Humble Leadership Skills

You’re never too important to be kind to people. The misconception? Kindness is a weakness. 
The reality? Kindness is wisdom. Natasha Mahajan said it best … It’s the foundation of leadership that doesn’t just command but inspires. The kind that doesn’t demand respect but earns it effortlessly. No title, no corner office, no accolade makes unkindness acceptable. True leaders - the ones whose teams follow them not out of obligation but out of belief - lead with humanity, not just authority. Here’s how to lead with kindness that resonates deeply: 1/. Listen like they’re the only person in the room. 
Put the phone down. Look them in the eye. Ask thoughtful questions. Listening is more than hearing words - it’s valuing the person behind them. 2/. Celebrate the details. 
“Good job” is a checkmark. Highlighting what they did well and why it matters is impact. Let your praise be specific, intentional, and memorable. 3/. Protect their time and energy. 
Meetings that don’t need to happen? Cancel them. Deadlines that aren’t reasonable? Adjust them. Respecting their bandwidth shows you value their humanity over their productivity. 4/. Own your mistakes. 
Leaders don’t deflect - they take responsibility. A simple “I could’ve guided you better” builds trust faster than any excuse ever could. 5/. Remember the moments that matter. 
Birthdays. Anniversaries. Firsts and lasts. These moments may seem small, but they’re reminders that your team is made up of people, not just roles. 6/. Be tough but thoughtful. 
When hard conversations come, focus on behaviors, not character. Collaborate on solutions. Toughness doesn’t have to cut - it can build. Kindness isn’t soft.

Your success as a leader comes down to how well you set others up to succeed. And I’ve gotten this wrong more than once. When onboarding new leaders, I would give them a stack of docs, send them on a listening tour, and check in often. I assumed that was enough. It wasn’t. I gave them information—but not context. And context is what actually drives clarity, confidence, and results. I’ve since rethought my entire approach to onboarding leaders. This year, when two fantastic leaders joined our team, I did something different: spent a week on providing context. No shortcuts. We talked through: Our mission, strategy, and priorities What success looks like in their first 90 days, 6 months, and year What’s worked—and what hasn’t—in these roles before How we’ll share feedback and stay in sync The shift? Less “onboarding” as a task. More “transferring judgment.” We left with shared context. And here’s what’s interesting: the same thing applies when onboarding AI agents. You can’t just dump data into a system and hope it performs. AI needs context too—about your customers, your voice, your goals, and what “good” looks like. Whether you’re onboarding a new employee or a new AI teammate, the principle is the same: Context isn’t a nice-to-have. It’s the difference between getting started and getting results.

For over 20 years, I've coached and consulted with some of the most successful leaders in the world. The world's most successful leaders all have one thing in common: They never believe they’ve “arrived.” They don't settle. They grow. They learn. Great leadership is a daily practice of learning, reflection, and growth. And the leaders who stand out the most aren’t just sharpening technical skills… they’re constantly working to become more emotionally intelligent. Here’s what lifelong learners in leadership consistently do: ✅ They study themselves first They reflect on their reactions, decisions, and impact. Self-awareness is their foundation for growth ✅ They seek feedback, even when it’s uncomfortable Emotionally intelligent leaders invite honest input because they know feedback accelerates growth and builds trust. ✅ They stay curious about people They don’t assume. They ask open-ended questions and listen. They seek to understand perspectives, motivations, and emotions. ✅ They invest in emotional intelligence skills They work on empathy, communication, self-regulation, and relationship management because leadership is about people, not control. ✅ They learn from every experience Wins become lessons. Challenges become teachers. Mistakes become fuel for improvement. Here's the leadership truth you won't always hear: The moment a leader stops learning is the moment they stop leading effectively. The leaders who make the biggest impact stay humble, curious, and committed to becoming better. They lead with emotional intelligence. Keep learning. Keep growing. Keep leading.

