Category: Leadership

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365 Coaching Tips: 205th, 206th & 207th

July 24th Coaching Tip: Ask Questions, Solve Problems.

Today I was asked to be a part of a “sales training” program with a goal of helping sales personnel learn how to ask better questions. If great questions are asked, this typically helps identify pain or problems that need to be addressed; these problems that need solved many times can trigger an emotional response from the buyer/prospect/client. As a salesperson, if you can help solve a problem and build trust, at a cost that is acceptable to the buyer/client, then you are adding value. If you can NOT solve a problem nor build trust or the cost is too high, the buyer may delay, drag their feet, distrust you, select someone else, etc.

What are some questions that you might ask? Try these on for color: what is it that you’re wanting to get accomplished? How committed are you to achieving this? What’s been in the way of this not getting resolved in the past? If I take the time and give you a practical solution and fair cost, are you willing to move forward? I’m sure that you have solid questions that work for you. Really pat attention and take notice when you help create an emotional response from the client, i.e. a joyous smile, a deep breath or sigh of relief, a stream of tears, etc. Stay present, in silence. They will usually open up and tell you more. Ask questions, solve problems.

July 25th Coaching Tip: Annual Infusion of HOPE.

In 2018, I was diagnosed with osteoporosis. My bone density test results were conclusive, and the treatment plan began. For a number of years, I took some daily meds and it also helped reduce my hot flashes. But in 2023, it was time to stop the daily meds (now that the hot flashes are gone) and move to an annual infusion for treatment. The first infusion hit me like a ton of bricks, i.e. couldn’t move for a couple days. Then in 2024, I drank more water and also took some Tylenol prior to receiving the infusion, and I felt much better after the infusion. Today was the day for my 3rd annual infusion; I intentionally hydrated well, did not work out, stayed out of the sun, and took some Tylenol. Hoping that these infusions will help stabilize my bone density; both my mother and grandmother shrank as they aged. I’m trying to be proactive by 1) ensuring my calcium input is at least 1,200 mg/day, 2) vitamin D is at good levels, 3) staying active and moving daily, and 4) strength training 2-3 times/week to help ensure the muscles around the bones are “in shape.” This infusion and these four items are my five-point plan of HOPE for my ongoing wellness fight vs. osteoporosis.

July 26th Coaching Tip: Etiquette Matters.

Open doors. Smile at strangers. Allow others to merge. Merge in wisely. Take your turn in lines. Return dirty dishes to kitchen sink or dishwasher. Pick up your trash. Greet others. Wave willingly.

Etiquette matters, and people see what you do in how you act and in how you leave things. There’s a phrase about staying at someone’s home: “leave it in better shape than the way you found it.” This etiquette might be as simple as leaving one fresh flower in a glass, and then cleaning up the house as you depart, leaving it like you found it. Etiquette matters on the golf course. Let others play thru, if you are playing slowly. Let the person putt who is farthest away. Be quiet when others are stepping up to take their golf swing.

Etiquette matters; it is witnessed, even if no words are spoken. Actions matter.

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365 Coaching Tips: 202nd, 203rd & 204th

July 21st Coaching Tip: Keep Doing It.

During one of my team coaching conversations today, I noticed a common thread that all five team members were mentioning: we are having crucial conversations and it’s working! So, I simply said, after listening to all of their examples for more than 20 minutes, to “keep doing it.”

They had a crucial conversation with a teammate who was way behind on work, and explained how it was impacting clients negatively and which was also leading to questions about his current and future role on the team. They had another key convo about processes that needed to be adhered to, and now they are adhering to their processes better. They even discussed compensation and how to get their thoughts and examples in writing.

Crucial conversations are worth it, if done with proper prep, calm delivery, and transparent thought. Leaders should not shy from having intentional and purposeful convos; these should definitely help the team meet goals, address problems, and help the entire team jump over barriers. Keep doing it, if it’s working.

July 22nd Coaching Tip: Ask For Help.

