Executive Promotion Pathways

"Why aren’t your ideas getting approved?”😭😭😭🙌🙌🙌 When I took on my first director role at the age of 26 I was certain I was smart, prepared, and performance-driven. I brought bold, thoughtful proposals into the boardroom. And..then....... silence.😭😭😭 Or polite deferrals. Or “let’s revisit this next quarter.” I thought results would speak for themselves. They didn’t. It wasn’t until my coach said: “You’re playing chess, but you’re only looking at the board not the players.”😭😭😭😭😭 That’s when I learned: Organizational politics isnt dirty . It’s reality. And ignoring it doesn’t make you principled it makes you ineffective. I learnt then that being Politically Savvy is actually a leaderboard Competency for C- Suite leaders. Here are 10 aspects of organizational politics that I have learnt over my 22 years of working that no leader can afford to ignore : 1. Informal Power Brokers Some of the most influential people don’t have big titles. They have trust, access, and networks. Find them. 2. Gatekeepers Every room has people who control the flow of ideas and people. If you don't have them onside, you're not getting through. 3. Timing & Influence Even brilliant proposals fail when they land at the wrong time or haven’t been seeded properly behind the scenes. 4. Don’t Surprise the Boardroom If your idea is being heard for the first time in the meeting, it’s already in trouble. Pre-socialize. Test reactions. Secure allies.People won't attack your ideas if you have them a chance to add their thoughts beforehand. 5. Hidden Agendas Everyone has priorities. Some are declared, some aren’t. Don’t be naive—figure out what really drives each stakeholder. 6. Alliances & Coalitions You can't drive change alone no matter how smart you are . Have people who are willing to go to bat for your idea when you're not in the room 7 .Narrative Control You may have the numbers, but do you have the story?🥹🥹 Decisions are made based on stories people can believe in. 8. Loyalty & Trust Boardroom influence is built outside the boardroom. Over coffee, in quiet crises, through shared wins. Relationships matter. 9. Change Resistance Is Political, Not Logical Silence, delays, and vague pushback? That’s not confusion it’s calculated resistance. Learn to see it for what it is. Politics doesn’t mean playing dirty. It means playing smart with integrity. It took me a while to embrace that. But once I did, everything changed: My ideas got traction. My confidence grew. And I finally understood how to lead not just with intention but with influence. To any leader especially women—feeling stuck at the table: You don’t need to change who you are. But you do need to understand the game you’re playing. If you are not navigating the politics the politics is navigating you . Winfield Strategy & Innovation #Leadership #OrganizationalPolitics #WomenInLeadership #ExecutivePresence #PowerAndInfluence #strategy

I got fired twice because I had poor soft skills. Then, I became VP at Amazon, where my job was more than 80% based on soft skills. This was possible because I stopped being an outspoken, judgmental critic of other people and improved my soft skills. Here are 4 areas you can improve: Soft skills are one of the main things I discuss with my coaching clients, as they are often the barrier between being a competent manager and being ready to be a true executive. Technical skills are important, but soft skills are the deciding factor between executive candidates a lot more than technical skills are. Four “soft skill” areas in which we can constantly improve are: 1) Storytelling skills Jeff Bezos said, “You can have the best technology, you can have the best business model, but if the storytelling isn’t amazing, it won’t matter.” The same is true for you as a leader. You can have the best skills or best ideas, but if you can’t communicate through powerful storytelling, no one will pay attention. 2) Writing Writing is the foundation of clear communication and clear thinking. It is the main tool for demonstrating your thinking and influencing others. The way you write will impact your influence, and therefore will impact your opportunities to grow as a leader. 3) Executive Presence Executive presence is your ability to present as someone who should be taken seriously. This includes your ability to speak, to act under pressure, and to relate to your team informally, but it goes far beyond any individual skill. Improving executive presence requires consistently evaluating where we have space to grow in our image as leaders and then addressing it. 4) Public Speaking As a leader, public speaking is inevitable. In order the get the support you need to become an executive, you must inspire confidence in your abilities and ideas through the way you speak to large, important groups of people. No one wants to give more responsibility to someone who looks uncomfortable with the amount they already have. I am writing about these 4 areas because today’s newsletter is centered around how exactly to improve these soft skills. The newsletter comes from member questions in our Level Up Newsletter community, and I answer each of them at length. I'm joined in the newsletter by my good friend, Richard Hua, a world class expert in emotional intelligence (EQ). Rich created a program at Amazon that has taught EQ to more than 500,000 people! The 4 specific questions I answer are: 1. “How do I improve my storytelling skills?” 2. “What resources or tools would you recommend to get better in writing?” 3. “What are the top 3 ways to improve my executive presence?” 4. “I am uncomfortable talking in front of large crowds and unknown people, but as I move up, I need to do this more. How do I get comfortable with this?” See the newsletter here: https://lnkd.in/gg6JXqF4 How have you improved your soft skills?

