Roger Osorio, Founder of The School of Reinvention, faculty member at the University of Pennsylvania and Sarah Lawrence College, and former globally-recognized executive coach at IBM launched a course on How to Coach Your Teammates or Employees. This special training is designed for any leader, individual contributor, or sales managers interested in developing their leadership style and communication skills in order to drive employee engagement, talent development, or a coaching culture in their organization. Enroll now for free access to the course!

For as long as I can remember, I loved helping people around me overcome challenges.

Specifically, I focused on helping people in math since that was my favorite subject and the one I performed best in. I figured if I’m going to help people in something, I better have some credibility. Math was my subject. I remember my first couple of tutoring experiences when I was in 7th or 8th grade and I was sent down to help some of the 5th graders. This desire to help people in math continued for decades and with time, I got better at it.

One of the biggest lessons I learned was that I didn’t need to have a math degree or teaching degree to successfully help people in math.

In 2008, I chose executive coaching as the focus of my M.S. in psychology. Equipped with effective coaching skills, I took my work in math education to new levels. Most importantly, I realized that I didn’t need to be an expert in a topic in order to help someone grow in that topic. Instead of an expert or mentor, I could be a coach. 

In my masters program, I learned fundamental coaching skills and a coaching process to extract increasing levels of performance from people. Since 2010, I have had the pleasure and honor of coaching over 3,000 professionals, leaders, executives, educators, students, entrepreneurs, and athletes.

But it seems I started learning coaching strategies much earlier than that.

While I didn’t know it at the time, high school helped me develop several effective coaching skills for becoming a successful coach.

In high school, I was fortunate to have the opportunity to advance quickly in math and take Calculus 2 in my senior year.

Mr. Diaz, whom I still can’t call by his first name out of deep respect, offered to teach Calculus II at a college level. He did not want to teach the lighter version that’s designed for the Advanced Placement Calculus BC exam. That wasn’t motivating enough for him to take on this teaching challenge and the incredible amount of preparation that would be required of him.

He said that if he decides to offer this course to us, it’ll be on his terms and that we must fully agree. For us, a bunch of inner city kids, this was quite the offer to get a course like this taught at the highest level. Of the 12 eligible students in our school, 6 of us took the challenge. Settings terms…sounds like something a coach would do before starting an engagement! What did I get myself into?!

Mr. Diaz always said that anyone can memorize formulas and learn how to “plug-and-chug” their way through math, but that to truly get all the value out of math, you have to learn how to massage and manipulate the problems until they give you the answer. He said, when you learn how to derive the formulas you need, in the moment, you will always be able to figure out problems, no matter what formulas you might have forgotten.

Mr. Diaz was my First Coach and Neither of Us Even Knew It

I didn’t know it then, but Mr. Diaz was empowering us to solve our own problems, an essential coaching skill. He used to tell us that we won’t always have him or our calculators or our calculus notebooks. Yet, we’ll still need to solve problems. This is why he was so passionate about teaching us how to figure it out on our own.

Mr. Diaz was my first coach – I just didn’t know it. His underlying assumption was that we had it in us to be great at this and it was his job to teach us how to get it out, anytime, no matter what the circumstances. And that is exactly what he did for me.

Mr. Diaz taught us the entire Calculus II course without graphing calculators. Since those were pretty expensive, I didn’t know what it was like to have one anyway, so I didn’t really know what I was missing. He got us to the point where doing everything by hand was the most normal thing for us.

We could look at a quadratic equation (i.e f(x) = ax2 + bx + c) and sketch the graph just from looking at it for a few minutes. Some might say that isn’t necessary because tech is available to do that for us. But that wasn’t the point…

Mr. Diaz was empowering us. He was building something far greater than an A+ student or a human calculator. He was building us into problem solvers for life.

Mr. Diaz taught me some of the most effective coaching skills

  • Always assume the answer is in your client and it is the job of a good coach to help the client uncover it.
  • Empower your client to solve their own problem – ask them what they think and what they could possibly do next. If necessary, meet them where they are and begin empowering them from there to take small steps forward. For effective coaching, a great coach assumes the answer is within their client.
  • If you teach anything in your coaching conversation, teach the skills that empower your client to solve their own problem. An effective coach shares the tools, strategies, and frameworks to empower their clients to solve more of their own challenges or opportunities. Perhaps even teach some of the coaching skills that make you a good executive coach.
  • Set the highest standards for your client and never let them slip below those standards. Challenge your clients to give their absolute best in the coaching session. Don’t allow a client to fall below that standard. The coaching relationship may only be a few hours per month. Make it count. Your client will be glad you did later.
  • Respond to questions with great coaching questions first. Embrace a coaching style where you consistently empower your client to answer their own question by asking powerful questions. This is where a great open ended question can create space for innovation.
  • Challenge your client to take on at least one scary and bold challenge.

Successful Coaching Strategy – The Impact of Setting BOLD Challenges

Mr. Diaz always included one BOLD challenge in each test he gave us. There was always one question to “separate A students from the B students.”

We were forced to stretch beyond our current skill level.

Basically, that meant even if you were doing great, you might only get as high as a B+ on the test (high 80s of 100 points). That final question would require us to dig for something that forces us to stretch if we wanted an A (or high 90’s of 100 points).

His tests were all take-home, which seems crazy now. Back then Google was barely a newborn. Plus, he took questions from his old Cuban calculus books, translated them, and then edited them to his liking. Imagine trying to find some of those questions on Google, even today.

In one test, I encountered the most difficult challenge question I had seen until that point. I set out to answer this question no matter how long it took. In all, it took me 24 hours, across a few days to answer that question. The answer eventually came to me in a dream the night before the test was due back. Waking up from that dream, I turned on my lights and resumed working on it. I had a deep sense of confidence that I was right and this was the correct answer!

First thing the next morning, I turned in my test and asked him if it was the right answer. He said that won’t matter until he looks at the work, but he looked anyway and said, yes, that’s it. After which, he stood up from his desk and shook my hand; he said I was the only one to get it right. At that moment I realized that I could do anything if I pursue it with absolute intensity.

This coaching technique can make the difference between a good coach and a great coach because it directly contributes to transformation.

Mr. Diaz’s Impact as a Coach Still Resonates Today…

Almost 10 years later, I applied for a job to teach math part-time at an after-school learning center. In my cover letter, I told a version of my Mr. Diaz story. That letter violated every rule of cover letter writing, but I needed something special to make up for lack of credentials. My Mr. Diaz story was going to be that special factor.

The executive director of the center booked me for an interview a day after I sent my cover letter. They said they wanted to hear the rest of that story in person and I got the job! When it came time to recall 4 years worth of math 10 years later, I didn’t have to recall anything because…

I derived everything I needed.

Ten years later, Mr. Diaz was right, it was always inside of me and now I knew how to get it out, any time, in order to help others.

Thanks to Mr. Diaz’s great coaching skills, I was able to reinvent myself into a math teacher without a single official credential. I spent 10 unforgettable years teaching math is a variety of settings, 4 years of which were in the classroom.

Every now and then, someone will ask me for help with a math problem and almost 25 years later, Mr. Diaz’s impact on me is still felt.

The key coaching skill of a successful coach is being able to make an impact for life.

Course Available

Roger Osorio, Founder of The School of Reinvention, faculty member at the University of Pennsylvania and Sarah Lawrence College, and former globally-recognized executive coach at IBM launched a course on How to Coach Your Teammates or Employees. This special training is designed for any leader, individual contributor, or sales managers interested in developing their leadership style and communication skills in order to drive employee engagement, talent development, or a coaching culture in their organization. Enroll now for free access to the course!

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