Category: Coaching

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

March 17th Coaching Tip: Go Green!

It’s St. Patty’s Day and many cultures embrace and 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 wearing some “spring green” feels good and fresh. St. Patty’s Day is always around college basketball’s March Madness, which is win and advance -or- lose and go home = green flag, go for the win! Lastly, green is my favorite color. Green was a favorite color of my grandfather (George), and he and I were 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. This isn’t my first rodeo of doing home remodeling projects. Thus, I 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 than 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 just one test, but two tests. 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 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 rest, 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. He was 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 for him to remain in his current role.

We will talk again in a couple weeks, as I gave him some follow up work to be completed. 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. Health matters.

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 the lease 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 selections can be overwhelming. For years, I’ve shared with many that my brain thinks in threes or like the triangle figure. The triangle is the strongest structure, and it helps bring focus to me 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 has been chaotic recently 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 New York City 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 two healthy and superb 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. My 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 stop, ask two colleagues what they would do. With good intentions, they quickly recommended a route with four steps that would allow me more comfort, less cost, and a quicker trip. Now I faced a new problem with these four, unfamiliar 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 pocket 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 three is also a game changer for basketball teams. If a team has some players that can hit the three point shot, 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 three point shots are made, it just takes four of these three point shots to get 12 points…while six two-point shots equate to 12 points. The power of three 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, 5) develop themselves thru coaching and practice, and 6) deal with the second graders’ 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 leadership skills and even learn from the kids, too. Today I watched two of my very special friends coach second graders, and they both were so good with them. One of them is a referee for kids’ games, while the other is now the director of a youth basketball league. Coach, referee, and director roles are great ways to improve your leadership skills.

When I was 24 years old, I coached sixth and seventh 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 impressive 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 and as a business owner, you know it’s coming. This evening, I got one last list of questions from my CPA on remaining items that needed to be 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. It also allowed me to rest and have a clear mind. Decades later, I do this same tactic when I am asked to speak: I will work one 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 her team was requesting my input on a Letter of Intent to potentially buy another business. I received it(the draft LOI) 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. She called me today, wanting to know if I could meet her tonight in Miami. I explained that I’m in New York City, but I gave her options on when we could connect. It was apparent she wanted to talk privately about something very important, and do it 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 these leaders coaching and developing their teammates? what would the teammate say about the leaders and do the leaders give clear and fair instructions to complete tasks?” Both the leader and the teammates need to step up. If, and only if, after all the 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 see if anyone else noticed it or even recorded it. Sure enough, within a few minutes, figured it out: the SpaceX Starship had a fiery breakup, after launching from TX and flying over the Gulf. 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 Univ. of Southern California team the second-round game of the Big Ten tournament. USC had much more talent than IU, but the IU women never 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, selling something at a lower price, advertising more, etc. It maybe 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.

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365 Coaching Tips: 61, 62 and 63

March 2nd Coaching Tip: REST.

REST. I learned that acronym from a four-star general who spoke to leaders at Caterpillar over 15 years ago. And here we are 15 years later, and I can easily recall the essence of his message: take time to Read relevant and timely information, ensure you get your Exercise (150 minutes/week), get enough Sleep (7-8 hours), and Take Time To Think.

This general reinforced that the easy decisions are already made at an individual, lower or intermediate level. The decisions that get to you as a high-level leader or business owner are more significant and difficult; it’s imperative that you have time to think clearly about important decisions and all the potential and unintended consequences. REST, because it matters to your results, personally and professionally.

March 3rd Coaching Tip: Draft It Up.

Today was my third coaching conversation with a future leader, and he has big plans for his current team, his succession plan, and the future growth opportunities that actually made him giddy with excitement. He had been talking a lot about it, quickly, and excitedly, but he wasn’t clearly articulating it. In our 2nd conversation, his homework was to draft/sketch what was in his head and put it on “paper”.

I was so proud of him today; prior to our meeting time, he emailed me his draft plan, and it was simple with just 4 pages. He had already used this draft with the local management team; he had talked to his current team, and now ready to share the draft with others, too. As we both spent 70 minutes really digging into it today, we further improved his draft and added a few more details. He also agreed to keep it updated, adding a date on each version so that he can keep track of the progress and plans, and be able to share the history with anyone who may join the team. Draft it up, it will help bring clarity to you … and others.

March 4th Coaching Tip: Time is Money.

Got up early today, drove to Coral Gables, FL to meet a colleague so that we could coach a number of leaders and advisors. We were there, on time, and ready to roll. The admin team had sent out the emails and reminders and ordered a lovely lunch. However, the office manager/leaders had NOT done the appropriate prep, didn’t have enough appointments set up for us, thus, it was an average day of efficiency. Actually, it was below average. For an upcoming two-day trip to New York City with this same admin team, you bet that I will be confirming the appointments on my schedule BEFORE we leave, so that others understand how valuable my time is. My schedule should be filled with high priority clients who want coaching and improvement. My time is valuable, business travel is difficult, and time is money.

