A Leader’s Holiday, 5 Steps to Lead Through the Stop & Starts of the Holiday Season!

As a leader within an organization, you know the craziness that comes with holidays; employees taking off, your vacation days, canceled meetings, rescheduled meetings, remembering where you and your team left off after the holiday, and chasing to follow-up or reschedule! The list goes on and there’s no more intense Holiday Time than the weeks between Thanksgiving and Christmas… at least in the United States and depending on when your Holidays may fall. So, how do you lead through the inevitable and enhance not only your Leadership & Work/Life Harmony, but also that of those you’re leading and your clients/customers?

Know Your Wins!

Monday through Friday, before I jump out of bed and my feet hit the floor, I say two things to myself… Number one, “Let’s be great and have some fun today!”. There’re a lot of people being their definition of great, but not having any fun… and too many people having fun and not being great. Do both, enjoy, and evolve! The second thing I say to myself is a question, “What are my wins for the day?”. Having an answer to this question allows enhanced awareness of what’s important, why it’s important, and a plan to achieve it! My list usually consists of 20 things I get to do to effectively run my business daily… it’s important to be careful that my list and your list is making you, your team, and your organization BETTER, not just BUSY!

Most organizations have a process of closing out the year; therefore, what are your wins for the Holiday Season? I suggest having an answer to this question and implementing my simply daily question to yourself before your feet hit the floor in the morning. For me… let’s say I have 15 prospects interested in bringing me in to present Leadership for their organization by year’s end or the following year; my win for the Holiday Season is to of course close them all, but that’s not always likely. My Holiday Season Win may become to have signed Agreements with more than half of the companies before the Holidays end, a scheduled Virtual Call to officially meet and speak before years end, and a scheduled follow-up Virtual Call post-holiday. For me, that’s my Holiday Win which leads us to the next Step!

Your Executive Assistant

If you’re lucky enough to have an Executive Assistant, great for you! If you’re not one of the lucky ones, no worries… the truth is, we all actually have an Executive Assistant and it’s called your phone, tablet, or laptop. Leaders anticipate… we know the Holidays are coming, the professional chaos that comes with it, so let’s not be surprised and negative about it… let’s beat it!

Weeks before the Holiday Season begins, bring awareness of the upcoming season with your clients/prospects and be sure to schedule meetings in advance; placing the dates and times into your calendar with alerts. I usually make my alerts two hours before and 30 minutes before; allowing you to be where you said you were going to be and maintaining your professional reputation at all times. I often place the meeting in my phone in front of the person while on a virtual call or face-to-face meeting to model the practice. Before the call or meeting ends, I usually ask “How would you like to best move forward or when is best to meet again? I look forward to hearing what you liked and anything you’d fine-tune to best move forward. Do you mind if we schedule it now so I’m not chasing you or you chasing me?”. Feel free to reframe this question and make it your own. The point is, you’d be surprised how many leaders never ask me first… leading to the biggest mess of “Let’s circle back”, or you chasing them and losing your power, or the least likely… them chasing you… negatively impacting your reputation as the person that never gets back to people. This leads us to Step 3!

The Inevitable Misses

No matter how perfectly you do Steps 1 and 2, Step 3 is inevitable! During the Holiday Season, the people you so intently scheduled with will cancel, reschedule, or flake. This happens for many reasons; they’re as busy if not busier than you and attempting to tame their ever-growing tornado of things to do before, during, and after the Holiday Season. Meetings, expected and unexpected, continue to pile up to take over their day, they have people calling off or on vacation to make up for, their kid’s school play was at 9:00am on a workday… who knew, Lol! The list can go on, but I’m sure you get the point. So, what to do?

  1. Know most people feel terrible for having to cancel or that they forgot. You know how you feel when you forget about a meeting, how it made you look, or that you wasted someone’s time? They feel the same. Therefore, connect to make them aware you were on the call and at the meeting and understand these things can happen. You look forward to reconnecting before or after the Holiday Season, whichever is best for them and offer two dates. One date and time within the Holiday sphere; some leaders and employees would like to include what you offer in their end-of-year planning or budget… YOU and what YOU OFFER may be their WIN! Offer a second date post-Holiday and see which they select.


