Strategies for Communicating Confidently with Senior Leaders

That VP who barely knows your work just vetoed your promotion. "Not enough strategic presence," they said. After coaching Fortune 100 leaders, here's what I've discovered: ➟ Strong team results ➟ Outstanding metrics ➟ Top performance reviews Yet when promotion time arrives, someone in the leadership room says: "I'm not sure they're ready." What's really happening? The Executive Trust Gap. Take Sarah, a Senior Engineering Manager who led a $14M product launch. Despite stellar metrics (98% team retention, 42% faster delivery), her CPO said: "Great execution, but I need to see more strategic leadership." Three months later, using what I'm about to share, she got promoted and now leads high impact meetings which opens doors to career-defining opportunities. The truth? Trust influences promotion decisions more than performance metrics alone. Here are 7 strategic moves that turn skeptical executives into your biggest champions: 1. Master the executive language shift ↳ Junior leaders talk about activities ("I completed the project") ↳ Senior leaders talk about outcomes ("This delivered 20% growth") ↳ Top leaders talk about strategic implications ("This positions us to...") ↳ Frame your updates at the highest appropriate level 2. Volunteer for cross-functional initiatives ↳ Creates visibility with multiple decision-makers ↳ Shows your impact beyond your immediate role ↳ Proves you think about the broader business 3. The "Preview" Strategy ↳ Brief key stakeholders before big meetings ↳ "I want to share our approach first and get your input" ↳ Eliminates surprise (which executives hate) 4. Create "Trust Deposits" before needing withdrawals ↳ Share relevant industry insights without asking for anything ↳ Congratulate executives on company wins ↳ Build the relationship when stakes are low 5. The 10-minute rule for executive meetings ↳ Practice delivering your message in 10 minutes ↳ Then practice delivering it in 5 minutes ↳ Then practice delivering it in 2 minutes ↳ Be ready for any time constraint 6. Demonstrate intellectual honesty ↳ Address problems before they're mentioned ↳ Acknowledge limitations in your recommendations ↳ Shows judgment and builds confidence in your thinking 7. The "Proxy Champion" technique ↳ Identify who already has the executive's trust ↳ Build strong relationships with these proxies ↳ Their endorsement becomes your shortcut to trust The most qualified person rarely gets the promotion. The most trusted one does. Which of these 7 moves will you implement this week? ♻ Repost to help someone bridge their trust gap. ➕ Follow me for more proven leadership strategies that create real career momentum.

How to Brief Senior Leaders Effectively: Lessons from a U.S. Diplomat In my over 16 years working in the field of diplomacy, I’ve developed and refined the art of delivering concise, actionable briefings to senior leaders, from ambassadors and cabinet members to decision-makers in high-pressure environments. Serving as a member of the leadership team and Acting Deputy Ambassador in my most recent assignments, I’ve led efforts on public affairs reporting, managing Embassy resources, risk assessment, and strategic communications. Here are three principles I’ve found essential for success: 1. Tailor the Message: Understand the leader’s priorities and decision-making style. Every briefing must align with their needs, goals, and the context in which they operate. 2. Clarity is Key: In high-stakes settings, time is limited. The ability to distill complex issues into clear, actionable points is critical. 3. Prepare for the Tough Questions: Senior leaders rely on experts who can anticipate risks, offer solutions, and provide insights that go beyond the surface. Throughout my career, I’ve briefed on critical global issues, including counter-disinformation strategies, human trafficking interventions, migration, and economic empowerment programs. Whether engaging with local stakeholders or presenting to top officials, my approach has always been rooted in precision, adaptability, and results-driven insights. These experiences have equipped me with the ability to provide clarity amidst complexity, a skill that translates seamlessly to senior roles in public affairs, risk management, and strategic communications.