I remember I was heading into a board meeting when our office janitor, Mr. Ellis, stopped me. He said, "Your name tag's upside down." My first instinct? → Brush it off. → Pretend I didn't need help. → Protect my pride. Instead, I paused and said, "Thanks for looking out for me." He smiled and replied, "Doesn't matter your title. You represent all of us when you walk into that room." That single moment with Mr. Ellis's big brown eyes shifted how I viewed leadership forever. Six months later, I stood in that same boardroom, presenting a critical strategy. Not because I knew everything. But because I walked in carrying the quiet confidence that comes from respecting everyone who makes our work possible, from the janitor to the CEO. And respect carries more weight than any title ever could, regardless of the room you're in. Here's what most professionals get wrong: They think career growth is about impressing those above them. They forget that everyone, from the janitor to the CEO, sees how you really show up. They underestimate the wisdom in people that society often overlooks. But the highest-impact leaders I've coached share one trait. They lead with respect. → They treat every person like they matter. → They know trust isn't reserved for titles. → They understand influence starts with how you make people feel. That's how careers grow, not just in skill but in humanity. The C.H.O.I.C.E.® Framework makes this real: Courage: Stand for dignity, even when no one's watching. Humility: Know you're not above anyone. Openness: Learn from every voice. Integration: Turn respect into everyday actions. Curiosity: Ask people about their stories. Empathy: See the person behind the role. Here's how to start leading with respect and grow your career: ✅ Start small. → Thank someone whose work often goes unseen. → Respect is built in micro-moments that matter. ✅ Listen deeply. → Instead of dismissing someone's input, ask: → "What do you see that I might be missing?" ✅ Model humanity. → Show others how to treat people well, no matter their title. → Respect shapes culture and careers. The more senior you become, the more your treatment of junior staff defines you. Your peers judge your character not by how you handle power but by how you treat those without it. 💭 Who's someone "behind the scenes" who taught you about leadership? ♻️ Tag someone who leads with humanity. ➕ Follow Loren Rosario - Maldonado, PCC, for career coaching that's human to the core.

Your first job out of college can feel overwhelming. I still remember joining IBM as a fresh grad, unsure of what to expect but eager to prove myself. While I had worked hard to earn that opportunity, I quickly realized that succeeding in your first job takes more than just technical skill. Here’s my biggest piece of advice to new grads stepping into their first role: 𝗗𝗼𝗻’𝘁 𝘄𝗮𝗶𝘁 𝘁𝗼 𝗯𝗲 𝘁𝗼𝗹𝗱 𝘄𝗵𝗮𝘁 𝘁𝗼 𝗱𝗼. Be proactive, not reactive. That one shift in mindset changes everything. Instead of just doing what was assigned to me, I started thinking about: → How can I make my manager's job easier? → What’s slowing the team down? → Is there a process that can be improved? → Can I learn from teams outside my own? 💡 I wasn’t confined by my job description- I explored! I reached out to people beyond my immediate team, set up 1:1s to learn what they were working on, and asked where I could contribute. That helped me meet incredible people like Armand Ruiz, Dr. Seth Dobrin, Priya Krishnan, Shadi Copty, and so many more! That habit of thinking beyond your role, and then sharing your thought process and actionable ideas, is what builds credibility early on. It also helps you get noticed. 🌱 Having a growth mindset was key. I didn’t wait for opportunities, I created them by showing initiative and being vocal about how I could help. 🤝 Networking inside your company is as important as networking outside. Many of the best career moves I’ve made happened because I nurtured relationships beyond my team. Don’t underestimate the power of a coffee chat with someone in a different org. If you’re just starting your career, remember: → Speak up even if you’re the most junior person in the room → Share ideas that benefit your broader org → Learn fast, ask smart questions, and stay curious → Build relationships early and intentionally → You don’t need to have it all figured out. You just need to start showing up like someone who’s ready to grow. 𝗬𝗼𝘂𝗿 𝗰𝗮𝗿𝗲𝗲𝗿 𝗱𝗼𝗲𝘀𝗻’𝘁 𝗴𝗲𝘁 𝗯𝘂𝗶𝗹𝘁 𝗶𝗻 𝗮 𝘀𝗶𝗻𝗴𝗹𝗲 𝗱𝗮𝘆, 𝗯𝘂𝘁 𝗲𝘃𝗲𝗿𝘆 𝗱𝗮𝘆 𝗯𝘂𝗶𝗹𝗱𝘀 𝗶𝘁. 💼 #Classof2025

