MSMP 88: Timothy Colson on Trusting Your Team

What Does MSMP 88: Timothy Colson on Trusting Your Team Talk About?

In this episode of the Mads Singers Management Podcast, host Mads Singers welcomes Timothy Colson, an experienced leader who has worked in retail and insurance before founding his own financial services firm in New York. The conversation centers on building a strong team culture through trust, empowerment, and situational leadership. Timothy emphasizes that culture is shaped by core values like creativity, honesty, and fun, and that attracting A-players becomes easier when those values are prioritized. He and Mads discuss how performance and happiness are linked, and why underperformers must be addressed for the health of the team. The episode also explores the concept of situational leadership, where leaders assess the most critical issues and deploy the right people to handle them, fostering trust rather than micromanagement. A key story involves Timothy supporting a high-performing team member who used unconventional methods, choosing to seek forgiveness from higher-ups rather than stifle her success. The hosts critique the outdated management adage of treating everyone the same, advocating for tailored approaches to individual team members. The episode concludes with insights on the dangers of micromanagement and the importance of self-knowledge for effective leadership.

We sell commodities. There’s no need to take that so very seriously. I want a team that values creativity, honesty, and having fun.Timothy Colson

Who Is Featured on MSMP 88: Timothy Colson on Trusting Your Team?

Timothy Colson is the guest on this episode. He spent nearly a decade in leadership at a big box retailer before moving to a nationwide insurance company. Today, he runs his own insurance and financial services firm based in New York, about an hour outside Manhattan. Timothy is passionate about organizational culture and how it shapes team performance. He believes that great culture arises when people enjoy their work, feel trusted and empowered, and have a sense of belonging. His leadership philosophy centers on situational leadership, where he assesses the most important issues and empowers the right team members to address them. He shares a personal story of supporting a high-performing employee who used unconventional methods, demonstrating his willingness to take calculated risks for his team's growth.

What Are the Key Takeaways From MSMP 88: Timothy Colson on Trusting Your Team?

• Culture is built on core values like creativity, honesty, and fun, which attract and retain top talent.
• High performance and happiness are closely linked; underperformers negatively impact culture and must be addressed.
• Situational leadership involves identifying the most critical issue and deploying the right person to handle it, fostering trust and empowerment.
• Treating everyone the same is outdated; effective leaders adapt their approach to individual team members' needs.
• Micromanagement is detrimental to team morale and performance; leaders should trust their team and avoid controlling every detail.

I want a team that values creativity, honesty, and having fun.Timothy Colson

Is MSMP 88: Timothy Colson on Trusting Your Team Worth Listening To?

This episode is highly recommended for managers and leaders who want to build a thriving team culture. Timothy Colson's practical insights on situational leadership and empowerment offer actionable strategies for avoiding micromanagement and fostering trust. The discussion on treating team members as individuals rather than applying a one-size-fits-all approach is particularly valuable. The episode is engaging and filled with real-world examples, making it easy to apply the concepts. Whether you are a new manager or a seasoned executive, you will find useful takeaways that can transform your leadership style and improve team performance.

Who Should Listen to MSMP 88: Timothy Colson on Trusting Your Team?

• New managers seeking leadership guidance
• Experienced leaders wanting to improve team culture
• Entrepreneurs building their first teams
• HR professionals focused on organizational development

What Are Listeners Saying About This Episode?

Today’s guest for the Mads Singers Management Podcast, Timothy Colson, has spent many years in leadership, first in a big box retailer for almost a decade, then for a nationwide insurance company.  Today he runs his own insurance and financial services firm in New York, about an hour outside Manhattan.

Part of why Timothy runs his own firm today is his love of culture and the way that it can shape a team.  “We sell commodities.  There’s no need to take that so very seriously.  I want a team that values creativity, honesty, and having fun.”  Timothy noted that when he emphasized those core values, it wasn’t difficult to attract A-players to his team. 

Timothy noted that great culture happens when people enjoy their work, feel trusted and empowered, and come to work every day feeling like they are part of something.  I noted that that goes hand in hand with performance.  People who are performing well tend to be happier.  Those who are not performing well know they aren’t performing, and are a drag on themselves and the culture.  If they can’t get with the program, they have to go (and it’s better for them too!).

We also discussed “situational leadership” as a topic that is getting more attention these days.  Timothy sees that as assessing what is the most important issue in a given day or week, identifying the right person to deal with it, and then deploying that person to do so.  This fosters trust and empowerment in a team, as opposed to micromanagement, which tends to discourage team members.

Timothy and I also enjoyed roasting the old and outdated chestnut that, in management, you should always “treat everyone the same.”  The reality is that different people need different techniques and approaches.  Timothy talked about one particular scenario in which one of his team was performing very well, but not using the methods that had been determined as the “right way” by the higher ups.  After spending some time with her, he decided to ask for forgiveness instead of asking for permission from the higher-ups and leaned into the methods she was using to win.  He then documented those and passed them up the chain for approval.  Rather than insist that there was only one right way to do things, he took a gamble and helped coach his employee.

Timothy has a clear passion for the science of leadership and it was a pleasure to get to know him well.  Enjoy this episode!

Key Learning Points:

1. Timothy notes that it only takes one person to poison the culture of an entire company - 4:00

2. Timothy shares what he thinks a great culture does - 5:15

3. Mads reminds us that people who perform tend to be happy - 6:56

4. Timothy gives us his definition of situational leadership - 16:50

5. Mads warns that “treat everyone the same” as an idiom in management is outdated thinking - 19:00

6. Mads stresses the importance of self-knowledge to complement knowledge of your team - 21:32

7. Timothy shares how he found a way to help one of his team members grow in an unconventional way - 27:44

8. Timothy talks about an “aha” moment in regards to micromanagement - 33:03

9. Mads notes the biggest danger of micromanagement - 35:11

Connect with Timothy Colson

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