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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, there were a bit hesitant in working proactively with the current business owner. They hadn’t done the due diligence, and 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 said then asked, “You’re about to buy a business. Act like you own it. What do you want to know about it, similar to the car washes?” 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 fast 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 understand. He quickly went back to the kitchen, got the answering, wrote them on his order pad, and came back to the table with the answers. We ordered that soup of the day and the fried calamari. He checked on us without being too nosey, filled 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 a friend, help a guy out.

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 5 “leaders” and 3 “staffers” had explosive growth in 2024, and are on track to do the same thing again in 2025. However, they all were complaining about workload, capacity, lack of accountability, shocked by what their “staffers” told them recently about fairness, etc. It was quite clear to me after listening to the 5 “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, how to communicate with their leaders. There was limited to no 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 and clarity, and fairness.

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365 Coaching Tips: 46, 47 and 48

February 15th Coaching Tip: Squeeze It In.

Today was a day with a full list, but I was operating on less than five hours of sleep. Instead of having an intense workout, I chose instead to squeeze in my workout throughout my day. For an hour, I organized and moved some furniture around in our small condo, went on a walk to check the boat dock and to take the trash to the dumpster. Then during a college basketball game, I did my 3 sets of squats, crunches, pushups and lunges during the game’s timeouts. During halftime of the game, I went on a 12-minute walk. Then, 10 minutes before my mom arrived, I knocked on my neighbor’s door to get caught up with them and also carried a bag of snow melt for them, since a storm is on its way. Squeeze it in; you can do so many things that keep you motivated, organized, and purposeful in a matter of a few minutes.

February 16th Coaching Tip: Reward Them.

It’s 9am on a winter morning and I hear a few knocks at my front door, after a late night of freezing rain and 2-3″ of snow. The two 14-year-old boys are standing there with their new snow shovels, and one asks, “can we shovel your driveway and sidewalk?” I almost said no, but then I thought for a quick second: here are some kids that want some spending money and are working early on a Sunday morning. “Yes, you can shovel my sidewalk, and all around my mom’s car in the driveway.” The two got to work, and even their nine-year-old brother had a shovel and was shoveling. When they knocked on the door for their $20, I went out and inspected their work. Good work; but gave them some tips on straighter lines, and asked them to use a broom to knock the snow off of mom’s car. We then talked about all the businesses that they could start, and by simply looking around us, we saw a fencing business, car detailing business, painting business, landscape and snow removal businesses, etc. It was fun for me watching their creativity blossom. Reward the ones who show up early, and ready to go to work. Reward them!

February 17th Coaching Tip: Safety First.

Overnight, we had freezing rain and then it snowed 2-3 inches. The wind was blowing 15-20mph all day, and it was below 30 degrees. Getting my mom safely to her car was a top priority; we warmed up her car, defrosted the windows, put some snow melt down to help ensure there was no icy surface. We left plenty early, to get to my brother’s home and visit w/ the family, have lunch, and see the two new babies. We were able to drive slowly and safely and embrace the “defensive driving” lesson we all learned in driver’s training. When we got to see the babies, we washed our hands before holding them, again, to be safe and keep them healthy. On the way home, I helped mom by leading the way as she followed behind. As she went north and I proceeded south and got home sooner, I utilized the “find my” App on my iPhone to keep track of her progress. We all had a safe day, because we had a safety-first mindset. It’s worth it; take you time, prep, think about others. Safety first.

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365 Coaching Tips: 43, 44 and 45

February 12th Coaching Tip: Heads Up.

When I worked at Caterpillar for over 25 years, we embraced the heads up mentally. Work proactively by thinking ahead, looking out for others, letting your teammates know what’s about to happen or may happen or anything coming around the corner that you can’t quite see, i.e. give them a heads up. Today, during a coaching conversation with a highly talented, top female performer, she was beyond frustrated with her leader’s lack of understanding in her explosive growth and also her being down a couple teammates, due to health reasons and an upcoming retirement. She was wanting him to respect that she was giving him a heads up on her needs for talent, so that she can continue to grow, while allowing her colleagues to tend to health needs and plan to retire.

