Learning the art of asking good questions is one of the most valuable skills we can develop as Millennials. In fact, novelist Thomas Berger once said, “The art and science of asking questions is the source of all knowledge. The more practice we have asking questions and seeking wisdom early on in our journey, the better we’ll be at discerning wisdom and advice later in our career.

As Millennials, we must be intentional about seeking out the wisdom and advice of the leaders we admire. However, some questions are definitely better than others. There are questions that might provide answers to what we want to know, but only allow us to scratch the surface of the wisdom and knowledge they possess. If we truly want to learn from older leaders, we must learn how to ask the right question.

The Two Best Questions Millennials Can Ask Older Leaders

Over the course of the past several years, there are two questions that have proved to be invaluable during conversations with older leaders.

What have you learned from your failure?

Samuel Smiles once said, “We learn wisdom from failure much more than from success.” It’s easy to look at the different leaders and mentors we admire and think they have somehow avoided failure. However, in most cases, every great leader has experienced great failure at some point in their career.

Asking older leaders what they’ve learned from failure not only gives us an incredible perspective on their journey, it provides an invaluable understanding of things we wouldn’t know because we haven’t experienced them. While it might seem awkward to ask this question at first, I’ve found that most leaders are more than willing to share what they’ve learned from the seasons of life that no one really ask about.

Who do you know that I should know?

If success is more about who we know than what we know, then our network is one of our most valuable resources. And most successful leaders have incredible networks.

What I love about this question is that it puts the ball in their court. Most leaders expect to get questions like, “Can you help me connect with so-and-so?” This question allows them to make a connection that is mutually beneficial. The more you share your story, the better understanding they have to connect you with someone who could provide the most value. In most cases, the older leader will not only give you a name, they’ll be more than willing to make an introduction.

If we truly believe that leadership isn’t about always knowing the answer; it’s about asking the right questions, then it’s important to become experts at asking great questions. Asking these two questions on a regular basis will help us gain wisdom, expand our network, and increase our influence as we grow in our personal lives and careers.Become a Common Grounder

What questions can Millennials ask older leaders to find common ground and provide leadership insight?

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