During my early days at Davincified, I walked into a board meeting with a complete rebranding plan. Our customer acquisition costs were increasing and I was confident I had the solution, some substantial social media programs directed toward art enthusiasts. I was eager to get started. Halfway through my presentation, our CEO, stopped me, "Jacob, have you ever asked our customers directly why they're buying?" I had not. I was pitching a solution and proving my marketing capabilities, I had skipped over the listen phase. The following week, I dedicated my time to customer calls. It was humbling to learn, a total disconnect from what I thought. Rather than looking to buy art, they were seeking to connect to family members, create gifts with impact, look for something to do when distracted, and meditative activities to relieve stress. My targeting of 'art enthusiasts' would have ignored the core customer. That experience taught me, the credibility of an executive, is not found in finding the answer first, it can be built by asking better questions first. For now on, in any new environment, I spend my first 21 days being a listener. Here is what I learned, the very moment you begin to believe you are the smartest person in the room is the very moment you become the most dangerous. Leadership is not about demonstrating what you know, its about learning what you don't know. And, sometimes, that humility is the difference between program beauty and destruction of something the customer held as value.
After nearly 30 years in architecture, I've learned that prescribing solutions before understanding kills deals faster than anything. When I was establishing KDG, I walked into meetings armed with design ideas and construction knowledge, ready to impress with my expertise. The turning point came during a residential project where the clients wanted to tear down an existing cottage in Oakwood. Instead of immediately presenting my grand vision for a replacement, I simply asked "What don't you like about the current house?" That question changed everything. I spent two weeks really listening to their concerns and studying what they already had. Rather than the new construction they expected, I proposed changing their American cottage into a craftsman style that addressed every issue they raised. When I presented those sketches, the homeowner cried tears of joy. That project taught me our tagline should be "designing with--not just for--clients." Now I spend entire first meetings just listening, and our close rate jumped dramatically. The clients who hire us consistently say they chose KDG because we were the only firm that truly understood their needs before proposing anything.
When I joined Lusha's leadership team, I felt the urge to suggest new sales processes right away, but I held back. I started asking our sales leaders what patterns they noticed in stalled deals and where they felt blocked by the CRM. The real headache with scaling was cultural resistance, not the tools themselves. By listening first, I shaped a rollout that blended into their workflow and made adoption smoother, which ultimately strengthened my credibility.
In my early days of leading SaaS teams, I thought jumping in with solutions right away showed strength, but I quickly learned it had the opposite effect. During a leadership transition at CLDY.com, I spent weeks just listening to the existing engineers and product managers describe their workflows before suggesting any changes. Between you and me, this patience uncovered pain points I would have missed, like minor process bottlenecks that looked small but created a huge ripple effect. Holding back my expertise didn't weaken my standingit actually built trust and made them more open to my eventual strategies.
Once, I went into an interview with a blockchain project prepared to show my strategy, but I did not. I asked about the campaign metrics they utilized to measure the effectiveness of their past campaigns, how much they spent, and what they thought was missing. They even mentioned that they had spent almost $100k on multiple agencies, but they received very little measurable value. That changed the entire dynamic, because I was listening more than speaking, I could identify gaps in their project's internal communication, and I could see their current investors outreach campaign was failing. When I eventually shared my plan, it was rooted in their reality, instead of theory, which made me a more enticing option.
When I was being interviewed for SonderCare, I was ready with lots of ideas but chose to listen instead. The team opened up about their struggles on how to position the brand as a trusted name in the home healthcare. Knowing those things has enabled me to see the areas the brand struggled with before offering solutions. I wanted to build with them, not over them. Once I took on the role, I did the same with our clients. I took the time to listen first so I can explain how our beds could provide safety and dignity. I truly believe that listening before taking action has made my leadership stronger and it helped me guide the company through consistent growth. Listening first has become the foundation of how I approach every decision I make today.