3 Speed-Bumps That Almost Derailed a Leading Voice in Product Growth
"I didn't handle feedback very well"
"One day, my CMO sat me down and said, 'I can't stop thinking about what you said in that meeting a week ago'"
It wasn't meant as a compliment.
Aakash Gupta is a former VP of Product and Growth, turned creator. Today he publishes of one of the largest Product Growth newsletters in the world. But before all of that, he faced one of the toughest feedback moments in his career that forced him to completely re-evaluate his leadership style.
Aakash was working in growth at thredUP, an online thrift store, and they had just hired a new Director of Brand. One day, Aakash was in a meeting with the new Director when he shot down one of her ideas in an unprofessional way.
"In retrospect, I wasn't being open to their ideas or opinions."
"I was in full founder mode, just dropping bombs and zingers every other sentence," he shared during our conversation.
"It was always for the reaction, always for the boom. I was a debater in high-school so it was a big part of my identify at that time."
Afterwards, the CMO cared enough to pull Aakash aside to have a conversation about his actions. But, he didn't respond well to that feedback either."
"I managed to have the most immature response ever," he said.
So not only did Aakash not present himself well in the original meeting. His reaction to the feedback wasn't great either. A double-whammy.
Although it was painful at the time, he referred to the moment as a "wake up call" that transformed his management and leadership style forever.
Here’s how Aakash changed his leadership style (that you can apply too).
Leading with integrity: being a leader is more than making strategic decisions and executing well against your goals - the way you get there matters. How people feel along the way really matters. Prioritize a team environment that brings out the best in everyone.
More inward attention: pay attention to how you represent yourself in meetings and conversations to identify where you need to evolve. In addition to the direct feedback from his CMO, Aakash spoke about how getting more sleep and a daily meditation practice gave him the mental space to evaluate his actions more objectively - and more frequently.
Shifting from founder mode to manager mode: Aakash stopped being the person who tried to have every answer and solve every problem himself - and instead started helping other people solve problems.
These changes have enabled him to be less combative - and more effective.
We all face career challenges that test our confidence and self-worth. How we navigate these moments shapes who we become as leaders.
Other highlights in our conversation:
Navigating the ego hit of a failed startup in his twenties.
When putting a team member on a PIP goes horribly wrong.
His tips for managing imposter syndrome while leading fast-growing teams.
This episode is perfect for team leads, new managers, and anyone navigating leadership challenges, self-doubt, and personal growth.
Catch our full convo to hear Aakash’s full story.
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