5 Questions Everyone Should Ask

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I’m a fairly unlikely success on paper. I made average grades in school, attended a fairly average college, struggled with ADHD and bouts of depression, and am not some sort of second-generation anything. But despite my struggles, I don’t know that I would describe myself as an unlikely success. Why? Because I was raised by a mother who always told me I must and a sweet, Midwestern Daddy who always told me I could.

This combination has had an immeasurable impact on my life because it forced me to always continue the chase, to always feed my curiosity, and to always believe I could. Second, only to my upbringing, these five questions have allowed me to grow and develop and I hope they can do the same for you.

Where do I want to go?

While this question may seem pretty straightforward, the answer isn’t always as straightforward as we may want it to be. Still, without your initial direction, you cannot build, implement, and execute a plan because you’ll have no idea where you’re going. Here’s my advice…while you may not know what the answer to this question is without a shadow of a doubt, answer it anyway. It doesn’t mean you can’t pivot or adjust after you’ve started. Heck, it doesn’t even mean you can’t change your mind. But, by starting with a clear direction, you’ll prompt action, which is 80% of the battle!

What do I lack?

Knowing what you lack isn’t about self-deprecation, it is about awareness. For instance, we have all of our coaching clients take an initial assessment to identify their CliftonStrengths® as a tool of self-awareness and self-discovery. Much like knowing where you want to go, this is about identifying where you are so you can be clear about what skills you need to work on, who you need to meet, what you need to implement, etc. But let me be clear: do not get stuck on what you lack! While self-awareness is an important element of growth, it is also a paralyzing fear that far too many of us succumb too. Where you are today does not define where you can go, it merely states your starting point. The rest of the story is yet to be written.

Who can help me grow?

Look at any successful person by any measure and I can tell you a single truth that they all share - none of them got there alone. While success certainly has a lot to do with talent and grit, it also has to do with gumption. Identifying people who possess strengths you want to build, roles you want to have, or even lifestyles you aspire to and seeking out their wisdom is a huge part of your growth. While many of us will look up to certain people, far too few of us seek them out and inquire about their advice. Don’t hold back. Most of the time, people are anxious to share their thoughts and help others. Ask!

What’s holding me back?

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While this question may seem similar to “what do I lack?” it is distinct in its’ own way. Identifying what is holding you back is more about your mindset than your actual ability. Our own self-doubt, our thoughts, and even our resources can make a big impact on our growth if we let them. My dear friend Vanessa Bergmark recently shared a talk at WomanUP!® about “fear-setting” where she outlined identifying your fears, playing out the worst-case scenarios and working backward to show ourselves that the likelihood of the worst-case scenario being the outcome is actually quite small. This small exercise can push us further and to develop in ways that our fear often won’t let us.

Is fear holding you back? Watch Tim Ferris’ TED Talk outlining exactly how to complete fear setting.

What’s next?

If I had waited for the right moment to take most of the leaps I’ve taken in my career, chances are…I’d still be waiting. The truth is, there is never a good time to take a leap of faith but the advantage of that is that there is also never a bad time either. By constantly asking yourself “what’s next?” you force your brain out of complacency and into action. You begin to define your next steps and always be in a growth mindset. That, my friend, will be what makes all the difference.

When I initially wrote this list, I wrote it as “5 Questions Every Leader Should Ask”; however, after putting the list together, it occurred to me that maybe we would have more leaders if more individuals asked these questions. I don’t mean to imply that my confidence has been what has allowed me to overcome my obstacles. In fact, I have struggled the same as everyone else; however, deep down, I know that forward progress is the key to success so instead of asking “what if I fail?” what if you asked, “what if it works?”