Category: Coaching

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365 Coaching Tips: 91st, 92nd and 93rd

April 1st Coaching Tip: Ask For An Exception.

Recently was working with an advisor who is 3-4 months from announcing his retirement. He received a major curve ball: his succession plan (with a female advisor that has been his business partner for more than 13 years) is in limbo. The female advisor now faces an existential health situation. It’s drastic for her, and for the soon to-be retiring advisor. After we discussed this tragic situation, we thoughtfully started discussing options. By the end of our very important and focused call, we had identified seven options. And the 7th option ended up being the “ask for an exception to the policy.” He’s now working the details on that option even further, because as he says, desperate times require desperate actions. He’s going to ask for the exception; my bet is that he will get it due to his story and prep, and his relationship with leadership.

April 2nd Coaching Tip: Those “T” Words

As the workday wrapped up on April 2nd, threatening weather with severe thunderstorms and tornadoes scattered from Dallas, TX to Toronto, Canada. And in Indiana, there were multiple sightings and touchdowns of tornadoes within one mile of our rental homes in Carmel, IN. But before all of this threatening weather started occurring around 8pm, the United States announced new and higher tariffs, after the stock market closed. There was an immediate and thunderous loss in the markets across the globe. Lots of “T” words, that can and will drive anxiety, fear, anger, and isolation. Think of how when a tornado is closeby, we quickly move to isolate inside in a safety room/basement/closet. When it thunderstorms, we tend to get inside, too. When tariffs are announced, this tends to drive isolation by countries…self-preservation versus decades of collaboration.

April 3rd Coaching Tip: Hopeful “T” Words

Today, I’m thankful that none of my friends, family, and rental homes were impacted by the tornadoes in Central Indiana last evening. It’s Taco Thursday and Thirsty Thursday, so let’s make it through the day to celebrate an upcoming weekend. With the tariff announcements came a sell off of the stock market; this timing might just be a good time to jump in the market and buy when prices are lower. I sure took advantage of it!

How YOU respond to daily and weekly announcements, happenings and untimely realities that impact your world is on YOU. It’s YOUR decision. Your attitude and how you respond will be remembered by others, but more importantly, it will help you be resilient thru these times.

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365 Coaching Tips: 88th, 89th & 90th

March 29th Coaching Tip: 2.8 Seconds.

My uncle texted me and said, “looks like overtime!” He was assuming that 2.8 seconds wasn’t enough time for the University of Houston to score and beat Purdue. After a timeout, both teams came out on the court, Houston got the ball under their basket. All Purdue has to do is defend well, since the score is tied. Official hands the ball to the Houston inbounder. He ball fakes, makes the Purdue defense move, and then he waits even longer to survey his 3-4 options, and right in front of him a few feet away, is his open teammate. He throws a perfect pass to his center, then the inbounder expertly jumps inbounds, and the center throws his back a perfect pass…and that inbounder scored. Game over, Houston wins by two points, and only 0.8 second left on the clock.

What happened to allow Houston to make not one but two passes? A complete breakdown by the Purdue defense and perfect execution that had been practiced numerous times by Houston. The Purdue defender who was guarding the inbounder actually turned his head AWAY from that inbounder/the bal, and was then consumed with the other players moving. Then two other Purdue players didn’t switch well on defense, which allowed the passes and the shot to be made. Know your job and do it. Had Purdue better defended the inbounder, the result most likely would have been “overtime”. A lot can be accomplished in 2.8 seconds.

March 30th Coaching Tip: That Letter “C”

Met with one of the largest advisors in the firm today, and after approximately five hours together, we landed on a list of 8-10 items as next steps. She has a team of 10 teammates, and 7-8 are highly committed and talented. The remaining 2-3 are not as committed or not as talented. We identified next steps, which revolved around words that begin with the letter “C”.

Improve the team Culture. Interview 100% of the team’s Colleagues, to help drive Cohesiveness. Increase Capacity by Coaching up under-performing teammates. Recognize Collaboration and equalization of workload. Segment and vet the Clients. Identify a future Chief Operating Officer (COO). Review the team and individual Compensation. Bottom line: as meetings are happening every single day, how will you summarize it for easier and clearer understanding? I chose to embrace letters or words, so that recall is clearer. Go C’s!

