Executive Director, Entrepreneur, and Business Coach at Darby Integrative Counseling, LLC
Answered 6 months ago
As both a Psychotherapist and Executive Coach, I am trained to recognize the profound value of silence and attunement, but I was reminded of its power most vividly when restructuring my organization from a contractor model to an employment-based practice. As the CEO of my group psychotherapy organization, I entered a staff meeting intent on unveiling a carefully crafted organizational restructure, including all the bells and whistles of an employment benefits plan. Yet upon my initial announcement of the change, I immediately sensed the room was saturated with unease and unvoiced questions. In that moment, I paused and told myself, "Andrew, this is not a time for declarations, listen to your staff!" I set aside my agenda, allowed their concerns to unfold, and listened not only to their words but to the emotional timbre beneath them. That pause created a crucible for trust, transforming the meeting into a dialogue rather than a monologue. Only then could I frame the changes as a shared path forward, one grounded in both business opportunities and respect for my staff's questions & concerns. The experience reaffirmed what my dual vocations teach, and that which is so easy to forget: true authority is not asserted through the swift display of expertise, but through the disciplined art of listening, where credibility and collective commitment are quietly but indelibly forged.
Earlier in my career, I made the mistake of walking into high-stakes interviews eager to prove my value by immediately outlining solutions. I thought showcasing expertise upfront would demonstrate confidence, but instead it sometimes came across as prescriptive or tone-deaf, because I hadn't yet earned the context or trust to make those recommendations. The turning point came during an executive-level interview where, instead of jumping in with frameworks and strategies, I deliberately shifted my approach to listening. When asked about challenges, I responded with curiosity rather than immediate answers: "What's driving that issue internally? How has the team been approaching it so far? What's worked and what hasn't?" That line of questioning opened the conversation in a different way. The executives on the other side leaned in, shared more candidly, and I could see the dynamic shift—they weren't evaluating me as a consultant pitching solutions, they were experiencing me as a leader who wanted to understand their world before shaping a path forward. Ironically, holding back my expertise strengthened my credibility far more than showcasing it would have. It signaled respect for the existing leadership, empathy for the people on the ground, and the awareness that lasting solutions rarely come from quick fixes. When I did eventually share perspectives, they landed better because they were connected to the specific context I had taken the time to uncover. That experience taught me that executive leadership isn't about proving how much you know in the first five minutes—it's about demonstrating judgment. Listening first shows that you're not just smart, but wise enough to build trust before prescribing change. In the long run, that credibility is what sets strong leaders apart.
I learned this lesson early in my executive journey, and it completely changed how I approach leadership and interviews alike. I once interviewed for a senior strategy role at a growing tech firm that was struggling with profitability despite rapid expansion. Eager to impress, I initially went in with a long list of "fixes" and frameworks I'd used successfully elsewhere. Within minutes, I realized I was talking more than listening—and watching the leadership team's expressions, I could sense I was missing the mark. So, in the second round, I completely shifted my approach. Instead of showcasing my expertise upfront, I focused on asking thoughtful questions: What do you see as the biggest barriers to sustainable growth? What's worked so far, and what hasn't? The conversation transformed. Their tone relaxed, and they opened up about internal tensions, cultural challenges, and gaps that weren't visible from the outside. By the end, it wasn't an interrogation—it felt like a collaborative strategy session. That experience taught me that restraint can be a form of strength. Executives don't need to prove how much they know right away; they need to demonstrate curiosity, emotional intelligence, and strategic listening. When I finally shared ideas, I could tie them directly to the organization's pain points because I truly understood them. Ultimately, I got the role—not because I had the flashiest solutions, but because I showed respect for their journey and a willingness to learn before leading. Since then, I've made it a rule: listen first, diagnose second, prescribe last. It's a simple mindset, but it's what earns trust and credibility faster than any impressive resume ever could.
Yes. Early in my career I thought credibility meant proving expertise fast. I'd show up with solutions in hand. It backfired—leaders didn't feel understood. What changed was when I began working as a fractional CMO. CEOs would come to me drowning in data. My instinct was to prescribe fixes right away. But I realized most didn't need a marketing playbook in the first meeting. They needed someone to listen, to understand their language, and to see their world first. So instead of leading with my knowledge, I borrowed from my years as a professor. I'd frame a simple hypothesis—"Here's what I think might be happening, but let's see if the data agrees." That approach showed them I wasn't rushing to be the smartest person in the room. I was there to help them make sense of complexity. The result: stronger trust, faster buy-in, and contracts that grew into long-term partnerships. It taught me that listening first isn't passive—it's the most strategic move. When executives feel seen and understood, your expertise lands ten times harder.
