What I had to unlearn when leaving a Fortune 500 company

After a long career in Fortune 500 companies, I found myself in a startup where I was invited to deliver a keynote speech in Paris. At first, my instincts told me that I should accompany the CEO, but I chose not to. Instead, I focused on crafting the speech, coordinating with the conference team, and ensuring the CEO's notes would be displayed on a monitor.

The talk was one of the best I've seen him deliver, and two years later, our team still references it. However, the downstage monitor I had planned did not materialize. This experience taught me a valuable lesson: unlearning some of the practices that were ingrained in me from my previous career. Over the years, I had built storytelling, judgment, creativity, customer understanding, and trust as the fundamentals of my leadership.

These skills remained important, but some of the scaffolding that supported them was outdated. Here are four things I had to unlearn since transitioning to a startup:

1. Don't rebuild the organization you left. A startup offers a clean slate, but it can also feel overwhelming when you realize certain roles are missing. The urge to fill these gaps can be strong, but I asked myself: "If we were starting this process from scratch, would we build it the same way?" The answer was no. I had spent years developing specialized expertise, such as shaping executive narratives and preparing leaders for critical moments.

At a startup, my focus was on creating a system where this expertise could travel and be easily adapted by others.

2. Don't just make the old job faster; redesign it. While using AI to expedite tasks can be beneficial, I became more interested in exploring how teams could reimagine their work processes. The questions I kept asking were: What context can we teach the system, where is human judgment most crucial, and how can we leverage expertise that once resided in another person's mind?

I had a marketing team member who wanted to transition into communications. Rather than solely teaching her new skills, I mentored her on preparing executives for podcasts and building social platforms. By sharing how we train our brand and executive voices, she gained the ability to adapt these skills independently. Her efforts led to the creation of a full thought-leadership campaign, and she even began developing platforms for other leaders.

3. Speed is about getting it right, not just faster. In the startup culture, speed is highly valued, and AI has amplified this need for instant results. However, I discovered that an AI workflow, although taking a few minutes to produce results, yielded a more accurate output compared to the usual instant response. The emphasis was on accuracy rather than speed alone.

I realized that taking a few extra minutes to ensure the correct output was more valuable than spending an hour on constant prompting and rewriting. Ultimately, the goal was to deliver high-quality results efficiently.

4. Being a strong leader doesn't mean being in every room. Reflecting on my experience in Paris, I realized that my job was to help ensure the CEO didn't need me. This realization extended to my team at Typeface. Sometimes, an opportunity that I would have traditionally owned was better suited for someone else. Sometimes expertise was more valuable when taught or embedded into a workflow that others could utilize.

Scaling oneself meant creating impact in rooms that I was not physically present in. In conclusion, my experience as a leader taught me that leaving a Fortune 500 company allowed me to unlearn certain practices and approach leadership differently. By questioning the systems built around the skills I had developed, I discovered the importance of democratizing expertise, emphasizing human creativity, and creating impact beyond the confines of my physical presence.

This journey of unlearning has given me confidence, curiosity, and the willingness to embrace change in both the work we do and the systems we rely on.