25 Critical Questions While Hiring Super Leaders

Determined to find a star for Super Leader role? Jeff Weiner, former CEO of LinkedIn, suggests you must ask your candidate “What’s your dream job?” and see if their answer aligns with the job on offer or not.

However, evaluating the right CEO is much trickier than that. Well, Jeff Weiner was himself appointed as CEO of LinkedIn after Reid Hoffman spent 40 hours with him. That makes it clear that spending time with your potential hire is crucial and a single short interview won’t cut it.

A. Let Your Network Help You Amplify Your Decision-Making For Hiring!

Reid Hoffman, Founder of LinkedIn, PayPal, and Inflection AI, on being interviewed about hiring top-level executives put forward some key factors to consider. Let’s take a quick look:

Step 1

Don’t ask yourself “Who are the best people I know that I can hire?”

Ask yourself “Who are the best people I know?”

Step 2

Get in touch with them and understand who have worked out to be the right fit from their perspective and why. This way you get a template of what to look for in a candidate.

Step 3

Use the template to filter your candidates and then as you boil down the list. Ensure you spend fruitful time with your potential hire and evaluate them beyond an interview.

B. Right-Fit Factors To Evaluate During The Interview

The Leader you hire will be responsible for the long-term success of the company. Well, ideally of course. Therefore you must take every measure to ascertain the candidate you hire is not only passionate for the role but s/he also embodies hard skills, behavioral skills and soft skills necessary to lead the company without personal bias.

Foregoing the quick-onboarding process, these are the metrics based on which you would want to judge your potential hire:

Identity

Integrity

Ambition

Culture Fit

Leadership

Empathy

Strategic Approach

Employee-Company Balance

Board Fit

We have curated the best possible interview questions across trusted domains to help you find your company’s Leaders for growth and sustainability.

C. Asking Right Questions

1. Assessing Identity

✅ “How would you describe yourself in one word?”

💡 Traits in the spotlight: Self-reflection

What you want to know:

• The word is unimportant.

• Your candidate can present a unique perspective to his/her association with the word.

This interview question, one of the favorites of Dara Ruchardson-Heron, former CEO od YWCA, helps you kickstart an interview with broader perspective on the candidate.

✅ How would you spend and what would you want to know in your first 30 days?

💡 Traits in the spotlight: Readiness, Quick, Organizational skills, foresight.

What you want to know:

• Entering a new company can bring big responsibilities all at once: surprise factors, pending decisions, unhappy candidates who were hoping for the same promotion, information overload, and multitudes of things.

• A hire-worthy candidate would have researched and understood the upcoming priorities in the organization already.

• An organized Executive would have a plan in place to get on speed with each segment seamlessly.

2. Assessing Integrity

✅ Don’t you think all-round success of a company is an ideal case scenario and almost never true? In real world we often need to compromise on one front.

💡 Traits in the spotlight: Unmovable ideals

What you want to know:

• Your candidate should not bow to the opinion.

• How one defines success with metrics?

• Does the candidate include the success of company, stakeholders , and employees?

✅ When tied in a difficult spot, which existing leaders come to your mind and guide you through the challenge?

💡 Traits in the spotlight: ideals, personality traits.

What you want to know:

• Here you aren’t looking for wrong or right answers.

• Consistency in his persona and his ideal leader.

• A candidate may lie about his own ideals and values, but knowing the personality who drives his leadership you can asses the ideals & philosophies your candidate is striving for.

• If they can’t justify their choice, perhaps there are no other questions need to be asked.

✅ What are your career regrets that you carry till date?

💡 Traits in the spotlight: Willingness to learn, experience.

What you want to know:

• How the candidate approaches their failure & disappointment.

• Bigger learning come with bigger failures and challenges.

• So, if your candidate hasn’t faced a tough situation to crack, s/he should ideally not crack this interview.

Other questions to ask:

✅ Have you exited the right employees?  Or have you made mistakes?

✅ Why not pursue a leadership position at your previous company but ours?

3. Assessing Ambition

✅ If you were hired, what would be your immediate goals for this role and the company? What about the next three years?

💡 Traits in the spotlight: Long-term vision, risk appetite, commitment to YOUR company.

What you want to know:

• The candidate understands the trajectory of your company.

• Ambition to become your YOUR company’s leader.

• This also answers if a candidate is serious about committing to the company in the long run.

✅ Explain a time when you implemented a major change that helped the company.

💡 Traits in the spotlight: Opportunist, open-mindedness, gap-identification, vision.

What you want to know:

• Elaboration on WHY the major change was a sound move?

• Why it hadn’t been done before?

• How did s/he ensure a fail-proof execution of the change?

• Was the change a success?

4. Culture Fit Questions

✅ If we switched places, what would you want to know before you handed over this company to me?

💡 Traits in the spotlight: Aligned values, strong connection with your company, seriousness of the candidate

What you want to know:

• This helps you check if one has taken the time to not only go through but also understand the company’s values.