March 31st Coaching Tip: Consider It A Gift

Consider it a gift when someone is asking for time with you. They are willing to share something with you that’s very important to them, and they are entrusting you with this information, insight, advice, or problem.

Recently, I had a popular person (so called, “public figure”) reach out to me and say that she wanted to run an idea by me. She asked when I was available, and we got that on our calendars. But the most important thing that I noticed was that she didn’t want to text the topic. That is a clear indication to me that it’s important, or new, or highly confidential. The fact that she is entrusting me to discuss it is truly a gift. When we meet soon, my whole goal is to stay present and truly listen, remain curious, and have zero of my own intentions cloud or confuse my ability to listen. Consider it a gift, when someone needs your presence.

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365 Coaching Tips: 85th, 86th and 87th

March 26th Coaching Tip: Find The Yes.

Too many of my coaching conversations revolve around people’s frustration from being told “no” or “nope, can’t do that” or “no way”. For example, today I had two different leaders being told that they can NOT hire additional employees. Instead of being told “no”, I coached them to figure out how can they get a “yes, you can hire”. As we looked thru their business, it was evident that their competitive metrics as compared to others were quite average, i.e. 40-50% on a 1-100% scale vs. competition. And then we dug deeper, and their development of a current newer hire has not gone as expected, and that individual is failing. My coaching question was pointed: “what do you own in getting the answer, “no”?” After some silence, the leader admitted that he hadn’t run his business like he was intending. And after some more intentional questions from me and answers from him, we developed a monthly accountability plan for him to run his business better and to more intentionally develop his teammates. Time will tell, but figure out how to find the yes.

March 27th Coaching Tip: Don’t Rain…

Don’t rain on other people’s parade. When someone is really excited about something that they deeply care about and are telling you all about it, listen, smile, and celebrate with them. Whether you like it or not, it is important to THEM. Be curious, ask questions, learn more about them and their “parade”, and they will think you are a rockstar. Why? Because you listened to them and didn’t rain on their parade. For example, my oldest brother and mother own harness horses together and love to talk and share about their horses, race results, and the new baby foals. All I have to do is listen, ask questions, and then celebrate their successes…or be empathetic when things don’t go well. For example, recently one of their favorite mares died as it was having a baby foal, and the foal died, too. They were grieving, and so we all started sharing photos of this super special, winning racehorse when it was winning, training, and enjoying it’s pasture. Don’t Rain on other people’s parades. Just don’t.

March 28th Coaching Tip: End of Quarter.

How did your quarter go? This was a question that was asked every single 90 days when I worked as a leader at Caterpillar. Same thing now happens at Bank of America/Merrill Lynch. Let me ask you: How was your quarter? What did you intentionally get accomplished? What slid and didn’t get executed to meet your expectation? What are you most proud of? What is the biggest disappointment? How did your personal goals progress? How did you celebrate others’ goals?

We just intentionally had dinner outside and talked about what we are proud of since the beginning of the year. We started with personal priorities, then pivoted to professional and work priorities. Overall, even though we both battled bronchitis and Covid, we beat it and remain standing strong. I also made substantial progress on my real estate businesses, with getting one home under contract (to close in mid May), another home will be listed in mid May, and the remodel project is right on track for completion in late summer. Regarding my coaching work, today I summarized all the coaching engagements that I started in 1Q2025. The impact that I’ve already noticed with these leaders and advisors is off to a great start, and by YE2025, results will be substantial. Look at your results, at the end of every quarter.

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365 Coaching Tips: 82nd, 83rd and 84th

March 23rd Coaching Tip: Friends First.

As I watched my IU Hoosier women’s basketball team wrap up their loss to South Carolina, I noticed that one of our IU players stopped and truly hugged one of the SC players. And then, after all the players shook hands, the SC player came back thru the line and hugged, then quickly gave a sweet cheek-kiss to the IU player. Why would they do that, aren’t they competitors? Yes, of course they are competitors. But they are friends first and have been friends for years. It was a pleasant site to witness, and the TV cameras even showed the parents of both of these players hugging each other. As you compete, remember to remain friends with those who really are friends. I’ve learned that I now have friends that I competed against or with daily in practice, and I’m so glad that many are still my friends. Friends first!

