What's it like being on the other side of me?
Every other week my 14 year old son and I go out to grab some food late night. There are two stipulations to this time. He has to come with a question he wants to ask me, and I have to come with something I want to teach him. This triggers a very intentional time of deep conversation and growth for the both of us.
One night after we had wrapped up our conversation and we were on our way home I looked over at him and asked him "What's the hardest part about being my son?" The silence was deafening. It persisted for quite a while until I nudged him again for an answer. "That's a really hard question to ask someone" he said timidly. “I wouldn't have asked you the question if I wasn't prepared for your answer." I responded.
"The hardest part about being your son, is you're always here...but you're not always here."
I think at any other point in my life that would be a hard thing to hear. While I am with my family almost 24 hours a day, I'm often consumed in my thoughts and am not always mentally present. His comment didn't hurt near as bad because it was something I was already committed to working on that year. It was affirmation that I was focused on the right things.
While this specific conversation was rewarding, questions like this have led to harder conversations and difficult truths to hear. In addition, there are other people in my life that haven't even received the benefit of a question like this.
Have you ever asked:
What is it like working with me? Have you ever asked your coworkers what it's like being on the other side of a project with you? Am I collaborative or bossy? Am I patient or in a rush? Do I cut corners or produce good work?
What is it like being married to me? Have you ever asked your spouse what it's really like? The longer you've been married the easier it is to brush off bad habits and quirks as if it's forever acceptable. Justifying a fixed mindset. The one's we love the most and are closest to us we tend to lean on in our weaknesses. We expect them to "love us for who we are" and spend most of our time trying to impress people we barely know. What if we flipped that and spent our time looking to impress the one's we love the most? They, above anyone else, deserve your best.
What is it like working for me? Here's a big one. As a leader, how big and consistent is your feedback loop? The higher we climb in leadership the less our team will be willing to give us feedback. Those we lead often hesitate to speak up to leadership about personal improvement areas due to fear of judgment, potential career repercussions, or the belief that their concerns may be dismissed as naive. If we do not proactively solicit feedback from the people we lead the natural result will be growing blindspots and a cyclical regression.
What's it like being my friend? This is a rabbit hole most won't be willing to go down. How often do we reach out to our friends...when we don't need something? Do we know what they are passionate about? Do we sit with them in their pain no matter how big it is? Do we cheer for them in their wins no matter how small they are? It's scary to ask this question, but I encourage you to do it, and challenge you to accept the response.
Introspection is a healthy habit, but without external evaluation we will do nothing but self-justify and at best self-medicate. You will never truly know what degree of self awareness you're operating at without the solicited input of the people you engage daily.
Through routine it's common for us to believe that the way we act is acceptable, cordial, good, great even. We all live in our silos though and the person we talk to the most? Ourselves. It doesn't take much to convince ourselves that we like the way we are, that we do a good job, that we're a great friend, colleague, or spouse.
I challenge you to ask one of these questions today. Most people you ask will start with niceties, complement your positive attributes and so on. Ask them to stop. Ask them to be candid about who you are to them and how you can be better. Engage someone with a strong desire to be a better version of you. Not to try to clarify, justify, or down play the way you've been, but to sit and listen with an eagerness to be better.
These conversations don’t just happen by accident. They require intention. If you wait for the “right moment” to ask hard questions, you’ll likely never ask them. Life will always provide a reason to delay: too busy, too tired, not the right mood, not the right setting. Growth often hides inside the conversations we’re most tempted to avoid.
When I think about that night with my son, I realize it wasn’t the question itself that made it powerful, it was the posture we’d built around our time together. He knew our conversations were a safe space. I wasn’t asking to trap him or to prove a point. I was asking because I genuinely wanted to know. That’s the environment where truth can surface.
The same principle applies in every relationship you have. If people in your life aren’t giving you honest feedback, it’s worth asking: “Have I created a space where they feel safe enough to tell me?”
Asking someone what it’s like to be on the other side of you is an act of humility. It’s an admission that your perspective of yourself is incomplete. That’s hard for our pride to swallow, but the alternative...living blind to how we affect others...is far worse.
Why? Because everyone around us deserves a better version of us.... We deserve a better version of us.
Today’s Forced Challenge: I want you to FORCE yourself to attack at least one of these challenges:
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Go home tonight and ask your spouse, What’s the hardest part about being married to me?...and don’t flinch.
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Sit across from your kid and ask, What’s the hardest part about being my son/daughter?...then shut up and listen.
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Call your closest friend and ask, When have I failed you as a friend?...and mean it.
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Look your direct report in the eye and say, What do I do that makes your job harder?..then fix it.
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Text your mentor and ask, What blind spots do you see in me that I don’t?...and brace yourself.
If you choose to take one of these challenges, remember:
Be ready for discomfort. Real answers may sting.
Resist the urge to defend. This isn’t a debate, it’s a gift of insight.
Act on what you hear. Feedback without action is just noise.
In the end, the courage to ask is matched only by the courage to change. And when you do, the people around you will notice, not because you told them you were working on yourself, but because they’ll feel the difference.
"Criticism, like rain, should be gentle enough to nourish a man’s growth without destroying his roots." – Frank A. Clark
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