Permission to fail

Leaders often grapple with the challenge of finding the right balance between micromanaging and giving their teams the freedom to learn from their mistakes. Early on, my own approach involved identifying risks, discussing mitigation strategies, and, when things went wrong, issuing the dreaded “I told you so.” Over time, I’ve learned the importance of fine-tuning my communication to make it constructive throughout the process, but it’s still a delicate balance.

This dynamic is very similar to parenting. As parents, we frequently find it easier to set boundaries for our kids than for our team members. At home, things feel more straightforward—if you drop a plate, it breaks; if you touch something hot, you get burned. Consequences are often immediate and clear-cut. The longest delay might be failing a test due to a lack of studying, but even then, it’s a direct and teachable moment.

When my oldest child, who has always been interested in cars, started practicing for their driver’s test, they already had extensive experience with different types of vehicles—from golf carts to dump trucks. In contrast, my youngest, who’s just starting to learn to drive, feels nervous behind the wheel of a car. My first instinct was to let them learn through trial and error, but then I paused. Unlike a broken plate, mistakes on the road could have far more serious consequences, including injury.

At home, we constantly communicate what’s safe and what isn’t, where are the boundaries, and what are the consequences for crossing them?

But what about at work? How often do we, as leaders, clearly define boundaries? How frequently do we give our teams permission to explore and take risks, and do they know where the limits lie?

AND Interestingly, there’s often an assumption that engineering teams will naturally push the boundaries. But I’ve seen the opposite too: teams that are so comfortable that they hesitate to take any risks at all, like a teenager who isn’t interested in getting a driver’s license or can't decide what to do post highschool. In life, milestones like buying a first car or home are built-in motivators that help measure growth. But at work, someone could stay in the same role for years without feeling motivated to try something new or push past their comfort zone.

So, what do you do as a leader to cultivate growth in your team?

For me, I value teams that have a range of risk-takers. It challenges me to set thoughtful boundaries while also encouraging creativity. I want a team that understands the business and can see both its present and future needs. Part of my role is ensuring they have the right information and reminding them of it when needed.

It’s easy to assume that as teams mature, leading them will get easier. But, much like with kids, the challenges only seem to grow.