𝐖𝐡𝐲 𝐝𝐨 𝐬𝐨𝐦𝐞 𝐩𝐞𝐨𝐩𝐥𝐞 𝐠𝐞𝐭 𝐩𝐫𝐨𝐦𝐨𝐭𝐞𝐝 𝐟𝐚𝐬𝐭𝐞𝐫, 𝐡𝐞𝐚𝐫𝐝 𝐦𝐨𝐫𝐞 𝐨𝐟𝐭𝐞𝐧, 𝐚𝐧𝐝 𝐭𝐫𝐮𝐬𝐭𝐞𝐝 𝐦𝐨𝐫𝐞 𝐝𝐞𝐞𝐩𝐥𝐲? Of all the topics people ask me about, executive presence is near the top of the list. The challenge with executive presence is that it’s hard to define. It’s not a checklist you can tick off. It’s more like taste or intuition. Some people develop it early. Others build it over time. More often, it’s a lack of context, coaching, or exposure to what “good” looks like. Here’s what I’ve learned over the years, both from getting it wrong and from watching others get it right. 1. 𝐋𝐚𝐧𝐝 𝐲𝐨𝐮𝐫 𝐦𝐞𝐬𝐬𝐚𝐠𝐞 People early in their careers often feel the need to prove they know the details. But executive presence isn’t about detail. It’s about clarity. If your message would sound the same to a peer, your manager, and your CEO, you’re not tailoring it enough. Meet your audience where they are. 2. 𝐔𝐩𝐥𝐞𝐯𝐞𝐥 𝐭𝐡𝐞 𝐜𝐨𝐧𝐯𝐞𝐫𝐬𝐚𝐭𝐢𝐨𝐧 Executives care about outcomes, strategy, and alignment. One of my teammates once struggled with this. Brilliant at the work, but too deep in the weeds to communicate its impact. With coaching, she learned to reframe her updates, and her influence grew exponentially. 3. 𝐔𝐧𝐝𝐞𝐫𝐬𝐭𝐚𝐧𝐝 𝐭𝐡𝐞 𝐬𝐮𝐛𝐭𝐞𝐱𝐭 Every meeting has an undercurrent: past dynamics, relationships, history. Navigating this well often requires a trusted guide who can explain what’s going on behind the scenes. 4. 𝐏𝐫𝐨𝐯𝐢𝐝𝐞 𝐜𝐨𝐧𝐭𝐞𝐱𝐭 Just because something is your entire world doesn’t mean others know about it. I’ve had conversations where I assumed someone knew what I was talking about, but they didn't. Context is a gift. Give it freely. 5. 𝐂𝐨𝐦𝐞 𝐰𝐢𝐭𝐡 𝐬𝐨𝐥𝐮𝐭𝐢𝐨𝐧𝐬 Early in my career, I brought problems to my manager. Now, I appreciate the people who bring potential paths forward. It’s not about having the perfect solution. It’s about showing you’re engaged in solving the problem. 6. 𝐊𝐧𝐨𝐰 𝐰𝐡𝐚𝐭 𝐭𝐡𝐞𝐲 𝐜𝐚𝐫𝐞 𝐚𝐛𝐨𝐮𝐭 Every leader is solving a different set of problems. Step into their shoes. Show how your work connects to what’s top of mind for them. This is how you build alignment and earn trust. 7. 𝐁𝐮𝐢𝐥𝐝 𝐜𝐨𝐧𝐧𝐞𝐜𝐭𝐢𝐨𝐧 Years ago, a founder cold emailed me. We didn’t know each other, but we were both Duke alums. That one point of connection turned a cold outreach into a real conversation. 8. 𝐃𝐫𝐢𝐯𝐞 𝐭𝐨 𝐜𝐥𝐚𝐫𝐢𝐭𝐲 𝐚𝐧𝐝 𝐝𝐞𝐜𝐢𝐬𝐢𝐨𝐧 Before you walk into a meeting, ask yourself what outcome you’re trying to drive. Wandering conversations erode credibility. Precision matters. So does preparation. 𝐅𝐢𝐧𝐚𝐥 𝐭𝐡𝐨𝐮𝐠𝐡𝐭 Executive presence isn’t about dominating a room or having all the answers. It’s about clarity, connection, and conviction. And like any muscle, it gets stronger with intentional practice.