• Instant demonstration of whether the candidate and your company’s goals are in line or not.

✅ How do you build rapport with the management team? What role do others play in actualizing your strategies?

💡 Traits in the spotlight: Inclusivity

What you want to know:

• Management is the link between micro tasks performed by employees and executives responsible for macro developments.

• The right candidate should have already researched the management in place within your company.

• Preaching inclusivity kept aside, this should give a clear roadmap on how the candidate goes about bringing team members on board with a vision, while equally stepping into the culture of people who have already been working for the company.

Other questions to ask:

✅ If you must name one thing that makes you unfit for the Leadership role at this company, what would that be?

5. Leadership Questions

✅ When you strongly believe in an organisational-wide change, how will you go about it?

💡 Traits in the spotlight: leadership style: participatory or autocratic?

What you want to know:

• An answer referring to past experience.

• Do they have the necessary experience required to succeed at the job?

• Is the leader bringing a biased opinion or is s/he open to discussion with management on receiving diverse opinions and consensus before moving ahead?

• If the change affects employees, what measures will the leader take to get updated on their opinion?

✅ How do you match your expectation from employees with reality?

💡 Traits in the spotlight: Awareness, flexible management approach, motivation building strategies.

What you want to know:

• Expectation vs. Reality can be very contrasted at times.

• How does your candidate discover the root cause behind the gap?

• It is an Executive’s responsibility to ensure that the goals set for employees also match their motivation. Right expectations from the employees ensure a seamless flow of tasks, and goal achievements internally in the organization, which is vital to overall success.

Other questions to ask:

✅ How have you managed teams in the past? Can you give an example of a time when you had to resolve a conflict within your team?

✅ In the past, how have you resolved any fundamental disagreements in strategy or direction with the CEO or others in the C-suite, or on the executive team? [COO role]

6. Empathy Questions

✅ Can you go above and beyond for an unhappy employee?

💡 Traits in the spotlight: Empathy in line with company’s boundaries, interpersonal skills.

What you want to know:

- Does your candidate work out a solution that is beneficial both for the company and the employee without hurting one’s sentiments?

- Here you would be looking for a flexible approach, as different solutions will work with different individuals.

- Every Executive comes across employees who go through a tough time. In those times, how has the candidate approached the issue at hand, gone the extra mile, and resolved it while maintaining the best interests of the company?

✅ Have you dealt with an employee who just wouldn’t do what you require of him/her?

💡 Traits in the spotlight: Perceptive & observant

What you want to know:

- What questions did the Executive candidate ask to understand the situation from the employee’s position?

- What were the measures taken?

- Which measures failed and why?

- Besides empathy, does your candidate understand the value of firing an unruly employee?

7. Strategic Questions

✅ Sometimes there won’t be time to evaluate multiple options. How do you act in the face of ultra-tight deadlines?

💡 Traits in the spotlight: Spontaneity, experience, data-driven approach

What you want to know:

- The candidate should already have an experience to refer to where he was quick in decision making with the help of data available.

- Ask a follow up question on the outcome of the decision taken and if the candidate thinks he should have done things differently. If so, then why.

✅ What’s the biggest challenge you’ve faced so far? How did you handle it?

💡 Traits in the spotlight: Perspective shift, analytical abilities in challenging times, learning attitude

What you want to know:

- What is their strategy towards evaluating different options?

- The key metrics that define their decision making in crisis also unfolds a lot about their leadership in practice.

Other questions to ask:

✅ As you set objectives and develop strategies, what information do you consider? What role do other department team members play in the process?

✅ What is the most essential aspect of managing a corporate budget?

8. Employee-Company Balance Questions

✅ If employees are demanding a perk but that requires a considerable sum out of profits, would you do it?

💡 Traits in the spotlight: Equal value for both dynamics

What you want to know:

- An ideal candidate will strive to find if the demand is justified.

- If yes, then what is the motivation behind such a demand?

- Secondly, they would see if the motivation can be met with an innovative solution.

- A quality leader always endeavors to build sustainable solutions beneficial to both employees and the company.

✅ Tell me about a situation when management had a conflict with an employee. How did you handle it and what was the resolution?

💡 Traits in the spotlight: Ability to listen to both sides, conflict resolution, a plan to avoid similar conflicts in the future.

What you want to know:

- When matters escalate, some conflicts reach the Leaders to be resolved. Is your candidate prepared to handle such issues?

- How does your candidate decide which tactic should be used for conflict resolution?

- How has his techniques worked out in the past?

- Does his decision involve bias or favoritism?

9. Board Fit Questions

✅ Describe a time when the management board was struggling to reach a decision. What did you do?

💡 Traits in the spotlight: Data storytelling, financial projections, convincing prowess.

What you want to know:

- This is an opportunity for the candidate to showcase how s/he can use data, trends, demands, projected outcomes, and numbers to evaluate a decision and thereby help the board members reach a decision, based on consensus.

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