When Should You Stop Trying for VP?

 

"I've been trying to become a VP for a year. When should I stop trying for it?"   A client inside my program asked me this recently. And it stopped me for a second - because that's not really a tactical question. It's an emotional one.   It's what people ask when they've tried everything they think they're supposed to do… and it's still not working. It's the moment when ambition meets exhaustion.   My honest answer? If this milestone matters to you - never. Not because I believe in endless hustle.   But because the right question isn't "When should I stop?" It's "What do I need to do differently?"   The Hidden Truth About "Trying" My client wasn't chasing VP for the title or salary (though she deserved both). She had a 10-year vision - she wanted to build her reputation inside corporate first, then transition into consulting.   So when she said "nothing's working," I asked a simple but uncomfortable question: "What exactly have you tried?"   We made a list. She networked… with about five people - all year. She had a few "fun" coffee chats, but no real plan. She posted occasionally on LinkedIn - mostly random thoughts. And she had one recruiter interview for a role she didn't even want.   If you've ever been in this situation, you know how frustrating it feels. You're doing things. You're putting in effort. You're technically trying.   But without the right strategy all of your effort doesn’t get you the right results. Let’s change that.

What a VP Strategy Actually Looks Like Getting to VP isn't a waiting game - it's a campaign. And like any good campaign, it needs a plan, clear positioning, and consistent action.   Here's what I told my client to do instead:   Step 1: Turn Networking into a Strategy Talking to five people a year won't move the needle. You need consistent, intentional outreach. Reach out to 20 VPs every month. Not for favors - for insight. These conversations are where you learn how people actually made the leap.   Here's how to make those calls count: Listen more than you talk. Spend 80% of the conversation understanding their path, the shifts they made, and what leaders looked for when promoting them. Ask smart questions. "What do you think made leadership see you as ready?" "What skills mattered most?" "What advice would you give someone preparing now?" Build momentum. End every call by asking, "Who else would you recommend I talk to?" - and keep the chain going.   Within a month, you'll have real data - not assumptions - about what it takes to reach VP in your company or industry. Plus, a hot network of VPs who would think about you when opportunities open up or when they are leveling up.   Step 2: Know Your Value If you can't clearly articulate who you are and the unique value you bring, it will be hard to stand out and explain why you are the best person for the job. Avoid the trap of trying to be good at everything and focus on highlighting one thing that matters.   Your positioning statement should answer three questions: What problem do you solve? What impact do you create? Why does that matter to the business?   For example: "I help product organizations turn customer data into strategic decisions that drive growth."   Now you're not just a Director who's great at execution - you're a strategic operator with a business lens.   Once you're clear on your message, make it visible. Use LinkedIn to share insights, results, or patterns from your work that reinforce your value narrative. Visibility builds credibility.   Step 3: Create Your Own Opportunities Most people wait for the perfect job description or for recruiters to DM them. But that's how you end up waiting years.   Instead, make a dream list of companies and CEOs whose problems you can solve. Then, reach out directly - not with a resume, but with a short message that articulates your value proposition.   Something like: "I've been following your company's growth, especially your recent expansion into [X]. I specialize in helping teams operationalize that kind of scale efficiently. Would you be open to a short conversation about how I could help?"   That's how senior hires happen. Quietly. Through proactive, thoughtful outreach - not job boards. (If you are a Director just swap CEO with VP and voila!)   Why Quitting Your Dream Isn’t The Answer Here's the hard truth: most people give up right before things start to move. When a few months pass without progress, they assume they're not good enough.   That maybe they don't have "it." But that's rarely true. They don't lack potential - they lack a process.   Just because you know the ingredients - hard work, networking, visibility - doesn't mean you know how to bake the cake.   It's the same with your career.   You need to know how to combine your skills, relationships, and visibility in the right order to create results.   That's the strategy I used to land my second VP role - and the same one that helped two of my clients get promoted to VP this year, despite a tough economy and fewer opportunities than ever before.   No magic. No shortcuts. Just the right ingredients, in the right order.

Your Next Steps If you've been working toward VP and it feels like nothing's clicking - pause and ask yourself: Are you busy or are you strategic?

13 lessons life has taught me

 #1. Excellent things happen to people who do excellent things.

#2. Morning exercise is a game-changer.

 

#3. The game of leadership is helpfulness.

#4. The things that are hardest to do are the things that are generally the wisest to do.