As an executive coach, I've had the privilege of guiding senior leaders through the complexities of their roles. One critical skill I developed as Chief of Staff at AT&T is how to effectively brief a leader in 30 minutes or less. By the way, these work for any level of leader no matter who you are prepping to meet with. Here are 6 strategies that work: 1. 𝗕𝗲𝗴𝗶𝗻 𝘄𝗶𝘁𝗵 𝘁𝗵𝗲 𝗲𝗻𝗱 𝗶𝗻 𝗺𝗶𝗻𝗱 (from Stephen M. R. Covey’s 𝘛𝘩𝘦 7 𝘏𝘢𝘣𝘪𝘵𝘴 𝘰𝘧 𝘏𝘪𝘨𝘩𝘭𝘺 𝘌𝘧𝘧𝘦𝘤𝘵𝘪𝘷𝘦 𝘗𝘦𝘰𝘱𝘭𝘦): Start your briefing by clearly defining the desired outcome. This sets the direction for the conversation, helping the leader to quickly grasp the purpose and make informed decisions. 2. 𝗞𝗻𝗼𝘄 𝘆𝗼𝘂𝗿 𝗼𝗯𝗷𝗲𝗰𝘁𝗶𝘃𝗲: Ensure the leader gets the essential info to make a decision. 3. 𝗣𝗿𝗶𝗼𝗿𝗶𝘁𝗶𝘇𝗲 𝗲𝘀𝘀𝗲𝗻𝘁𝗶𝗮𝗹𝘀: Focus on what truly matters. Leave out the unnecessary unless asked. 4. 𝗔𝗻𝘁𝗶𝗰𝗶𝗽𝗮𝘁𝗲 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀: Prepare for insightful questions and be ready with solid responses. 5. 𝗘𝗻𝗴𝗮𝗴𝗲: Make it a two-way dialogue for richer, more impactful discussions. 6. 𝗦𝘂𝗺𝗺𝗮𝗿𝗶𝘇𝗲 𝘄𝗶𝘁𝗵 𝗮𝗰𝘁𝗶𝗼𝗻𝘀: End with clear actions, so the leader knows what’s next. In today’s fast-paced world, concise communication is key. How do you prepare for crisp updates? Share your thoughts below! #ExecutiveCoaching #LeadershipDevelopment #EffectiveCommunication

Complexity kills action. Especially with senior execs. Early in my career, I said too much. I assumed detail meant I was prepared. But in exec conversations, it often backfires. Senior leaders don’t need all details. They want what matters. Why it matters.  And fast. When I treated executive time like prime time, I quickly added value and became a trusted partner. Here’s the approach I still use today: (It’s how I earn trust in rooms that move fast.) 𝗧𝗵𝗲 𝗖.𝗟.𝗘.𝗔.𝗥. 𝗙𝗿𝗮𝗺𝗲𝘄𝗼𝗿𝗸 (𝘍𝘰𝘳 𝘩𝘪𝘨𝘩-𝘴𝘵𝘢𝘬𝘦𝘴 𝘤𝘰𝘯𝘷𝘦𝘳𝘴𝘢𝘵𝘪𝘰𝘯𝘴) 🧠 𝗖 = Clarify what matters now Start with the core issue or opportunity Be direct about what’s on the line 🗞 L = Lead with your recommendation “This is what I’d recommend we do next…”  Frame the why in 1–2 sharp sentences 🎯 𝗘 = Emphasize the takeaway Make the key point easy to repeat  Signal what you want them to remember 👁 𝗔 = Anticipate what they’ll ask Prep the