Leadership Pitfalls and Challenges

I was shadowing a coaching client in her leadership meeting when I watched this brilliant woman apologize six times in 30 minutes. 1. “Sorry, this might be off-topic, but..." 2. “I'm could be wrong, but what if we..." 3. “Sorry again, I know we're running short on time..." 4. “I don't want to step on anyone's toes, but..." 5. “This is just my opinion, but..." 6. “Sorry if I'm being too pushy..." Her ideas? They were game-changing. Every single one. Here's what I've learned after decades of coaching women leaders: Women are masterful at reading the room and keeping everyone comfortable. It's a superpower. But when we consistently prioritize others' comfort over our own voice, we rob ourselves, and our teams, of our full contribution. The alternative isn't to become aggressive or dismissive. It's to practice “gracious assertion": • Replace "Sorry to interrupt" with "I'd like to add to that" • Replace "This might be stupid, but..." with "Here's another perspective" • Replace "I hope this makes sense" with "Let me know what questions you have" • Replace "I don't want to step on toes" with "I have a different approach" • Replace "This is just my opinion" with "Based on my experience" • Replace "Sorry if I'm being pushy" with "I feel strongly about this because" But how do you know if you're hitting the right note? Ask yourself these three questions: • Am I stating my needs clearly while respecting others' perspectives? (Assertive) • Am I dismissing others' input or bulldozing through objections? (Aggressive) • Am I hinting at what I want instead of directly asking for it? (Passive-aggressive) You can be considerate AND confident. You can make space for others AND take up space yourself. Your comfort matters too. Your voice matters too. Your ideas matter too. And most importantly, YOU matter. @she.shines.inc #Womenleaders #Confidence #selfadvocacy

If you’re a PM leader at a tier 1 company, your life probably looks like this: there is great pressure to - know every detail - always be on top of everything - attend various staff meetings (and say something clever in them) - ensure every team member rates you 10/10 in the annual employee engagement survey - while flawlessly running your team’s execution at 100 mph. While the core product work might be fun, most PM leaders barely touch it anymore. While their LinkedIn title looks great, there is chronic inner conflict about imbalance in other parts of one’s life. This conflict persists even when one manages to get a lot of likes on Insta after posting a Sunday picnic photo of the family and claiming “feeling so blessed. don’t forget folks, you too can have it all”. There is no solution, no silver bullet for this struggle. But, there are 2 ways to relieve the unhealthy stress and inner conflict: 1) Understand that trade-offs must be made: You cannot have it all. So what matters more than anything else is to have clarity about what you truly want out of your work & life over the long-term and what that means for the trade-offs you must make right now in the present. Without that clarity, most people get manipulated by the seduction of getting to the next rung of the ladder or getting the rare "greatly exceeds expectations" rating in Q3. 2) Make better decisions in your job: It turns out that a large part of what makes you busy in your PM leadership job is: (a) nonsense work you’ve created for yourself, and (b) work you can delegate, if you have the courage Regarding (a), you must be able to see that a large fraction of your time (for most PM leaders I’ve known, it’s a majority of their time) is spent on: i) fighting fires that shouldn’t have started in the first place or shouldn’t be fought and instead should be left burning ii) working on projects, offsites, meetings, processes, etc. that might appear to provide positive ROI but also come with a very high opportunity cost In other words, these are things that seem like a good use of time, but they are not a *great* use of *your* time. This also includes features / initiatives / projects you greenlighted that you should never have greenlighted and decisions you made quickly that you should have percolated on for a few hours more or a few days more. I know you think that is impossible and your case is special (of course it is), but that is also called a self-fulfilling prophecy. The reason you aren’t seeing the reality here is that perhaps there’s a deficiency of courage or perhaps there’s a tendency within you to be a conformist. Are you ready to accept this? No one can write a few words and make any of this easy for you, because no one can instill courage within you, no one can give you the judgment to understand when to conform and when to be a non-conformist. That is a struggle that belongs to you and you alone. I hope you choose your struggle wisely.

