Lessons on Trust from Corporate Experience

I’ll never forget something a CEO taught me early in my career. He would stop by my desk regularly. No agenda. No formalities. At first, it felt routine. But over time, I began to see the pattern. Just a simple, “How’s it going?” At the time, it seemed insignificant – a polite hello. But now, I see it for what it was: a trust-building moment. His casual approach made it easier for me to open up, share my concerns, and speak honestly. It wasn’t about the words.  It was about the intention behind them. Trust doesn’t just happen. It’s built with consistency, action, and a lot of listening. As a leader today, I do my best to do the same. If your team isn’t approaching you, here’s what may help: - Be present.  ↳ When someone comes to you, put everything else aside and truly listen. - Avoid shutting them down.  ↳ The first “no” can be the last time they trust you with their ideas. - Go to them.  ↳ Don’t wait for trust to walk through your door, go and build it where they are. Here’s something not many will tell you: If your team isn’t coming to you, it’s not on them. It’s on you. So go to them. Because trust isn’t a gift – it’s a responsibility.

Trust isn’t built through perfection. It’s built through authenticity, vulnerability, and humility. In the best teams, people don’t need to have all the answers. They need to show up honestly, ask good questions, and stay open to learning. That kind of culture only works when leaders model it from the top. When they don’t, it creates distance. People start managing impressions instead of solving problems. Energy gets spent on appearances instead of outcomes. I once worked for a boss who really wanted to be a great leader, but never quite showed up fully. He said all the right things about collaboration, strategy, and innovation, but there was always a filter. Something about him felt slick. I remember inviting him to an offsite about our product roadmap. It was an early-stage, messy kind of conversation: technical debates, half-formed ideas, back-and-forth about what might work. Inviting him was a bit of a risk, given what I’d observed. He sat in, but you could tell he was uncomfortable. He wasn’t used to that level of transparency. He was used to polished slides and confident answers, not the raw process of figuring things out together or dealing with uncertainty. That moment stuck with me. I realized he maintained trust by appearing right and in control. He saw our openness to uncertainty as a weakness, when in reality, it was how we built great products and strong teams. That’s when it clicked: I couldn’t work for someone who equated vulnerability with incompetence. Real trust requires showing up as a human. And if you can’t do that, no amount of talk will prove you are qualified.

When Integrity Prevails: Lessons from an Unexpected Twist In leadership, unexpected challenges can test resilience and integrity. Recently, I had a client whose situation highlighted both. Her team was thriving, delivering beyond expectations. Yet, out of the blue, her boss urged her to resign, citing the CEO’s supposed request. Rather than accepting this without question, she decided to seek clarity directly from the CEO, only to uncover a startling reality: the CEO had been told by her boss that she wanted to leave, not the other way around. Once the truth came out, it was her boss who was dismissed, and she was promoted. This experience underscores several powerful lessons for professionals at any level: 1. Transparency is Key: When something seems off, seek clarity with those who matter. In this case, a direct conversation with the CEO revealed the truth. Transparency can quickly dissolve misunderstandings and reveal agendas. 2. Trust but Verify: Even senior leaders can have misaligned motives. When life-altering decisions hinge on someone’s word, it's wise to confirm critical details, especially if they significantly impact your career. 3. Speak Up Early: If something doesn’t feel right, don’t ignore it. Addressing concerns openly—sooner rather than later—can prevent larger issues from unfolding. By speaking up, my client preserved her career and reputation. 4. Maintain Senior Connections: Cultivating relationships with key executives fosters alignment and offers support in challenging situations. This network can be crucial, especially when intermediaries may misrepresent intentions. 5. Integrity Wins: Ultimately, her track record and ethical approach worked in her favor. This situation reinforces that consistent performance and integrity are the best safeguards against misrepresentation. In the corporate world, challenges like these can seem daunting. However, by staying true to our values, prioritizing transparency, and advocating for ourselves, we not only protect our careers but also model resilience for our teams. This story serves as a reminder: in the end, integrity has a way of winning out.