After a lengthy coaching discussion with her, we landed on her putting together a timeline to clearly indicate what is currently happening (massive growth), about to happen(losing two teammates), what could happen (further growth w/out client service), how to support her(request getting the interviews for new talent started), and by when(beginning of 2nd quarter). She is also going to include how she is ready to coach and develop others on her team and spread the workload proactively, before either of the two depart. Heads up, they work.

February 13th Coaching Tip: Don’t Fall Behind.

Got a reminder today that I needed to submit some expenses for recent business travel. Utilizing a couple 30 minute slots throughout the day, I was proactive and leveraged those two windows of time to get all the expenses and receipts organized, and then at the end of the workday, I submitted the three expense books. In all, it took me about 2 hours to get five different trips submitted, however, I made the decision to do it all at once, because I was prioritizing my coaching work over the last month. The people came first, and I didn’t want to fall behind with them. Nor did I want to fall behind with submitting my expense books; I had given myself 30 days from the start of the first trip to get them submitted, and I did just that, i.e. flew out of town on Jan 14, and submitted the expense books on Feb. 13.

Prioritize what is most important to yourself and your clients, and don’t ever fall behind on submitting expenses or invoicing your clients for work completed or following up with clients who are past due. In my coaching work, I see many who fall behind, become frozen, and unable to catch up. Don’t let the piles stack up and overwhelm you. Don’t fall behind.

February 14th Coaching Tip: Love People.

Valentine’s Day reminds us to spread the love with your sweethearts and those you love. However, today I made the decision to spread the love even further, with the men who are working on a complete remodel in one of my homes. We had three plumbers, two carpenters, an architect, and a floor specialist working away, and I was grateful for their expertise. Thinking that I probably said, “Happy Valentine’s Day” up to five times, I also brought some fresh-made donuts, reminded them to love on their loved ones, and leave work a bit early today. Also asked each of them about themselves; I learned so much. One guy had 3 kids; another had been married 30 years; another was a nutrition major in college; one had 2 sick kids; one was vaping and struggling with his desire to quit. When I left, one of them said, “I love being around you and your energy.” That energy is LOVE. Love People!

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365 Coaching Tips: 40, 41 and 42

February 9th Coaching Tip: Set High Standards.

Yesterday, I witnessed an uncomfortable moment. During a college softball game, the batter laid down a bunt, and then slowly ran towards first base, almost turned out of the baseline. It appeared to everyone at the game that the batter had already told herself that she would be thrown out and had convinced herself not to run fast to first base. Meanwhile, the defense/3rd baseman mishandled the bunt and had an errant throw to first base. Frustration sat in quickly by the batter’s teammates, as they screamed at her for not running hard to first base. And then the uncomfortable moment really happened: the head coach, standing in the 3rd base coaching box, shouted across the field to her team’s dugout, and said, “Stop…stop screaming at her (the batter). Seniors, you set the culture, step up and don’t allow this lazy culture to sneak in.” The entire crowd was in a bit of shock.

However, it worked. The next inning, these same gals went out and got hits, loaded the bases, and then a senior hit a triple that knocked in 2 more runs. That’s responding to an uncomfortable moment, by the seniors. The seniors did know the standards and responded to the accountability that the coach called out. What makes this special is that there was a high standard that was set, and the seniors quickly realized that they were the problem, and they fixed it immediately. Set high standards.

February 10th Coaching Tip: Clarify Goals.

As we are now in the 10th day of the 2nd month of the new year, recommend that it’s a great time to ask your colleagues and teammates IF they have 100% clarity on the goals. If they do have clarity, have them state what are the goals and their roles in making those goals happen. If they do NOT have clarity, then help them gain clarity. For example, ask what else do they need to understand, repeat what the goals were, ask them to rephrase how those goals impact them in their role, etc.

