Author: Jen Wilfong

Jen Wilfong Lake Worth Beach, FL Carmel, IN
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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.

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365 Coaching Tips: on to 19, 20 and 21

January 19th Coaching Tip: Friends Matter. We’ve all heard that phrase, “Sunday Funday!” Today, we rolled out of bed, didn’t take showers, and started whipping up some gluten free pancake mix, baked some bacon, got the omelet ingredients all prepped, and set out the dishes for a scheduled brunch with our best friends. They rolled in with similar hairdo’s, and somehow beautifully displayed a colorful platter of fresh fruit and brought an old-school orange squeezer to make some orange juice for mimosas.  We had this brunch planned for a week, as temperatures were plummeting and we decided to stay inside instead of going to see a college basketball game.  Glad that we stay committed to our bond of having a homemade brunch.  Brunch was plentiful and scrumptious, the food and friends, the warmth of the fire, the catching up, as it had been a few weeks since we all had been together.  Recent research is indicating that people are spending more time alone; more time on social media than ever before; depression and anxiety are both on the rise; and mental illness is now commonly discussed.  My recipe for a lot of these trends is to have something to look forward to, and do it with people that you love and care about.  Planning a simple lil Sunday brunch while wearing zero makeup with bad hair, allowed us to naturally connect, cook, and share. Plan things with your friends.  Friends matter.

January 20th Coaching Tip: Leverage Experts. In tackling a huge remodel of a 95-year-old home, I realized that I needed experts.  The ceilings were bowing, the floors were not flat, the stairs were not safe, the house was chopped up, and we are adding a garage, as well as some new windows, siding and doors.   I needed help! Enter in a general contractor, an interior designer, and an architect.  In working together, them listening to me and what I want in this farmhouse, and then hearing them regarding their ideas, we are really bringing this project together nicely.  With the architect’s quick eye, he gave the GC some ideas on how to improve the bowed ceilings and the uneven floors.  It’s done already.  The interior designer is pushing us all on functionality as well as the latest fashions, with the right flow.  I’m grateful for smart people, who can work collaboratively. Embrace others and improve results by leveraging expertise.   

January 21st Coaching Tip: Keep On-Track.  In my coaching work, many of my colleagues/coachees set goals…and then they don’t track results frequently enough.  As they get in to March and move thru May, they are already telling themselves if they can or cannot make their yearend numbers.  For the teams that I coach who set a goal to accomplish their results by summer or no later than Labor Day, they typically do it. How? They track their results daily, and definitely weekly and monthly. Many people annually give up on their new year’s resolution between January 18-27, so now is the time to keep and stay on track. Develop yourself a daily or weekly scorecard, and you will be amazed what you can accomplish. Keep on-track!

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365 Coaching Tips: here’s 16, 17 & 18

January 16 Coaching Tip: Clear Goals. In coaching a few teams in the last couple days, it was very evident to me that the team nor its leaders had any clear goals. In asking questions like, “what are you most pleased with from your work in 2024? where are you headed in 2025? And what will you do the same and also different in 2025?”, it really helped the teams figure out their goals. It also helped that we had plenty of time and were not rushed, so that we could really discuss and prioritize the goals. Truly asking questions, listening to their responses, giving time for all to speak, allowed for well understood goals that were much more cohesive and focused than the beginning of the coaching sessions. As we wrapped up, their three main goals started with the number eight: 80%, $800,000, and $80mil. I was so delighted that they were ready to meet again and continuously throughout 2025 to share their progress on their results. We went from having no goals to identifying well understood goals, and sensed a strong commitment to achieve them; this made me smile. Get clarity on your goals, whether personally or professionally.

