Stepping into a sales leadership role isn’t just about managing people or coaching your team to close more deals. It’s a complete shift in how you think, operate, and handle responsibilities. The skills that helped you crush it as a closer are valuable, but they won’t be enough to lead a team, especially in a remote setting.

Before making the leap, it’s critical to ask yourself: Do I have what it takes to lead? In this newsletter, I’ll walk you through a self-assessment that will help you evaluate your leadership potential and uncover any areas you might need to work on before stepping into a management role. This isn’t about perfection—it’s about being honest with yourself and knowing where you need to grow.

The Biggest Misconception About Leadership

Many closers think that the only thing they need to do as a leader is get their team to close better deals and stay on top of the pipeline. While that’s part of it, being a leader means seeing the bigger picture: how the offer is performing, how the team is functioning, and what data points are telling you about performance.

It’s not just about being a better closer—it’s about making data-driven decisions, empowering your team, and addressing challenges before they become problems.

The Hardest Shift for Most Leaders

One of the hardest shifts I had to make when transitioning to leadership was letting go of taking calls myself, even when I knew I could close them. Instead, I had to let my team handle the calls, assess their performance afterward, and coach them from the background. That shift—from being the one closing to empowering others to do it—was tough, but necessary.

The truth is, leadership means trusting others to do the job you used to do and coaching them to get better, rather than taking over.

Take This Self-Assessment: Are You Ready to Lead?

Now, let’s get practical. Here’s a self-assessment to help you determine if you’re ready to take on a leadership role. Answer each question honestly to see where you stand.

1. Can You Trust Others to Close, Even When You Know You Could Do It Yourself?

• Letting go and allowing others to step up is crucial. Can you take a step back and guide them instead of jumping in to close the deal yourself?
• Rate yourself:
  [ ] Struggle to let go
  [ ] Can delegate but check in constantly
  [ ] Trust my team and coach from the background

2. How Well Do You Communicate with Your Team?

• Leaders communicate expectations clearly, offer feedback consistently, and create an environment where team members feel comfortable asking questions. Do you?
• Rate yourself:
  [ ] Rarely communicate clearly
  [ ] Communicate but often need to clarify
  [ ] Clear communicator who fosters openness

3. Are You Data-Driven?

• Leadership is about more than just gut feelings. Are you able to make informed decisions by looking at data points like show rates, close rates, and team performance metrics?
• Rate yourself:
  [ ] I don’t focus on data
  [ ] I look at data occasionally
  [ ] I consistently use data to drive decisions

4. How Do You Handle Underperformance?

• Great leaders don’t avoid tough conversations. Are you willing to address underperformance directly, hold your team accountable, and provide support where necessary?
• Rate yourself:
  [ ] Avoid difficult conversations
  [ ] Can handle conflict but get uncomfortable
  [ ] Address underperformance directly and constructively

5. Do You Put the Team’s Success Over Personal Wins?

• As a leader, your team’s success should be your priority. Are you able to shift your focus from personal achievements to ensuring your team thrives?
• Rate yourself:
  [ ] I still focus on my personal success
  [ ] I try to balance personal and team wins
  [ ] I prioritize the team’s success over my own

6. Do You Stay Up-to-Date with Industry Regulations and Best Practices?

• Leadership requires staying informed, especially about regulations like FTC guidelines. Do you stay current with industry practices and lead by example?
• Rate yourself:
  [ ] I’m unaware of current regulations
  [ ] I know some but not all regulations
  [ ] I stay up-to-date and keep my team informed

What Your Results Mean

If you scored low on any of these questions, don’t worry—it just means there’s room to grow. Leadership is a journey, and the more you develop your communication skills, your ability to make data-driven decisions, and your comfort with addressing underperformance, the more effective you’ll be when you step into that role.

Remember: it’s not about being perfect. It’s about being aware of your strengths and weaknesses and having a plan to improve.

What to Do If You’re Not Quite Ready

If you’re not quite ready to lead, that’s okay. Leadership is a skill that develops over time. Here are a few steps you can take to start preparing:

• Shadow a leader: Spend time with someone who’s already leading a remote team and observe how they handle challenges.
• Get comfortable with data: Start tracking performance metrics across your team or account. The more you understand the data, the better prepared you’ll be to lead.
• Work hand-in-hand with decision-makers: Learn how decisions are made at a leadership level and what factors are considered when making strategic moves.

By doing these things, you’ll develop the skills and mindset needed to step confidently into leadership.

Conclusion

Being a leader isn’t just about doing more of what you did as a closer—it’s about thinking bigger, making data-driven decisions, and guiding your team to success. The self-assessment you took today will help you identify areas where you can improve and grow as you work toward becoming a high-performance leader.

Next week, we’ll dive into how to build critical thinking in your team and why coaching your reps to make better decisions is more effective than micromanaging their every move.

Call to Action

If you’re serious about leveling up your leadership skills, I’m creating an exclusive community designed to help you grow faster. Inside, you’ll get:

• Custom GPT tools to enhance your decision-making and leadership.
• Step-by-step ClickUp setups to streamline your team’s processes.
• In-depth leadership strategies to help you build high-performing remote teams.

If you want early access, reply to this email and I’ll make sure you’re first to know when we go live!