Freestyle Fridays: Leadership, Relationships, and Honest Evaluation
Freestyle Fridays are uncut, uncensored, unedited, and unscripted. No notes. Just real-time reflection. This episode was recorded on January 6th, just after finishing my morning routine, coffee in hand and workout still ahead. I had already spent time reading and journaling, including diving deeper into a book that has resonated strongly with me lately, How to Work with Complicated People by Ryan Leak. It is a reminder that people are different by design, and leadership requires understanding, patience, and clarity. That idea sets the tone for today’s message.
The Question Every Leader Needs to Ask
If you are running a business, leading a team, or managing people in any capacity, here is a question I want you to sit with honestly. Knowing everything you know now about the people on your team, would you still hire them today? I recently asked this question to several VIP clients, and many answered no. But that is not the point of the question. The real purpose is to evaluate differences. How are they different from you? Are those differences helping you grow? Are they bringing a perspective, skill set, or lens that you do not have?
Why Differences Matter More Than Similarities
Being surrounded by people who think exactly like you may feel comfortable, but it rarely produces growth. Collaboration requires contrast. Push and pull. Different ways of thinking. Different strengths. The people who challenge you, when aligned with your values, often help you see blind spots you would never uncover on your own. The key is learning to appreciate those differences instead of resisting them.
Evaluating Relationships in Business and Life
This question does not apply only to work. It applies to life as well. If you knew then what you know now, would you still choose certain friendships or relationships? In many cases, the answer may be no. But there are always a select few where the differences are exactly what make the relationship valuable. Those people help you see the world through a different lens. They expand your thinking. They push you forward.
Knowing When It Is Time to Move On
Over the last few weeks, I have watched many professionals in the mortgage and real estate industry make major career moves, leaving companies they had been with for decades. Every time I have left a long-term role in my career, I have looked back with gratitude for what I learned, but also with clarity that I stayed longer than I should have. That reflection matters. Evaluate the people and situations in your life. Embrace differences when they add value, but do not tolerate misalignment that keeps you from moving forward.
Use Third-Party Perspective to Remove Emotion
One of the most effective strategies I use with my clients is removing emotional attachment from hiring decisions. When key roles are being filled, I often conduct interviews myself because I have no emotional stake in whether the candidate is hired. The business owner does. That emotional attachment can cloud judgment. Bringing in a neutral third party, such as a coach or consultant, can save months or years of frustration by ensuring the right people are in the right seats.
Playing to Strengths and Reassessing Annually
At least once a year, reevaluate your team. Are people still aligned with where you are going? Do their strengths outweigh the challenges they bring? If the answer is yes, pour into them. If the answer is no, have the hard conversation. Most people are only meant to be part of your journey for a season unless they are growing alongside you. High performers move fast. Not everyone wants to run at that pace, and that is okay. But clarity is required.
Vision and Communication Are Non-Negotiable
If you expect people to run with you, they need to understand the journey. Where you are going. Who you are becoming. What the vision looks like. This applies to business and personal relationships alike. Your spouse or partner must understand where you are headed, and you must support where they want to go as well. Communication is everything. One of the most important lessons I ever learned about communication came early in my career. The biggest mistake in communication is thinking it happened. Clarity must be intentional and repeated.
Final Thoughts: Evaluate, Communicate, and Lead With Clarity
Take time to evaluate the people in your life and business. Appreciate differences when they add value. Address misalignment when it holds you back. Communicate clearly and often. Leadership is not about comfort. It is about responsibility. When you lead with clarity and intention, everything else begins to align.
Upcoming Speaking Engagement and Invitation
This episode will be released on January 9th, and I will be speaking on January 16th in Orlando at the Rosen Shingle Creek during the National Association of Mortgage Brokers Focus Conference. I will be on stage from 1:00 to 2:00 PM. If you would like to attend and receive a free ticket, reach out to Taylor at welton.live and she will provide the details. We would love to see you there, meet you in person, and spend time connecting throughout the day.