As co-guardians of my uncle, my mother and I have to stay on the same page with all things pertaining my uncle. It’s our responsibility to do that for his overall well being and financial affairs. We are getting some items more organized and reducing unnecessary clutter, but one small $800 issue has now drug on for the third month. We both were told that we needed to send in a notarized letter with our signature. I don’t have a lot of time to handle items like this during the workday, but when you need something notarized, I asked my lawyer’s assistant and she was very willing to help…and did it. We got it notarized efficiently. Don’t be afraid to ask for help.

July 23rd Coaching Tip: Get Your Confidence Back.

In one of my coaching sessions today with two highly accomplished leaders of a team, I let them vent for more than an hour. It went something like this: “Now what do I do? I’ve tried everything. It’s just not working. I’m losing hope. My confidence is waning. Our colleagues are taking advantage of us. And I’m really good at what I do, I just want to be able to go do it.” By the 90th minute, I was ready to wrap up the call and I asked for next steps. Believe it or not, they had none. So together, we worked on next steps. We identified three for them to do; I agreed to sleep on it, and bring in two other colleagues that can give me insights on when they worked with these two leaders in the past.

When your confidence is low, reach up and ask for help. As my mother would say, “if you’re in a hole, quit digging. Put the shovel aside and use it as a ladder to get up and out of the hole.” Proud of these two leaders asking for my help and knowing that they needed help for themselves, and it should also help their entire team. The team is feeling overwhelmed, not saying much in team meetings, and not showing up consistently. It’s going to take some one-on-one conversations and a gathering of multiple inputs, but our goal will be to help them get their confidence back. If your confidence is dropping, change things up and ask for help.

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365 Coaching Tips: 199th, 200th & 201st

July 18th Coaching Tip: Early Dinner, then Walk.

As we wrapped up the week, we decided to do our early Friday evening dinner. Eating earlier in the evenings and enjoying lighter foods helps us both 1) feel better, 2) sleep more soundly, and 3) spend less money. When we arrived back home, it was only 6:00pm. I headed out on a walk and grabbed my phone to give a call to my mom to check up on her. Why walk after a meal? It’s a new routine/habit that I have implemented after wearing my glucose monitor this past Spring and also learning about ways to help reduce glucose spikes after eating. A stroll of three to five to up to 15 minutes helps me bring the spike back into the normal range. And since I grabbed my phone, I got two things done.

Wellness is more than going to the gym. It’s connecting with those that matter; it’s taking a stroll after eating; it’s winding down with friends on a sunset cruise. My tip for today is eat earlier and eat less, then go on a walk. You never know, you might even begin to notice that you see your neighbors outside more, too.

July 19th Coaching Tip: Laugh Daily.

We all have “stuff” that hits us daily or weekly, at the very least. We make it a point to laugh daily, especially as we are getting older and been together for eight years now. We don’t want to become the crusty, grouchy old people. We want to embrace life and what comes at us, but we also are making the choice to laugh a lot every single day. For example, a couple nights ago, we stayed up until 11pm recapping the day, hysterically laughing about all the stuff that happened. We could have chosen to whine, be upset or even angry, and quietly go to bed. Today, I’ve laughed multiple times watching a funny video that was set up by the Philadelphia Phillies baseball team. Their two mascots went in to the crowd, acted like they were a couple, and then ducked when the “Kiss Cam” got them on camera. It’s now a national meme that the nation is laughing about, as a married CEO was embracing his company’s HR leader at a Coldplay concert in Boston; once they noticed they were on the “kiss cam” they both ducked and turned around. Oops! They got caught which is serious business. But the meme and set up for the Phillies’ mascot was downright hilarious. A must see for your daily laugh!

July 20th Coaching Tip: Two Weeks To Go.

In two weeks, we pack up the car and head to Des Moines, Iowa, for my first-time competing in five events at the National Senior Games. Yes, I’m a bit nervous because I’m doing my research on what it will take to advance in the 100m, 200m and 400m sprints. I’m also realizing that I will need to hit 23/25, 24/25 or possibly 25/25 free throws and more than 9/15 in the 3-point shooting to place in the top three or potentially win the basketball shooting contests.

