Interviewing Your Future Boss? Ask These 6 Revealing Questions First

As job seekers, we’ve all grown accustomed to the rigorous vetting process companies put us through.

From comprehensive application forms to gruelling panel interviews, we practically bend backwards to prove our worth.

But when it comes to the person who will be managing us day-to-day – the one holding the keys to our career growth and happiness – how much effort do we put in? 

According to Gallup, people quit managers, not companies. And yet, we often make this critical decision based on a mere 30-minute interview. No wonder the “great resignation” is/was in full swing!

Let’s be honest – shouldn’t we treat this relationship with the same care and consideration as we do in our marriages?

Leverage May Be Skewed, But You Can Still Uncover the Insights You Need

I know what you’re thinking – “But Adrian, they’re the ones signing my paycheck, not the other way around. How can I possibly put them through the same wringer?”

You make a fair point. The traditional power dynamics of the employee-employer relationship certainly don’t lend themselves to a perfectly symmetrical vetting process. It’s not like you can demand your potential boss fill out a comprehensive questionnaire or do a presentation for your spouse and parents.

However, you can still resign to accept whoever the company deems fit to manage you unquestioningly. There are still ways to uncover critical insights about your future boss, even if the process could be more equitable.

The key lies in your interview questions…

From Fluff to Substance: Asking Questions That Reveal Their True Colors

Through my experience conducting countless interviews during my recruitment days and the hundreds of hours interviewing guests on different podcasts, I’ve learned that the quality of the questions you ask can make all the difference.

Good questions yield good answers, but great questions? They have the power to unlock transformative insights.

Too often, we fall back on the standard, surface-level queries – “What’s your management style?” “How do you handle conflict?” While these may provide some basic information, they’re ultimately just time-fillers that fail to reveal who this person truly is at their core.

Instead, I encourage you to take a page from Tim Ferriss’ playbook and ask questions that throw your potential boss off-script. Questions that force them to tap into their “inner compass” rather than a rehearsed response.

Here are some questions to consider and the purpose behind each of them:

1. What is their birth sequence? (Or are they parents)

  • Significance: This question aims to understand the manager’s personality and potential management style based on their birth order. The general idea is that older siblings tend to be more responsible and organised, while younger siblings can be more free-spirited and creative. Also read: What Can Leaders Learn from Parenting?
  • Purpose: By understanding the candidate’s birth sequence, you can gauge how they approach problem-solving, decision-making, and team management. An older sibling may be more inclined to take a more structured and disciplined approach, while a younger sibling might bring a more flexible and innovative perspective. Only child from a privileged household? Run.
  • Example Approach: Instead of directly asking about their birth sequence, try a more subtle approach, such as: “Could you tell me a bit about your family background and upbringing? I’m curious to learn more about the experiences that have shaped you as a person and a leader.”

2. Who they look up to as a manager/leader

  • Significance: This question provides insight into the manager’s values, leadership style, and the traits they admire in other managers or leaders.
  • Purpose: By understanding who the candidate looks up to, you can gain insights into the qualities they find important in a leader and how they might approach management. This can help you assess whether their leadership style aligns with the company’s culture and the team’s needs. A major red flag is if the role model is Kim Jong Un.
  • Example Answer: “I’ve always admired [name], the CEO of [company], for their ability to inspire a shared vision and empower their team to achieve ambitious goals. I’m drawn to their collaborative approach and willingness to make tough decisions when necessary.”

3. What is your toughest decision as a manager/leader?

  • Significance: This question allows the manager to share their real-world experience navigating difficult situations and making decisions as a manager or leader.
  • Purpose: By understanding how the candidate has handled tough decisions in the past, you can assess their decision-making process, problem-solving skills, and ability to balance competing priorities and stakeholder interests. As a friend said to a panel, “The day I leave the company is the day I realise my boss does not have the spine to make hard decisions.”
  • Example Answer: “One of the toughest decisions I had to make was letting go of a long-term employee struggling to meet the performance expectations of the role. It was a difficult conversation, but I had to prioritise the team’s and the organisation’s needs. Ultimately, it was the right decision but certainly not easy.”

4. How do you personally unwind from work?

  • Significance: This question provides insight into the manager’s work-life balance and ability to manage stress and burnout.
  • Purpose: Understanding how managers recharge and manage their well-being can indicate their overall approach to work and leadership. It can also help you assess whether they will be a good cultural fit for the organisation. Importantly, the lack of it may infer they would invest that time into work and expect their team to do likewise.
  • Example Answer: “I try to make time for various activities that help me unwind and recharge. I enjoy going for long walks or hikes on the weekends, as it allows me to disconnect from work and clear my mind. I also set aside time for hobbies, like reading or playing the guitar, which helps me maintain balance and perspective.”

5. What would you expect to see in 6 months for you to think it is a job well done?

  • Significance: This question helps the manager articulate their vision and goals for the role and their expectations for success.
  • Purpose: By understanding the manager’s short-term objectives and key performance indicators, you can assess whether their priorities and expectations align with the company’s needs and the position’s specific responsibilities. The lack of clear measurement may imply there isn’t one, which may mean a shifting goalpost.
  • Example Answer: “In the first six months, I would expect you to have a comprehensive understanding of the company’s key processes, workflows, and systems. I would want to see that you have identified the top three strengths and two areas for improvement within the team and clearly defined the three to five immediate priorities for the role. Establishing productive working relationships with at least 80% of the team would be a key focus.”

6. What systemic problems in the company could be fixed and would go on to solve 80% of the issues?

  • Significance: This question allows the candidate to demonstrate their problem-solving skills and ability to identify and address systemic issues within the organisation.
  • Purpose: By understanding the candidate’s perspective on the company’s challenges and potential areas for improvement, you can gauge their analytical skills, understanding of the business, and ability to think strategically about solutions. A follow-up question is how long the problem has existed. This shows the power that is or isn’t there to solve these problems.
  • Example Answer: “Based on my research and understanding of the company, I believe one of the key areas that could be improved is the communication and collaboration between different departments. I’ve noticed that siloed workflows and a lack of cross-functional alignment often lead to duplication of efforts, delayed decision-making, and missed opportunities. If we could establish more robust processes for information sharing, joint problem-solving, and shared accountability, we could address a significant portion of the company’s challenges.”

By incorporating these questions into your interview process, you can gain valuable insights into the candidate’s personality, leadership style, decision-making abilities, and strategic thinking. This information can help you identify the best fit for the role and the organisation, ultimately leading to a more successful hire and a more effective working relationship between the new employee and their manager.

Don’t Forget the Reconnaissance: Uncover the Dirt on Your Future Boss

Of course, the interview itself is just one piece of the puzzle. To truly understand your potential manager, wear your investigative reporter hat and start digging.

The secret? Contact someone who previously held that role and see if they’re willing to share their honest take. Think of it as a pre-employment background check鈥攂ut for the person doing the hiring.

Just be sure to approach it tactfully. You don’t want to come across as a total sleuth, so a simple template like “I’m interviewing for the [role] position and would love to get your honest perspective on what it’s like working with [boss’s name]. Any insights you can share would be hugely helpful!” should do the trick.

Securing the right boss is just as crucial as landing the perfect job. So why not put in the same level of diligence to vet them as they do you? Remember, most people don’t quit companies – they leave managers. You might make sure you’re not making that same mistake.

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