January 17 Coaching Tip: Set Expectations. Since November, I’ve been working with new contractors to help me with a significant farmhouse remodel. New general and sub contractors, new interior designer, and a new architect are all helping me do this, as I’m in Florida working. In meeting with all of them, I’m clearly letting them know my expectations of what I want and need from them, as we remodel a nearly 100 year old home. For example, this home is old, and I want to honor it’s 1930’s farmhouse legacy with some new yet timeless touches. I also want 1930’s crooked floors and ceilings to be straight and level, for fashion, functionality and also safety. I want it to be clean, safe, and dry, and get the water draining away from the home. I want it to be thoughtful and functional, with what we defined as A- workmanship. It does not have to be perfect A+ work, but it must be better than B or B+ work. This clarity has really helped my new colleagues/contractors as we all make decisions together. If others around you don’t understand what you need or are expecting, it might be wise to look in the mirror. Set expectations and reinforce them regularly. And reward/recognize when those around you when they absolutely nail them!

January 18th Coaching Tip: Embrace Tools. Over the last couple years, many of my coaching sessions have been about capacity. For example, I very frequently hear comments like, “we are overwhelmed, we are busy, we need more people, we don’t have time, etc.” As I ask more questions about capacity, many times I have found that tools are not being utilized enough, even though some tools/IT/processes/support have already been paid for. I use this example regularly: “who still calls the taxicab service, reserves a car, hopes that the taxi comes on time to the proper address, the driver is pleasant, the car is clean and safe, and you arrive at your destination on time?” Few still do this, very few. Most are utilizing their cell phone to arrange a ride (with Lyft or Uber), and it can be done within seconds, with complete transparency, and the payment is automated and more secure. When I use this example, all of the sudden, the brains in the room start cranking…”what can we use to improve our capacity? what should we stop doing? what must we continue? what do we need to learn and be trained on to implement quickly?” Within 5-10 minutes, we can quickly identify a number of tools or processes that should be implemented immediately to gain capacity. That metaphor of, “I’m busy sawing, don’t have time to sharpen my saw…” is at play in numerous coaching sessions. Take some time and figure out how to embrace new tools, and utilize the ones that are and have been available.

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365 Coaching Tips: the 13th, 14th and 15th Days

January 13th Coaching Tip: Family Talks. In our coaching work, we help our colleagues/coachees as they prep for crucial conversations. In Kerry Patterson’s book, “Crucial Conversations,” most of these crucial convos don’t even happen, and then when they do, they don’t go well. Thus, we as coaches help our colleagues practice these important convos. Today, a husband and wife indicated that they want to bring on at least one of their two sons into their business. And yet, they had nothing in writing, nothing that either of them could confidently replicate with clarity. The husband and wife soon realized that they weren’t even on the same page. The mother wanted the son(s) to be “hungry” and the father wanted to be more “helpful” to his son(s). Thus, I encouraged them to get on the same page, draft it up, and then have a family talk with both sons, so that both sons heard the same message. Then, if either son wants to enter the business in the future and they discuss the opportunity further, the four of them would potentially have a more solid foundation. Remember, have those crucial family talks.

January 14th Coaching Tip: Plan Ahead. Whether its travel for work or vacation downtime, or getting groceries for a Sunday brunch planned with friends, or an early morning Uber ride to the airport, plan ahead. This week I’ll be in a number of hotels, crossing multiple state lines, and in unfamiliar places with unfamiliar people. Thus, I planned ahead by truly looking at the map, understanding drive times and locations, and knowing when I need to be where. Thinking about my personal routines, I even bought my cold brew the night before, and got up this morning and was rollin’ with my favorite coffee while reading my devotionals. This allowed me to get ready and arrive to an unfamiliar office 20 minutes in advance (instead of rushing in to a coffee shop, and then being dissatisfied with my java). Knowing that I could walk to this office in just 2-3 minutes from the hotel that I picked (so that I wouldn’t even have to get in the car and drive/commute), I got my morning routine, breakfast, and workday started as normalized as I possibly could have done. Folks, plan ahead to help reduce stress and you’ll be surprised how much it increases your efficiency.

