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8 Questions to Ask a Managing Director in an Interview


As leading global headhunters, we’re asked to source at C-Suite level and are constantly asked what are the most probing questions to ask when headhunting a managing director? So, when sitting down for an interview with a Managing Director, it’s obviously important to know exactly what you want to ask them. But what’s the best way of getting the most important things you need to know out of your interviewee? As much as you might want to sit there and pick their brains all day, you only have a limited time conducting an interview, and the more detailed your interviewees answers are, the less time you have to ask the important questions. Efficiency is key to a successful interview for both you and the candidate, and the best way of achieving this is by making every question count.

With that in mind, let’s take a look at 8 key questions you might ask a Managing Director during an interview to help identify whether they are the natural leader your business needs.

1. What are your long term goals, did you achieve them, and how?

A fairly standard interview question, and for good reason. Every good leader should have a clear set of goals both for themselves and their business. You need to know what kind of expectations your interviewee sets for themselves, and if their goals align with yours as a company. Encourage them to elaborate on if and how they achieved these goals, with as much detail as possible. Make sure they explain how they achieved their goals or are on track to achieve them, or if not, why they think they didn’t. This is a fantastic method of gaining insight into your interviewee’s work process and achievements, as well as allowing the candidate to demonstrate their own self-awareness by acknowledging and understanding the reasons for their shortcomings.

2. What has been your biggest challenge, and how did you overcome it?

This can tie in nicely to the last question, and that’s because every Managing Director will have had to face significant challenges to achieve their company goals, and if they haven’t you’ll probably have to question if their goals were ambitious enough in the first place. We know that there’s nothing wrong with admitting to struggling or feeling challenged with something, and showing how you overcame such a challenge can be very impressive. Asking this is important to ensure that the person you’re interviewing is aware of and open about what they found to be challenging, and how they are able to tackle such issues in a way that will instil confidence in you should they face similar challenges in your role.

3. How important is company culture to you and what measures do you take to maintain your desired culture?

Every workplace leader should have a good awareness of their company culture and environment. By structuring some questions around this, you can find out if they view culture as important and what their ideal culture is. You can also find out about their adaptability, for example if they like their workplace to be a very specific environment, and how this attitude will transfer and adapt to your company. This is a good way of determining whether the candidate will thrive in your company or whether they will struggle to adapt or create influence in an unfamiliar work culture.

4. What are your values as a company leader? How do you ensure these values are upheld by employees?

Company values lie at the core of a well-functioning business, but attitudes to core values vary massively from company to company. Especially in customer or client facing businesses, many leaders like to build their business around such values, often highlighting them on their website, publications, around the offices etc. Ask the interviewee what, if any, values they have outlined either for themselves, or for their business, and what measures they take to uphold them.

You can start to piece together your interviewee’s priorities as a leader by inquiring into why their specific values are important over any others, and how this benefits their company. You can then find out more about their leadership skills and priorities by asking what actions they take to uphold these values with their employees across the business. If you want to go one step further, try and lead into a discussion about the values of your own company and how they would adjust to these, or what influence they would like to have.

5. What features make a good leader? Would you describe yourself as a good leader and why?

Think of this as a variation of the age-old ‘Name someone that inspires you’ prompt. Though you should feel free to utilise this, it may be more useful to focus on what qualities the candidate finds to be inspirational, as these qualities are what they are likely to try and emulate. Anyone can name someone who they think is a good leader, but it shows true insight for the candidate to be able to state why someone is a good leader. You can then inquire into how the interviewee views themselves, which of these qualities they share, or what other features they have that make them a good leader in order to get an idea of their perception of themselves.

6. Would you describe yourself as a risk taker? Describe some of the risks you have taken as MD and the results

This question usually garners divisive answers, but it can be an important factor to take into account. When hiring for a senior management or director level role, you’re probably going to want an individual who is not afraid to take risks, but at the same time one who isn’t careless or brash. How the interviewee answers this question will be interesting, as depending on the individual and the opportunity at hand, risk-taking can be perceived as a positive or negative quality. Asking them to describe risks they have taken to you also shows what actions they consider to be risks and for what reason.

7. How do you build rapport with your workers? Why do you think this is effective?

We know that, as managing director, the way you interact and build relationships with employees, other directors, and board members is crucial to your success. But relationships obviously aren’t just built overnight. Ask the interviewee what conscious efforts they made to build a rapport with workers in their business and why they think this method is effective. Find out if they like to be friendly, engaging, professional, distant, etc., and measure this against your company to see if their leadership style will fit with your current employees.

Other factors include whether they conduct rapport building in the office, or if they organise special team building activities out of office. Of course, if the candidate can fully justify the way they build rapport, they may still be a good fit for your business. It all revolves around solid, convincing justification.

8. What is your current and ideal work/life balance? What measures do you take to control the work/life balance of you and your employees?

It’s no secret that being a Managing Director takes a lot of work. It’s a busy job that offers very little downtime, and it’s easy for anyone to get burned out from overwork, no matter what your role is. To be successful in a senior role such as managing director it’s essential that you are able to balance your own work and personal life, as well as understand how other members of your business do this. Find out how your candidate manages their time, how much free time they afford themselves and for what reason it is or isn’t ideal. It’s also important to find out how they do this for their workers, for example if they expect employees to sacrifice all personal life, or if they value the importance of free time. Make sure to find out how they do this, via rules, incentives, or holidays for example.

Don’t Forget to Create a Dialogue

Most importantly, you shouldn’t feel the need to be too rigid with your interview questions. Trying to initiate a dialogue is ultimately the best way of allowing your interviewee to open up naturally and gives you a more complete view of who they are, how they think, and how they interact with other professionals. Allow yourself time when interviewing your candidate to have a more free-form discussion on a topic of your choice. This should give you a good idea of their critical discussion and conversational skills, even if the topic isn’t necessarily directly relevant to the job.

These are just some of the options you have when interviewing a Managing Director, but what’s important, no matter what specific questions you ask, is that you put your candidate to the test and get the information you need out of them to make sure that the candidate that you decide upon is the right individual to take your company to the next level.

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