Good ideas don’t only live at the top. This illustration captures the powerful truth about leadership and organizational success, which Lynn Perry Wooten and I uncovered in the research that fueled #ThePreparedLeader: Too often, organizations rely on a small circle of senior leaders to generate ideas – an approach that can surface solutions but also unintentionally stifle innovation by leaving critical insights on the table. The most resilient and dynamic organizations know better. Instead, they intentionally lift up voices at every level, creating space for ideas to emerge from those closest to the work, the customers, and the day-to-day realities of the business. Lynn and I viewed firsthand how much stronger leaders become when they listen across boundaries of role, level, or tenure. Especially in moments of uncertainty, this kind of broad engagement surfaces the ideas, patterns, and signals leaders might otherwise miss. (Illustration by Marissa Solomon Shandell – @ResearchDoodles on Instagram – as part of a monthly series with Knowledge at Wharton that I highly recommend you check out!)

THE FASTEST WAY TO DESTROY SOMEONE’S POTENTIAL IS TO PUT THEM UNDER THE WRONG MANAGER Some people leave companies. Most people leave managers. And nothing crushes a high‑performer’s confidence or creativity faster than being placed under the wrong leader. A manager can be a multiplier or a barrier. A builder or a breaker. A catalyst or a cage. And the difference shows up quickly. 1. The Wrong Manager Shrinks People Great managers stretch people. Toxic managers shrink them. Instead of coaching, they criticize. Instead of developing, they diminish. Instead of empowering, they control. Employees begin second‑guessing themselves—not because they lack ability, but because they fear the consequences of being visible. 2. Innovation Dies When Fear Leads People think boldly when they feel safe. They do the bare minimum when they feel watched or judged. A poor manager creates: • Fear of speaking up • Fear of mistakes • Fear of blame • Fear of being replaced Fear suffocates creativity long before performance drops. 3. High Performers Become Quiet Performers When strong employees suddenly go quiet, it’s rarely disengagement—it’s self‑protection. They stop sharing ideas. They stop volunteering. They stop challenging the status quo. Not because they don’t care, but because they’re trying to survive a leader who doesn’t value them. 4. The Wrong Manager Rewrites the Story Insecure managers often create false narratives. They label confident employees as “difficult.” Independent thinkers become “not team players.” Questions become “attitude problems.” These narratives spread quietly and damage reputations long before anyone notices. 5. Potential Doesn’t Disappear—It Leaves People don’t lose their potential under a bad manager. They take it somewhere else. They leave for leaders who: • See them • Hear them • Challenge them • Support them Organizations don’t lose talent because talent is weak. They lose talent because leadership is. 6. The Right Manager Changes Everything A great manager can transform an average employee into a star. A bad manager can turn a star into a resignation letter. The right leader: • Builds trust • Encourages growth • Sets clear expectations • Provides psychological safety • Celebrates strengths When people feel valued, they innovate. When they feel supported, they stay. Final Thought The fastest way to destroy someone’s potential is to put them under the wrong manager. The fastest way to unlock it is to put them under the right one. Leadership matters—more than titles, strategy, or policies. Because people don’t grow from positions. They grow from people.