Executive relationships aren’t built in boardrooms — they’re built in small, consistent moments of trust. Having worked closely with CXOs from Fortune 500 companies, I’ve seen firsthand how trust can translate into long-term business impact. Over the years, I’ve come to rely on what I call the PVR framework as my north star for building these relationships: 1️⃣Preparation: Do your homework. Know their story and know it well. That could mean reading their latest post, noting a book they’re working on, or simply being aware of what’s top of mind for them when you walk into a call. Executives can tell within minutes if you’ve come prepared — it sets the tone for respect. Before stepping into a conversation, ask yourself: what’s in it for them? 2️⃣Validation: In psychology, they say “to feel seen is to feel valued.” Show them you’re paying attention. If a recent idea, article, or insight of theirs resonated, bring it up in your next conversation. Not in a forced way, but in an honest, “this stayed with me” way — and here’s my take on it. Authenticity matters. For me, the goal has always been to grow relationships, not “nail” them. That’s the outcome, not the strategy. 3️⃣Recognition: Acknowledge what makes them stand out. Sometimes that’s celebrating a milestone, other times it’s reflecting back the unique perspective they bring. What I’ve found especially meaningful is noticing their unseen efforts; the way they back their teams and quietly create space for others to succeed. Even sharing a positive experience you’ve had with one of their team members goes a long way. It tells them you see the human behind the title and the difference they make every day. In my experience, what stays with leaders isn’t the polished deck or the perfect pitch — it’s the feeling of being seen, heard, and valued. That’s the real foundation of trust. I’d love to hear — what’s worked for you when it comes to building genuine executive trust? 🤝 #executiveengagement #csuite #strategicrelationships

I once worked with a team that was, quite frankly, toxic. The same two team members routinely derailed meeting agendas. Eye-rolling was a primary form of communication. Side conversations overtook the official discussion. Most members had disengaged, emotionally checking out while physically present. Trust was nonexistent. This wasn't just unpleasant—it was preventing meaningful work from happening. The transformation began with a deceptively simple intervention: establishing clear community agreements. Not generic "respect each other" platitudes, but specific behavioral norms with concrete descriptions of what they looked like in practice. The team agreed to norms like "Listen to understand," "Speak your truth without blame or judgment," and "Be unattached to outcome." For each norm, we articulated exactly what it looked like in action, providing language and behaviors everyone could recognize. More importantly, we implemented structures to uphold these agreements. A "process observer" role was established, rotating among team members, with the explicit responsibility to name when norms were being upheld or broken during meetings. Initially, this felt awkward. When the process observer first said, "I notice we're interrupting each other, which doesn't align with our agreement to listen fully," the room went silent. But within weeks, team members began to self-regulate, sometimes even catching themselves mid-sentence. Trust didn't build overnight. It grew through consistent small actions that demonstrated reliability and integrity—keeping commitments, following through on tasks, acknowledging mistakes. Meeting time was protected and focused on meaningful work rather than administrative tasks that could be handled via email. The team began to practice active listening techniques, learning to paraphrase each other's ideas before responding. This simple practice dramatically shifted the quality of conversation. One team member later told me, "For the first time, I felt like people were actually trying to understand my perspective rather than waiting for their turn to speak." Six months later, the transformation was remarkable. The same team that once couldn't agree on a meeting agenda was collaboratively designing innovative approaches to their work. Conflicts still emerged, but they were about ideas rather than personalities, and they led to better solutions rather than deeper divisions. The lesson was clear: trust doesn't simply happen through team-building exercises or shared experiences. It must be intentionally cultivated through concrete practices, consistently upheld, and regularly reflected upon. Share one trust-building practice that's worked well in your team experience. P.S. If you’re a leader, I recommend checking out my free challenge: The Resilient Leader: 28 Days to Thrive in Uncertainty  https://lnkd.in/gxBnKQ8n

