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25 Questions to Help You Be a Better Leader in 2019

by Verity Creedy

25 Questions to Help You Be a Better LeaderAccording to journalist and author Malcolm Gladwell, it takes around 10,000 hours to develop expertise in a skill or behavior, but the constant demands on leaders today makes it hard for them to carve out time to spend on self-development.

Researchers also indicate that you can create a habit within 21 days, which has become a format for various development activities (e.g. I recently did a 21-day meditation series from Oprah Winfrey).

Lastly, we know that the best way to develop your behaviors is on the job.

With these three things in mind—10,000 hours for mastery, 21 days for a habit to form, and development best on the job—I wrote 25 bite-sized questions to help leaders look at their role and responsibilities from various perspectives, and shared them on LinkedIn and Twitter, one question a day, for 25 days. The response to the series was incredible. I particularly loved how some readers used these daily prompts as a series within their organizations, sending them to leaders directly.

So, now here we are in 2019; and as many make New Year’s resolutions, I want to share these questions in their entirety for the benefit of those who selected “Be a Better Leader” as a goal for the year:

  1. Frequently during times of constant change, leaders struggle with demonstrating strength while remaining humble. How do you show your humility in the workplace? 
  2. Hard work and intellect aren’t enough to be a leader—you need EQ, too, whether in an office or on a race track. How emotionally aware (of yourself or of others) are you?
  3. Feedback is a gift, but remember it is only well received when well delivered. Feedback should be timely, balanced, and specific. Miss one of these, and your feedback may miss the mark. Do you have feedback to give to someone today? 
  4. Peter Drucker says, “Only three things happen naturally in organizations: friction, confusion, and underperformance. Everything else requires leadership.” Which of these three elements is most prevalent in your team now and how will you address it?
  5. How do you want to be described as a leader? What do you want your leadership legacy to be? Write a sentence or two to answer these questions right now—and then live that intention.
  6. How can you show vulnerability today? Spend 20 minutes on your personal development so you can share who you really are with your teams. Need a hint? Check out this TED Talk by Brené Brown on the power of vulnerability
  7. Are you developing a possible successor? According to the Global Leadership Forecast 2018, only 14 percent of CEOs have the leadership talent to execute their strategy. How can you ensure your business has a sustainable leadership pipeline?
  8. If you haven't seen Randy Pausch's "The Last Lecture," then check out YouTube for a humbling experience. One quote that really stood out to me: “When you’re screwing up and nobody says anything to you anymore, that means they’ve given up on you. You may not want to hear it, but your critics are often the ones telling you they still love you and care about you and want to make you better.” Are you giving feedback to your team or giving up on their growth? When did you last seek feedback?
  9. What is your “Why”? Never mind the “What” or “Where” or “How.” “Why” is the most important model for inspirational leadership. 
  10. Are you empowering the women on your team? Be purposeful about driving gender diversity in leadership. As DDI’s CEO Tacy Byham says, “If you’re lucky enough to be a woman leader who has made it to the top, look down and make it important to ‘pull others up the elevator with you to get to the top of the building.’”
  11. Imagine that your work day finishes in three hours—what do you really need to achieve before you leave your desk? Do that first.
  12. Author Stephen Covey wrote, “Seek first to understand, then to be understood.” How well do you understand those you lead? Or do you treat all team members as one and miss their unique skills, motivations, and abilities? 
  13. In today's stressful world, leaders are under pressure to achieve results quickly; which means they often focus on the practical needs of the conversations but miss the personal needs of the person they are conversing with. You can address the practical side of the conversation, but completely miss the other person’s need to feel valued or respected. Is this a pitfall into which you fall? How can you address both the practical and personal needs of the people on your team?
  14. Michael Jordan said, “I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that’s why I succeed.” What do you learn from the errors or mistakes that you have made? Do you make failing fun within your team or is it something that people fear?
  15. Are you unlocking the hidden potential in your company by leveraging diversity and inclusion? Check out DDI’s popular eBook “Unleash Hidden Potential: Build Your Competitive Edge Through Diversity and Inclusion” to learn more.
  16. Speaker and author Dave Ulrich says that, “Leaders who listen to their employees as much as talking to them learn to communicate in ways that matter to employees.” When you interact with your team members, what is the balance of you listening and you speaking?
  17. According to LinkedIn CEO Jeff Weiner, the biggest U.S. skills gap is not coding, but soft skills. When it comes to leadership development it is so easy to focus on technical skills and miss the "soft" skills (which are actually the hard skills!) How are you developing your interaction skills?
  18. The Wall Street Journal recently identified empathy as one of the most critical skills for leaders—and according to adventurer Bear Grylls, this applies to other extreme leadership situations too: “If you are stuck up a mountain for three months with someone, then the most important skill is not climbing. It’s empathy.” How effective are you at demonstrating empathy?
  19. If you haven't seen Sheryl Sandberg's TED talk on women leaders, stop what you’re doing and watch it. It's essential viewing for leaders who want to flourish through team diversity. One of my favorite quotes: “We need women at all levels, including the top, to change the dynamic, reshape the conversation, and make sure women’s voices are heard and heeded, not overlooked and ignored.” How can you apply this to your team today? 
  20. Are you effectively demonstrating empathy to bridge the gap between interacting with your team members and driving job performance? Read more on the topic here.
  21. Do you embrace the misfits and rebels, or do you fear them? The famous Apple “think different” ad campaign heralded these people as changemakers and revolutionaries. How can you leverage differences further within your team to drive change?
  22. Collective leadership is one of today's hottest topics. How are you encouraging that collective spirit within your team?
  23. How are you using data to drive leadership development and growth within your organization? Check out this article about how you can do so—and do it well. 
  24. How do you manage uncertainty and complexity? Do you have the leadership skills to stay on course during the storms?
  25. How will you continue your self-development, and how does your organization develop its leaders? Get some inspiration by attending our webinar on furthering leadership development and best practices on this topic. This webinar, “Ignore Frontline Leaders at Your Peril,” provides more details on alternative leadership development insights and approaches, and I hope you can join us for this event.

Wishing you all good habits, mastery development, on-the-job application—Oh, and a Happy New Year!

Reserve your spot in the “Ignore Frontline Leaders at Your Peril,” webinar on January 31st.

Verity Creedy heads up DDI’s European sales team and is based in London. When she’s not working with clients to identify talent solutions that address their business strategic aims, Verity can be found reading endless Bizzy Bear books with her young daughter, window-shopping at unusual shoe stores, and finding new ways to raise money for Cancer Research UK. If you have any Bizzy Bear favorites, shoe store recommendations, or fundraising ideas, please send them to

Posted: 16 Jan, 2019,
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