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5 Leadership Questions to Challenge Yourself and Your Business

AnonymousBy Reagan Cerisano 7 years ago
Home  /  Insights  /  5 Leadership Questions to Challenge Yourself and Your Business

A leader who aspires to achieve great success cannot afford to avoid personal or professional growth. It’s important to be constantly sharpening and adjusting your vision as you grow and build your organization. But in order to grow, you need to be able to challenge yourself with questions which may make you feel uncomfortable and will force you to be honest. As Voltaire noted, “Judge a man by his questions rather than his answers.” These five leadership questions below can help you organize your thoughts and refine your vision.

Image courtesy of Ethan Lofton via Flickr

“Why are we doing this?”

People don’t buy what we do but why we do it. All actions within a company should sit on a foundation of purpose. We’ve said this over and over again. If you still haven’t watched Simon Sinek’s TED talk on how great leaders inspire action, go do so now. Business need to focus on why they do what they do in order to have a core understanding of themselves, their employees, and their customers. As Sinek notes, ”The goal is not to do business with everybody who needs what you have. The goal is to do business with people who believe what you believe.” By asking yourself “why,” you set the foundation for any other leadership question you may ask.

“What are our strengths?”

Obviously, this means you understand what’s going on in your business. But it also helps point out where you need balance. Yes, it’s cliche to say that your strengths are also your greatest weakness, but to a certain extent, it’s also true. You need a balance of personality traits. According to an article by Inc Magazine, the best leaders today strike a balance between both stereotypical masculine and feminine personality traits. Scholars point to this historical proof in Abraham Lincoln, “Lincoln scholars have commented on the 16th President’s merging of masculine traits (strength of purpose, tenacity) with feminine ones (empathy, openness, and the willingness to nurture others). That combination ‘was central to his practice of great leadership,’ writes Frank J. Williams.” By understanding your company’s strengths, you set the stage to begin balancing the talent within the organization.

“Who will join us?”

This question should closely follow the previous leadership question about strengths. Hiring talent is critical, and you need to be sure that you hire people who support your vision. Many business leaders worry how they attract and retain client within the organization. If you haven’t answered the first two questions, then you won’t be able to answer this one properly either. Because as Sinek noted, “If you hire people just to do a job, they’ll work for your money. But if you hire people who believe what you believe, they’ll work for you with blood, sweat, and tears.” You must answer why you do what you do first, and then know who to hire based on your strengths. If people love your company’s vision, then they will be more inclined to join you.

“How am I serving?”

Be really critical with this leadership question. The servant leadership movement was initiated by Robert Greenleaf in 1970. According to Kent Keith, Greenleaf describes these leaders as:

[blockquote type=”left” style=”background-color:#f7f7f7; borde:1px solid #e5e5e5; padding:5%; font-size:20px; font-style:italic;”]”Servant-leaders are people who initiate action, are goal-oriented, are dreamers of great dreams, are good communicators, are able to withdraw and re-orient themselves, and are dependable, trusted, creative, intuitive, and situational.[/blockquote]

Analyze this in two distinct segments:“Am I serving my customers? And am I serving the people in my business?” As Isaac Newton stood on the shoulders of giants, business leaders are supported by their customers and the people who make up their organization. Without customers’ and employees’ loyalty and effort, a business could never accomplish anything of worth. But in order to maintain mutually pleasant relationships with these people, leaders need to make sure they serve the people who serve them. This leads us to the next leadership question…

“Am I actively listening?”

I’m not talking about the awkward, 30-second pause after a meeting when you ask “Any questions?” Are you actually listening to the voices of your people. These people are often experts and on the front lines of your business. But people don’t talk unless you’ve fostered a candid culture. In order to start doing so, go and pick someone’s brain one-on-one. As many of us have experienced, it can be easier to voice your opinion to one person, versus a group of people. Also, be willing to take criticism. If people people fear your response to criticism, they won’t say anything. And that will stagnate your company’s prosperity.

As mentioned in a previous post, disengagement is costly to your organization.In one of Gallup’s State of The American Workplace Report, it leads to more than $450 billion in lost profits in the U.S. annually. Obviously, that’s super risky for any industry to ignore.

While you may be able to touch base with a lot of the people in your organization, you may not be able to speak one-on-one with everyone. In order to still receive the depth of insight and analysis one might receive from these personal meetings, high performing leaders turn to the 9Lenses software platform to help collect a wealth of information across a broad set of stakeholders in the organization. At the same time, the software translates this qualitative information into quantitative data all by collecting, connecting, and automatically quantifying these insights in one central location. Ultimately, this allows you to listen to the people and sharpen your vision.


Nobody likes the hard questions. They’re uncomfortable and put us in a very vulnerable place if we don’t like the answers. But by asking the right questions, we come closer to setting ourselves and our companies up for success. Sometimes it’s within the parameters we expect, and sometimes it isn’t. No matter where your answer places you, strengthening the core of your organization is critical in order to gain or maintain forward momentum.

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