My Top 3 Challenges In Transitioning To Leadership

Transitioning into a leadership role is challenging…
 
When I started as a Senior Account Executive at my last company, I remember the day I told my CEO about my goal to one day have a seat at the boardroom table with the rest of the leadership team.
 
I loved being in sales, but I knew management was what I was working towards. I wanted to play a role in developing strategy and influencing the direction of the company. But I especially wanted to have a team of up-and-coming sales reps that I could help develop and coach. I was big on building a solid team that supported each other’s individual achievements and rose together as a group.
 
The opportunity to take on the leadership of the sales team came faster than expected. I was so excited, and I was fortunate to have an extremely committed leadership team that were focused on supporting me through the transition.
 
Here were the three biggest challenges in my first twelve months as Sales Director:

Transitioning from a peer to a boss

It’s normal for sales reps to have a complex relationship with each other. Our sales team was close; we had built friendships that existed beyond the office. But we were also competitive with each other, always striving to be the team’s top performer.
 
When I was promoted to the Sales Director role, I went overnight from peer to boss. At first, I struggled with wanting to maintain the strong relationships I had with the team but also step into this new role where authority and respect were necessary. I knew I was subject to “executive privilege” and there was information I would have access to that I couldn’t share with my team. This was challenging and isolating at times.

Redefining what “value” meant for my new role

Before I transitioned onto the leadership team, I was the top performing sales rep. The value I brought to the company and my success was determined by the amount of revenue I brought into the company. When I took over the sales team, I was no longer responsible for directly generating revenue. This was a challenge because for my whole career, the value I brought to a company was clear; the more I sold, the more valuable I was. In this new role, I was forced to redefine value without stepping on the toes of my team and becoming a micromanager.
 
My ego took a hit at the beginning. I was indirectly responsible for the entire revenue number, but in turn lost the status of top performer. I was happy for my team, but it took a few months to drop the competitiveness I was so accustomed to. I had to fully embrace the reality that my team’s success was my success.

Dealing with the voices in my head telling me I wasn’t good enough, old enough or experienced enough for this role

 Everything always comes back to mindset. Even if you have been working towards a goal for a while—and you do all the things you need to do to achieve it—once you “make it,” you often feel like an imposter. For the first few quarters, imposter syndrome followed me around. I would beat myself up for not having more experience. I would constantly wonder if the team was benefiting from my leadership. And, in my one-on-one’s with my boss, I would feel like I always had to prove my worth.
 
Stepping into a leadership role for the very first time can be exciting, motivating and rewarding. But it can also be challenging, draining, and isolating.
 
At the beginning of this transition, the way I showed up and the way I felt inside my head were very different. I showed up confident, appearing like this was a natural progression. But in reality, it was hard. It took a lot of mindset work to navigate through the challenges of this big career leap.
 
Now I’m able to help other leaders overcome their mindset blocks and show up confidently without losing themselves along the way. If you have made this jump to a leadership position—and you’re looking for some support to navigate the transition—reach out! I’d love to work with you!

chat soon!

Sylvana