To help improve employee engagement, clarify goals and roles. Today, I realized that I don’t have to do three things that I did in 2024. This give me more time and mindspace to work on coaching and speaking. I’m thrilled, as I was not aware of these changes…because they had not been communicated until today. Now I can truly focus my time on these new, fewer high priority goals, Clarify goals.

February 11th Coaching Tip: Say What?

Every now and then, we hear things and roll it around in our head for a few, and then say, “Say What?” It happened to me today. Overnight, I had received a couple emails about an important and urgent situation that just didn’t make complete sense. Then we found out more info, and yet more info. Recommend that if you are saying to yourself, “say what?”, dig in, find out more info, set up some quick meetings/conference calls with people who are aware of the situation to gain their insights, all in an effort to understand. This deliberate action of learning more will help you move on from “say what?” to “ok, now I understand.” In my coaching work, sometimes we see teammates become overwhelmed or frozen, and then they don’t do anything. Seek to understand when others are looking at you awkwardly, stunned with silence, or have no input. Help them move on from, “say what?”

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365 Coaching Tips: Here’s to 37, 38 and 39

February 6th Coaching Tip: Go See ‘Em.

Had the opportunity to work with a number of people in the Southeast and across the state of Florida since October 2019, and then six months later, COVID happened and changed my business travel for years. In December 2024, I made the decision to go see ’em. It was time to take all of the Zoom and Web-Ex virtual meetings, and bring those interfaces to life, in person. Over the last four weeks, I’ve been traveling to see those that I’ve been coaching, sharing with others what we do and how we help others accomplish goals, with our coaching. What a joy it’s been to meet everyone in person, hug, chat, and really open up further. Go see ’em!

February 7th Coaching Tip: Be Unrivaled.

When two women’s pro basketball players start their own league and name it “Unrivaled”, take notice. Think about this: they started Unrivaled in 2023 and launched this inaugural season in January 2025. Everything is new: new format with a smaller basketball court, shorter shot clock, two month season, three on three style, only six players, coaches wear black, all games are played on Friday, Saturday, and Monday evenings in the same venue, the venue is intimate, all games are televised in partnership with TNT/Tru, and the players are the focus!

We were so impressed by the fast-paced game, energy, talent, crowd engagement, the drone flying over the players showing unique TV angles, the colorful media and graphics, etc. And what we didn’t see, but the women players feel every day here in Miami is the warmth of their surroundings, and I don’t mean just the weather. Nutrition, recovery, safety, community of pro athletes, and childcare are all priorities to these gals, many who have children. Again, the players are the focus. If you have the courage to start something new, then…Be Unrivaled.

February 8th Coaching Tip: Celebrate Others.

For the weekend, we zipped over to Miami to watch some college softball. My beloved Indiana University softball team is playing in a tourney. We quickly noticed a few new players, and wow, are they talented and quick. The senior pitcher also is a strong batter, and she hit a two-run homerun today to crush Iowa State 9-1, ending the game early due to the 8-run rule after the 5th inning. At the game, a former assistant coach sat with me and we were just celebrating the gals, chatting it up about the program, the coaches, the talent, the love of winning, and that winning is just plain fun. On a Saturday morning, celebrating others got my mindset in a positive state for the rest of the weekend. Celebrate others.

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365 Coaching Tips: 34th, 35th and 36th Tips

February 3rd Coaching Tip: Utilize Timelines

During an initial consultation this week that was about hosting a summit for some large international teams, I quickly realized that all the leaders had good ideas for this summit, had determined the right audience, and provided thoughtful content. Now it was time to figure out when this will all happen, and who will do what. Thus, I recommended pulling together a timeline. Within a matter of minutes, we all were able to start slotting in the important deliverables so that all the prep could be done timely and yet it also gave us some flexibility. Here we are in early February planning for this leadership summit in early May, and because we utilized a timeline with the group on this initial consultation, we have a plan for execution that is well understood by all. Key deliverables were identified for mid-February, early March, late March, and so on. Utilize timelines to simplify understanding, improve accountability and execution.