March 24th Coaching Tip: Evolve.

My word for the year is Reduce. One of my colleague’s word is Evolve. I like it, because she is our senior coach, with incredible experience, and more senior than me and our manager. She wants to continue to evolve by embracing new ways of doing business, learning from others, and working a bit differently. If you were in the last few years or months of your career, how willing would you be willing to evolve?

Many of my elders have shared with me that when you stop learning and growing, you start slipping and dying. Now that I have more grey hairs, I truly support this thinking. Tonight, we watched “The Americas” series on Peacock, narrated by Tom Hanks. We kept watching episode after episode, consuming all of the incredible cinematography as well as the education on all of these animals, insects, and species. Keep evolving.

March 25th Coaching Tip: No 2am Texts.

My mother and I talk and text every single day. We share a lot and are very close. Over the last month, she has shared with me that someone in our family has texted her at 2am on a couple occasions and has also sent an additional 8-10 texts since March 19.

This is a coaching lesson in emotional intelligence: 1) when you want a senior/elderly/84 year old woman to help you, don’t text them at 2am. 2) when you want help, maybe call them and ask how THEY are doing and really care about what is shared. 3) if you are sending an additional 8-10 texts, look in the mirror, and ask yourself, “why aren’t I getting any response?” (from the 84 year old woman). 4) and don’t deny it when you are called out for doing it.

I have texted my family member twice now, and let them know that my mom is busy thru tax time (April 15) and managing over 10 farms. I also requested that the 2am texts stop. Due to al ack of emotional intelligence, the family member (of course) indicated that they don’t text much, didn’t do the 2am texts, wasn’t adding any stress to the situation, and indicated this was like high school drama. Bottom line: wake up, look in the mirror, own your errors, be more in tune with elderly people, and for goodness sakes, don’t be rude to them when you need a favor. Seniors (like my mother) have who multiple stents in their hearts and have had two hip surgeries in the last 2+ years, lost their husband of 63 years, keep their phone “on”, charged up, and nearby. and their Apple watch on their wrist. Just stop and think, no 2am texts.

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365 Coaching Tips: 79th, 80th and 81st

March 20th Coaching Tip: Two Minute Test.

One of the most common coaching discussions that I have with leaders revolves around their ability to get buy-in from their teammates and colleagues. When I ask them to explain to me what they want to accomplish, many have a challenge clearly articulating what they want to get done…and why. This question can also apply to people who lead groups or a family. Here’s an example in a family: “Our family listens and watches others, and then we are confident in how we execute. We take great pride in a preparation and calm execution, and that helps us know that we did our absolute best. We love. We learn.” You get the point.

Today I worked with two very talented leaders in Scranton and Philadelphia, PA. They have an incredible growth mindset, but are concerned that everyone around them are not as excited about the growth, which may mean more extra work and adding new/lazy teammates, etc. My assignment, after listening to them for 45 minutes, was to work with these two leaders and help them to be able to clearly and confidently articulate what they are building, and why, in two minutes. Looking forward to hearing them tighten up their message. Two minutes.

March 21st Coaching Tip: Move On.

The transfer portal in college sports is getting a lot of attention right now, since teams have been selected for the NCAA and NIT tournaments. In today’s world of college sports, the transfer portal allows student athletes to enter a transfer portal quickly to let other schools know that they are ready to “move on.” The sooner that someone wants to move on, the better. This applies in business, too. If an employee or teammate wants to move on, search for a new job, try a new career, take a few months off, recommend and encourage them to move on. Why? Because it will be better for the remaining team members. Those that “stay” want to know who is on the team and who is ready to get to work to achieve great things together. Move on when you know it isn’t right, simply move on.

March 22nd Coaching Tip: Tech Help.