The day I finally understood how trust really works, everything changed for me as a CSM. In my first Customer Success role, our leader had us read a book before our team offsite: The Trusted Advisor. Short. Simple. Game-changing. Inside was something that flipped a switch for me, the Trust Equation: Credibility + Reliability + Intimacy / Self-Orientation For the first time, trust wasn’t a feeling, it was something I could build intentionally. So I made a move, and this changed how I worked with customers: I wrote each element of the equation into their account. And every engagement became a chance, an opportunity to build on trust with purpose. Here’s what that looked like in real life ✅ Credibility Know your stuff. Speak with clarity. Bring insights, not just product updates. → When a customer asks how to achieve a specific outcome in your product and you clearly walk them through 2-3 workflows that get them there. → When they ask, “What are other customers like us doing?” and you give just the right amount of relevant context and detail. ✅ Reliability Do what you say you’ll do. No surprises. No dropped balls. → You follow through after every meeting. → You send the recap. → You make the intro. → You deliver on that one thing they asked for, even if it seemed minor. ✅ Intimacy Be human. Build connection. Care about what matters to them. → You remember their kid’s name. → You know they’re prepping for a board meeting next week and ask how it’s going. → You lead with empathy, not agendas. 🚫 Self-Orientation Don’t make it about you. Ever. → You don’t flex your product knowledge to sound smart, you share what helps them win. → You don’t push your goals, you stay focused on theirs. Every CSM wants trusted relationships. Not every CSM builds them on purpose. This equation gave me a new level of intention. What’s one small way you can build more trust? ________________________ 📩 If you liked this post, you'll love The Journey. Head over to my profile and join the thousands of CS professionals who are along for the ride as I share stories and learnings going from CSM to CCO.

Unpopular Opinion: It doesn't matter how many days a week you bring people back to the office if your organization lacks employee trust. I recently had a conversation with a young professional who believed that they couldn't speak up within their organization because, at one point, they were told by their manager that they didn't have enough experience to have an opinion. This type of behavior damages the individual's personal career growth, including their ability to develop the skills and experience if they don't feel like they can question their own assumptions and the assumptions of others. It also damages the overall organization's ability to succeed since it prevents people from bringing their best ideas forward and working together collaboratively and productively. Yet, in all the conversations around RTO from leaders, so much is centered around a need for more productivity and innovation. Trust is the glue that holds teams together, empowers individuals, and creates an environment where employees feel valued and supported. When employees trust their employers and colleagues, they are more likely to be engaged in their work, perform at their best, and take risks that lead to innovation. Numerous studies have highlighted the significant impact of trust on organizational success. According to a study conducted by the Harvard Business Review, companies with high levels of trust experience 74% less stress, 106% more energy at work, 50% higher productivity levels, and 76% higher engagement rates compared to low-trust organizations. So how can employers cultivate trust in the workplace? It's not by getting people to show up to the office more. Here are a few key strategies: 1️⃣ Lead by example: Trust starts at the top. Employers must demonstrate trustworthiness through their actions and decisions. When leaders consistently act with integrity, transparency, and fairness, it sets the tone for a culture of trust throughout the organization. 2️⃣ Foster open communication: Encourage open dialogue and active listening within teams. When employees feel heard and valued, they are likelier to trust their colleagues and share ideas freely. Regular team meetings, feedback sessions, and opportunities for collaboration can all contribute to building trust. 3️⃣ Provide autonomy and empowerment: Trust goes hand in hand with giving employees the autonomy to make decisions and take ownership of their work. When individuals feel trusted and empowered, they are more likely to go above and beyond, take calculated risks, and develop innovative solutions. 4️⃣ Recognize and reward trust: Acknowledge and appreciate trustworthy behavior. Recognize employees who consistently demonstrate trustworthiness and create a culture where trust is celebrated. This can be done through public recognition, rewards, or small gestures like a simple thank you. #management #leadership #returntooffice #employeeexperience #employeeengagment #trust