February 4th Coaching Tip: Culture Wins.

During my decades working at Caterpillar, we had a phrase that was repeated frequently in meetings: “Culture eats strategy for lunch.” For those who don’t quite understand what this phrase means, let me explain an example that I witnessed this week in the styles of two different leaders. One leader showed up early, welcomed me to his office, really spent time asking me about how I was, my hotel, my flight, my partner, etc. He was prepared for the all-day meeting, paced it well, asked alot of questions and listened to the answers, ordered healthy food, shared the stage and speaking assignments with many on his team; he was thoughtful and steady with his comments.

Contrast that to the other leader. He was not as organized, cut off some of his employees while they were speaking in mid-sentence, condescending to some team members, asked the same question multiple times, made some inappropriate comments about people and politics, etc. This 2nd leader gave us the feeling of frequently being in an erratic state, while the first leader was pleasant and calm, and had surrounded himself with highly skilled talent who exemplified calm and intelligence. Culture wins.

February 5th Coaching Tip: Quick Updates.

I’ve been traveling to multiple locations for the last four weeks. Haven’t had a chance to debrief my boss with a longer 30–45 minute update, so what works for us is quite simple: quick texts, one paragraph emails, and a quick phone call immediately after a conference call/webex that ends early. Don’t overcomplicate things. If a one-to-three-minute brief convo can update someone with a quick text, or a simple email, or a phone call, then do it. Remember, be specific, results oriented, and if there is an ask, state it. Quick updates work. If you don’t believe me, talk to a pilot during an emergency landing. Pilots are brief, calm, and exact with their communication in short statements with their co-pilot, the air traffic controllers, the passengers, etc. Quick updates.

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365 Coaching Tips: The 31st, 32nd and 33rd Days

January 31st Coaching Tip: Take The Call.

It was a Friday morning, and I was drinking my coffee (cold brew coffee, ice, with Fairlife chocolate milk) and moving slowly after an intense work week. My business phone rang, and something told me to get up and take the call. Although it wasn’t a priority for me, it was a high priority for the gal who called me. We had never met, but a common colleague connected us to talk about a potential new job for her. After explaining to her that I needed to get up and moving, she agreed to give me a minute to get moving and we ultimately had a 28 minute conversation while I walked outside and heard her story and excitement for the new job. Please don’t ever underestimate how important it is to give people time, take their call, hear them out, share some insights, and then smile as they flourish. Take the call!

February 1st Coaching Tip: Never Ever Give Up.

Alot of people in the USA right now, less than two weeks after the Presidential Inauguration, are scared about the amount of change that is happening via executive orders by the President. Each and every new leader implements change, sometimes leaders gather input for 0-100 days and others move quickly. In either case, those leaders think that they are doing what’s right. However, over the centuries, we have seen that surprises happen, unintended consequences happen, good results happen, etc. If you believe in something, don’t ever give up. If you believe in unions, then go support them. If you believe in immigration, get involved and learn the law. If you can’t buy a home due to bad credit, then start paying down debt and increase your income to pay debt down quicker. Bottom line, if you believe in something, don’t ever give up. It’s worth it!

February 2nd Coaching Tip: The Extra Mile.

The extra mile is…lonely. Very few people are there. So what do I mean? Here are a few examples that I’ve witnessed over the decades in the business world. Seems like we know who are the hard workers who show up early, and stay a bit later than everyone else. They seem to get their work done, and thus get more work to do, which leads to opportunities. The leader who is speaking on the main stage for a large event, and he really focuses on his stage presence, his timing, his pace, his tone; his preparation is taken seriously. Outside of work, I see it personally as I try to be a role model of senior wellness. I’m training and running sprints at the local middle school track, and shooting baskets on the asphalt courts. How many people are also shooting and running? Few, very, very few. There are 8-10 basketball courts at this middle school, and no one has been there practicing shots for all the times that I have been there.