January 15th Coaching Tip: Stop Burnout. Start saying “no” to certain things and start saying “yes” to yourself. Today, I coached two teams who were “burned out, bored, (not thriving).” After listening to what was going on, they shared that they have too many clients, and many of those clients don’t pay them or are so simple and could be served by someone else more effectively and happily. Gently, we all looked at one another after I had them repeat what they said, “we have too many clients who consume our time and don’t pay us (much).” In my coaching work, we remind our coachees that it is YOUR business. You make the decisions. You select your clients. You can say “yes,” and you can also say, “no”. My recommendation is for you to clearly identify WHO you want to serve and then stick to it. Serve clients that make you smile, that you truly want to help, that take your advice/pay for your expertise, and you both grow from helping each other. Say YES to the right clients, and that will help reduce burnout.

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365 Coaching Tips: Days 10, 11 & 12

January 10 Coaching Tip: Practice. Yes, I said practice. This week, I had a number of people call me to practice their upcoming crucial conversations or new scripts that they want to utilize in 2025 to help grow their business. In a matter of just a few minutes, confidence grew. One person needed help pulling together their talking points and a timeline for the huge decision they are making to retire in about 18 months; I listened to them as they practiced, and they became more and more confident as they got more clear and organized in their thoughts. Another person needed help with removing exhausting clients who pay very little but take a lot of time; after a few practice conversations, he felt affirmed in what he was saying and was ready to share it with the exhausting clients. As for me, practicing my sprints a couple times a week in helping me build confidence that I can run sprints in my 60’s without getting hurt. So, bottom line: Practice!

January 11 Coaching Tip: Challenge Yourself. It’s amazing what you CAN DO, if you just challenge yourself a bit more. For example, if you only have 15 minutes to get a task done, isn’t it amazing how efficient you can become and get the bulk of the task done? I find this in my life if friends are on their way/close by/gonna drop in for a quick visit. I say yes, and then quickly get stuff picked up and organized a bit more. Also find this now as I’m training for the National Senior Games; my ability to do multiple sprints as a 60 year old is encouraging. Now I’m checking other sprinters’ times, just to see how much quicker I need to be. Challenge yourself, or hire a coach to challenge you and help hold you accountable.

January 12 Coaching Tip. Help Others. The fires in Los Angeles, CA are apocalyptic in nature, and I feel like there is absolutely nothing that I personally can do. And yet there IS something that I can do. After watching closely which organizations were “showing up to help others”, I chose to support the World Central Kitchen. During a time of a disaster of this magnitude, the state of someone’s food, water, and housing security are second to none. Find a way to “help others” (instead of complaining about this or that or pointing the finger at what should have been done or at certain people). We all want angels/people to help us when we are down; so, “help others.” Find your way to help, in your own way.

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365 Coaching Tips: Now on day 7, 8 & 9

It takes commitment and consistent execution to implement a new habit, and I’m really liking this new habit of identifying a coaching tip (or trend) daily. We have made the first hurdle of a new habit, and that’s doing it intentionally for at least one week.

January 7 Coaching Tip: Be Specific. With the new year beginning and my coaching work is now ramping up, a number of my coaching sessions have been focused on “I want to grow my business.” I simply ask, “can you be more specific?” That’s when it can get quiet. The silence spurs more questions. Ultimately, these type of questions get asked: “how will you grow”, “how will you spend your time differently”, “who are you targeting”, “what should you not do this year”, “which type of clients do you want to replicate”. The more specific that you can be about what YOU want to accomplish, I find it’s more likely that you will be successful. And further research indicates that if you write the goal/specifics, you are much more likely to succeed. For example, I have post-it notes on my mirrors and desks that remind me of my quarterly goals. Everyday, I am looking at those specific goals.

January 8 Coaching Tip: Backup Plans. We don’t want to think about backup plans, but when we have them, we sure are happy when we can quickly and somewhat effortlessly put them in motion. Today, on two different occasions, I was working with coaching situations where there was no backup planning by the coachee; they had one plan and just assumed it would go the planned way. As I asked a few questions, I could quickly tell that they needed to think more broadly and thoughtfully, regarding a backup/2nd or even a 3rd scenario. One situation was already in turmoil and they were in triage mode, losing sleep, begging for assistance, etc. We quickly put together a plan for a 2nd and 3rd option in both cases. Backup plans are necessary for many stages in our life journey; don’t be surprised when things re-route you. Have a plan and be ready, or at least somewhat ready.