Today, one of my colleagues helped me with some quick tech issues quite efficiently. We were able to jump on a Zoom, share screen views, and get 3-4 resolved quickly. If you need tech help, go to someone younger (typically) who is really good at it. They can do it rapidly, and kinda get a kick out of helping you. Makes them look good, and you get your problems solved…without being on a 1-800 tech support line for minutes, hours, etc. Ask someone younger for your tech help. My mom does it frequently, and I can help her with almost every single item with her iphone, ipad, or laptop. My god daughter jumped in my Tesla the day I got it at the Tesla dealership nearly three years ago, and she quickly touched the screen and took us to multiple restaurants that were within a quick driving distance. She also was curious to many of the items on the Tesla dashboard/dashpad. So she started touching and investigating, and in the process, I was learning. Get tech help.

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365 Coaching Tips: 76th, 77th and 78th

March 17th Coaching Tip: Green!

It’s St. Patty’s Day and many cultures act like the Irish characters all around the globe. I made it a point to wear green and always have done so. It’s fun, unique, and honors a culture and country. And I really like this special day because it hints of springtime, so sporting some “spring green” feels good and fresh. St. Patty’s Day also is always around college basketball’s March Madness, which is win and advance -or- lose and go home = green for go win! Lastly, green is my favorite color. Green was a favorite color of my grandfather George, and he and I are buddies. Green signals a sign of life to me. Green is that hint of money, and when people have some green in their pocket, they have an extra kick to their step. Celebrating St. Patty’s is always fun for me. Go Green!

March 18th Coaching Tip: Trust Your Gut.

Currently in the middle of a remodel project of a 95-year-old home. And from the beginning, we have been working with one subcontractor that just didn’t quite sit right with me. Fast forward a few months to now. We received his quote for new cabinets in the kitchen, bathrooms and the laundry room. The quote was as much as a new car, and it wasn’t complete and a bit suspect. Thus, I really trusted my gut and reached out to some cabinet suppliers that I utilized back in 2004. Sure enough, my gut was correct; the second quote was much more detailed, included taxes and installation, and was still 20% lower than the quote from the questionable contractor. Trust your gut, especially when it impacts three things: 1) YOU, 2) YOUR FAMILY, and 3) YOUR MONEY. No one will care more about those three things that YOU.

March 19th Coaching Tip: Ask For Flex.

The last couple mornings, my Oura ring was clearly indicating that something was off with me, i.e. elevated temp, high heart rate, poor sleep patterns, recommending rest mode. Yesterday, I tested positive for COVID. Not once, but twice. I actually thought I only had a cold, since I have been traveling steadily for 60 days and had just returned from New York City. Life goes on, and so it’s my responsibility as a coach to be proactive. Before 9am daily this week, I’ve reached out to all of my coaching appointments letting them know I need some flexibility and gave them a couple options: email me an update or reschedule for the next two weeks. Quickly they responded with complete understanding, and most were willing to wait to talk to me/reschedule for next week. When you need, ask for flex.

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365 Coaching Tips: 73rd, 74th and 75th

March 14th Coaching Tip: Health Matters.

Today I received a call from a leader that I’ve known for nearly a decade. Looking for advice on next steps for a work/career change, we discussed these three questions: are you living where you want to live, are you doing what you want to be doing, and are you with who you want to be with? After talking thru those questions, then we dug a bit deeper and discussed: are you living a healthy life? are you at the health and fitness level that you desire? Suddenly, the conversation turned to, “no, I’m not…I’m not happy with my lack of exercise and sleep, poor nutrition, less than normal vitals (weight, blood pressure, cholesterol).” Of course there are other considerations like annual compensation, long term or deferred comp, risk, management style, outstanding debt, buy-in from the family, etc., however, this leader realized that it was unhealthy to remain in the current role.

We will talk again in a couple weeks, as some assignments were given. With a number of my coaching clients, the conversations start in one direction (about a job or a situation), but then it turns into a much deeper situation. In this case, health matters more than anything else. As a coach, it’s my responsibility to stay present to hear the nuggets of the true problem.

March 15th Coaching Tip: Communicate in Advance.

Sometimes we have contracts or situations where we need a 60-day in advance notice. I have those with my tenants, as leases come up for renewal, i.e. 60-day notice if the tenant expects to exit the lease or 60-day notice if I decide not to renew or sell the property. How do I stay on top of these 60-day notices? I put a reminder in my iphone calendar that is approximately 75 days in advance. This allows me to give plenty of a “heads up” to the other party, and it is usually met with a response, “thanks, I had forgot, let me/us get back to you.” Communicating in advance can typically help things move along smoothly and with less stress.