In the early days of Eprezto, as a first-time founder, I often felt the urge to come across as the one with all the answers, especially when meeting potential partners or investors. Over time, I learned that listening first often carries more weight than prescribing solutions too soon. A good example came when we were in talks with a major insurance carrier about integrating our platform. My instinct was to pitch features and processes we thought were best. Instead, I chose to hold back and spent the first meetings asking detailed questions about their workflows, pain points, and compliance constraints. By doing that, we discovered that their biggest barrier wasn't what we had initially assumed, it was how their internal underwriting process worked. Had I rushed to prescribe our solution, we would have come across as misaligned and risked losing the opportunity. That experience taught me that credibility as a leader doesn't come from having all the answers upfront, but from demonstrating that you understand the context before proposing change. Listening first not only strengthened our partnership but also shaped a more effective solution.
In a recent executive interview I felt the urge to jump in and start solving the problems they mentioned. Instead I paused and asked lots of questions about their business, culture and priorities. By listening closely I was able to uncover things that weren't obvious from public information. This allowed me to provide thoughtful insights later in the conversation rather than generic advice. The interviewers later told me they appreciated my measured approach and ability to absorb context before acting. It increased my credibility because it showed patience and strategic thinking - things they valued in a leader. I learned that holding back from the urge to "fix" the problem can actually show confidence and adaptability - you lead by understanding first, then act with precision.
I remember an interview for a leadership spot in the trading tech world. My first instinct was to just unleash everything I knew about forex and digital marketing strategies. But I caught myself. Instead, I genuinely focused on hearing their real pain points, trying to understand the nitty-gritty of their challenges. I quickly learned they were struggling with growing their user base while keeping everything compliant. By truly listening, I uncovered blind spots I never would have guessed, such as their limited use of data-driven insights. When I eventually shared my perspective, it landed because it was custom-fit to their exact situation. This approach didn't just boost my credibility; it demonstrated my capacity for building essential trust in business development and trading circles.
Throughout my career Trading, especially when moving from Business Development Director to Chief Executive Officer at TradingFXVPS, I absorbed the significance of initially hearing out others to genuinely grasp a company's requirements and hurdles. For instance, during a critical client collaboration discussion, my initial instinct was to propose solutions immediately based on my expertise. However, I held back and prioritized comprehending their operational difficulties and distant objectives. This approach not only solidified confidence but also enabled me to customize a tactic that surpassed their anticipations. This experience reinforced the value of patience and listening as foundational to leadership credibility and building lasting relationships in trading.
After graduating, I built Kate Backdrops and quickly learned the importance of listening before assuming. I recall a client with very specific event backdrop needs. My first thought was to suggest one of our ready-made designs that seemed suitable. As I listened more closely to their needs, I realized they were seeking something unique and personalized—a custom design that truly reflected their brand and theme. Rather than imposing my ideas, I stepped back and focused on fully understanding their vision. After several meetings and discussions, we came up with a completely customized backdrop design that exceeded our client's expectations. They were thrilled with the end result and it truly elevated their event to the next level. This experience taught me the importance of active listening and truly understanding a client's needs before offering solutions. It also showed me the value of creativity and thinking outside the box when it comes to designing for events.
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.
Early in my career, I made the mistake of jumping too quickly into "solution mode" during executive interviews. I thought demonstrating expertise meant prescribing fixes right away. What I learned later is that this approach can unintentionally signal arrogance or a lack of respect for the organization's unique context. One pivotal moment came during an interview for a senior strategy role. Instead of outlining a 90-day plan on the spot, I shifted my approach: I asked thoughtful questions about the company's culture, its pain points, and what success looked like to the board. I listened more than I spoke. At the end of the conversation, one of the panelists remarked, "You didn't try to fix us—you tried to understand us. That's what makes you credible." The result was not only a job offer but also a stronger foundation of trust when I stepped into the role. Because I hadn't overpromised, I had the space to co-create solutions with the leadership team. Within six months, we launched a new client retention initiative that improved renewal rates by 18%. The key takeaway: executive credibility is built on curiosity and restraint, not quick fixes. By holding back expertise until you fully understand the organization, you demonstrate humility, emotional intelligence, and the ability to lead collaboratively—qualities boards and teams value far more than instant answers.