Your manager just excluded you from the C-suite strategy meeting. Not by accident. By design. You earned your seat at that table. But they're keeping you in the shadows. Here's the truth: Your growth became a threat. I watched this unfold with Chen, a Director of Product at a Fortune 500 tech company. For two years, his VP championed every idea. Invited him to executive briefings. Praised his strategic thinking publicly. Then Chen started getting direct recognition from the CEO. Everything changed: → His 1:1s got rescheduled constantly → His proposals sat "under review" for weeks   → He stopped getting invited to senior meetings → His VP started taking credit for his frameworks Chen wasn't failing. He was succeeding too visibly. When you outgrow your manager's comfort zone, they don't usually sabotage you openly. They just quietly remove your oxygen. Here's how to protect your trajectory: 1. Document Everything → Keep records of your work, ideas, and impact → Use email to confirm verbal agreements   → CC relevant stakeholders on key updates → Your manager controls the narrative until you create your own 2. Build Relationships Above Your Boss → Volunteer for cross-functional projects with executive sponsors → Offer to present your work to senior leaders directly → Share insights that help them hit their priorities → Your value needs visibility beyond one gatekeeper 3. Make Your Boss Look Good Publicly → Credit them in meetings → Frame your wins as team wins they enabled → Reduce the threat by making them feel secure → The less threatened they feel, the less they block you 4. Create External Options Quietly → Update your network outside the company → Take calls with recruiters   → Build your personal brand → Having options changes how you show up 5. Know When to Escalate → If they're actively undermining you, document it → Request a skip-level meeting with their boss → Sometimes the only move is an internal transfer or strategic exit Chen did all five. He built relationships with two other VPs. Started presenting product strategy directly to the CPO. Made his boss look brilliant in every meeting while quietly building external options. Eight months later, a VP role opened in a different division. The CPO recommended Chen directly. Your manager doesn't own your career. They just control one pathway. When that pathway closes, build three more. 🔔 Want my complete Political Navigation Blueprint that's helped 10770+ leaders handle difficult manager dynamics and accelerate past roadblocks? Join my inner circle. Link to my newsletter below.

Did you know most Director+ hires in big tech never even apply for the role? Here’s the playbook hiring managers don’t tell you. I’ve talked to hiring managers at Meta, Google, Amazon, and Microsoft, and here’s the truth: You can’t just land a Director+ role, even with years of experience under your belt. It’s about understanding their playbook and playing the right game. Here’s how you can do it: — 𝗧𝗵𝗲 𝗟𝗼𝗻𝗴 𝗚𝗮𝗺𝗲 𝗼𝗳 𝗚𝗲𝘁𝘁𝗶𝗻𝗴 𝗥𝗲𝗰𝗿𝘂𝗶𝘁𝗲𝗱 Most successful Director+ candidates don’t apply cold. They’re recruited. Here’s what that means: Hiring managers trust internal networks more than any recruiting pipeline for such roles. Example: → A Google Director “intentionally” spent two years writing blog posts about scaling engineering teams (which Google values), which even caught their hiring manager’s attention, and he got hired. Actionable Steps: → Focus on showcasing your expertise in high-impact areas like scaling, decision-making, and cross-functional leadership. → Build relationships within your industry before you even think about applying for a role. — 𝗕𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗧𝗵𝗲 𝗥𝗶𝗴𝗵𝘁 𝗧𝘆𝗽𝗲 𝗼𝗳 𝗣𝗿𝗼𝗳𝗶𝗹𝗲 Your profile is your first impression and it needs to scream scope, scale, and credibility. What This Means: Hiring managers want to see specific evidence of your impact. Example: → A Meta Director highlighted their experience leading initiatives at scale: "When we hit 100M users, I wrote about it. When we had a major outage, I spoke at conferences." Actionable Steps: → Update your LinkedIn with quantifiable results: team size, budget, user growth, or revenue impact. → Publicly share your work — updates, blog posts, talks, and even internal wins (if possible). — 𝗧𝗵𝗲 𝗔𝗿𝘁 𝗼𝗳 𝘁𝗵𝗲 𝗜𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄 They don’t just assess what you’ve done; they also assess how you think and lead. Three ways to win: 𝗥𝗲𝗳𝗿𝗮𝗺𝗶𝗻𝗴 𝗬𝗼𝘂𝗿 𝗦𝘁𝗼𝗿𝗶𝗲𝘀 Your stories need to shift from execution to strategy. → Example: Instead of “I led a team to redesign our app,” frame it as: "I identified mobile as a strategic gap, grew a 50-person mobile team, and drove 60% of company revenue from our mobile-first strategy." 𝗧𝗵𝗲 𝗗𝗮𝘁𝗮 𝗦𝘁𝗼𝗿𝘆 Numbers matter but not just any numbers. Example: "Grew the team from 20 to 100 while reducing time-to-hire by 40%" stands out more than product-level metrics like engagement rates. 𝗛𝗮𝗻𝗱𝗹𝗶𝗻𝗴 𝗧𝗵𝗲 𝗣𝗿𝗲𝘀𝘀𝘂𝗿𝗲 𝗧𝗲𝘀𝘁 You’ll face intentionally tough scenarios to test how you handle ambiguity and pushback. → Example: One Amazon candidate was grilled about a delayed launch. He stayed calm, explained his reasoning, and stuck to data-driven answers and got the job! — If you want the full guide, check out the comments!

