Thinking Bigger

I’ve had hundreds of conversations with executives over the past year. Naturally, I like to ask them what their most significant current challenges are and how they intend to improve their organizations or companies. Frequently, the answers are very milquetoast, without a scintilla of genuine aspiration. The usual suspects include “improve quality of service X,” “have happier people,” or “deliver the roadmap.” Like people deep in the trenches, they are missing the bigger picture. When you are thinking too small, you limit your possibilities and, in my opinion, your eventual improvement.

After all, thinking small is like looking for local optimizations. You might make things better but miss out on the major opportunity around the corner. When your biggest wish is to make your team improve quality standards, what are the odds that they’ll suggest a new way of automating half of the day-to-day customer success requests? A team that is told achieving what it commits to in sprints is likely to become really good at buffering rather than gain remarkable momentum.

Sometimes, you have to think big. Allow yourself to imagine what a truly remarkable year would look like and work backward from that. Yeah, you’ll likely realize significant portions of that vision are not doable, but what about the things that are?

Examples of Teams Crushing It

I want to provide you with three cases where teams I worked with recently made real leaps in productivity.

Realignment on value: One newly-appointed VP I was working with talked to me about a slew of goals, initiatives, and tasks he was juggling. Edging him to think bigger, we worked to distill the areas that would provide the business the most impact and clarity in their stage (working toward product-market fit). Instead of imagining a “perfect path,” he started by painting a picture of the wanted future state and worked from that. Fast forward a bit, he told me their R&D team crushed it and achieved its objectives two months early.

Redoing it all: Another startup I was working with was going through growing pains, and things seemed to be getting slower and worse rather than improving. The executive team spent a couple of quarters attempting iterative improvements, which were not moving fast enough. Again, I urged the entire company’s leadership team to collaborate and think bigger. They reimagined the entire product-engineering flow from the ground up. Teams were reforged, processes swapped, role definitions changed, and the strategy was adjusted. Shortly after, one of the executives told the team, “Do you realize we just moved 3-4 times faster this sprint?”

Smarter, not harder: A CTO was racking his brains about scaling the team’s ability to onboard new clients. It has become a bottleneck for the business, and he consulted me about streamlining the process to solve the issue. Thinking bigger, we imagined, “how would Amazon/Meta/Stripe solve this?” That unlocked a different way of thinking. We were no longer looking for ways to type faster. That resulted in some clever innovations for automating significant parts of it and systematizing the others. That portion of tech capital probably saved that company 30-50% of its R&D time.

Your Turn

Each of these stories is different and shows that innovation can come in many shapes and sizes. However, it won’t happen if you don’t make the space for it. Talk about thinking bigger to your directors and your executive team peers. Avoid the urge to just double down and try harder when things are challenging. Get some external perspective. If you cannot work with a trusted advisor like myself, find peers you can talk to. For example, I invite you to join my new community for execs in tech. It’s closed and free; details here.

Once you spot an opportunity, put all your attention there. A new point of leverage means you should place yourself as the fulcrum. Real executives should not be bogged down with busy work but enable precisely these sorts of leaps forward for the company. Don’t do your role a disservice.

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