𝗪𝗲 𝗹𝗼𝘀𝘁 𝗵𝗶𝗺 𝗯𝗲𝗳𝗼𝗿𝗲 𝗮𝗻𝘆𝗼𝗻𝗲 𝗸𝗻𝗲𝘄 𝘁𝗼 𝗹𝗼𝗼𝗸. Not physically. Not professionally. But quietly — to disconnection, exhaustion, and an invisible kind of burnout. He was a top performer. He showed up to every meeting. He hit his numbers. He made the team laugh. But one day, he simply stopped engaging. Then he left. And no one really knew why. The truth? No one asked. Because no one knew they could. In too many workplaces, 𝘴𝘪𝘭𝘦𝘯𝘤𝘦 𝘣𝘦𝘤𝘰𝘮𝘦𝘴 𝘵𝘩𝘦 𝘴𝘵𝘢𝘯𝘥𝘢𝘳𝘥 — especially among senior leaders. Mental health becomes a private matter. Support becomes something “others” need. And the people carrying the greatest weight stop feeling safe asking for help. That silence doesn’t just cost us people. It costs us culture. It costs us creativity. It costs us connection. It creates environments where: – Stress is mistaken for strength – Performance is rewarded, regardless of cost – Struggle is seen as a personal failing, not a leadership signal When leaders don’t talk about the pressure, they teach others to hide it too. 💬 𝗥𝗲𝗺𝗶𝗻𝗱𝗲𝗿 𝘁𝗼 𝘀𝗲𝗹𝗳: 𝘚𝘪𝘭𝘦𝘯𝘤𝘦 𝘩𝘢𝘴 𝘢 𝘤𝘰𝘴𝘵. 𝘈𝘯𝘥, 𝘢𝘴 𝘭𝘦𝘢𝘥𝘦𝘳𝘴, 𝘸𝘦'𝘳𝘦 𝘰𝘧𝘵𝘦𝘯 𝘵𝘩𝘦 𝘰𝘯𝘭𝘺 𝘰𝘯𝘦𝘴 𝘸𝘩𝘰 𝘤𝘢𝘯 𝘢𝘧𝘧𝘰𝘳𝘥 𝘵𝘰 𝘣𝘳𝘦𝘢𝘬 𝘪𝘵 𝘧𝘪𝘳𝘴𝘵. #ExecutiveLeadership #MentalHealthAwareness #BurnoutPrevention #CultureChange #ModelTheWay #LeadershipSeries

I once worked with a #team where the top performer—let’s call her Anita—was the go-to person for solving problems, mentoring juniors, and making impossible deadlines happen. She didn’t just “do her #job,” she raised the bar for everyone around her. Then came promotion season. Everyone assumed Anita’s name would be on the list. Instead, the #promotion went to someone who spent more time impressing upper management in meetings than actually delivering results—someone who was an expert in office politics, not in the work itself. The fallout was quick: Anita stopped volunteering for extra projects. Morale across the team dropped. Within 3 months, Anita had an offer from another company that valued her #skills and #leadership. By the time leadership realized what had happened, they had lost not only Anita but also two more top performers who followed her out the door. The lesson? Promotions send a powerful message—about what an organization truly values. If you reward politics over performance, favoritism over fairness, you’re telling your best people that their hard work doesn’t matter. #Leaders, please remember: ✅ Recognize and reward those who actually build your company. ✅ Promote based on merit, not manipulation. ✅ Protect your culture by putting the right people in the right positions. Because when the wrong people get promoted, you don’t just lose employees—you lose trust, morale, and the very foundation of a high-performing workplace. LinkedIn

We primarily celebrate the big wins in D2C: the valuation, the market share, the funding rounds. But as leaders, we need to acknowledge a silent, shared challenge that comes with hitting a major business milestone early in our journey, which often triggers deep professional self-doubt in founders. You’d think massive success would bring total confidence. Instead, when a company scales fast, the founder's role changes completely, and they can lose the connection to what they started. This feeling is a natural consequence of shifting from a hands-on start-up parent to a long-term strategist. The founder who builds the brand is often not the same leader required for the next phase. 1. From Hands-On Creator to Strategic Director In the early days, the founder is formulating products, writing the first copy, and handling every detail. That’s the passion stage and successful leaders still champion creation every day. But at scale, the primary duty shifts from doing the creation to directing the creative vision and safeguarding its integrity across the organization. The necessary shift is the intentional step-back. Founders must learn to delegate the daily doing so they can hold the broader vision. 2. The Weight of Purpose A brand's purpose is its biggest asset but sometimes the scale makes it heavy. For purpose-driven brands, every major operational decision, from sourcing materials in bulk to changing packaging, becomes a moral choice. I have seen founders struggle under the ethical pressure of maintaining integrity across a huge supply chain and hundreds of products. It is isolating to be the final gatekeeper. D2C leaders must institutionalize their purpose. We've done the same for each brand under Honasa Consumer Ltd.. Brand values must be written into operational SOPs, not just left as motivational concepts. This protects the mission and eases the ethical burden on the founding team. 3. Maintaining Connection and Speed The first team operates like a small, fast-moving crew, everyone is aligned and can adjust quickly. The later team of 500 is a large organization—it needs complex systems, clear communication protocols, and structure. Founders have to evolve from being the charismatic leader to being the architect of the system. This can feel distant at first, and leaders often worry about losing that intimate connection and the early-day speed. But it's just what is needed at the time. What was the biggest internal identity change you had to embrace when your team grew from a small start-up crew to a large organization? #D2C #StartupFounder #Entrepreneurship

