Six Lessons I Wish I Learned Sooner as a Supervisor

I will never forget my first days as a supervisor. I was stepping into uncharted territory, feeling equal parts eager and unprepared. It had been nearly eight years since I left the Marine Corps, where leadership was a part of everyday life. Back then, leadership was all about decisiveness, discipline, and building trust through shared hardships.

But transitioning into a corporate role? That was a completely different challenge. Suddenly, I was in a world where leadership was not clearly defined. Instead of leading people, I felt more like I was managing tasks. No one hands you a guide for this kind of leadership, and for a while, I was stuck unsure how to bring the skills I had honed in the military into a workplace that seemed to value process over people.

Everything shifted when I attended a workshop called “Making the Transition from Staff to Supervisor.” It was not just about learning techniques; it was a wake-up call. It reminded me of the qualities I already possessed but had buried under doubt and hesitation. For the first time in years, I felt equipped to step up and lead, not just manage. That workshop reignited my passion for leadership and clarified what it truly takes to lead well.

Looking back, these are my favorite six lessons I wish someone had told me when I started my leadership journey. They are not theories. They are practical truths forged through trial, error, and reflection. My hope is that sharing these will help you navigate the challenges of leadership with more clarity and confidence.

1. Define the Standard of Communication You Want

Here is a hard truth. If you do not intentionally set the tone for communication, the default will almost always fall short of what your team needs.

I learned this the hard way. Poor communication is not just frustrating. It erodes trust, kills momentum, and breeds unnecessary conflict. As a supervisor, you have to decide what kind of communication culture you want. Is it rooted in transparency, regular feedback, or open collaboration? Whatever it is, you have to model it consistently.

For me, that meant scheduling regular check-ins, being clear about expectations, and practicing active listening. It is not always easy, but when your team sees you setting the standard, they will follow suit.

Takeaway: Be intentional about communication. It is the foundation of trust and alignment.

2. Relationships Are the Bedrock of Leadership

Leadership is not about the title on your business card. It is about the relationships you build.

Strong relationships with your team are the key to earning trust, navigating challenges, and driving results. But here is something people often overlook. Your relationships with leadership matter just as much.

I learned this when I struggled to secure resources for a key project. I realized I had not invested enough in building trust with upper management. Once I focused on improving those connections, not only did I get the resources I needed, but I also became a better advocate for my team.

Takeaway: Invest in your relationships, both with your team and those above you.

3. Identify the “Doers” on Your Team

Every team has unsung heroes. They are the ones who deliver results without drama or excuses. These are your “doers,” and they are invaluable.

Spotting them early is critical. They are proactive, consistent, and often the glue that holds projects together. Once you identify them, do not just rely on them. Empower them. Give them opportunities to lead, recognize their contributions, and trust them with responsibility.

Takeaway: Find your go-to people and make them your allies.

4. Never Stop Asking for Help

As a new leader, it is easy to fall into the trap of thinking you should have all the answers. Let me tell you, nothing could be further from the truth.

Asking for help is not a sign of weakness. It is a sign of strength. It models humility, encourages collaboration, and creates a culture where it is safe to admit when you are stuck.

I have faced plenty of situations where I felt out of my depth, like implementing new systems or navigating difficult conversations. Each time, asking for guidance from someone with more experience not only solved the problem but also made me a better leader.

Takeaway: The best leaders do not know it all. They know when to seek support.

5. Your Mental Health Sets the Standard

Your team looks to you for cues about how to navigate work-life balance and manage stress. If you are constantly burned out, they will assume that is the price of success.

What kind of culture are you modeling? If you want your team to prioritize their well-being, you have to start with your own. Showing up as your healthiest and most grounded self is one of the most powerful ways to lead.

For example, I learned to set boundaries around email after hours and to take mental health days when I needed them. Over time, my team began doing the same, and we saw a noticeable improvement in morale and productivity.

Takeaway: Lead by example. Prioritize your mental health, and your team will feel empowered to do the same.

6. Set Boundaries Without Losing Yourself

One of the hardest lessons I learned is that leadership requires boundaries. That does not mean you stop being your authentic self. It means protecting your energy and ensuring you are fully present when it matters most.

Balancing approachability with professionalism is key. You can care deeply about your team while still enforcing boundaries that keep everyone accountable. For instance, set specific times for availability or delegate tasks when you are overextended. Being transparent about your boundaries helps others respect them without feeling alienated.

Takeaway: Boundaries are not about creating distance. They are about protecting your ability to lead effectively.

?? Cold Hard Truth

Leadership is not about being liked. It is about being effective and getting results. Sometimes, making the right call means disappointing people, saying no, or enforcing standards. Growth rarely happens in comfort zones, and as a leader, you are in the business of growth.

Reflection Questions

Take five minutes today to reflect on these questions:

• How would you describe your team’s communication culture? What is one thing you could do to improve it?
• Are your relationships with your team and leadership as strong as they could be? What could you do to strengthen them?
• Do you feel comfortable asking for help? Why or why not?
• How are you modeling work-life balance for your team?
• What boundaries could you set to protect your energy while staying authentic?

?? Resource Recommendation

"Dare to Lead" by Brené Brown

This book dives into vulnerability, courage, and authenticity as cornerstones of effective leadership. If you are looking to deepen your leadership skills, it is an invaluable guide. Amazon

If you are struggling with some of these lessons, you are not alone. Leadership is not something you master overnight. It is a journey of constant learning and adjustment. The good news is you do not have to go it alone.

If you would like personalized coaching or guidance on building a thriving team, let’s connect. Whether it is one-on-one coaching or workshops, I am here to help you lead with confidence and purpose.

Keep leading boldly,

Ben