March 16th Coaching Tip: Three Options.

Ever walked down a grocery aisle and notice that there are 40-50 different types of whatever? Tortilla chips and bread are examples and the options go on and on in other categories. The mass amount of selection can be overwhelming. For years, I’ve shared with many that my brain thinks in threes or like the figure, a triangle. The triangle is the strongest structure, and it brings me focus quite quickly. You may witness me bringing my thumbs and pointer fingers together to form a triangle, as I summarize or articulate three points. With my real estate remodeling projects, I tell my contractors to get me three options, and I can decide quite quickly. Figure out what works for you. How do you simplify how you make decisions. Embrace a way to make decisions. For me, it’s three options. Make your decision and move on. Rarely do I have regret.

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365 Coaching Tips: 70th, 71st and 72nd

March 11th Coaching Tip: Take A Break.

The stock market was chaotic due to a multitude of national and global situations. I was in back to back meetings with leaders who are leading themselves and their teams thru anxious and challenging times. All day, I was working in a beautiful office overlooking the Statue of Liberty to the south and the 9-11 Memorial to the east. As it was approaching 5:45pm, I realized that it was time to grab a cab and go to the hotel. While in the cab, I called a friend who always makes me laugh…hysterically. She and her daughter had just returned from NYC and saw a Broadway show. Quickly I pivoted from work stuff to fun stuff. And by the time the cab dropped me off at the Bryant Park Hotel, it was game on: I’m checked in quickly, put on some comfy clothes and running shoes, and headed to see MJ, The Musical. It was a healthy and superb two decisions: take a break. Call a friend to laugh.

March 12th Coaching Tip: Good Intent.

After coaching all day in back to back meetings, it was time to head to JFK airport. Problem was that it was rush hour, and I was at Rockefeller Plaza in NYC. I packed up my gear, started to head out and catch a cab. But, I decided to ask two colleagues what would they do. With good intentions, they quickly recommended a route with four steps that would allow me more comfort, less cost, and a quicker trip. The problem was the four steps, so I asked one of them to write down those four steps. He gave it to me on a post it note, I slide it in my briefcase and away I went. The four steps: Cab to Penn Station; grab the Long Island Railroad to the Jamaica exit; go up the escalator to the AirTrain and take it to Terminal 5. Perfect instructions that had good intent, saved me money and time.

March 13th Coaching Tip: The Power of 3!

Earlier in the week, I was entrusted to read a Letter of Intent regarding a purchase. It was a thorough and well written, four-page LOI. But after reading it a couple more times, I felt that it might be best to summarize it with three words: scale, grow, win. When I received the LOI later, sure enough, the LOI had been simplified a bit, and the scale, grow, and win was a highlight.

The power of 3 is also a game changer for basketball teams. If a team has some players that can hit the 3, it stretches out the court and makes the defense guard more of the court. This stretching of the court opens up the easier shots closer to the basket. And when 3-point shots are made, it just takes four 3-point shots to get 12 points…while six 2-point shots equate to 12 points. The power of 3 in basketball is game changing. And it’s also powerful when leaders are communicating in business.

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365 Coaching Tips: the 67th, 68th & 69th

March 8th Coaching Tip: Coach Kids.

If you want to improve your leadership skills, coach kids. Yep, I said it, coach kids. If you can get second graders to 1) listen to you, 2) execute what you ask them to do, 3) have fun doing it, 4) win and lose, and 5) develop themselves thru coaching and practice, and as coach, deal with the parents with calm, integrity, and respect, then you can lead adults. You might just find that coaching other parents’ kids is the best way for you to fine tune some skills, and even learn from the kids, too. Today I watched two of my very special friends coach 2nd graders, and they both were so good with them. One of them is now a referee for kids’ games, while the other is now the director of the youth basketball league. Coach, referee, and director roles are great ways to improve your leadership skills. Coach kids.

