Strategic Questions All Leaders Should Ask

“Judge a man by his questions rather than by his answers.” –Voltaire

Einstein urged us to “question everything.” Persistent questioning keeps the mind flexible, feeds creativity, reveals unexpected options, and prevents inertia. But business requires more of a Voltaire approach—it’s all about asking the right questions. The right questions inspire thoughtful answers and motivate action. So let’s discuss the questions great leaders ask to elevate business, empower employees, and advance themselves.

Questions to consider for your business

Are we relevant? Will we be relevant in five years?

Markets expand and contract. Technology continues to disrupt and overturn. New competitors materialize overnight. Consumers have more options—and opinions—than ever before. In the face of constant change, great leaders question the relevancy of the business often and honestly, from the products it sells to the brand it wears.

What could we do differently?

You don’t have to start over to start doing things differently. Whether it’s done as a creative exercise or as precursor to a strategic move, this question puts the status quo to the test in ways that can positively impact employees, partners, customers, and communities, as well as the business.

What critical performance metrics are we tracking?

Set goals, delegate responsibility, and track the results. Measuring critical performance sounds simple enough, but it’s all for naught if you focus on the wrong performance metrics. Questioning those metrics can help ensure you’re tracking the right things for both your employees and your business.

Questions to ask your team

What do you like to do outside of work?

Asking your employees (especially potential employees) about their passions and hobbies outside of work gives you a sense of their personal values, goals, and level of enthusiasm, which can often be indicative of whether or not they’re a good fit for their roles, or a good fit for the company. Involvement in a community, school, or philanthropic organization could indicate a high-level of intrinsic motivation that will have a tremendous ripple effect on your company.

What do you think about ______?

The savviest leaders recognize that they don’t have all the answers and readily seek out the opinions of others. Turning to your team for counsel offers dual benefits. It leads to better ideas and solutions, and it empowers team members who feel they have a voice and that their opinions matter.

How can I help you?

Recruiting a great team is just the beginning. The best leaders understand that it’s what you do to inspire and motivate that team that counts. One of the most effective ways to engage employees is by helping them define their goals and articulate what they need to be successful.

What impact did you have this week?

Studies show that motivation impacts performance. Inspirational leaders build and channel motivations focused on purpose and potential to bring out the best in a team. Asking employees to quantify their impact isn’t about making employees feel pressured to prove their worth, but rather about helping them feel empowered. According to the Harvard Business Review, purpose is one of the primary elements driving high-performing cultures

Questions to ask yourself

What can I delegate?

As a leader, you have to recognize that some things aren’t worth your time, and just let go. Focus your energy on tasks that are profitable and that only YOU can do. This Inc. article offers some excellent advice about what you should be delegating and how to go about doing it.

What kind of leader do I want to be?

If you haven’t thought about it, it’s time to. If you have, ask yourself this question: Does my leadership style align with my company’s vision? Regardless of how carefully you’ve seeded your company’s culture, your leadership style impacts the climate and the results. Once your vision and style are fully aligned, you can begin working on that legacy.

What can I do today to help make my company better?

Each day is an opportunity to improve something, no matter how small the deed. Write down one goal or aspiration as a reminder and make it a point to give yourself a celebratory pat on the back when it’s complete. Daily or weekly accomplishments, even small ones, build better organizations.

It’s easy to become immersed in day-to-day operations. What separates good leaders from great leaders is the ability to step back, ask the right questions, and be willing to hear answers that might provoke or challenge your notions about your organization and your teams. In the long run it will be worth it as you identify ways to grow your business, your employees, and your own leadership skills.

The author, Cory Jones, currently serves as Vice President of Commercial Marketing for Frontier Communications. In his role, Cory is responsible for all facets of business-to-business marketing for the company, including acquisition, retention, digital, social media, lead generation, and marketing communications.

Cory holds a bachelor’s degree in advertising from Texas Tech University. He lives in the Dallas area with his wife and two children, and is on an eternal quest to finally break par on the golf course.


Frontier Communications offers voice, broadband, satellite video, wireless Internet data access, data security solutions, bundled offerings, specialized bundles for small businesses and home offices, and advanced business communications for medium and large businesses in 29 states with approximately 28,000 employees based entirely in the United States.

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