The Why of a much older “son” ~

Oliver Keller
Oliver’s Blog about Nothing
3 min readNov 8, 2018

Recently I was confronted by one of our team members, let’s just call him Bill, who came to my office armed with a multitude of why questions in his arsenal. Interestingly though, compared to my why conversation with Jake, this individual was so uncomfortable in presenting his questions. Thanks to Jake, my personal heart over ego coach, I was able to put him a bit more at ease, encouraging him to stump me, ask away freely and if I did not the answer, that we would explore finding one together, or at a minimum find out, together, that there just was not one to be seen.

Remember when I shared how Jakes, why questions invoked fear and by proxy made me uncomfortable because it required me to be real and honest? I learned that allowing yourself to be real, vulnerable and honest, actually creates higher respect from those around me, so rather than hiding behind my ego and pretending to be the smartest guy in the room, I set the foundation for a crucial and emotional conversation, not governed by position or title.

As we started our conversation we established a few ground rules. The most effective was to give him complete permission to make me uncomfortable, not to mice words or be politically correct and ask away. Btw wtf does that actually mean? Are we actually saying politicians are so polished and always correct, truthful and should be emulated, I do regress. Back to Bill and me. So retrospectively, I think he was not sure what to do with that comment, as such an offer had never been extended to him.

After fighting off the butterflies Bills why’s were flying at me in rapid-fire succession, and I shared what I knew to be my truth. We went on like this for about 30 minutes until we were both drained, yet energized because of the depth of the conversation. There were plenty of I do not knows, none of which we could even answer together.

What we did gain by having this learning moment, was respect on a human level and not from CEO to associate, but the start to living our approachable culture where why’s and crucial conversations are not only encouraged but expected. This sincere and honest conversation my associate and I shared would not have been possible if it were not for the education I received from Jake, my 5-year-old step son, and his need to quench his curiosity and create a framework for a greater understanding.

Take Away:

Trust is built on honesty. The ability to check egos at the door creates an environment of openness and vulnerability where all agree that sometimes there’s just not a right or wrong answer to be had, heck, any deep or sound answer really. It sets the stage that “I do not know” is as acceptable as the possible deep-rooted and researched answer. “I do not know” is actually perfect in its own right. It merely is about this moment in time, life as it is and is not. That’s it. The end.

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Oliver Keller
Oliver’s Blog about Nothing

Managing Partner & C.E.O. of Synlio. Synlio addresses one inarguable fact, #RFPsSuck. See how Synlio’s RFP Automation solution has reimagined the RFP Process.