What am I doing to reduce my nervousness? Prep, just like in my coaching. I’m practicing with more intention and higher demands of myself. I was shooting around 21/25 in my FT’s recently, but the last two days, I hit 23/25. That’s what it will take to medal, and I want to medal. In my running, I’m working on my start, relaxing my face and hands more as I’m “sprinting”, and I’m trying to run faster at the end of the sprint.

I’m not sure how this will all turn out, but in two weeks, I’ll have the results. I’ve put in the work for more than 18 months, and I hope to reward myself for all this practice and prep. Two weeks to go…is not the time to stop. Now is the time to make it ALL count.

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365 Coaching Tips: 193rd, 194th & 195th

July 12th Coaching Tip: Keep An Eye On Trends.

Someone today asked me how to start an LLC. My very quick response was to leverage AI. Why did I respond that way? Because the last time I started an LLC was years ago, with an professional expertise of an attorney, and he just took care of it. I also watched the CEO of a large corporation today talk freely and confidently about how he expects his company’s employees to learn and leverage AI. He wasted no time in saying that replacing their Microsoft Outlook system with Microsoft’s new 365 system that has AI embedded will cost more. He is expecting to have employees leverage it to help improve productivity and the client experience. (And I’m expecting it to ultimately replace employees who do NOT learn it and do NOT leverage). I may be wrong; I may be right. I’m making the commitment to keep on eye on trends and stay aware of AI’s developments and embrace it to be more productive personally and professionally.

July 13 Coaching Tip: Assists Indicate Alot.

The Indiana Fever women’s basketball team played the Atlanta team today and crushed them. What did they do so differently? They set a team record in assists; assists are when a player passes the ball to another, and that person scores. The unselfish and fast pace of play was exciting, and the Fever dominated the game, winning by 19 points and scoring over 100. The Fever also had only 8 turnovers. So there were lots of assists, few turnovers, all meaning the players were really looking for each other and making great decisions.

In life, assists indicate a lot, too. When someone is willing to help you look good, that’s positive. When a colleague is willing to pass the praise and give another person the credit, that’s an unselfish human. Assists indicate a lot and they feel good when you assist others.

July 14 Coaching Tip: Productivity Gains.

Today I was prepping for a virtual event that was available nationally for our colleagues. About 30 minutes prior to the start of the event, I double checked a few things: did our guest speakers have the invite? No. Did our speakers ever receive the final deck of visuals to support our conversation? No. As we were approaching one minute to go, our producer finally got one of the speakers dialed in to the event.

This all could have been avoided if the production invite was smoother and included the speakers and the visuals, instead of just completing the task of setting up the invite. In your line of work, always be on the lookout for ways to improve and identify productivity gains.

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365 Coaching Tips: 184th, 185th & 186th

July 3rd Coaching Tip: Be a Favorite Customer.

As our friends and family were prepping for the upcoming long July 4th weekend, we decided that we wanted some healthy Mediterranean food. I raised my hand to cater in some yummy gyro meat, salad, rice, hummus, sauces, and pita bread. At 3pm today, I called my favorite Med restaurant, verbally told them what I wanted, and they said, “we’ve already started your order; it’ll be ready in 15 minutes.” I got there in 22 minutes, walked in, the owner greeted me, I paid them, and he told all of his workers, “she is one of the best and favorite customers.” (He trusted me last August 2024 and catered my birthday party for over 100 people. Plus, we go there every couple weeks for carry out.) After I paid, he asked where I parked, then he and another employee carried out the trays of food, put them in my car, and smiled as they walked back into their restaurant. Be a favorite customer.

July 4th Coaching Tip: Laugh Alot With Friends.