As someone who's been running Loudoun Roofing for over two decades, I learned this lesson the hard way during a major commercial project in 2018. The property manager called about "obvious water damage" and I showed up ready to pitch a full membrane replacement based on their description over the phone. I started explaining TPO vs EPDM systems and throwing around technical terms about ponding water and flashing details. The manager kept interrupting with budget concerns, but I kept pushing my expertise until he finally said "Do you even know what building this is?" Turns out it was a historic property with strict preservation requirements that made my standard solutions completely unusable. When I stopped talking and started asking questions, I finded they'd already gotten three quotes for full replacement but needed someone who understood historic building codes. By listening first, I learned about their real constraint--maintaining the building's historic designation while solving drainage issues. That project became a $180K job using specialized materials I wouldn't have considered initially. More importantly, that property management company has referred us for 15+ additional projects since then. Now I always start consultations by asking "What's your biggest concern?" instead of launching into solutions.
As founder of ilovewine.com, I learned this lesson the hard way when I first approached California wineries for partnerships. I'd walk in armed with analytics about our 500k community and immediately pitch collaboration ideas. The breakthrough came during my early meetings with Central Coast producers who seemed polite but unengaged. Instead of pitching our platform's reach, I started asking what challenges they actually faced in connecting with consumers. One Paso Robles winemaker revealed they were drowning in requests for generic coverage but starving for storytellers who understood their terroir. That conversation completely shifted how we approach partnerships. We developed our destination travel guides and food-first features specifically because winemakers told us they needed content that captured their craft's cultural context, not just tasting notes. Our most successful collaborations now come from wineries who feel we truly understand their story first. This approach transformed our editorial strategy too--when covering wine festivals like Emily Kaufmann's California Wine Festival, I spend time understanding their vision before suggesting coverage angles. The result is content that serves both our audience and partners authentically.
As a wedding photographer who's built Candid Studios from a local Fort Collins operation to a multi-state company documenting 1,000+ weddings, I learned this lesson the hard way during a consultation with a high-end Denver couple planning their $80K wedding. I walked in ready to impress with our AI-improved editing capabilities and cinematic techniques. Within minutes, I was showing portfolio examples and explaining our advanced post-production workflow. The couple seemed polite but distant, and I could feel the energy shift. Finally, I stopped talking and asked what their biggest fear was about their wedding day. The bride broke down explaining how her sister's photographer missed capturing their grandmother's reaction during vows--their last family wedding before she passed. They didn't care about AI editing; they needed someone who understood the irreplaceable human moments. I shifted completely to listening about their family dynamics, who the key people were, and what moments mattered most beyond the standard shot list. We spent an hour creating a personalized approach around their grandmother and family story. They booked our premium package that same day, and that wedding became one of our most referred projects, directly leading to 12 additional bookings worth over $60K.
As someone who handles client services and marketing outreach for Limitless Limo in Columbus, I learned this lesson during my first major corporate account pitch with a Fortune 500 company needing executive transportation. I walked in ready to showcase our Mercedes Sprinter Executive and started pitching luxury amenities before understanding their actual needs. The executive stopped me and explained they were dealing with consistent late arrivals to board meetings due to unpredictable traffic patterns around their downtown location. I shifted to asking about their current transportation challenges, typical routes, and meeting schedules. Turns out they needed reliability and local traffic expertise more than champagne service. By listening first, I finded they valued our flight tracking technology and chauffeur knowledge of Columbus traffic patterns over flashy vehicle features. This approach helped us secure a $50,000 annual contract because we addressed their real pain point - punctuality for high-stakes meetings. Now I always start client consultations with questions about their specific transportation challenges before proposing any vehicle or service solutions.