“You’re the one who closed it. You’re the one who owns it.” That’s what I was told after closing my first seven-figure enterprise deal—into a market our company had never sold into before. I assumed there’d be a handoff. Instead, I became the face of the partnership. Onboarding. Product delivery. Executive alignment. Renewal strategy. All of it. We had committed to roadmap work and new workflows. Expectations were sky-high, and we were building as we went. There was no process for handling escalations. So I wrote one. There was no precedent for how to communicate when we missed. So I set the tone. I remember one of our first post-sale calls. The customer asked me to send a recap. I had taken notes—but I hadn’t expected to be the one sharing them. That moment reshaped my thinking. In the post-sale phase, the expectations aren’t lower. They’re higher. The details matter more. And how you follow through becomes the measure of trust. Then came the moment I’ll never forget. At the customer’s annual conference, one of their daily users approached me during a happy hour with a list of concerns. I listened, acknowledged, and promised to follow up. She kept going—not because she didn’t believe me, but because she needed to believe someone would act. That’s when her CEO stepped in and said: “If Sarah says she’ll follow up, she will. I’ve seen it firsthand—she delivers.” That moment stayed with me. Because trust may begin in the sales cycle, but it’s earned through execution—especially when things don’t go according to plan. Years later, at another event, a different end user from that same customer came up to me and said: “Thank you. What we’re doing together is making a real difference in people’s lives.” I managed that relationship for over a decade. What started as a new market experiment became a flagship account and a defining chapter in my career. Here’s what I’ve learned: * Set the tone early. The way you show up during the sales process shapes how customers experience everything that follows. * Think long-term. It’s not just about the close. It’s about building value that compounds over years. * Own the outcome. When issues arise, don’t deflect—lead. Be the steady voice that drives solutions. * Build trust that lasts. Trust is earned through consistency. Deliver on what you say, especially when it’s hard. Because the best sellers don’t just hit quota. They lead. They deliver. They become the reason customers stay.

He looked up from the memo and said it quietly—almost to himself. “𝗔𝗿𝗲 𝘄𝗲 𝗼𝗸𝗮𝘆?” Not “Is this legal?” Not “Will this hold up?” Just: “Are we okay? Am I okay?” I’ve been asked that a dozen ways: → When a product launch hit a regulatory snag no one saw coming → When a marketer needed to retreat without losing face → When an exec’s voice cracked after reading a hostile headline All human moments, sandwiched in legal advice. When people ask Legal for answers, they’re also asking for something deeper: Reassurance. Judgment. A steady voice when everything feels shaky. These aren’t rules (I’ve broken some of them myself). But when I remember them, things go better: 𝟭. 𝗖𝘂𝗹𝘁𝘂𝗿𝗲 𝗶𝘀 𝗮 𝘀𝘆𝘀𝘁𝗲𝗺, 𝗻𝗼𝘁 𝗮 𝘀𝗹𝗼𝗴𝗮𝗻 • What we allow once becomes policy and precedent • People learn more from what we tolerate than what we say 𝟮. 𝗟𝗲𝗴𝗮𝗹 𝗶𝘀 𝘁𝗵𝗲 𝗰𝗼𝗻𝘀𝗰𝗶𝗲𝗻𝗰𝗲 𝗼𝗳 𝘁𝗵𝗲 𝗰𝗼𝗺𝗽𝗮𝗻𝘆, 𝘄𝗶𝘁𝗵 𝗯𝗼𝘁𝗵 𝗲𝘆𝗲𝘀 𝗼𝗽𝗲𝗻. • When fear drives speed, someone has to ask: “At what cost?” • If the answer is “We don’t know yet”—help them figure it out 𝟯. 𝗧𝗿𝘂𝘀𝘁 𝗶𝘀 𝗯𝘂𝗶𝗹𝘁 𝗼𝗻 𝗮𝘂𝘁𝗵𝗲𝗻𝘁𝗶𝗰𝗶𝘁𝘆 • Not when we're right, but when we’re real • “Here’s what I’m worried about” opens more doors than “Here’s the policy” 𝟰. 𝗖𝘂𝘁 𝘁𝗵𝗿𝗼𝘂𝗴𝗵 𝘁𝗵𝗲 𝗻𝗼𝗶𝘀𝗲 • People don’t need 10 risk scenarios; they need a path forward • I once sugarcoated a risk to preserve harmony. When it blew up, they didn’t blame the risk. They blamed me for not being clearer 𝟱. 𝗥𝗶𝘀𝗸 𝗶𝘀 𝗲𝗺𝗼𝘁𝗶𝗼𝗻𝗮𝗹, 𝗻𝗼𝘁 𝗷𝘂𝘀𝘁 𝗮𝗻𝗮𝗹𝘆𝘁𝗶𝗰𝗮𝗹 • They’re not just asking, “Is this legal?” They’re asking, “Are we okay?” 𝟲. 𝗖𝗹𝗮𝗿𝗶𝘁𝘆 𝗶𝘀 𝗸𝗶𝗻𝗱𝗻𝗲𝘀𝘀, 𝗲𝘃𝗲𝗻 𝘄𝗵𝗲𝗻 𝗶𝘁 𝘀𝘁𝗶𝗻𝗴𝘀 • A well-placed question can reassure or shift a strategy • Long emails and texts are often ways to hide. It’s better to speak face to face 𝟳. 𝗜𝗻𝗳𝗹𝘂𝗲𝗻𝗰𝗲 𝗶𝘀 𝗾𝘂𝗶𝗲𝘁 𝗽𝗼𝘄𝗲𝗿 • When we're the calmest voice in the room, people listen • Our role isn’t just to stop bad decisions; it’s to help shape better ones 𝟴. 𝗙𝗼𝗹𝗹𝗼𝘄 𝘁𝗵𝗿𝗼𝘂𝗴𝗵, 𝗮𝗹𝘄𝗮𝘆𝘀 • Spotting an issue doesn’t earn trust, but solving it does 𝟵. 𝗡𝗮𝘃𝗶𝗴𝗮𝘁𝗲 𝘁𝗵𝗲 𝗰𝗼𝗮𝗹𝗶𝘁𝗶𝗼𝗻 • Companies are often made up of competing interests, not shared vision • It helps to show people how their goals align with doing the right thing 𝟭𝟬. 𝗧𝗶𝗺𝗶𝗻𝗴 𝗶𝘀 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴 • Know when to raise the flag, and when to let things play out • The difference between being consulted and being included? Timing 𝟭𝟭. 𝗔 𝘀𝗽𝗼𝗼𝗻𝗳𝘂𝗹 𝗼𝗳 𝘀𝘂𝗴𝗮𝗿 𝗵𝗲𝗹𝗽𝘀 𝗹𝗲𝗴𝗮𝗹 𝗺𝗲𝗱𝗶𝗰𝗶𝗻𝗲 𝗴𝗼 𝗱𝗼𝘄𝗻 • How we show up often speaks louder than anything we say • Don't be the person who "told them so" be the one who shows them how Which of these resonates most with your experience? What would you add to this list?  #inhousecounsel #lawpractice