Friends, fireworks, fun, freedom and family! It’s what July 4th is all about here in the USA. Today we celebrated my oldest brother’s (Brett) 64th birthday; we had nearly the entire family there, except for one niece and her man. Mom and her seven great grandkids were there, and all adults in between, to celebrate Brett at my other brother (Grant) and his wife’s lake home. It was the first time that the entire family got to hang out at this new “lake home” family destination.

Throughout the entire day, we also had friends at our lake condo, just a few miles away from my brother’s lake place. Our friends were enjoying the lake views, kayaking, swimming, eating, chatting it up, etc. Before the end of the evening and the fireworks, did we ever have some stories? We poured a beverage and walked up the stairs to our friends’ condo directly above us to watch the fireworks, as they were popping up from multiple locations. It was easy to watch and also spectacular. Then we sat on their back deck laughing our heads off until well after midnight. One of my friends named herself the “camp counselor” for the day; that will be her new nickname as we all head into our Golden Girls years together. Laugh a lot with your friends; we have been thru some stuff together these last couple years, and we know that we’re all in for a lot more challenges. Keep laughing with your friends to maintain your wellness.

July 5th Coaching Tip: Heavenly Sent.

The Punkin Vine Fair in Kentland, IN, is something that my family and I have been going to since the 1970’s. Today, I intentionally joined my mom at the Fair as we helped organize the fun during the 13 harness horse races; it’s our job to get the audience involved. We interview them and the Fair queen, we recognize the oldest and youngest fans, we allow everyone to put their name in a bucket each race to select the horse they think will win, and then we pick one winner, give out small gift bags and tickets to other Fair events.

To our surprise, the Fair Board agreed to have the second annual Lynn Wilfong Memorial Race. How exciting, because we were not expecting it. My brother (Brett) brought a horse to race, and by golly, it was in the LW Memorial Race. And what do you know, Brett’s horse was in second the entire race, then came roaring down the final stretch to win the race. It was a magical moment, my mom was shaking and my brother was smiling. We got the win, and we all realized that this day was heavenly sent. I’m so glad that I was there for this magical moment.

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365 Coaching Tips: 181st, 182nd and 183rd

June 30th Coaching Tip: Midyear 5R’s.

With it being June 30th, now’s the time to ask yourself and your team some questions. How much time did you take today or will you take (soon) to your reflect on your progress of what you wanted to accomplish in 2025? Who helped you accomplish key priorities? Who have you thanked? Who have you coached and further developed? What goals and priorities came up a bit short during these first six monthly of the year? And what might you continue to excel with during the 2H2025?

Now’s the time to review the first six months of the year by embracing five R words: Reflect. Recognize. Reward. Restart. Recommit.

July 1st Coaching Tip: Be Your Own Advocate.

As a 60-year-old with osteoporosis, I must advocate for myself. What does that mean? My primary care physician nor my endocrinologist did not call me to 1) schedule my annual blood test, 2) schedule an in-office appointment, and 3) schedule my annual infusion. I called them multiple times. My two previous annual injections were done in mid-May 2023 and June 21, 2024, so it’s time…right now. But first, the doc wants to see me and have my blood test results. And I want another bone density test, since it’s been three years (July 2022), to see if the two annual injections actually helped, stabilized or had no impact on my bone density. Advocate for yourself; if you don’t, who will be your wellness advocate? Have the courage to do it yourself.

July 2nd Coaching Tip: Stuff Happens. How do you respond?

How do you respond when “stuff” happens? Today, as I inspected the work on a project, I noticed three things: two were easy decisions, but the third could have been close to catastrophic. Calmly handling all three with good listening skills, I asked more questions to gain agreement on next steps. That allowed us to get all three situations taken care with no drama. The potentially catastrophic issue was actually done by a third party; I slept on it and then felt like they needed to know about it. Drafted an email and sent it to the third party. They responded professionally, didn’t “own it”, but they do now know that something happened. Bottom line, remember that stuff happens. How you respond is crucial; people may judge you during those moments and choose later to be a bit cautious with you. Respond calmly, get buy in, and have a plan.