pushbacks before they ask  Think like them, not just like you 🧭 𝗥 = Read the room in real time Watch tone and body language, not just words  Ask: “What questions do you have at this point?” Senior leaders don’t need every answer,  they want clear actionable information. How do you build trust with senior leaders? ♻️ Share this with someone ready to level up their career 🔔 Follow Justin Hills for insights to grow your influence

When the CEO asked me, '𝙒𝙝𝙖𝙩 𝙙𝙤 𝙮𝙤𝙪 𝙙𝙤?'  I was ready with a response that left an impression. I didn’t say how many years I had been with the company. 🙄 Or recite my role description. I communicated my VALUE. This sparked an engaging conversation, that allowed him and other leaders to learn more about me, creating a memorable interaction that helped me stand out.  Here’s the framework I used to confidently articulate my value: 1️⃣ 𝗦𝘁𝗮𝗿𝘁 𝘄𝗶𝘁𝗵 𝘄𝗵𝗮𝘁 𝘆𝗼𝘂’𝗿𝗲 𝗸𝗻𝗼𝘄𝗻 𝗳𝗼𝗿. Titles can be misleading. Think about your biggest strength and the impact of your work day-to-day. Including metrics or measurable results when talking about what you’re known for shows how you are delivering to company goals. 2️⃣ 𝗦𝗵𝗮𝗿𝗲 𝘄𝗵𝘆 𝗽𝗲𝗼𝗽𝗹𝗲 𝗰𝗼𝗹𝗹𝗮𝗯𝗼𝗿𝗮𝘁𝗲 𝘄𝗶𝘁𝗵 𝘆𝗼𝘂.   What makes you great to work with? This is an easy way to highlight your skills and why people trust and value your input.  3️⃣ 𝗘𝗻𝗱 𝘄𝗶𝘁𝗵 𝘄𝗵𝗮𝘁 𝗲𝘅𝗰𝗶𝘁𝗲𝘀 𝘆𝗼𝘂.  Tie it to your passion or what drives you professionally and/or personally.  Here is an example of what I would say today: 𝘏𝘪, 𝘐’𝘮 𝘚𝘦𝘭𝘤𝘩𝘪𝘢, 𝘵𝘩𝘦 𝘌𝘮𝘱𝘭𝘰𝘺𝘦𝘦 𝘌𝘹𝘱𝘦𝘳𝘪𝘦𝘯𝘤𝘦 𝘓𝘦𝘢𝘥 𝘧𝘰𝘳 𝘓𝘈𝘛𝘈𝘔. 𝘐’𝘮 𝘬𝘯𝘰𝘸𝘯 𝘧𝘰𝘳 𝘤𝘳𝘦𝘢𝘵𝘪𝘯𝘨 𝘰𝘯𝘣𝘰𝘢𝘳𝘥𝘪𝘯𝘨 𝘢𝘯𝘥 𝘦𝘮𝘱𝘭𝘰𝘺𝘦𝘦 𝘦𝘹𝘱𝘦𝘳𝘪𝘦𝘯𝘤𝘦 𝘴𝘵𝘳𝘢𝘵𝘦𝘨𝘪𝘦𝘴 𝘵𝘩𝘢𝘵 𝘨𝘦𝘯𝘶𝘪𝘯𝘦𝘭𝘺 𝘤𝘰𝘯𝘯𝘦𝘤𝘵 𝘰𝘶𝘳 𝘱𝘦𝘰𝘱𝘭𝘦 𝘵𝘰 𝘵𝘩𝘦𝘪𝘳 𝘸𝘰𝘳𝘬 𝘢𝘯𝘥 𝘩𝘦𝘭𝘱 𝘵𝘩𝘦𝘮 𝘴𝘶𝘤𝘤𝘦𝘦𝘥 𝘧𝘳𝘰𝘮 𝘥𝘢𝘺 𝘰𝘯𝘦. 𝘐 𝘳𝘦𝘤𝘦𝘯𝘵𝘭𝘺 𝘪𝘯𝘤𝘳𝘦𝘢𝘴𝘦𝘥 𝘯𝘦𝘸 𝘩𝘪𝘳𝘦 𝘱𝘳𝘰𝘥𝘶𝘤𝘵𝘪𝘷𝘪𝘵𝘺 𝘪𝘯 𝘵𝘩𝘦 𝘳𝘦𝘨𝘪𝘰𝘯 𝘣𝘺 𝘱𝘢𝘳𝘵𝘯𝘦𝘳𝘪𝘯𝘨 𝘸𝘪𝘵𝘩 𝘐𝘛 𝘵𝘰 𝘦𝘯𝘴𝘶𝘳𝘦 𝘯𝘦𝘸 𝘩𝘪𝘳𝘦𝘴 𝘳𝘦𝘤𝘦𝘪𝘷𝘦𝘥 𝘦𝘲𝘶𝘪𝘱𝘮𝘦𝘯𝘵 𝘰𝘯 𝘋𝘢𝘺 1, 𝘪𝘮𝘱𝘳𝘰𝘷𝘪𝘯𝘨 𝘧𝘢𝘷𝘰𝘳𝘢𝘣𝘪𝘭𝘪𝘵𝘺 𝘳𝘢𝘵𝘪𝘯𝘨𝘴 𝘧𝘳𝘰𝘮 84.1% 𝘵𝘰 88.5% 𝘵𝘩𝘪𝘴 𝘺𝘦𝘢𝘳. 𝘗𝘦𝘰𝘱𝘭𝘦 𝘤𝘰𝘭𝘭𝘢𝘣𝘰𝘳𝘢𝘵𝘦 𝘸𝘪𝘵𝘩 𝘮𝘦 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘐’𝘮 𝘢𝘱𝘱𝘳𝘰𝘢𝘤𝘩𝘢𝘣𝘭𝘦, 𝘮𝘺 𝘤𝘰𝘮𝘮𝘶𝘯𝘪𝘤𝘢𝘵𝘪𝘰𝘯𝘴 𝘣𝘢𝘤𝘬𝘨𝘳𝘰𝘶𝘯𝘥 𝘢𝘭𝘭𝘰𝘸𝘴 𝘮𝘦 𝘵𝘰 𝘱𝘳𝘰𝘷𝘪𝘥𝘦 𝘤𝘳𝘦𝘢𝘵𝘪𝘷𝘦 𝘴𝘰𝘭𝘶𝘵𝘪𝘰𝘯𝘴 𝘢𝘯𝘥 𝘐 𝘣𝘳𝘪𝘯𝘨 𝘢 𝘨𝘭𝘰𝘣𝘢𝘭 𝘱𝘦𝘳𝘴𝘱𝘦𝘤𝘵𝘪𝘷𝘦—𝘸𝘩𝘪𝘭𝘦 𝘬𝘦𝘦𝘱𝘪𝘯𝘨 𝘵𝘩𝘦 𝘦𝘮𝘱𝘭𝘰𝘺𝘦𝘦 𝘦𝘹𝘱𝘦𝘳𝘪𝘦𝘯𝘤𝘦 𝘢𝘵 𝘵𝘩𝘦 𝘩𝘦𝘢𝘳𝘵 𝘰𝘧 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨 𝘐 𝘥𝘰.  