  1. Keep a list of missed or requested rescheduled meetings: Their names, date of the missed meeting, and email address. I’m honored to work with and speak with many organizations around the world and it’s inevitable one or more will fall through the cracks as leaders and companies ask to reschedule numerous meetings or virtual calls throughout the Holiday Season… It’s nothing personal; simply inevitable. Remember, leaders anticipate! Therefore, maintain that physical list at your desk and be ready to reach out with A Leader’s Two Dates and Times as listed above when the Holiday Season comes to an end.

Include Your Team

As a leader and as an employee during the Holiday Season… I know you’re busy! It’s important to remember “Winning” isn’t only about YOU. It’s about your team winning both professionally and personally! Professionally… does your team know what the wins are? Do you know what winning may mean for them individually? How will you celebrate your team in our new hybrid world? The leadership skills you’ve learned here or other trainings, have you shared it with your team; allowing them to enhance their Leadership & Work/Life Harmony?

Personally… work/life harmony matters for you and your family; especially during the Holiday Season! It would be a shame to hit the mark at work and miss the mark at home with those that matter most. Yes, the Holiday Season will inherently involve time spent with loved ones… time we usually take for granted. By all means, do that time and enjoy that time. As a leader, can you and will you Make Time and Take Time for meaningful moments during the Holidays with your significant other, Date-Day with your children 1-on-1, or time with your friends… instead of exhaustingly preparing for the Holiday and returning back to work even more exhausted than you left! My wife and I hosted our first Annual Friendsgiving this year and all I could thing was, “Why haven’t we done this sooner?”. What a wonderful time and I felt lucky and joyful returning back to my work!


My 2-year-old daughter can make a mess like no other. When she colors, it’s inevitable she’s going to dump all of the crayons onto the floor, then become 10-Second Tom; inevitably running off to make a mess somewhere else for 10 seconds… and repeat! it’s adorably crazy and crazy adorable all at the same time, Lol! When it’s time to clean up, we play the Clean Up Song! If you’re unfamiliar or don’t have kids, you ask your Alexa or Siri to play The Clean Up Song and all kids magically stop in their tracks, start dancing, and cleaning up voluntarily… it’s a true WOW moment to witness for the first time!!! Why do I mention this?

It always makes me giggle a bit when companies say, “Let’s get together after the holidays, we’ll be less busy then”. Part of me fully understands; as there so much to do before, during, and right after the Holiday Season to close out the year… I get it! The other part of me knows, everyone will be as busy… if not more… with their organization’s Quarter One goals… all the while taking care of the loose ends of the previous year. Therefore, it’s important to play that Clean-Up Song in your head as a leader when returning from the Holiday Season! Remember that list you kept at your desk of clients/customers/employees/etc. that missed or wanted to reschedule their meetings. Make Time and Take to clean up and reconnect; as these are the people already dialed in as an asset to give you money, time, or whatever you were asking for and planning. Clean Up with your team to tie up any and every loose end. Lastly, evaluate YOU as a leader from last year… what did you do great? What would you like to fine-tune? What was your biggest mistake and what did you learn from it? What’s your dream? What’s your vision and 3-5 things it’s going take for you and your team to achieve it? Clean-Up-Time is essential for your leadership & Work/Life Harmony, your people’s, and your organization. Enjoy it, Apply it, and Evolve it!

“It’s important to be mindful that your list is making you, your team, and your organization BETTER… not just BUSY!” – Andre Young

Written by: Andre Young

Click www.youevolvingnow.com to find out more about Andre Young’s Leadership & Work/Life Harmony Trainings, Speaking Engagements, Books, and more; evolving your organization, your leaders, employees, and teams!

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