Two years ago in the midst of a career change I sat down and sent an email to a guy whose career I admired requesting a chance to meet.

To my surprise, he agreed, and a few weeks later we met on a Friday morning for a coffee.

Forgetting my wallet, and making him float the bill, topped off a laundry list of mistakes I made during our conversation. In addition to trying to act cool, I even disrespected him at times by interrupting him to demonstrate my vast knowledge on the topics we were discussing (something you probably should not do to a communication coach).

Despite acting like an idiot, he remained cordial, even humouring me at times. However, as thick as I was that morning, the message that I was not making the impression that I had set out to make came in loud and clear and I had blown the opportunity to build a relationship with a person I knew I could learn a great deal from.

I went home thinking to myself that I had not lived up to my potential, but after a few months I came to a hard conclusion: even if I was on top of my game that day, I had not been ready to meet with him and that I had made the mistake of reaching out too soon.

Since that day I have used that conversation at a measuring stick to gauge my growth.

Was I ready to contact him again?

Was the work I was doing good enough to request a second meeting?

Each time coming to the conclusion that the answer was “No. Not yet. Get back to work.”

All the while this was happening I began writing more and more in my secret blog and time and time again the one person that checked in and left the occasional encouraging comment was the man whose time I had wasted months before.

I knew that he was not the type of guy that gave compliments lightly or wasted time on someone he did not see something in. So slowly, the very man that I had prematurely tried to impress — ultimately making me question my own confidence and abilities — was the very person that was building it back up again, whether he knew it or not.

After two years, recently I got a shot at round two.

After speaking for 90 minutes I closed the video chat with the feeling that I still had much to learn. However, a big part of me felt like both us of had benefitted from the conversation, and that he had finally met the person I thought I was two years prior.

Since that meeting I have learned a great deal about myself, and through his subtle actions, a great deal about leadership and building relationships.

Below are the 6 main take-aways I have learned since making the mistake of contacting Conor Neill, the guy I admired too soon, which inadvertently turned out to be one of the best mistakes I have ever made.


Relationships and reputations are often build by what some would consider inefficient actions.

Conor is a very busy man with little time to waste. That said, his actions told me that he knows that we must be open to possibilities and that helping others is always the right thing to do in so many ways.

A favorable nod, a pat on the back, or a word of encouragement energizes and empowers others and through Conor´s subtle actions he reminded me of the golden rule in not only relationship building, but career building as well: The best way to clear your own path is by helping others clear theirs.”


If each of us lives a full life, the odds are high that we will work for 50 years, each year representing roughly 2% of our overall career. By reaching out to Conor when I did I demonstrated to him that I wanted everything at once and that I was willing to cut corners to reach my goals.

Bill Gates said that, Most people overestimate what they can do in a year and underestimate what they can do in ten.” During our conversation Conor subtly reinforced this notion by reminding me to slow down. I did not understand that then, but I do now.


Prior to meeting my wife, I had allowed my weight to get out of hand and I was stuck in a career that had I had allowed to run me into the ground. Yet if during that time you had asked me to describe my “dream girl”, the words “in shape” and “successful” would have topped the list. It was not luck that we met after I had begun to take care of myself again and begun to focus on work that mattered.

The same goes for my relationship with Conor.

I represented someone who had not yet done the work, expecting to connect with someone who already had without properly identifying how I could benefit him also, and you cannot do that.


The more people I meet like Conor, the more I have come to realize that success often comes down to the word, “AND.”

Good with numbers “AND” great at building relationships.

Inspiring writer “AND” patient teacher.

Even in relationships it is often the “AND” that keeps us awake at night; Beautiful AND great sense of humor.

Successful people always have an “AND,” and observing Conor move from a successful blog to an incredible video series shows me that no matter what level of success he has achieved, he is still chasing the next “AND” to add to his skill set, and that I better keep moving if I hope to get that third conversation.


Conor had every right to never contact me again and I would not have blamed him in the least if he hadn’t. But by sticking with me and checking in on my progress Conor taught me an invaluable lesson about building relationships: not everyone is going to get it right the first time, but that does not mean that they do not have something to teach me.

Too often we rush to dismiss an idea or an acquaintance based on hurried or shallow assessments, something I was guilty of in the past, but much more conscious of now moving forward.


Last December I reached out to Conor to get his opinion on the bones of an article that Fast Company had expressed interest in. Prior to submitting the final draft to the editor I went with my gut, contrary to one piece of advice that Conor had offered, and according to the editor it was the tipping point in him running the article.

This may seem trivial, but this was a big thing for me, and once again it came back to our first conversation where Conor encouraged me to listen to myself more than others, and for one of the first times in my life I went against the grain and it paid off.

A few days after our second conversation my feeling that I had indeed added something to the conversation was confirmed when Conor was kind enough to mention me in a part of his video series. Having a guy who I obviously admire demonstrate that I am not wasting his time, but adding to it will be one of the highlights of my career.

John Maxwell got it right in his book entitled, “Sometimes You Win, and Sometimes You Learn.”

The first meeting with Conor, I lost. But by him taking the time to guide me through the process, in the end, I learned, which the older I get, the more I realize is the same thing for winning.

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