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365 Coaching Tips: 178th, 179th and 180th

June 27th Coaching Tip: Keep At It.

Some days aren’t the best for energy. Today was one of those days for me. Some days I just have to tell myself to “pace myself, pace.” It’s like jogging or walking for exercise, you’re out there, at your pace. But you’re out there doing it, keeping at it. Even with work, sometimes if you let your colleagues know that you’re operating at a “6/10 or 5/10”, you will get some grace. And if you keep at it, your colleagues will appreciate your honesty, and most likely will say, “I got you.” Then when they are running a bit low on energy at a “5/10”, you will be more apt to help them out, too. The point is keep at it; don’t just stop.

June 28th Coaching Tip: It’s Fun Until It Isn’t.

My mom used this phrase today: It’s fun until it isn’t. I had never heard her say it before but it was so accurate for what was happening. My partner is realizing that utilizing her RV is quite a bit more work now that it used to be. As a kid, she loved trekking from TX to MI during the summer vacations. She has been utilizing her RV for trips and transporting dogs the last 5-10 years. I’m realizing that jogging is ok, up to 2-3 miles, and then I’m good.

Now, I have zero desire to run a half marathon, like I did when it was fun running half marathons regularly about 15 years ago. My partner will soon be selling her RV. Know your “no”; it’s ok to change. It’s ok to embrace Mom’s phrase: It’s Fun Until It Isn’t. You’re not giving up on your dream; you’ve already done it. Now might be the time for a new dream.

June 29th Coaching Tip: Change It Up.

Sometimes changing it up can really produce some better results. For example, I have a tendency to do the similar workout routines across a two week period. It’s my belief (and many health and wellness experts) that doing a variety of exercises can help reduce fatigue and potential injuries due to overworking an area. Today I jumped in the swimming pool and decided to tread water in the deep end for 10 minutes; my left ankle had just a hint of soreness, so my gut instinct was to change it up and exercise with a lower impact. I plan to swim more in the next few weeks to just give that ankle some recovery time, but keep my cardio workouts going. Don’t be afraid to change it up.

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365 Coaching Tips: 175th, 176th and 177th

June 24th Coaching Tip: Review Expenses Quarterly.

Take time quarterly or at least every six months to review all of your expenses. This one habit, done every 90 days, will help you manage your budget and may free up a bit of cash that was once unavailable. For example, I noticed that my ATT internet rate jumped from $50/mo to $70/mo. And another subscription jumped from $10 to $20/mo. As I investigated other options, I realized that I could get 3X’s faster internet service for $50/mo for up to three years AND it lowered my iPhone mobile bill by $10/mo, too. I made the switch over a couple months. Question is: was it worth it? Yes it was. $30/mo is saved over a three year period for my internet and iPhone, and the other subscription will save me $10mo/, which equals $1,440 over three years. Plus, I have much better and faster service.

If you found nearly $1,500 laying on the ground, I’m confident you would quickly grab it. It took a couple phone calls, approx. two hours of my time on these phone calls and then self-installing the new internet. Check those expenses quarterly to understand your budget. It’s like paying yourself.

June 25th Coaching Tip: Embrace Cancellations.

What the heck does embrace cancellations mean? When I have a coaching appointment that postpones or cancels, I embrace that opportunity of 30-60 minutes to get work done that had been getting pushed back. For example, I had a list of over 25 colleagues to reach out to who wanted coaching. Because I had a couple cancellations today, I was able to focus on those 25 people and reach out to them. The targeted effort worked, and many of the 25 responded quickly to set up time in July. Embrace cancellations; it can lead to other opportunities to help and coach others.

June 26th Coaching Tip: Coach or Consult.