"I have a bone to pick with you." That's how I opened a recent conversation with an executive. Spoiler: It didn't land well. 🫠 (𝘐’𝘮 𝘴𝘸𝘦𝘢𝘵𝘪𝘯𝘨 𝘴𝘩𝘢𝘳𝘪𝘯𝘨 𝘵𝘩𝘪𝘴 𝘰𝘯 𝘓𝘪𝘯𝘬𝘦𝘥𝘐𝘯, 𝘣𝘶𝘵 𝘐 𝘣𝘦𝘭𝘪𝘦𝘷𝘦 𝘪𝘯 𝘯𝘰𝘳𝘮𝘢𝘭𝘪𝘻𝘪𝘯𝘨 𝘮𝘪𝘴𝘵𝘢𝘬𝘦𝘴, 𝘴𝘰 𝘩𝘦𝘳𝘦 𝘪𝘵 𝘨𝘰𝘦𝘴.) I came in with a strong point of view, ready to advocate for my position. It was in opposition to a decision she made but that could still be changed. "She'll appreciate that I have conviction!" I thought confidently. But instead of sparking a productive debate, I miscalculated. The executive gently stopped me. She offered advice I'll never forget and have been thinking about days since: "Consider the context around how I made this decision." In that moment, I realized I'd skipped a crucial step: curiosity before challenge. Here's what I learned about challenging up, why my approach was all wrong, and what you can learn from my mistake. This advice is great if you're a current or aspiring #chiefofstaff but also applicable to anyone working to improve their persuasion skills. 1️⃣ 𝗟𝗲𝗮𝗱 𝘄𝗶𝘁𝗵 𝗰𝘂𝗿𝗶𝗼𝘀𝗶𝘁𝘆 𝗯𝗲𝗳𝗼𝗿𝗲 𝗰𝗼𝗻𝘃𝗶𝗰𝘁𝗶𝗼𝗻. Instead of jumping in with a firm stance, start with, "I'm curious how you landed on this decision." This simple shift creates space for dialogue. It might even change your perspective before you voice your challenge. (In my case, as soon as I had more context, I changed my tune. If only I had led with curiosity...) 2️⃣ 𝗞𝗻𝗼𝘄 𝘄𝗵𝗲𝗻 𝘁𝗼 𝗯𝗿𝗶𝗻𝗴 𝗮𝗻 𝗶𝗻𝗳𝗼𝗿𝗺𝗲𝗱 𝗼𝗽𝗶𝗻𝗶𝗼𝗻 𝘃𝘀. 𝗮 𝘀𝘁𝗿𝗼𝗻𝗴 𝗣𝗢𝗩. Here's how I think about the difference: An informed opinion means you've thought critically but remain open to learning; a strong point of view (POV) usually means you've already decided the best course of action and are looking for buy-in. Generally, if the decision is in your domain/area of expertise, it's good to have your recommendation (POV) ready. For broader strategic decisions, almost always seek to understand first. 3️⃣ 𝗙𝗿𝗮𝗺𝗶𝗻𝗴 𝗺𝗮𝘁𝘁𝗲𝗿𝘀 — 𝗮 𝗹𝗼𝘁. Compare "I disagree with this approach" to "Here's something I've been thinking about. Could I share my perspective?" Both convey your conviction, but one does it WAY more effectively. The former shuts down dialogue; the latter invites discussion. This experience taught me an important truth: The most effective persuaders aren't just those with strong convictions. They're the ones who master the dance between inquiry and advocacy. 💃 And even in an AI-driven world, persuading other humans will continue to be an in-demand skill. Whether you're early in your career or sitting at the executive table, understanding this balance can transform how your points are received. It might even change some strong opinions you thought you had. It did for me. (𝘛𝘩𝘪𝘴 𝘱𝘰𝘴𝘵 𝘸𝘢𝘴 𝘸𝘳𝘪𝘵𝘵𝘦𝘯 𝘣𝘺 𝘢𝘯 𝘰𝘷𝘦𝘳𝘵𝘩𝘪𝘯𝘬𝘪𝘯𝘨 𝘩𝘶𝘮𝘢𝘯, 𝘯𝘰𝘵 𝘈𝘐.)

Want to lead better? Start by acting like a human. Forget your title, your role. Be a human. And start treating your people like humans. It’s not about head or heart. It’s about being real. If you had a guest at your home, you’d feed them. Host them with care and make them feel welcome. Why does that disappear at work? Why do we lead with power instead of presence? You can be firm and kind. You can be strategic and human. In fact, the best leaders are both. It’s not a weakness to be warm. It is deep wisdom. And here’s how you start: 1. Before giving feedback, pause and ask: “Would I say this to someone I care about?” 2. When someone makes a mistake, don’t react. Respond like a mentor, not a judge. 3. In meetings, stop talking first. Start listening better. 4. When tension rises, lower your voice. Not your standards. 5. And when things go well, Acknowledge effort. Emotion. Humanity. People don’t remember your title. They remember how you made them feel. So the next time you lead… Don’t ask, “What should I say?” Ask, “What would a good human do?” Because that’s where real leadership begins. And that’s what people will follow.