'My executives are all A-players. They just don't trust each other.' That's what a $60M CEO told me over coffee this morning. His revenue was up 40%, but his leadership team was falling apart. Sound familiar? Here's the counterintuitive truth I've learned after working with dozens of scaling companies: High performers often create low trust. Not because they're untrustworthy, but because they're too capable. Think about it. When you stack your leadership team with ambitious, competent executives, each one is used to being 'the person with the answers.' They've built careers on being right. But scaling a business isn't about being right. It's about being aligned. Last month, I watched a Chief Revenue Officer and COO nearly sink a $100M deal. Not because either was wrong - both had valid concerns. But their inability to trust each other's judgment created decision paralysis. The real cost of low trust: - 3x longer decision cycles - Duplicated efforts across departments - Missed market opportunities - Rising stress, falling margins Your smartest executives are often your biggest trust barriers because: - They have the strongest opinions - They're used to being proven right - They've succeeded through individual excellence - They struggle with shared vulnerability Want to build trust between high performers? Start here: ✅ Create shared defeats, not just shared victories. Nothing builds trust like failing together and recovering stronger. ✅ Stop celebrating individual heroes. Start rewarding collaborative wins. ✅ Make decisions visible. Trust grows in transparency and dies in darkness. ✅ Build accountability around team outcomes, not departmental metrics. Remember: You don't have a trust problem. You have an alignment challenge. Your executives don't need trust falls. They need a compelling reason to depend on each other. Curious: Have you ever had a high-performing team that struggled with trust? What turned it around? #Leadership #OrganizationalDevelopment #ExecutiveTeam