The extra mile is lonely; however, commit to YOU and YOUR development, and you will shine. Even if no one is there to see you shine. YOU will see yourself shine, and that’s what matters most.

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365 Coaching Tips: Day 28, 29 and 30

January 28th Coaching Tip: Exude Positivity.

Today, I listened to an accomplished leader who had led large groups of people in Washington DC and Miami. He and his wife made the decision years ago, after losing their son, to remove all negative people in their life. Intentionally, they were making the decision to include and keep people in their lives that exude positivity. How do you respond when you are supporting someone: positive or negative? How do you show up at a meeting at work: positive or negative? How do you show up for a family dinner: positive or negative? Research indicates that you are more likeable if you are positive, ask questions about others, listen to the responses, and remember the details. Embrace and exude positivity.

January 29th Coaching Tip: More Cowbell!

Celebrate your wins. Hit the cowbell. Celebrate a tiny, small win. Hit the cowbell. Celebrate someone else’s big promotion. Pound that cowbell. Celebrate a new baby born. Again, more cowbell. Affirmation and recognition are deep-rooted needs within our souls. And today, I was reminded just how important recognition is. Picture a room full of highly confident leaders and wealthy individuals, who are in the top 1% of income earners in the USA. And yet, none of them were recognized for all of their hard work and efforts accomplished in 2024 (year prior). This was a huge miss by the leader running the meeting, because everyone was gathered for this “2025 Kickoff”. Recommend that you never miss an opportunity to recognize people, to hit that cowbell. No matter the place on earth, people want to be seen, be heard, and hear their name being recognized. More cowbell is like love, just never ever too much of it.

January 30th Coaching Tip: Develop Others.

Couple of my coaching meetings this week have been pleasantly surprising, as a couple senior leaders were planning for the legacy of their business, and we were openly discussing the development of the next generation. As leaders age and get asked, “when are you going to retire?”, it’s such a pleasant and affirming conversation to have with clients (and your team) about your intentional plans for the next generation. Both of these teams have added the next gen and have given them big jobs and significant responsibilities.

Someone probably gave you a shot or believed in you at some point, that may have changed your life. Return the favor as you age and give the same kind of development opportunity to someone younger. My godson reminded me recently of a business trip that he joined me on in the Fall 2015; we cris-crossed 6 states, visited offices, leaders, businesses, ate at nice country clubs, stopped quickly at gas stations to gas up and grab a drink, checked in to numerous hotels, etc. My godson indicated it was a life changing few days for him, and he learned so much in how to manage time, effort, clients, energy, and business. Take some time to develop others. We all deserve it.

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365 Coaching Tips: Here’s to 25, 26 and 27

January 25th Coaching Tip: Leadership Matters.

In many of my coaching sessions lately, leaders are frustrated with employees and teammates who leave their teams, and some of these leaders also claim that there’s no talent out there to replace them. As we dig into what happened and what drove the teammate to depart the team, rarely does the leader indicate that it was him/her. It’s usually something like the teammate left for more money, they had a baby, they are relocating, they, they, they. It’s my responsibility, as a coach, to ask compelling questions. For example, “what did you learn from this? what do you own in this? how were you developing this teammate? how are you attracting talent to be ready for teammate exits? ”

Leadership is hard, Leadership really matters to those who follow you. I’d encourage you to ask the questions: How are you investing in yourself, especially if you lead others? What are you reading, and then implementing? Who is a leader that is mentoring you or could mentor you? Are you a good boss, and how do you know that you’re a good boss? Are you easy to follow? Do you truly connect with your teammates? Do you micromanage or coach, develop and empower?” Leadership matters, and if you master it, teammates will stay and be loyal.

