A tweet from Kelsey Hightower has been living rent-free in my brain:

Learn from the mistakes of others, because you can’t make enough mistakes of your own.— Kelsey Hightower (@kelseyhightower) May 8, 2024

One day at the beach, I laughed when my wife tripped in the sea. Minutes later, I tripped in the exact same spot. As I helped my dignity up, I remembered Kelsey’s tweet and wondered: Can we actually learn from others’ mistakes?

As a manager, being aware of and knowing how to handle diverse challenges (e.g., performance issues, internal conflicts, burnouts) is an essential skill. You can only run into a few of these challenges early on in your career. That’s why exposure to other people’s challenging situations can be extremely valuable in accelerating your growth.

All of this made me think of two recommendations that I’ve first heard from Lara Hogan here. I’ve found them very effective to get exposed to other people’s struggles and learn from their experiences: Manager Voltron and leadership dens. Let me explain.

Manager Voltron

A “Manager Voltron” is a diverse support network of trusted peers, mentors, and coaches that helps a manager navigate and overcome various challenges in their role.

Much like how the components of Voltron come together to form a stronger robot, building a diverse support network is vital to become a stronger manager.

I’m fortunate to have close friends in similar roles in different tech companies–they are my go-to people when I need to vent, and I learn a ton from them. I’m also in touch with a former manager I’ve considered an exceptional mentor. And I have a coach—another of Automattic’s perk—who helps me through all kinds of challenges, but especially stressful situations.

If you lack such a network, be intentional about cultivating relationships at your current company. Attending workshops at leadership conferences can also be a good start—the setting can definitely help create strong bonds.

Engineering Leadership Dens

Another way to learn and build your network is through leadership dens. A leadership dean is a group setting that allow leaders to discuss challenges, share experiences, and gain insights from different perspectives in a safe environment.

Initially skeptical, I’m now a convert. People will share their real struggles if they find themselves in a safe space. That’s when these calls become more valuable. Performance issues, conflicts among peers, burnouts. The juicy stuff. I also must confess I’ve left some of these calls feeling relieved not to have to deal with some of these challenges yet. But I always leave learning something new. My favorite part is hearing from people with different levels of experience and leadership styles.

I also enjoy suggesting things I’ve read in books but never had a chance to put into practice. And then following up to see how it went. It’s a low-stakes way of learning through others.

If you have a similar initiative at your organization, join it. Thank me later. If you don’t, it’s super easy to replicate: Vegas Rules, an agenda, and someone taking the facilitator role.

Conclusion

As I stated initially, I’m unsure if we can learn from others’ mistakes. However, being exposed to other people’s experiences can definitely help you grow faster in a leadership position. Here I shared two of the ways that I’ve found effective in my career:

• By cultivating a support network you can become a stronger manager. Surrounding yourself with trusted peers, mentors, and coaches builds your resilience and decision-making skills. This network becomes your sounding board—offering advice, sharing lessons learned from their own experiences, and providing emotional support when things get tough.

• And by taking advantage of leadership dens you get exposure to a wide variety of issues, how people with different management styles deal with them, and you get a chance go give back by sharing your own experience.

I’m sure there are other effective ways out there. What were yours?