I was promoted 3x in five years at Microsoft. That led to ~$200k+ of additional comp. Here are 6 principles I used to make it happen: First, some context: Promotions at Microsoft happen in two ways: 1. Internal level bumps 2. Traditional role changes Two of my promotions were level bumps and one was a role change. All three came with increased responsibility and compensation. On to the principles. 1/ Get Clear On Where You're Going I spent my first six months figuring out exactly where I wanted to go. That way I could quadruple down on my goal. The relationships I built and projects I took on all happened with that goal in mind. Compounding applies to careers too. 2/ Be Vocal About Your Goals! I told everyone about my plan: "I want to be a Director of Partner Development." I brought it up in my 1:1s. In my performance reviews. And in convos with colleagues. People can't help you if they don't know your goals. 3/ Build Up Your Social Capital I identified people who could impact my ability to get promoted. I'd talk to them about their challenges and goals. Then I'd work to help solve that problem or support their initiatives. When you show up for others, they show up for you. 4/ Create A Specific Plan With Management Every quarter, I'd ask my manager 3 questions: 1. What skill gaps do I need to fill to get this promo? 2. What results do you need to see as evidence? 3. What projects can I join / start to get those results? Then I'd get started. 5/ Overdeliver On Value And Results I consistently came in over quota. I helped my teammates level up. I helped colleagues on other teams solve problems. Asking for a raise is a lot easier when you generate 10-100x+ what you're asking for. 6/ Ask For The Promotion Finally, make the ask! When the job becomes available, let everyone know two things: 1. You want it. 2. How they can help you (putting in a good word, etc.) Too many people don't get promos simply because they don't ask or ask at the wrong time.

Before becoming an Executive, I was an INVISIBLE contributor for the first 10 years of my career. (you probably are too) I was: Dreaming of recognition but → keeping my head down and hoping someone would notice Dreaming of promotions but → waiting for my turn instead of advocating for myself Dreaming of leadership roles but → staying quiet in meetings to avoid rocking the boat Dreaming of making an impact but → underselling my achievements to appear humble Turning point? I got snubbed for promotions not once, not twice but THREE times. Staying quiet was getting me a first-class seat at my DESK. After the third snub, I realized: I can't stay quiet and expect someone to notice me. I will always care more about my career than anyone else. I can't expect someone to articulate our value for me. I worked on: Actively sharing my accomplishments: "Our team's productivity increased 30% last quarter due to the new process I implemented." Clearly communicating my career goals: "I expressed my interest in leading the upcoming project to my manager, highlighting my relevant skills." Volunteering for high-visibility projects: "I took charge of presenting our department's quarterly results to the executive team." Quantifying and presenting my contributions: "I created a dashboard showing how my initiatives saved the company $500K annually." I eventually became an executive once I put these into practice. You don't need to change jobs every time you hit a roadblock. Or throw money at the problem with another degree or certificate. Learning to articulate your value can make all the difference. To master value articulation: Keep a detailed record of your achievements Align your work with company objectives and highlight this connection Practice describing your impact in concise, compelling ways Seek opportunities to present your work to leadership Regularly update your manager on your progress and aspirations Remember: "Your work speaks for itself, but only if you give it a voice." #aLITTLEadvice