👗"Jingjin, what are you wearing right now?" The question caught me off guard. It was eight years ago. I was in the office preparing for the upcoming QBR, when my phone rang. It was our division VP. “Can you be in a client meeting this afternoon?” he asked. One of the world’s largest automotive OEMs. High stakes. 200 people are working around the clock to close the deal. I had 6 hours to prepare. My heart raced. This was the kind of meeting that could change many things! Of course, I said yes. Then came the pause. And that question: “What are you wearing right now?” "Is there a dress code?" I laughed. "Kind of..." He continued, a bit apologetically yet firmly: “I need to tell you that the president has a reputation for hitting on women. I want you to be prepared.” Suddenly, my job wasn’t just to represent the business. It was to calculate risk. To protect myself in the room. In those five hours, I still worked on my talking points. But I also asked a junior male colleague to join me, as a buffer and braced myself for inappropriate comments. The meeting went well. I delivered. There were no inappropriate comments But that experience never left me. ... If you're a woman in leadership, you need to prepare for two battles: The work, and the room. And if you're a male leader, your silence is complicity. Here’s what I now teach women privately, and what I wish someone told me earlier: 1. 🛡️ Bring your buffer.    Don’t be afraid to request someone in the room with you, not to assist you technically, but to dilute the power imbalance. It’s not weakness. It’s strategy.     2. 🚫 Pre-empt boundary crossing.    If you’re warned someone is inappropriate, name it before it happens. “Just to clarify, I’ll be focused strictly on business today.” Let them know they won’t get away with casual harassment cloaked as banter.     3. 📍Control the setting when you can.    Suggest public venues, group meetings, or shorter time slots. Private dinners and “casual drinks” are not neutral spaces. Stop feeling guilty for adjusting logistics to protect your dignity.     4. 📝 Write it down.    Any inappropriate comment, no matter how subtle, goes in your private log: date, time, what happened, and who else was there. Not because you’re planning to report it. But because memory fades, and patterns matter.     5. ⚖️ Stop normalizing it.    You’re not “too sensitive.”    You’re not imagining it.    You’re managing two jobs: your work, and your safety.    And the latter is unpaid labor.     If you're still wondering whether gender equity has arrived, ask yourself who’s planning their safety before they speak. And who just gets to speak. 👊 Until the answer is “everyone,” we’re not done.

It's time we talk about how Black women face hyper-visibility & invisibility simultaneously at work. Black women in leadership are asked to be the representative of diversity and inclusion, but the irony is we’re often left stuck in the same roles without the growth we deserve. The constant push and pull between being both overexposed and overlooked takes a mental and emotional toll. I was talking about this on X and someone commented: “And unfortunately this is reality in most spaces in which we navigate and involve ourselves. It's heartbreaking (and deeply concerning) that a great deal of us possess a number of stories about these experiences.” I couldn’t agree more. The number of stories I’ve heard from professionals across industries, stories of being praised for the very things that make us stand out, only to be dismissed when we ask for the same respect, promotions, and growth opportunities. If you want to build inclusive workplaces, we must begin by valuing and compensating the contributions of Black women fairly.