January 9 Coaching Tip: Measure Frequently. If any of my coachees want to execute on a new goal, I ask them, “what are you measuring, and how frequently are you measuring it?” For example, one of my coachees wants to grow their business by 15% in 2025. We talked about reviewing the results monthly, measuring progress weekly, and assessing and tracking daily activity that contributes to growth. For me, I have some goals this summer to be able to run faster. Therefore, I’m tracking three things daily: my VO2MAX level on my Apple watch, my weight every morning, and my times when I run sprints weekly. If my VO2MAX increases, and I weigh a bit less all while continuing to run my sprints, I should be running faster this summer that I ran in June 2024. Guess what, 9 days into the new year, and my VO2MAX has increased and I’ve dropped a pound or two. Progress, bit by bit.

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365 Coaching Tips: For Days 4, 5 & 6

We’re on a roll here, and the coaching tips are evident.

January 4 Coaching Tip: Stay connected. Friends and family really matter to your overall wellness. The Blue Zones research by Dan Buettner indicates that having a purpose and regular social connections are two of the most important keys that Buettner revealed. I find that I thrive on getting my crew together; today, I had the opportunity to attend a ball game with two of my Indiana University teammates. Plus, gave two tickets to my high school basketball coach. Then, looked up and there was one of my high school teammates. And lastly, in the stands, there was a gal that I used to ride the school bus with. We all connected, smiled, and are intentionally staying in touch via getting out of the house, going to support college women play basketball…something that we all did years ago.

January 5 Coaching Tip: Make Plans. My vacation days are already booked on my personal and work calendar, and shared with my partner. Why? Because vacations and memories, while healthy, are a huge contributor to my overall wellness. Another tip that I have implemented for years is to take four days of vacation, but get 9-10 days off. How? Utilize the 3-day weekends with holidays to maximize your vacation, i.e. Memorial Day is always the last Monday in May, so take the Tuesday thru Friday off in late May. You will have a great start to your summer, and only utilized four vacation days.

January 6 Coaching Tip: Get Organized. Most people establish “New Year’s Resolutions” at the beginning of the year, and then most resolutions dissipate by the end of January. My recommendation is to get organized. What does that look like for me? Yesterday, I spent the bulk of the workday creating high priority Outlook email folders, and deleting years of irrelevant or outdated folders. The clutter went away quickly, and it did not take that long. Also did that with my personal Gmail account. Less clutter, more organized, and more focus on your priorities are easily reinforced now.

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365 Coaching Tips: Let’s Get Started

In mid-November 2024, I decided to set my goals for 2025. One of the 10 most important goals was to “blog regularly (daily and weekly) about relevant topics and my coaching work.” Setting the goals, then putting them in motion before the end of 2024 allowed me to get rolling along. Must admit, I’m proud of my progress as we all launch into 2025.

So, let’s get started.

January 1 Coaching Tip: Pick one word. One word that YOU can leverage throughout the year, that will empower you, motivate you, slow you down, or speed you up, or help you make decisions. As shared in my January 1, 2025 post, my one word for 2025 is REDUCE. (see it for more on why the word REDUCE)

January 2 Coaching Tip: Explain why. If you want something done or need to delegate or have to reschedule, quickly explain why and/or what’s going on. Most and nearly all humans with a heart (and a brain, with some type of empathy) will understand, and be flexible. Already in the new year, I found myself having to change a few appointments, and when I quickly shared that my 84-year-old mother wanted to have lunch with her three adult kids, everyone I spoke to quickly realized, “moms win!”

January 3 Coaching Tip: Find your best times. Find your best times to work, when you’re really uninterrupted and in flow; when your body thrives on exercise; when you need some downtime. In wearing my Oura ring now for nearly 5 years, my most active time is around 9:00am E, and my best work is done in the morning, right after my important, quiet time reading my devotionals while enjoying my cold brew(s).

One of my priorities in 2025 is to share what I learn in my coaching, to help you in your leadership, life, parenting, family, etc. journey. Let’s keep these coaching tips rolling all year long. Hold me accountable.