Practicing intellectual curiosity is critical to a leader’s journey of continuous learning and growth. We must ask questions, listen actively, seek out different perspectives, and challenge our assumptions. Many leaders read voraciously, reflect regularly, and engage with coaches and mentors to ensure we are exposed to new ideas, insights, and feedback. One practice that has helped me learn and evolve over the years is tracking and analyzing the outcomes of my decisions. This is not about dwelling on mistakes but about accountability, continuous improvement, and leading with intention. I started this as a mid-level manager, thanks to a great boss who taught me how to balance data and instincts—a critical skill to have when you need to make a decision urgently in the absence of a complete set of facts. He coached me to start recording my gut instincts whenever I had to make a decision. I would do a quick gut check and put that insight aside. I would then approach the decision analytically, weighing all the available data to make a determination. Over time, we’d compare the two approaches, tracking the success rate through the years. This practice has stayed with me—in fact, I’m still tracking business decisions I made in Southeast Europe, Germany, and Southeast Asia over the years! As importantly, I track the successful careers of employees I hired, coached, and promoted. This is not only a useful learning exercise of what worked and what didn’t, but also a wonderful way to celebrate the success of others. What are some practices that help you continuously learn and grow? #Leadership #Development #Curiosity #ContinuousLearning #DecisionMaking

A new VP introduced "radical candor" - direct feedback, public disagreement, transparent conflict. Exactly what worked at her last company. Six months later, she was isolated. The team nodded, said feedback sessions were "really valuable," then kept operating as before. By month nine, she was gone. Her mistake wasn't the strategy. It was assuming the environment would cooperate with it. 👉The Generic Leadership Trap Most leadership advice is context-free. "Be transparent." “Create psychological safety.” "Empower your team." All of it sounds right. None of it tells you whether it will work here. Every environment has unwritten rules that override your written ones, historical patterns that resist your direction, invisible incentives that reward behaviors you're trying to eliminate. 📍Leaders without context clarity treat these as obstacles to overcome. They're not obstacles. They're the terrain. 📌 What Context Clarity Actually Is The ability to read the system you're operating in, not the system you wish you were in. What is the real history here? What happened the last time someone tried to change things?  - What does this system actually reward? ❓What are the unspoken rules? "We don't challenge the CFO in meetings." "Engineering always wins." "The CEO's opinion is the last opinion." ❓How does power actually flow? Not the org chart. Who influences decisions? ❓What is this environment optimized for? Speed or stability? Innovation or risk management? You can't change what something is optimized for by wishing it were different. 📍The Cost of Context Ignorance When leaders ignore context, they fail slowly. Your initiatives get quiet resistance. People say yes and do nothing. You become "the outsider who doesn't get it." Even if you've been here for years. You waste influence on unwinnable battles. 📌 The Test Can you explain why your last three decisions failed, not because of your execution, but because of the environment's response? If you can't, you're not reading the context. You're just reacting to it. 📍Leaders with context clarity: Work with the grain of the culture, not against it. Plan moves based on what the system can absorb. Translate generic leadership advice into local strategy. They stop trying to lead the organization they wish they had. They lead the one that actually exists. 👉 Context clarity is what makes leadership intelligent. You can have perfect identity clarity, know exactly who you are. But if you don't know where you are, your clarity just makes you confidently wrong. It's the difference between conviction and naivety. Between vision and delusion. Context clarity ≠ Context Acceptance. Tomorrow, I share more. ---- This is a framework I’ve developed over a decade of working with leaders and companies globally. In this 21-minute solo episode of Overnight Wisdom, I break down the three clarities. Whether you lead 2 or 2000, have a listen and let me know what resonates. 🎧Spotify: https://lnkd.in/dvr8zGUr

A fundamental principle for psychologists is that the quality of the therapeutic relationship is EVERYTHING. If clients don't feel safe and supported – if they can't be "real" with you – nothing else matters. So, we quickly learn to notice when something doesn't feel quite right – when words and body language don't match, when everything is always "fine", when there's reluctance to share what isn't working. We learn to lean into that discomfort, gently sharing observations and asking curious questions… 💬 "I could be way off here, but it feels like there's something you're not saying. Am I getting that wrong?" 💬 "I'm sensing there's something difficult here – what's on your mind?" 💬"Just now, I noticed you took a breath as though you were about to say more, then stopped. I'd love to hear what that was...?" These are small acts of humility that signal: "It's okay to say what's really on your mind..." and "I know that I don't always get it right..." and "You won't be punished for disagreeing..." 💡Leaders need the same skill. When your team always says "yes," always reports things are "fine," always praises your ideas – you might not have engaged or aligned employees. You might have people-pleasing instead. The best leaders, like the best psychologists, tune in and start noticing those moments – and then importantly, reinforce honesty when it shows up: 💬 "Thank you for being straight with me – it's really important that I understand a range of different perspectives." What do you think? Have you worked with any leaders who do this particularly well? #PsychologicalSafety #Leadership #Humility #LeadershipDevelopment #OrganisationalPsychology