How to evaluate your next leadership role
Observation 🧐
I had a coaching conversation with a former sales leader.
Here's his story: After years as a successful AE, he stepped into his first management role, which he did for a year. Then, due to some corporate restructuring he went back to carrying a bag. Now he's questioning everything. Is he cut out for leadership? Should he try again or just stay as an AE for the foreseeable future?
The situation he inherited would challenge even seasoned managers. An underperforming team. A toxic team member who had applied for the same role and was actively undermining him. Impossible targets. A lack of support from above.
His experience got me thinking: How many talented people write off leadership entirely because of one difficult first experience? And more importantly, how can we better evaluate whether management is truly for us?
In our conversation, I shared with him the framework I use to evaluate any new leadership opportunity. This framework can help assess any new leadership role you're considering.
The 3 P's Framework
Your management experience is shaped by three critical factors that are largely out of your control. Here are the decision criteria I use to assess new opportunities:
1. People - Who are you Leading?
The team you inherit makes or breaks your management experience. There's a world of difference between:
The Dream Scenario: Leading high performers who are coachable, collaborative, and hungry to grow
The Challenging Scenario: Managing underperformers, dealing with toxic team members, or navigating complex personality conflicts
My client had inherited someone who felt passed over and entitled to his role. That person spent months undermining every decision, poisoning team dynamics, and creating an environment where progress was nearly impossible.
The other driver of performance is the tenure and skill level of your team. Leading a team of junior sales people in their first closing role is very different from leading a group of mature reps who are selling to Enterprise customers. It’s like a teacher deciding whether or not to teach kindergarten versus high school. Very different students, yet each experience is rewarding in its own way.
The lesson: If your first management experience involved difficult people dynamics, that says more about the situation than your leadership potential. The caliber of talent you’re leading also matters. The tenure of your team will greatly impact your experience.
2. Product - What are you selling and do you enjoy the sales motion?
The complexity of your go-to-market motion dramatically impacts your management experience:
There is such a spectrum here from
Simple, Proven Products: Clear value props, established processes, predictable sales cycles
Complex, Emerging Products: Undefined markets, evolving messaging, longer deal cycles, more rejection
There’s no right or wrong here, rather you need to understand what you enjoy most as a seller. If you hate prospecting and you’re leading an outbound SDR team, there’s a misalignment with your skillset.
If you thrive when you are the key salesperson, you may struggle if you’re leading a team of specialist sellers who are brought into a deal cycle already in flight.
The lesson: Product complexity and market maturity create different management challenges. You need to find the selling motion you will thrive in.
3. Performance - What is the baseline?
The performance baseline of your team sets the entire tone of your management experience:
High-Performing Teams: You're coaching from strength, optimizing what works, managing up-and-to-the-right trajectories
Struggling Teams: You're in crisis mode, having difficult conversations, rebuilding confidence while hitting numbers
Taking over a team that just crushed their goals versus one that's missed three quarters in a row are completely different jobs requiring different skills and creating different stress levels. Some managers love the challenge of a rebuild, others don’t.
The lesson: Turning around underperformance is one of the hardest aspects of management. If that's what your first experience demanded, you were essentially starting on expert mode.
You need the right environment to thrive as a leader.
For those new to leadership: don't judge your leadership potential based on one challenging situation shaped by factors outside your control. Instead, focus on the fundamentals. Leaders must enjoy the fundamentals of coaching and developing talent.
Did you care about your people's success and development?
Were you willing to have difficult conversations?
Did you take ownership of results, even when circumstances were tough?
Are you energized by helping others win, or do you prefer individual achievement?
Leadership isn't for everyone, and that's perfectly fine. Some of the best individual contributors I know have tried management, realized it wasn't their path, and returned to roles where they could maximize their impact and satisfaction.
But if you're writing off leadership because your first experience was difficult, consider this: you might have just been dealt a challenging hand in a complex game you were still learning to play.
The right question isn't "Am I cut out for leadership?". It's "Given different circumstances (the right people, product, and performance baseline) would I want to try again?"
Sometimes the answer is still “no”, and that's valuable self-knowledge.
But sometimes, it's a “yes” because what you really need is another shot with a better hand of cards.
Thought Starter 🤔
Love 🥰
For Mother's Day this year, my husband gave me a book “Decisive” by Chip and Dan Heath. The subheading reads “How to make better choices in Life and Work”. I'm not going to lie, I was mildly offended (Does my husband think I make bad choices? I did chose him…) but once I started reading, I became grateful. The book opened my eyes to the flaws in typical decision making processes (and why Pros and Cons lists are problematic) and how to open up the aperture to find the best path forward.