  3. How do you handle failure and setbacks?
  4. How do you give and receive feedback?

Phil Jackson

Here is a list of three interview questions for an executive candidate at a tech startup that would assess the values put forth by Phil Jackson:

  1. How do you create a team culture that is based on trust, respect, and a shared sense of purpose?
  2. How do you empower your team members to take ownership of their roles and make decisions?
  3. How do you balance individual and team success?

Steve Jobs

Steve Jobs is known for his values of innovation, simplicity, and focus. Here are three interview questions for an executive candidate at a tech startup that would assess these values:

  1. How do you create a culture of innovation at your company?
  2. How do you simplify complex problems and solutions?
  3. How do you stay focused on the most important things, even when there are many distractions?

These questions are designed to assess the candidate’s understanding and commitment to Jackson’s values of teamwork, empowerment, and balance.

In addition to these questions, you may also want to ask the candidate to share stories or examples of how they have demonstrated these values in their previous roles. For example, you could ask them to tell you about a time when they had to overcome a challenge, build a team, or make a difficult decision.

By asking these types of interview questions, you can get a better sense of the candidate’s values and how they align with the values of your company.

More Thorough List of Interview Questions that probe Jim Collin‘s Leadership Values

Below is a more thorough list of deeply thought-out interview questions for an executive candidate at a tech startup that would assess the values put forth by Jim Collins. Note again, as will all of the above, these questions were arrived at by taking Jim Collin’s proclained leadership qualities into consideration. These are not actually questions coming from Jim Collins unless it so happened purely out of coincidence.

Vision and Purpose

  • Tell me about a time when you helped an organization develop or achieve a bold vision.
  • How do you ensure that everyone in the organization is aligned with the vision and purpose?
  • How do you measure the success of your vision and purpose?

People

  • How do you create a culture of high performance and continuous learning?
  • How do you develop and promote leaders from within the organization?
  • How do you create a diverse and inclusive workplace?

Execution

  • How do you set clear priorities and goals for your team?
  • How do you track progress and make adjustments as needed?
  • How do you create a culture of accountability and ownership?

Disciplined Thought

  • How do you make decisions in a data-driven way?
  • How do you challenge the status quo and think outside the box?
  • How do you learn from your mistakes and failures?

Discipline

  • How do you build and maintain a culture of discipline and execution excellence?
  • How do you deal with difficult decisions and trade-offs?
  • How do you stay focused on the long term, even when faced with short-term challenges?

Technological Leadership

  • How do you invest in and leverage technology to achieve your business goals?
  • How do you create a culture of innovation and experimentation?
  • How do you ensure that your organization is at the forefront of technological change?

In addition to these general questions, you may also want to ask the candidate about their specific experience with some of the key concepts in Collins’ work, such as those below. For candidates not familiar with Jim Collins’ work, you may need to explain things (like the Hedgehog principal).:

By asking these types of questions, you can get a better sense of the candidate’s understanding of Collins’ work and how they would apply his principles to lead your tech startup to success.

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