When I was 24 years old, I coached 6th and 7th grade girls basketball. These gals had little confidence, but the parents really wanted me to coach them. I agreed, and we got to work, had a blast, and won. How did we win? We ran simple plays, played intense defense, and made our layups. To win, we realized that that we had to improve our dribbling and passing the ball better, so that we could hit the layups after creating steals with our defense. The kids had fun winning and developing their skills; the parents enjoyed watching their girls’ confidence skyrocket. Coach kids.

March 9th Coaching Tip: Don’t Delay.

Tax Day (approx. April 15th) comes every year here in the USA, without fail. And as an adult or business, you know it’s coming. This evening, I got one last list of questions from my CPA on remaining items that needed to be provided or questions that needed answered. What a relief, it’s all darn near done, and I’m not rushing to get it submitted.

For me, getting important projects done a bit early started back in college. By my junior and especially my senior year, I was prioritizing my surge of studying two evenings before exams. For example, if the exam was on a Wednesday, I was doing the bulk of my studying on Sunday and Monday evenings. This allowed me to think thru the materials on Tuesday, and if need be, it allowed me more time to dig in to the areas that I needed to tighten up. Decades later, I do this same tactic when I am asked to speak: I will work a week to two weeks in advance to fine tune the exact timing of the topics, how and when to intertwine the audience, and when to ask my colleagues on stage questions. This prep feels natural, and allows me to be smiling with calm instead of being anxious and underprepared. Don’t delay!

March 10th Coaching Tip: Here for you.

There’s that phrase that many people use when offering help, “I’m here for you.” How do you respond when they do need you? Today, this happened three times in my orbit. One was at work, with a very significant leader and team requesting my input on a Letter of Intent to potentially buy another business. I received it last week, printed it off, read thru it twice, and provided feedback. I was there for them when they needed me. Then my mother was called by her neighbor, and my mom said, “well of course I will take you to get your bloodwork done. I’m here for you.” And the third example was a public figure called me today, wanting to know if I could meet her tonight in Miami. I explained that I’m in New York City, but gave her options on when we could connect. It was apparent she wanted to talk face to face; we will make that happen. As a reminder, when you tell people that you are there for them, then make sure you honor that and be a model of integrity: here for you.

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365 Coaching Tips: 64, 65 & 66

March 5th Coaching Tip: Step Up.

In a couple of my coaching conversations today, the advisors that were leading their teams were frustrated with the lack of consistent high-level execution by their teammates. As I listened to them, it was clear to me that it was time to have the discussion, “step up or step out” with these underperforming teammates. However, as I drove home, it got me thinking, “what has the leader done to help them execute better? how are he/she coaching and developing them? what would the teammate say about the leaders and their instructions to complete tasks?” Both the leader and the teammates need to step up. If after all coaching and developing has been done, then it may be time for the teammate to “step out” and find a better role or fit elsewhere.

March 6th Coaching Tip: Remain Curious.

As we were driving to the airport this evening, we looked out the window to the south and there was something we had never seen before. It looked like a drone with lights was falling and spinning a bit out of control. We just couldn’t figure it out. Once I got to the airport, I started reading online to seeing anyone else noticed it or even recorded it. Sure enough, with a few minutes, figured it out: the SpaceX Starship had a fiery breakup, after departing from TX. This is the second explosion in the last two launches. Thank goodness there were no humans on board. For all of us, remain curious if you see something different or out of the ordinary. This applies to darn near everything in your life…including the engineers at SpaceX. I’m sure they are now very curious about why their efforts failed two times in a row. And it applies to your life, your personal safety, your kids, your home. Remain curious.

March 7th Coaching Tip: Keep it close.

You can’t win everything and always be atop the leaderboard on everything. With life comes losses. With life comes challenges. With life comes new or younger talent. If you can’t win, keep it close. My beloved Indiana University women’s basketball team really gave an outstanding team effort against the team from Univ of Southern California in the second round game of the Big Ten tournament. USC had much more talent than IU, but the IU women never ever gave up, kept up their intensity high until the end, and only lost by five points.

With basketball or business, it’s challenging. Be ready, as someone or some other company or team is always after you/your business. It might be developing a better product, at a lower price. It maybe a new, younger and quicker talent on the court; or more mature players who can execute under pressure. Bottom line, it’s hard to win at everything, all the time. If you do lose, do it with class: learn from it, evaluate your next steps, and keep it close. Always.