Why You Should Ask More Questions

Asking questions is one of the most underrated activities of a leader; however, I believe asking questions is the cornerstone of all leadership. There are at least two reasons why leaders don’t ask questions:

  1. Pride prevents it – As leaders, we feel like we’re supposed to have all the answers. In my experience, though, the best leaders don’t have the best answers, they facilitate the process of discovering the best answers. There have been many times where I have come up with awful solutions that could have been prevented if I had just asked a couple questions.
  2. It takes a lot of time – Question asking takes a lot more time than directing people to do your will. Leadership is relational, though, so I challenge you to take the time to ask the hard questions.

And there are two reasons why you should ask many questions:

  1. It creates trust – Craig Groeschel always says that “people would rather work for someone who’s always real than one who’s always right.” People trust people who ask questions and care about what they have to say. It shows authenticity and vulnerability.
  2. It helps you get to the source of issues quickly – instead of speculating about issues, a few well pointed questions (as hard as they may be) will get you to the source of issues you may not even know about. The operative words: well pointed.

When’s the last time you asked one of your team members a question and genuinely cared about the answer? What are some ways you can improve your question asking abilities?



How to Fight Insecurity

If I’m honest, insecurity is my biggest struggle as a leader. I don’t know what it is, but when I see someone doing something better than me, I get angry. Beyond that, if I see someone doing something that I’m not able to do at all, I envy that person. I sincerely hope I’m not alone in this feeling.

What’s interesting about this is that each and every one of us has a specific set of skills that we’re meant to use in order to contribute to society. We’re not all meant to have the same set of skills, and even for those of us who have similar skills, we’re still differentiated enough that we each have our own specific impact. My speaking or writing style is my own, and I don’t need to adjust it to how someone else speaks or writes because I’m not them.

You have a specific impact you’re meant to have on this world. No one can lead like you can. No one can speak like you can. No one can do what you do like you can, and that’s what makes life beautiful. Be secure in who you are and how you lead. Craig Groeschel, one of my favorite speakers, always says, “Be real. People always prefer to follow a leader who is always real than one who is always right.”

Have your aspirations; be inspired to learn something new; continue to grow, but be yourself in whatever you do. Be secure in who you are and confident in the fact that you have significance and the ability to make the difference.

What are some ways that insecurity creeps into your life? How can you prevent jealousy from influencing your leadership?

Why Your Ideas Don’t Land

Communication is an extremely part of life, and not just in leadership. Really, anyone can talk about anything, but it takes special practice to get your ideas across in an intelligible way. What this boils down to is being concise.

I think we’ve all experienced the leader (and been the leader) who rambles on and on to try and make a point, but by the time their point is made, you’ve lost focus because you couldn’t keep up with their multiple trains of thought. We have good ideas and good intentions, but sometimes the message gets muddled up in an excessive string of words. Even if you have the best, world-changing idea, it won’t matter if you can’t accurately and concisely convey that message in a way that is understood by the other person.

This is something that I often struggle with, and it’s honestly why I try to keep my blog posts at about 300 words. It forces me to focus in on my message and only pick the most appropriate pieces of stories that will get my point across. I often feel like I have a lot to say, but what good is it if I cloud my point with unnecessary words that will only lead to confusion.

Part of being concise is choosing the right words to say in a certain context, which is another thing I really struggle with. Mark Twain said, “Don’t use a five-dollar word when a fifty-cent word will do.” I think sometimes we all want to feel like we’re smart, and an easy way to do that is to use big words. While big words have their place, they’re not always necessary and can often detract from the conciseness of your message.

As I wrap up this post, I want to leave you with a question: What are some things you can do to make yourself more concise? Do you feel you are too longwinded and vague? How do you think that affects other people?


There’s Something More Important Than Listening. Here’s what and why…

I listened to a podcast by Gary Vaynerchuk today, and he hosted one of my leadership heroes, Simon Sinek. Something they were talking about really stuck out to me, and that is that there is something more important than listening in leadership. That something is being the last to speak.

I’ve been reflecting on this statement for a good part of today and felt I needed to write about it. Here are three of my thoughts.

1. Leadership isn’t about coming up with the solutions. 

We must be secure enough to understand that we won’t have the best answer to everything.

2. Leadership isn’t about domineering a conversation.

If you’re doing a good chunk of the talking, that means you’re not listening. Foster an environment where your people can think and speak without fear of judgment.

3. Leadership isn’t about influencing another person’s idea when you face a problem. 
This is why you speak last. Since you’re in a position of authority, you’re more likely to change your peoples’ minds if you speak first or intermittently. The only thing you should be doing is asking questions to clarify a point.

Do you agree with their point about waiting to speak last? Have you ever felt implicitly influenced by a leader of yours in such a way that you changed your mind about contributing to a solution?

Leaders Are Focused

Have you ever been distracted? If you’re reading this, chances are you have been – this post may even be what’s distracting you. Being distracted – I think we can all agree – is frustrating, especially being easily distracted. It seems to only happen when we’re determined to do something or remember something or write something down or commit to something; we never seem to be distracted from daydreaming, only when we need to focus.

This topic of an inability to focus for the individual is frustrating to the individual, no doubt. However, when a leader is unable to focus, it is frustrating for the organization. Now, I’m not talking about an occasional bout of self-diagnosed ADD. I’m talking about when a leader has a list of 6 or more things they want to do and no vision to do any of it. To express the severity of this problem in the context of leadership, I need to modify the above quote: If you pursue too many things, you will fail them all.

I’ve read that it is recommended that an organization (or individual) should not have more than five (preferably three) big and important goals (I’ve also read this figure for metrics). Anything beyond five will most likely be forgotten or treated as less important. To further drive the point home, consider this story. It’s fabled that when Steve Jobs returned to Apple after a brief hiatus, he sat down with all his staff and drew a large square with two lines through it to form four quadrants. On the axes he wrote “Consumer” and “Professional” on one axis, and “Desktop” and “Portable” on the the other. While Apple has several other products on the market, the main push will always be with these four products. Apple is a focused company.

I’ve been a part of organizations that want to measure everything and put in place measures to ensure that the metrics are met. However, if every metric is important, then no metric is important. If everything is important, then nothing is important. This is why we need to take time to differentiate what’s important to us and what’s not. We need to set goals, values, and metrics that matter in and to our organizations.

As the old Proverb says: where there is no [focus, vision], the people perish.

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