Executives: If you rely on job boards to land your next role, you may undermine your search. I know... it feels productive: tailoring résumés and hitting the "apply" button. But for most executive-level roles, this approach doesn’t move the needle. Here’s why: 1. You’re invisible in a sea of applicants. Executive roles attract hundreds, sometimes thousands, of candidates. Your experience may be impressive, but if it doesn’t match the algorithm, it won’t make the cut. 2. Your broad, cross-functional background may be penalized. Executives often have rich, varied experiences. Ironically, that complexity doesn’t always score well in automated systems designed for narrower roles. 3. Many jobs are already filled before they’re posted. Job descriptions are frequently written after a preferred candidate has been identified. The listing is often a formality to meet compliance requirements. 4. Applying online creates a false sense of momentum. It feels like progress, but leadership roles are secured through conversations, not clicks. 5. Job descriptions don’t reflect what hiring managers truly want. Many job listings are “wish lists” that don’t reveal the actual challenges of the role. You need to speak with someone inside the organization to learn the real story. 6. Lack of salary transparency wastes valuable time. Without a clear compensation range, you could spend weeks pursuing a role that doesn’t meet your expectations. So what should you do instead? Executives who land faster—and better—roles aren’t applying more. They’re positioning better. • Consulting as a bridge: Stepping into fractional or project-based work helps companies see your value before a permanent role is available. • Thought leadership: Publishing, speaking, or participating in industry conversations raises your visibility and authority. • Referral networks: Most executive roles are shared through trusted introductions long before a listing is written. I break all of this down in my latest Forbes Coaches Council article: 6 Ways Job Boards Are Slowing Your Executive Job Search (And What You Should Do Instead). 🔗 https://lnkd.in/gPdFJur2 If you’re serious about shifting from passive to strategic, now is the time to rethink your approach. The right executive role won’t come from applying, it will come from aligning, positioning, and being seen before the search begins. If you need help with your strategy, please reach out to connect with me. #QualfiedIsntEnough #CareerVelocity #jobs

The skills that make someone an exceptional individual contributor often become limitations in senior leadership. Consider Sarah (composite of many real examples): - Crushes every metric - Works longest hours - Knows every answer - Solves every problem personally - Team depends on her for everything Passed over for VP multiple times. Here's the pattern I've observed: High Performers Often: - Execute personally - Protect their expertise - Measure effort - Create dependency - Focus on tasks High Leaders Typically: - Execute through others - Share knowledge freely - Measure outcomes - Create capability - Focus on people The coaching insight we shared that changed everything for Sarah's trajectory: "What if you stopped being the best player and started being the coach?" Her shift over 6 months: - Delegated strategically - Developed team capabilities - Led cross-functional initiatives - Focused on multiplying impact The result: Finally promoted to VP. This is much easier said, than done. While the specific actions are easy. Internal beliefs, patterns, habits, routine and skills are much harder to change. A step-by-step approach with proactive coaching every step of the way, Made this change possible. The uncomfortable truth I share with clients: If you're the hardest worker on your team, you might not be ready for executive leadership. Leaders create capacity. They don't just consume it. What's your experience with this transition? #Leadership #ExecutiveDevelopment #ManagementInsights #CareerGrowth

Searching for senior executive roles is an entirely different game than most career moves. At this level, the right strategy goes beyond updating your resume and LinkedIn profile. Some insights on building a targeted approach that gets results: 💲 Define Your Value Proposition Senior roles require clarity on your unique impact—think about the transformation you can drive. Reflect on your leadership strengths and the core expertise that sets you apart. This will form the foundation of your story. 💲 Target Specific Companies Don’t wait for opportunities to appear in job postings. Identify 10-20 companies where your experience would add specific value. Tailor your outreach to these organizations, emphasizing the problems you’re uniquely equipped to solve. 💲 Activate & Expand Your Network At the executive level, most roles are filled through connections. Connect with leaders in your target industries and companies, attend relevant events, and leverage connections you may have overlooked. Cultivate relationships—not just for job leads, but to understand industry needs and pain points. 💲 Build Your Brand Thoughtfully Position yourself as a thought leader in your space. Publish articles, comment thoughtfully on industry news, and consider speaking engagements. This isn’t just about visibility; it shows prospective employers your expertise and strategic thinking. 💲 Work with Executive Recruiters & Firms Build relationships with executive search firms that specialize in your industry. They can be invaluable resources, but remember, they work for the hiring company. Stay in touch, keep them updated on your progress, and be selective in who you approach. 💲 Be Prepared for a Lengthy Process The search for executive roles can take longer than anticipated. Focus on keeping momentum and staying positive. Your strategy will yield results if you remain consistent and committed. 🌐 The path to a senior role is nuanced and requires intention, patience, and resilience. Commit to a proactive strategy, and remember: the best roles often come through the relationships and trust you’ve built over time. #executivecareers #careers #jobsearch #strategy