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365 Coaching Tips: Here’s 58, 59 and 60

February 27th Coaching Tip: Do Due Diligence.

Today, I met a leader who has the opportunity to buy a business. As I asked him questions, he indicated that it’s a smaller business and about 1.5 hours away. The one employee isn’t very happy and feels overworked and the current owner is ready to check out and be done. As I listened, the leader then pivoted into the true details: what is he buying? what is in the business? what can he eliminate with minimum effort? how old are the assets and clients? how much potential is in the current business? what can he grow quickly to produce a higher gross margin? does he have other team members that can take care of this small business, so that the leader can be free to deal with bigger clients and deals? By the end of the conversation, he had a gameplan. He realized that he needed to drive to visit this small business owner in three days and start digging into what he is potentially buying.

When you’re buying a business, many larger companies take at least 100 days to complete the due diligence, and that’s after signing an LOI (letter of intent). Make sure that you do your due diligence.

February 28th Coaching Tip: Need Ya!

Coached a leader today with a highly talented team of 20 people. This leader had alot going on, like a lot! For example, his wife was on the west coast with her mom because of her mother’s transition to hospice. The leader was now taking care of three kids, and he needed to travel for business to Florida. Then, his middle child was admitted into the ER, so he had to ask his 14-year-old son to take care of their youngest child overnight and also get them both to school on a Friday. I was proud of him, as we figured out a way to get him more help over the next three weeks. He called his mother, and said, “Mom, I need ya!” He then made a plan to talk to key members of his team and his executive assistant to also tell them, “I need ya.” It will be two to three weeks of asking others to help and they will step up. Don’t be afraid to say “Need Ya” when you truly have a lot going on and need help.

March 1st Coaching Tip: Help Out!

Just the opposite of the post above (Need Ya) is the offer to quickly help out. By asking some simple questions or reading an invite/email/text, you can really figure out how to help out quickly. Today we are having a block party, and my neighbors are helping arrange it. While on my walk today, they asked me if we are going; I said yes. Then I came back to our house, re-read the block party invite, and noticed that they were requesting neighbors to bring paper plates, napkins, and silverware an hour early. This made it simple for me: open up the cabinets, see what I have that is still packaged up. I will now bring napkins, paper plates and some plasticware. A popular quote is, “look for the helpers, look who is helping.” Don’t overcomplicate things; ask a question or read something quickly, and you can figure out how to “Help Out”.

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365 Coaching Tips: 55, 56 and 57

February 24th Coaching Tip: Talent Everywhere.

Tonight, I had the difficult challenge of selecting four deserving winners of four scholarships from over 94 applicants. Why so difficult? Because the talent on these scholarship submissions was beyond impressive. There’s talent everywhere, it’s all around us. These were written by the high school seniors, and a recommendation letter was also included from their high school administrators. These kids were 100% student athletes, and shared numerous examples and stories of how they are learning how to: be disciplined, be a good teammate, serve others in the community, keep their grades in good check, win and lose, deal with injuries, deal with coaching changes, and on and on.

On a scale of 1-10, with 10 being the highest score, I mostly awarded the applicants with 7, 8, and 9’s. It was difficult to select the 10’s for the four scholarships, but I did it. The lesson that I learned here is that our kids today are juggling a lot and delivering in a very social world. There’s talent everywhere. Question: are you taking the time to witness them in action, mentoring them, and helping them become the adults that they want to become? They are ready!

February 25th Coaching Tip: Hold Yourself Accountable.

During three of my coaching calls today, it was all about helping the leader figure out what he/she could do to hold himself accountable to important goals. After listening and asking some clarifying questions on their priorities, one indicated that he wanted to add $1million in new money from clients by the next time we talk. And before the end of the day wrapped up, he sent me an email indicating he had already done over $150k of that $1m goal. Another picked up on the number three. He needs to develop himself as a better leader, while coaching his two new associates. All three need to develop; he agreed to spend three to five minutes/day with them both. He embraced the ‘rule of three’ to help them develop. The rule of three encourages new colleagues to try to figure out the answers to questions or problems that they are facing, by digging in and being resourceful in three different manners. They must do this BEFORE asking the boss for help. It teaches them to “fish” and be resourceful, instead of interrupting someone else and getting the answer quickly. The third leader that I coached had made great progress since July 2024, and yet he didn’t feel that good about it. We summarized all that he has accomplished, and then he pivoted and was ready to continue to be held accountable through yearend 2025. Hold yourself accountable, whether you have a coach or not. Accountability works.

February 26th Coaching Tip: Leverage Partners.

Today I had to coach myself. With three projects coming up in the next 90 days, I had to take some time to figure out WHO can help me, identify WHAT can they help me with, and WHEN do I need their assistance. We had an effective conference call at 9am, and by 10:15am, we had the plan regarding who’s going to do what by when. I was relieved to have these talented partners to work with.