January 26th Coaching Tip: Fundamentals Matter.

Today I watched a college basketball team come back, score 5 points in the last 23 seconds, and win a game on the road in a loud environment. I also watched a team lose the game, who gave up 5 points in the last 23 seconds. This losing team had a lack of clarity on clock management, who should be fouled and when, who should not be left open, who to throw the ball to, how to score with less than 5 seconds in the game and down by 1 point. Whether it is basketball or going to a networking event or driving a car, execute on fundamentals. Networking event: set a goal of meeting new people, ask questions and truly listen, then remember it is not about how much food you can eat. Driving a car: drive defensively, stay to the right if you’re going slower, look left then right and then left again before proceeding thru a stop sign or green light. Fundamentals matter. By not looking left to see oncoming traffic before proceeding into an intersection can potentially kill you. Contrast that with taking 1-2 seconds and clearly knowing that no one is coming at you.

January 27th Coaching Tip: Stay Sharp.

Today, the stock market was impacted by one announcement in the artificial intelligence (AI) space. According to news reports, one company lost over $600 billion in value in one day. By the next day, $200 billion had already been reinvested back into this company. With these type of swings, some may say to just ignore it, keep your head in the sand, etc. However, recommend that you stay somewhat aware, stay sharp on what’s happening around you and what’s impacting the business world. Why? As we age, it’s common for me to hear our seniors say, “I’m a dinosaur. I’m not very techy.” Dinosaurs died and are gone. Tech is here and not going away. Stay relevant, embrace what is happening in the world around you. That doesn’t mean you have to agree with everything, but be aware and stay sharp. In your kitchen, dull knives need sharpened from time to time…or they just stay dull and go unused. Keep ’em sharp!

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365 Coaching Tips: Day 22, 23 and 24

January 22nd Coaching Tip: Be Seen.

As I was watching a leader today, the day after a 3-day weekend, I noticed how she intentionally walked thru the office area and said hello, stopped and truly talked to her colleagues. They actually stood up and talked to her, shared what they did during their long weekend; smiles and laughs were present. Whether you’re a leader or a colleague, ask people about themselves and their lives. They appreciate being “seen”. As I watched the leader step away, a couple people said, “thank you for talking to us…it shows us that you care.”

January 23rd Coaching Tip: Be Heard.

Received an urgent Skype message today, i.e. “we need to get some time with you today to discuss an important situation.” This team is one who came to me 6 months ago and really shared their WHY and WHAT they want to accomplish. Thus, when they needed time today, we squeezed it in from 4-430pm on a Zoom. Indeed, it was important; they want to promote one of their colleagues and they wanted to practice and run-through the new role and gain clarity for her. After 25 minutes of listening to them and asking questions, they had the role clarified, were smiling, and a bit relieved as we wrapped up the call. If someone needs time with you, consider it a gift. They need someone to be “present”, and the best gift that you can give them is your “presence.” Let me them be heard, to help increase their confidence.

January 24th Coaching Tip: Be Efficient.

As a week winds down, it’s a common tendency to have the mindset of “let’s push it to early next week.” In my coaching work, I actually find that I can get a lot done before 10am on Friday mornings and also between 2-5pm. For example, I was able to squeeze in three, quick, efficient coaching sessions today. In a matter of 15-33 minutes, I was able to help all three situations.

Everyone is busy. Who has ever approached you in the last few years and said, “hey…I just don’t have enough to do” ? Like, let’s get real, no one. In being efficient today, I found that telling all three of them yes, I had a few minutes, we immediately became efficient with our time. They truly felt not only seen but heard, and realized I was ready to potentially help them thru their coaching situation. The greatest gift you can give to someone is your time, i.e. being present. And then when you can help them work thru a situation or two, and they can sleep better over the weekend, you have truly added value. Be efficient, and others will likely mirror your behavior, and be efficient, too.