𝘐’𝘮 𝘱𝘢𝘴𝘴𝘪𝘰𝘯𝘢𝘵𝘦 𝘢𝘣𝘰𝘶𝘵 𝘣𝘶𝘪𝘭𝘥𝘪𝘯𝘨 𝘸𝘰𝘳𝘬𝘱𝘭𝘢𝘤𝘦𝘴 𝘸𝘩𝘦𝘳𝘦 𝘱𝘦𝘰𝘱𝘭𝘦 𝘧𝘦𝘦𝘭 𝘷𝘢𝘭𝘶𝘦𝘥, 𝘢𝘯𝘥 𝘣𝘶𝘴𝘪𝘯𝘦𝘴𝘴𝘦𝘴 𝘵𝘩𝘳𝘪𝘷𝘦. 𝘞𝘩𝘪𝘭𝘦, 𝘩𝘢𝘷𝘪𝘯𝘨 𝘢 𝘵𝘰𝘥𝘥𝘭𝘦𝘳 𝘪𝘴 𝘸𝘩𝘢𝘵 𝘬𝘦𝘦𝘱𝘴 𝘮𝘦 𝘱𝘢𝘴𝘴𝘪𝘰𝘯𝘢𝘵𝘦 𝘢𝘣𝘰𝘶𝘵 𝘭𝘰𝘤𝘢𝘭 𝘤𝘰𝘧𝘧𝘦𝘦 𝘴𝘩𝘰𝘱𝘴. 𝘉𝘶𝘵 𝘴𝘦𝘦𝘪𝘯𝘨 𝘰𝘵𝘩𝘦𝘳𝘴 𝘴𝘶𝘤𝘤𝘦𝘦𝘥 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘰𝘧 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘐 𝘩𝘦𝘭𝘱𝘦𝘥 𝘤𝘳𝘦𝘢𝘵𝘦? 𝘛𝘩𝘢𝘵’𝘴 𝘸𝘩𝘢𝘵 𝘥𝘳𝘪𝘷𝘦𝘴 𝘮𝘦. ✨ 𝗣𝗿𝗼 𝘁𝗶𝗽: Tailor your pitch to the audience, too. For senior leaders, focus on outcomes. For networking, emphasize unique skills or passions.  Let’s practice, drop your introduction using this framework in the chat. ✍

Building relationships with company leaders outside your group is career-critical. These are the stakeholders who'll be in your promo conversations. I've observed that Supra members who consistently get promoted master three strategies for connecting with senior leaders: 1/ Approach with genuine curiosity and specificity The most successful PMs don't ask for "career advice" or generic meetings. Instead, they identify what the leader is known for excelling at: ↳ "I admire how you partner with Marketing. Could I get 15 minutes to learn your approach?" ↳ "Your strategic narratives are exceptional. Would you share how you structure them?" Everyone loves talking about what they're great at. The specificity demonstrates respect for their time. 2/ Provide unexpected value Leaders remember those who help them succeed. Supra members look for opportunities to: ↳ Share relevant market insights leaders might not see ↳ Connect dots between leadership priorities and their team's work ↳ Offer to lead cross-functional initiatives they care about When you consistently provide value, quarterly check-ins become natural. 3/ Find visibility through cross-team projects Volunteer for initiatives that cut across the org chart: ↳ Leading a PM community of practice ↳ Driving adoption of new tools or processes ↳ Creating templates that solve common challenges These give them authentic reasons to interact with senior leaders while demonstrating their skills. The goal isn't just face time — it's building genuine relationships where leaders see your value firsthand. What strategies have worked for you in building relationships with senior leaders?