I’m also remodeling a 95-year-old farmhouse, and boy, am I ever leveraging partners and specialists. At the end of nearly every day, my contractor will either text me with an update, send photos that are self-explanatory, or we facetime. He also does a great job of introducing me to all of his sub-contractors (partners), and my whole goal is to get to know them a bit, create a bond, and get a smile on their face. These men are helping me with electric, plumbing, demolition, roofing, siding, drawings, framing, drywall, leveling floors and walls, etc. You get my point; they are doing it all. I haven’t lifted a hammer yet and am 1,000 miles away keeping this project progressing. Leverage your partners and figure out how to get more done by leveraging their expertise.

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365 Coaching Tips: here’s to 52, 53 and 54

February 21st Coaching Tip: Recovery.

Some days, we just need some time to recover. After having two consecutive nights of less sleep than what I like to get, I decided to “recover” today. My exercise today included just one-mile of fast walking; I took a nap in the late afternoon by the pool and finished the evening with three short strolls before laying it down early. Even with my work today, I took a few less coaching calls, and I didn’t jam in things today due to my focus on my priority: recovery. I was still productive and ate balanced, just made the decision to turn down the dial a bit and recover. Prioritize yourself: you are your most valuable asset. Allow for time to recover. Your overall wellness depends on it.

February 22nd Coaching Tip: Text Real Quick.

If you’re trying to get ahold of someone, give them a quick text and simply ask, “are you free for 10 minutes?” or “is this a good time?” or “when do you have a solid 20-30 minutes? Need to run something by you.” Research indicates that a high percentage of our texts get answered in seven minutes or less. Seven minutes. If you want to connect with someone, give them a text, arrange a time, and then be ready to share your idea/question when you do get that time scheduled. It doesn’t work for everything or everyone, but for many, simply text real quick to get connected.

February 23rd Coaching Tip: Sunday Funday.

Sometimes, one just needs a beach chair and a sunset. And that’s exactly what we did today. We took it easy, enjoyed some “church time” at home, watched and listened to some relaxing geography and animal shows, did our workouts, ate well and prepped some meals for the week. But quiet time and the beauty of southwest coast of FL were calling our names. We threw a couple beach chairs in the car, grabbed a couple sweatshirts and some water, then drove to the beach. Heck, we even squeezed our convertible into a partial parking spot, and it worked. We just sat there for an hour and simply enjoyed all that the good Lord created. It was a wonderful way to end our Sunday Funday.

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365 Coaching Tips: 49th, 50th and 51st Tips

February 18th Coaching Tip: Own it.

Today during a coaching conversation with a couple men who are buying a business, they were a bit hesitant in working proactively with the current business owner. They hadn’t done the due diligence required to buy a business and they lacked a process for introducing themselves to the current business owner’s clients. They had no plan. After listening for a while, I leveraged an example from outside the industry, i.e. buying 25 car washes in a different state that we had never seen. They quickly knew what to do: fly to that state, rent a car, inspect all 25 car washes regarding all of their locations, better understand the real estate values, inspect the overall care of the car wash, interview key employees, evaluate how good is the drainage, how old/new is the car wash equipment, and on and on. Then I pivoted them. I asked, “You’re about to buy a business. Act like you own it. What do you want to know about it, similar our car wash quick exercise?” And they got it. They quickly realized that they didn’t know what they were truly buying and they weren’t acting like the new owners. Own it!

February 19th Coaching Tip: Been There.

We all have been on the job the very first day. All of us, every single one of us. Tonight, we walked to dinner and had a new waiter. He was pleasant and greeted us nicely, and of course, struggled answering some basic questions: “what’s the soup of the day? is the calamari fried or not?” We could tell he was new, and we smiled and said we understood. He quickly went back to the kitchen, got the answers, wrote them on his order pad, and came back to the table with the answers. We ordered the soup of the day and the fried calamari. He checked on us without being too nosey, refilled our drinks, and shared with us the gelato flavors. Of course, we ordered the mango sorbet. It was yummy, he was pleasant and learning quickly. We’ve all been there. Be kind; help a guy out on their first day at their new job.

February 20th Coaching Tip: Void? Lead.

When there’s a void, step up and lead. I saw it today in two of my coaching conversations. A team with five “leaders” and three “staffers” had explosive growth in 2024. They are on track to do the same thing again in 2025. However, they all were complaining about their workload, lack of capacity and accountability, shocked by what their “staffers” told them recently about fairness, etc. It was quite clear to me after listening to the five “leaders” share their insights, that they were most likely the bulk of the problem. No one was truly stepping up to lead. There was lack of clarity in compensation, roles, expectations, how to hold the “staffers” accountable and how to communicate with their leaders. There was limited to zero coaching or development of their best and their worst performing “staffers.”

Another example was in my own work. I was given the opportunity to present a quick summary to my boss about a complete plan to support a growing part of our business. In one page, I laid out the short-term plan with the resources needed and the budget. She read it and quickly approved it. Bottom line: when there’s a void, step up and lead. People want to be lead with simplicity, clarity and fairness.