There is a clear difference between coaching and consulting. Coaching is viewing your client/colleague as an equal partner, and with the right questions, truly believes that they do have the answers. These answers can many times be brought out of the client by the coach remaining present and curious, asking thoughtful questions. Consulting is listening and learning and then leaning in to giving advice and recommendations. Knowing the difference as a coach is important for me and my clients. Many times during the end of a coaching session, the client will look for reinforcement by asking, “am I on the right track…thinking about my plan correctly?” And then some are more direct, “what advice would you give me?” As a coach, it’s important to remain in the coaching mindset. However, if I do switch to consultant mode, I try to let them know that I’m doing that, by using the phrase, “let me take off my coaching hat and put on my consulting hat.” That slows me down, it also lets them know I’m doing it too. Know the difference between coach and consult mode. (Note: even when people receive advice, they go ahead most times and do what they want or what they are comfortable with. So be wise and infrequent when giving advice.)

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365 Coaching Tips: 169th, 170th and 171st

June 18th Coaching Tip: Write.

For years, I wanted to write more. That was my goal, “write more.” Why am I writing more in 2025? Because I have a daily goal of sharing a coaching tip. It’s really that simple. Once I identified a realistic goal of writing a coaching tip daily, that helped me to truly launch my writing. My coaching tip today: write. Write every day, even if it’s like me, a simple paragraph or two.

June 19th Coaching Tip: Keep Writing.

It’s one thing to write for a few days, and in the past, I would take a break. The break could last for weeks or months or even years. What have I done differently this year to keep writing? I have a reminder on my iPhone calendar to write on my JenWilfong.com blog every single day. It’s working; I keep writing and it actually makes it easier now that it’s a daily part of my routine. Keep writing!

June 20th Coaching Tip: Become A Better Writer.

Now that I’m writing and sharing coaching tips daily, I’m aware of how others write even more than ever. I’ve been asking myself what I appreciate about their style, their grammar, their asks, their summaries, their simplicity, their ability to reach all the senses, etc. It’s helping me become a better writer as I read others’ writings. Write, keep writing, and become a better writer. As I am writing more frequently, it’s also helping me with the questions that I ask during my coaching sessions. I’m really focused on simplifying questions, utilizing words that are easily understood, and summarizing with the client as we wrap up the coaching session. Writing is helping me in my daily work responsibilities. Write.

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365 Coaching Tips: 166th, 167th and 168th

June 15th Coaching Tip: Rest Before Trips.

Knowing it was the Sunday before heading to New York City for three days of work, it was time to rest. And when I say rest, I mean resting in bed for most of the day, doing absolutely nothing. This will be my third trip to the City in 2025. When I’m visiting NYCity, rarely do I sleep well, I almost always eat too much of the incredible food, and I walk a lot of steps. Knowing all of my tendencies, it was time to rest before this trip. And as you travel for your work trips or your vacations across the globe, the first couple days can be quite taxing on the body, i.e. new bed, new time zone(s), new social interactions, delayed flights, different transportation modes, etc. Rest before trips.

June 16th Coaching Tip: Listen Intently.

I have the pleasure of coaching a large team who helps guide and care for a small number of very affluent, large clients. This team has crushed all of its YE2025 goals, and it’s only mid-June. So now what? Coast til yearend? Improve on something? Keep growing?

We had each team member share their answers to 1) what should we double down on and do even more in the second half of 2025, and 2) what must be fixed that no one is taking the time to fix. As I listened intently and paraphrased back what we were hearing, the individuals on the team around the team felt heard, uplifted, and ready to keep growing in the 2H2025. The leader agreed to spend one on one time with everyone to assess their personal and professional growth. If you want buy-in, “seek first to understand to be understood.” Listen Intently.

June 17th Coaching Tip: Celebrate With Others.

One guy with over 40 years is setting off to his retirement. Another gal in the crowd was celebrating 38 years of service. And I was sitting there with 13 years. We all celebrated these decades of experience that we’ve shared with our colleagues, clients, and the Company. The retiree shared words of wisdom, even using the short phrase of “be decent.” Not at performing but being decent to one another. Celebrate with others as they achieve milestones. It’s their moment to shine. CELEBRATE!