15 Questions to Help Leaders Maintain Perspective

The quote, “It’s lonely at the top,” can unfortunately be the reality for some leaders. Successful leaders who have reached the top of their niche risk falling into the trap of self-sufficiency, alienating others and sometimes unintentionally rejecting further learning opportunities.

To keep themselves in check and maintain a down-to-earth mindset, business leaders should “check in” with themselves regularly. By asking the right questions, leaders will not only be able to keep their perspective, but also work toward constantly bettering themselves. We asked 15 experts from Young Entrepreneur Council to discuss some of the questions entrepreneurs should ask themselves every so often:

Q: What’s one question you regularly ask yourself to keep your perspective in check as a successful leader and make sure you’re being the best you can be?

Here are their thoughts.

1. Which Aspects Do I Need to Improve?

I regularly ask myself, “Which aspects of my character do I need to improve to be the person that I want to be?” The concept is straightforward: being honest with ourselves is a challenge, so we need to find time to review regularly. Work in that direction, align business and personal goals, and you will always have a path to follow. – Riccardo Conte, Virtus Flow

2. What Are My Weaknesses?

If you want to work on self-improvement, ask yourself, “What are my weaknesses?” Most of us know our strengths — it’s how we ended up in the position we are today. But understanding your weaknesses is the key to improving beyond your expectations. Think critically and honestly about where you would like to improve in your professional life, and bring those changes to life. – John Turner, SeedProd LLC

3. What Value Am I Bringing Others?

Ask yourself what value you’re bringing to others as their leader and as the leader of your company. Leaders always evaluate their teams, but how often do they evaluate themselves? As the leader of your company, it’s important to be honest with yourself about the changes you need to make in yourself to better serve others and drive results. – Jared Atchison, WPForms

4. Would I Want to Work for Me?

“Would I want to work for me?” is a frequent question I ask myself. I think back on old bosses I’ve had and, in my opinion, my best leaders were fair, reasonable, and had high standards. They knew what I was capable of and pushed me to be the best version of myself. It wasn’t always comfortable or easy but I respected them and I’m a better human as a result of it. – Ashley Merrill, Lunya

5. What More Can I Do to Help My Team?

At the heart of leadership is a deep focus on the people you lead: a focus on making them better and a focus on leading them toward a common goal. To succeed as a leader, I need the people around me to be as successful as possible. I continually ask myself and ask the members of my team how I can more effectively contribute to their experiences. – Adam Mendler, The Veloz Group

6. Have I Helped Someone Today?

My goal as a leader is to help people grow. Whether it’s to teach someone a new skill, a life lesson, or just to help someone in need, I want to look out for others in any way I can. For me, being a leader isn’t about just having authority; It’s about helping others and watching them grow so that one day, they can become a leader. – John Hall, Calendar

7. Am I Lifting as I Am Climbing?

I constantly ask myself, “Am I lifting as I am climbing?” If I’m not bringing folks with me as I build and grow my career, then I’m not being a very effective leader at all and have definitely lost perspective. – Andrew Schrage, Money Crashers Personal Finance

8. Are Leaders Born From My Leadership?

A question I ask myself is, “Are new leaders born from my leadership?” Do I lead people who eventually become stronger and better to the point that they can actually replace me in time? You’re only considered a successful leader if you are fruitful and your “fruits” have a good foundation. You have to lead by example and find ways to motivate your team to be better people — even if that means better than you. – Daisy Jing, Banish

9. How Can We Serve Our Customers Better?

A question all leaders should ask themselves is, “How can we serve our customers better?” As a leader, it is all too easy to lose sight of what really matters amid day-to-day administration and technical challenges. It’s important to take the time to realign goals with the real-world needs of customers and to ensure that our services meet those needs in the best possible way. – Justin Blanchard, ServerMania Inc.

10. Are My Decisions Aligning With Our Culture?

“Are my decisions aligning with our corporate culture and mission?” is a question that I ask frequently. Misalignment would require a closer look at the factors at play that I am weighing more heavily than others. Factors could be the current market for a product or some projections I am using as measurements that are not in the best interest of our culture and mission. – Matthew Capala, Alphametic

11. Would I Want This to Be on the Front Page?

“Would I want this to be on the front page of the news tomorrow?” This is a question someone shared with me when talking about decision-making in regards to how to treat employees, clients etc. If you wouldn’t be proud to have the decision you made broadcast to the public, you should reconsider the decision. – Kelsey Raymond, Influence & Co.

12. Why Did This Happen?

Whenever something goes wrong or goes into a different direction than I expected, I’ll ask myself, “Why did this happen?” The answer is usually that I didn’t know something. By acknowledging that I don’t know everything, it opens me up to being more humble, helps me ask better questions, and leads me to surround myself with people who know different things than me. – Thomas Griffin, OptinMonster

13. What Could I Have Done Better?

A question I ask myself is, “What could I have done better?” Hindsight is 20/20, and when we look back on our decisions, we usually think of ways we could have acted better. To be your best, you need to know there’s always room for improvement, which starts with these questions: How can you improve? What are the things you can do to make your team better as well? – Stephanie Wells, Formidable Forms

14. Am I Productive or Just Active?

Leaders should ask themselves, “Am I productive or just active?” There is a vast difference between staying busy and doing things that move the needle forward. When I need to check in on my success track, this question makes my calendar and to-do list for the day crystal clear around where I need to shift my focus to get back on track. – Matthew Podolsky, Florida Law Advisers, P.A.

15. Are the Critics Right?

Ask yourself, “Are the critics right?” Everyone loves to talk about their haters. It’s a common line, from radio stations to corporate offices. And those who don’t lament haters simply discard criticism as a distraction. Criticism is bittersweet. It’s like having diamonds under a pile of you-know-what. But who cares — you have diamonds. You can wash the manure off. – Samuel Thimothy, OneIMS

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