It was a few days into November of my 10th-grade year, and I had just put in work on the second day of basketball tryouts. I was sitting on a table in the gym lobby, feeling good about myself, watching the drizzle through the windows as I waited for the bus home. I balled out that day and felt like I was earning my spot in this new squad (I had attended a different school for my 9th-grade year, so I had to prove myself all over again). 

Just before the bus pulled up, our best player came up to me and said something I’ll never forget. “They ain’t cut you yet?”

The first words he ever said to me. 

Twenty-some years later, we’re still great friends. We went on to win a state championship together (albeit in football, not basketball). He went on to an NFL career. We shared plenty of adventures along the way.

Looking back, I believe that much of what made us successful on the field was our willingness to become comfortable with uncomfortable they-ain’t-cut-you-yet kind of feedback. We were ruthless. We had to develop thick skin to survive. And while most of it was standard fare adolescent shit talk, there’s no telling how much this served us when it came to pushing each other through the last sprint, studying extra film, or ego-checking whenever someone started puffing their chest a bit too much.

We had organically surrounded ourselves with a challenge network, decades before Adam Grant talked about it in Think Again. I hadn’t thought of my high school experience in that context until I read the book, and then it made so much sense. 

We naturally feel drawn to a support network–people in our orbit who complement, encourage, and give us confidence. But Grant argues that success is more often driven by a challenge network–the people we can surround ourselves with who will give tough love, disagree with us, point out blind spots, question our assumptions, and, ultimately, push us to greater heights.

This is where I’ve found that human-centered design and implementing a structured design thinking process can have an outsized impact.

It takes a special kind of confidence to be able to take they-ain’t-cut-you-yet feedback and use it as fuel. Most people don’t have it. I’ve found this to be especially true at work, where far too many ego-centric, ego-fragile “leaders” are shockingly incapable of taking any critical feedback.

Work should be all about building a challenge network–-I’d argue that building this might be the single highest ROI leadership objective and justification for what managers are paid. Unfortunately, many lack the confidence and self-awareness to do so. Instead, I’ve seen way too many use their direct reporting line as a support network, to validate their be right over do right attitude and protect their sensitive egos. Challenge their thinking or point out a blind spot, and you’ll find yourself looking for a new job.

A strong Design Thinking culture removes hierarchy-based fear and creates a safe cocoon in which to challenge ideas without the perception of challenging people (I don’t recommend saying “They ain’t fire you yet?” at work 🤣). But by stepping back and focusing on precise problem definition and then taking a structured, democratized, iterative path to a solution, the process inherently challenges everyone’s thinking regardless of rank or reporting line. 

In a nutshell, a Design Thinking culture normalizes the concept of a constructive challenge network in a way that doesn’t make anyone feel threatened, and that’s why I push to apply it all over any organization I work with.