When Structure Meets Ambiguity: How One Executive Adapted and Thrived in a Hands-Off Culture Some leaders walk into a new role and find their footing quickly. Others walk into chaos and ambiguity and have to build the map as they go. One of my clients, a seasoned executive, recently stepped into a senior role at a high-growth organization. On paper, it was a dream: global scale, high-impact responsibilities, and a boss with a reputation for giving his leaders full autonomy. But here’s the rub: her boss didn’t do onboarding. Or direction. Or detail. He was brilliant, fast-paced, and extremely hands-off. His philosophy: “Just handle it. Don’t tell me how. Don’t walk me through it. Just tell me when it’s done.” For a leader who excels with clarity, structure, and context, this felt like being dropped into deep water and expected to swim, sans a life raft. We worked together to help her reframe the situation and adapt her style of leadership. Today, she’s thriving. She’s earned high credibility across the enterprise, has positioned herself as a results-driven, trusted operator, and, most importantly, feels confident about her recently enhanced ability to lead through ambiguity. Here are 3 strategies we used that helped her succeed: 🔹 1. Translate Your Thinking Into Their Language Leaders who don’t value detail don’t want the story, just want the headline. My client learned to shift from explaining how to proving what. She used short, focused updates tied to outcomes: “Here’s what I’m doing, here’s why it matters, and here’s how we’ll measure success.” 🔹 2. Redefine Structure On Your Own Terms When leadership doesn’t provide structure, you build it yourself. My client created internal checklists, decision rubrics, and feedback loops to give herself clarity, even if no one else asked for it. The key? She never made her structure someone else’s burden. It was her tool for managing the chaos, not a tool for managing her boss. 🔹 3. Separate Your Need for Validation from Their Leadership Style Executives often equate silence with disapproval. But some leaders don’t give frequent feedback, not because you’re failing, but because they assume you’re fine unless they say otherwise. We worked on developing self-trust and seeking feedback through outcomes, not affirmations. Leading without a map requires a different kind of strength and an opportunity to grow. Unclear direction or an elusive boss doesn't have to stall success. With the right mindset and strategy, it can accelerate it.

If you want to be seen as a strategic partner, your message needs to land at the right altitude. For a long time, I thought that in senior leadership meetings, when I got asked a question, I had to answer immediately. ↳ The pressure to speak up was intense. ↳ That was the advice I kept hearing over and over ↳ “Jump in. Don’t stay quiet. Say something.” So I did. I’d jump in quickly. Not because I had clarity... But because I wanted to look confident. I wanted to do what I was told: speak up, sound impressive. But here’s what started happening: I over-explained. I stayed in the weeds. 🚫 Even when I knew my stuff, it didn’t land well. 🚫 It came off as tactical. 🚫 Not strategic. 🚫 Not well thought through. None of that was true... But it shaped how I was seen: - Not ready for bigger roles. - Not ready for real trust in the room. Here’s the problem: When your message lands at the wrong altitude, it reinforces the wrong narrative. You start sounding tactical even when you’re not. If you have a senior leadership meeting coming up, ask yourself: 1. What decision am I trying to drive in this room? 2. Is my message centered on this? 3. Is this connecting to what actually matters to the people at that table? 4. Are you leading with the core insight or am I walking them through every detail before I get to the point? If you want to be seen as a strategic sparring partner, you have to communicate like one. The altitude of your message shapes how you’re seen. 🔔 Follow me, Bosky Mukherjee, for more insights on breaking barriers for women in tech leadership. #womenintech #womenleaders #leadershipdevelopment #womeninleadership #careergrowth