What Is the Essence of a Great Adviser?

One of the very best mentors I ever had was Jim Porter. He came into my life when I was 28. He led the team which bought the company Richard Brock and I founded. Jim and I worked together for four years. One of my biggest regrets is that I didn’t stay in closer touch with him throughout my career. I believe I would have been a better man and better businessman with Jim at my side.

When Jim was retiring, I received a call from his son. He was creating a book of memories for his dad and asked me to write a letter of appreciation to his father.

I quickly agreed to write the letter.

In preparing my thoughts for this letter of gratitude, I asked myself, “What made Jim such a great adviser?” I flopped around on this question and never did come to a good answer.

But I’d agreed to write the letter, so I did. I was never satisfied with what I wrote. For twenty years, whenever I thought about Jim Porter, I would ask myself the question, “What made Jim such a great adviser?”

Then one day, I had the answer. It came to me in a conversation with my friend and life-long entrepreneur Jim Grady.

Grady nailed it.

He said, “The best advisers ask great questions which get me to think. Their goal is to help me get to my own opinion.”

Grady continued, “Our brains are basically lazy. They really don’t want to do any work. A great adviser engages our brains. The adviser makes us think, and think hard. The questions he asks and the conversation which ensues forces us to draw on all our experience and assumptions and come to our own conclusion, our own opinion.”

But this isn’t what I do, at least not all the time. I do this sometimes when talking, but most of the time I am giving advice.

I find myself starting sentences with, “You should…” “I think…” “If I were you, I would…”

I said to Grady, “You get it. You are on to something here. I’ve been leaving some of my conversations with entrepreneurs feeling unsettled, maybe even guilty. I haven’t been able to put my finger on what my problem is. Now I know.”

He said, “It takes patience to ask questions. To guide people to reach their own opinion rather than giving them yours.”

That’s when I knew the answer to the question I was asking myself about Jim Porter for the last 20 years.

What made Jim such a great adviser?

The answer: He asked the questions which helped me come to my own opinion, my own solution.

The adviser that engages with thought-provoking questions has patience.

This is patience born of humility.

Humility is the essence of the servant leader.

This was Jim Porter.

Thank you, Jim.

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2 thoughts on “What Is the Essence of a Great Adviser?

  1. Hi Charlie – great article, and I agree wholeheartedly!

    My rule of thumb for finding or measuring advisers is simple. I find people that are like our mutual good friend, the inimitable Michael Blake (@Unblakeable). He is my version of Jim Porter. He is completely unlike me. Not a software engineer. Not rambunctious. He is a finance guy, and patient in every regard. He always brings me around by asking me even-keeled, thought provoking questions. He’s a gem.

    Hope you are doing well, my friend!

  2. Great blog post. Learning to ask great questions is the foundation of learning. The average 4 yr old girl asks 40,000 questions in a year. Compare that to the questions that get asked in a retirement home. Continuing to ask provocative questions is the best rust-preventative I know. There’s a good book, “A More Beautiful Question” by Warren Berger that is great on this subject.

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