An excellent leader always thinks a few steps ahead. They keep the bigger picture on their mind while making everyday decisions, making sure that the team, department, or entire company follows the right direction, pursuing the long term goals of the business. Strategic planning is an important skill for all mid-level and top-level management jobs. It’s more than a skill–it’s a mindset, the way you approach your work.

Hiring managers and CEOs will typically ask you a few question that relate (directly or indirectly) to your ability to think strategically. Let’s have a look at 7 of them, and how you should answer them in order to make the right impression on your interviewers.


In your opinion, what role does strategic planning play in this managerial role?

If they ask about it, it likely plays a crucial role. But you should elaborate on this answer. Explain the responsibility you will have in the team, for setting the overall direction, for understanding the market trends, and predict the future.

You understand that without knowing the final destination the ship can hardly reach the harbor. And without knowing where you are eventually going as a team, you won’t be able to manage your people effectively.

But you also understand that things change quickly in the economic climate of 21st century. Strategic thinking is not a set and forget task for you. You will revisit your plans regularly, and make adjustments if the situation demands it.


Describe your process of setting long term goals for your team.

The key is to show them that you have some system in your strategic planning, and pillars you stick to. The overall vision and mission statement of the company can be one of your pillars.

Before deciding about the goals of the team, you consider the goals of the entire organization, the role your team plays (or should play) in achieving these goals, in attaining the lofty vision. Then you devise your goals accordingly, finding the sweet spot.

You understand that your team isn’t a stand-alone unit in the company, or in the entire economy. There are always bigger goals to follow, and everything relates to everything. You keep this on your mind while deciding about long term goals for your team.

What’s more–you try to be ambitious and realistic at the same time. It makes no sense to aim too low–that’s not why you became a manager. But you also want to set long terms goals your employees find viable, because if they struggled to imagine your vision, they would find it hard to work on it day after day…

How do you inform people about your strategic decisions?

It’s not only about form, or timing. Communication is also super important, and you should place the value on it in your answer.

Say that first and foremost, you make sure that everyone understands your decisions, the long term plan, ans what role they play in it. You may communicate this during managerial meetings, but you may also have one on one with the representatives of lower-management, explaining everything clearly, and with the help of follow-up questions ensuring that they got your point, and understand how it impacts their work.

Of course if we talk here about an unpopular decision–such as restructuring the company, or terminating contracts, or cutting salaries, timing is also important. What’s more, when announcing an unpopular decision you make sure that people understand why you had to make it, and that you did not really have another option.

* May also interest you: Creative thinking interview questions


Tell us about a time when you failed to achieve your goals in work.

The situation you narrate doesn’t interest the interviewers as much as the attitude you show, and the way in which you analyze the situation. Can you admit making a mistake? Can you identify the factors that contributed to the failure? And did you learn your lesson in the situation?

Try to go back in time, all the way to setting your goals. Describe the process of planning–what you had on your mind, what you tried to achieve, milestones and goals you set. But perhaps you underestimated something, or market conditions changed–and you didn’t have a plan B, or something else happened.

One way or another, you failed to reach the goal–and you take full responsibility for this as a manager. You understand what you did wrong, or neglected. You learned from the situation, and won’t repeat the same mistake again, while working on your strategic plans or setting your goals in your new job.

* Special Tip: Strategic planning isn’t the only tricky area they will inquire about in your managerial interview. You will face questions about adaptability, prioritization, dealing with ambiguity, and many other tricky questions. If you want to avoid “interview headaches”, and finally streamline your preparation for the big day, have a look at our Interview Success Package. Up to 10 premium answers for each difficult interview question will help you stand out in the interviews, impress the hiring managers, and get an amazing offer at the end. Thank you for checking it out!


If we hire you for this managerial job, what goals will you set for yourself and for your team?

This one is a bit tricky. Your ability to answer it correctly depends on your knowledge of your future employer, and their current situation. Needless to say, you should do an extensive research about your future place of work.

What they do, what they try to achieve, who their main competitors are, what is their position on the market. And of course, what role you can play in all this as their new manager. This should help you understand the basic direction, and perhaps even set some goals for you for the first year or two.

If you cannot find the information, however, and job description does not help you much, you still have two options for a decent answer.

First one is being honest and humble, and saying that before setting any goals, you have to talk to the executives, and understand what exactly they expect from you and from the team you will lead. Or at least your place in the company. Only when you understand such things will you be able to set right goals for yourself and for the team.

Another option is referring to general indicators of success. Increasing profits, reducing expenses, improving the customer satisfaction or retention, etc–depending the the position you have, the team you will lead. Of course each corporation will be satisfied if you reach such goals as a manager…


How do you measure the effectiveness of your strategy?

This isn’t always easy, especially if you work on something and the fruits of your efforts will become apparent much later–when everything eventually clicks together, and you will dominate the market.

Anyway, you can say that you will always try to set some partial goals, or point out certain indicators you can realistically measure, and will continuously monitor them while working.

While this isn’t a bullet-proof way of measuring the effectiveness of your strategy, it can definitely help you identify that things aren’t going the right way, and take action accordingly.

Of course when we speak about some specific strategy and position, when you can set very clear indicators (such as number of deals closed each month), it’s easier to measure the effectiveness of your strategy.


Tell us about a time when you demonstrated leadership at work.

More than anything else, true leadership (on the highest level of corporate hierarchy) is about making unpopular decisions, challenging the status quo, or setting overall direction for a team, department, company, or the entire country (if we talk about politics).

And that’s exactly what you should talk about–because they do not hire you to keep the status quo. They hire you to change and improve things, to set new strategic plans and take their company (or a team within it) to the next level.

Do not be afraid to talk about a time when you were bold in your decisions or expectations. It doesn’t matter whether others supported or opposed you, and whether your suggestion or decision eventually went through, and had a desired effect.

The most important thing is to show that you thought about the bigger picture, and did not mind challenging the routine in the place, the way they had done things before you came onboard…

* May also interest you: Are you a leader, or a manager?


Conclusion, premium answers to all questions

Strategic thinking and planning is an important skill, something we learn by experience. Interviewers may ask you several questions while trying to assess your ability to think strategically. Their questions may range from relatively simple (How do you set long term goals?) to tricky situational or behavioral questions (Tell us about a time when you failed to reach your goals in work).

Try to prepare a short answer to each question from the list, following my hints. And do not forget to do a throughout research about your future employer, their vision and goals, and the role you will play in the company. It will help you with your answers to the questions about strategic planning and thinking.

Last but not least, do not neglect your preparation for other tricky interview questions–questions about prioritization, dealing with pressure or ambiguity, and with many other situation you can experience in the workplace. If you need help, have a look at our Interview Success Package. Up to 10 premium answers to 31 tricky scenario based questions (+ more) will help you streamline your interview preparation, and eventually outclass your competitors and get the job. Thank you for checking out out, and I wish you best of luck in your interview!



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Matthew Chulaw
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