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Thinking about a leadership job? Here are questions to ask the hiring leader.

Updated: Sep 28, 2018

You have determined you're ready for a management and leadership role. The answers to these questions will help you determine if a specific job is right for you, demonstrate your thought leadership in the interview process, and once you get the job offer - will help you craft a plan to achieve early wins.

Congratulations on making the decision to go for it!

It's important to acknowledge that committing to your career change (some may call it an upgrade) is a milestone worth noting. Take some time to pause, appreciate yourself and how far you've come since you began your journey. It's been a path of many emotions: scary, exciting, stressful, frustrating, lonely, satisfying, and nervous - and you've been steadfast to make the decision.

Now it's time to take the next step. Ideally, it would be good to schedule an exploratory conversation with the hiring leader before you submit the job application. If that is a luxury that is not available to you, asking these questions during the job interview will be just as well. The answers to these questions will go beyond the often glamorized pitch of the job posting to determine your compatibility with the role and the organization, and also inform your plan of action once you start the job.

First, get the basic information about the posting: Why is this job/position open?

The details will give you a peek into the context of the role and the organization and will start to wet your appetite (or not).

  • It's a brand new position - You may have some room to define/redefine the job function once you start. There may also be an opportunity to hire the rest of the team members, and define their job responsibilities. There's more foundational work involved in a brand new position. Follow-up inquiry: is the job brand new because it consolidated 2 jobs in one?

  • The previous leader was promoted - Nice! That's a good sign of growth and opportunity. If the hiring leader is the one who previously had this job - that's great! This person will be able to provide useful guidance and lessons learned...and hope you don't get the "well that's how we've been doing it before" statement as you explore new ways to do things with your fresh perspective.

  • The previous leader left the company (or took a job at another department in the same company) - follow-up question: how long did that person have this job before leaving? Depending on how much additional information the hiring leader shares - the amount of time the last person held this job will factor into the morale of the team. Someone who didn't stay long = team is going through leader change again so be mindful of adjustment fatigue. Someone who was in the job for many years = team may have strong affinity for previous person (or they are glad to see the person go). Either way, it will affect your engagement plan for the first 3-5 months.

Role and Job Function Questions

1. What is the purpose and function of the team? Another way you can ask this - How does this team help the organization and the company achieve its results? You can follow-up with who are the internal and external customers, as well as other teams that are partners? This will reveal the scope of the job, and most importantly is it meaningful to you?

2. Ask the hiring leader to describe a-month-in-the-life of the job; a-day-in-the-life is too short - this should give you a glimpse into what is routine about the job. Based on how much detail is given, you can inquire more about scheduled or seasonal matters like what contributes to the busiest days/weeks; conversely, are there any slow days? The answers here will also give you an idea of the job's complexity.

3. How will success be measured? This is really a 2-part question. The success of the team, and the success of the leader (job you're applying for). What you should consider is how well defined are these measurements, and is there room for you to be able to give input or perhaps even transform. Take special note if many of the criteria for success are hard to objectively measure - like making your business partner happy. Watch-out for vague measures of success - you'll want to probe on this a bit more.

4. How large is the team? If the job posting didn't explicitly describe it, this is a good time to confirm that you will be leading people. It may sound trivial - but sometimes, management could mean process management, not people management. Where are the team members located? Many companies have globally dispersed teams and depending on what time zones they are in, that's going to indicate adjustments to your working hours. Also, ask if there are any virtual / work-from-home team members.

Even if the hiring leader's answers are not very generous in detail, the basic answers to these questions will give you enough information to decide if the job is fit for you in terms of meaningful purpose, demand for extra working hours, and added stress inherent to leadership roles. At best, it will trigger and inspire you to ask some follow-up questions to get a deeper understanding.

Company, Organization, and Culture questions

1. If the organization is given these statements, what is the percentage that would agree?

  • You have the tools and training available to perform your job well.

  • There is opportunity for growth and career path is clear.

  • Recommend the company as a place to work.

  • The senior leadership clearly communicates strategies to remain competitive.

2. What is the framework to recognize employee achievements?

3. What are the top 3 and bottom 3 dimensions of the last employee satisfaction survey?

4. Estimate - how many employee diversity groups are in the company? Some examples: Military Veterans group, Asian Network, Hispanic Community, Black Engagement Team, Women in Technology, LGBTQ, Parents forum...etc

5. What are some examples of innovation labs or similar programs that is in place today?

6. How would you characterize the senior leadership values of the company, of the organization, of the team?

Without the benefit of experience in the company, it is difficult to decide if the culture matches your own values. If you are applying for an internal company posting, you can answer some of these questions; however, each organization is a micro-culture, especially in large companies. Whether you are new to the company or new to the organization, the answers to these questions will give you a good enough sense about the culture and how well do they align to what is important to you.

It is vital to remind yourself that you are in the driver's seat of your career journey and you always have a choice. The company and organization have to audition to you as much as you audition to them. Often times, the hiring side is believed to be in control. Practice your self awareness as your prepare to ask these questions, and more importantly as you reflect on the answers.

As with many career change decisions and transitions, there is no manual that outlines every step you should take. Every situation is unique and circumstances play-out dynamically that it can sometimes be overwhelming and could lead to feeling lost. Let Lotus Beacon be the light to guide you.

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