As a clinical psychologist who's conducted hundreds of medicolegal assessments and relationship counselling sessions, I've learned that premature problem-solving destroys trust faster than any other mistake. Early in my career, I had a couple come in where the husband immediately described their communication issues, and I jumped straight into suggesting specific techniques from Cognitive Behavioural Therapy. The wife shut down completely. When I stepped back and spent the next two sessions just listening, I finded the real issue wasn't communication--it was unresolved trauma from her childhood that was triggering defensive responses. My initial "expert" recommendations had made her feel unheard and misunderstood. Now I structure every first session with comprehensive clinical interviews before any assessment or intervention. This approach has dramatically improved our client matching success rate at MVS Psychology Group, where we specifically focus on pairing clients with the right psychologist for their actual needs rather than assumed ones. The same principle applies in executive settings--whether you're a CEO or a clinician, people need to feel understood before they'll trust your solutions. I've seen this pattern repeatedly: the leaders who ask the deepest questions first are the ones who build the strongest therapeutic relationships and achieve the most lasting results.
As founder of tekRESCUE, I've learned that jumping straight into technical recommendations during client consultations is the fastest way to lose credibility. Early in my career, I walked into a potential client meeting with a San Marcos manufacturing company and immediately started outlining their obvious cybersecurity gaps and recommending specific solutions. The IT director's body language shifted immediately--arms crossed, checking his phone. When I finally stopped talking and asked about their biggest operational challenges, he revealed they'd just survived a ransomware attack that cost them $50K, but their real frustration was with previous consultants who "diagnosed" them without understanding their 24/7 production requirements. I spent the next hour just listening to how their night shift operations worked and why previous security implementations had failed. Turns out their biggest vulnerability wasn't technical--it was employee training during shift changes when people were rushing and clicking on anything. We landed a three-year contract worth $180K because I redesigned our entire approach around their shift patterns rather than pushing standard solutions. That client became one of our strongest references and directly led to our "Business of the Year" award from the San Marcos Chamber.
In my early days starting Tropic Renovations after getting my contractor's license, I thought my 20+ years of construction experience meant I should walk into client consultations ready to solve everything immediately. That approach nearly cost me a major bathroom renovation project in Venice. The homeowners were talking about a simple tub-to-shower conversion, and I started rattling off solutions about accessibility features and modern fixtures. They kept getting quieter until finally the wife said "we just wanted to see if you actually listen to what we need." I shut up and started asking questions instead. Turns out their real concern was that the husband had mobility issues they were embarrassed to discuss upfront. By listening first, I learned they needed wheelchair accessibility but wanted it to look neat, not institutional. That project became one of our showcase "Cave to Wheelchair Accessible" renovations and led to referrals worth over $200K in additional work. Now our entire consultation process starts with questions, not solutions--it's why we've completed 1,000+ successful renovations and won Venice Chamber's Business of the Year in 2022.
As a partner at Watson & Norris representing employees for over 20 years, I've learned this lesson from both sides of the table. Early in my career during depositions, I'd jump in with legal theories before fully understanding what actually happened to the employee. The game-changer came during a racial discrimination case in Jackson where I initially assumed it was about promotion denial. Instead of outlining federal remedies immediately, I spent three hours just listening to my client describe the daily microaggressions and documented incidents. What emerged wasn't a promotion case at all--it was a hostile work environment with clear retaliation patterns. By holding back my legal expertise and truly hearing her story first, I finded she had carefully documented everything for two years. That documentation became the foundation of our case strategy and led to a significant settlement. The client later said she chose our firm because I was the first attorney who didn't interrupt her story to explain the law. This approach has become standard in my practice now. Of my 1,000+ employment cases, the strongest outcomes consistently come from cases where I listen completely before offering any legal framework. Employees know their workplace better than any attorney ever will.
As CEO of an AI innovation platform working with Fortune 500 companies, I've seen executives crash and burn by leading with solutions instead of problems. My biggest lesson came during our early days when pitching to a major telecommunications company. I walked in with a polished presentation about our AI agents and use case database, ready to showcase how we could revolutionize their innovation process. Ten minutes in, the Chief Innovation Officer interrupted me: "This looks impressive, but we just spent $2M on a similar platform that nobody uses." I stopped pitching and asked what actually happened with their previous investment. Turns out their innovation team was drowning in startup outreach emails and couldn't validate which technologies actually worked. Their real problem wasn't finding startups--it was proving ROI to skeptical business units who'd been burned before. We completely rebuilt our approach around evidence verification and board-ready reports instead of just startup matching. That "failed" meeting led to a six-figure contract because I learned their innovation teams needed credibility tools, not more startup connections. Now our problem-first methodology is literally built into how Entrapeer operates--we always start with "what's the use case?" before showing any technology.