#5. Creativity shines brightest when we are alone. Make time for silence, stillness and solitude.

#6. Education is inoculation against disruption. Read for an hour each day to protect your hope, refine your craft and grow your knowledge.

#7. The fears you don’t face become your walls. And doubts are destroyed by strong action.

#8. What hurts us can help us. Leverage hardship to reclaim your natural heroism.

#9. Cheap costs more.

#10. Mastery takes massive practice, unrelenting patience and vast devotion. It’s a very difficult obsession. And one of the best commitments you can make.

#11. An amazing family life sets you up for a glorious business life.

#12. Keep your promises. Never lie. Outwork your peers. Deliver beautiful value. People watch what you do. Even if you think they don’t.

#13. You can’t inspire others if you are uninspired. Actively work to keep your enthusiasm and inner fire high. Be with art. Go to conferences. Travel. Explore.

What to Do When There’s No Path to Promotion

 

The 3 Most Common “No-Growth” Scenarios Let’s call them out.   1. The Structural Ceiling There’s only one Director or VP above you, and they’re not going anywhere. Unless they move or retire, there won’t be an opening.   2. The Reorg Loop The company keeps changing priorities, but not creating new leadership roles. You’re having to build your reputation over and over again for new leaders, but that feels like treading water.   3. The Cultural Block Promotions go to the “next in line” not the most qualified. That is actually a red flag not just for your promotion, but the culture in general. “Butt in seat” promotions are archaic and often deliver poor leadership.   If any of these sound familiar, it’s not a reflection of your readiness. It’s a sign you’ve reached the natural limit of growth there.

The Mindset Shift: Stop Waiting, Start Designing Most people assume their next step will come from proving themselves harder. But you don’t have to wait to be picked. You can design your next move.   Here’s what that shift looks like: From Earning to Positioning: You’ve already earned it. Now your job is to signal readiness through how you talk about your work and show up as a leader. From Loyalty to Leverage: Staying too long doesn’t prove commitment. And loyalty is rarely rewarded. What you need is to create leverage for yourself somewhere else. From Patience to Proactivity: Promotions aren’t fair. They’re strategic. And the people who get them are the ones managing their career like a business. Stop waiting and start taking action.   These mindset shifts earned me most of my promotions and at least 6-figures in raises. Every time I got stuck and there was no room for growth (despite trying) I stopped waiting for a mircle, changed companies and moved up. Here’s how you can do that too.   How to Move Up (Not Sideways) When You Change Jobs If you’ve hit a ceiling, changing companies can absolutely be a promotion. But only if you approach it strategically. Here’s how to make your next move count.   1. Find Proof You’re Already Operating at the Next Level Before you update your résumé or LinkedIn, get clear on what “the next level” actually looks like. Look up job descriptions for the role above yours—Director, VP, or whatever’s next. Or better yet, talk to people already in those positions. Ask what success looks like in their world. Then go back to your own work and find proof that you’re already doing some of those things. Leading cross-functional initiatives. Driving strategic priorities. Managing leaders, not just individual contributors.   This step does two things: It helps you see yourself differently, as someone already playing at that level. It gives you the language and evidence you’ll need to position yourself that way publicly.   You’re not inflating your story. You’re finally articulating your value at the right altitude.   2. Reframe Your Narrative: Speak Like the Level Above You When you’re ready for a step up, your story has to shift from “Here’s what I’ve done” to “Here’s what I can do for you next.” Executives don’t get hired for their past. They get hired for their potential impact.   That means: Speak in terms of outcomes and strategy, not just execution. Frame your work around business results, not personal achievements. Tell stories that show how you think—how you connect dots, influence direction, and make decisions.   The next level isn’t about doing more. It’s about thinking differently.   3. Position Yourself as the Obvious Choice This is the part most people skip. Instead, they try to be everything to every company and end up being ignored or rejected. I get where this is coming from. Especially in this economy, you want to cast a wide net and create more opportunities… except this approach is the reason you’re not getting approached.   Think of it this way: If you had a serious heart issue, you wouldn’t call your family doctor — you’d call a cardiologist. Both went to medical school, both are qualified, but one has built depth in a specific area.   That’s exactly how senior leaders think when they’re filling top roles. They’re not looking for someone who can “do a bit of everything.” They want the person who can diagnose the real problem, lead the treatment, and deliver results in their domain.   Positioning yourself means identifying the big need at the next level, and crafting a story that shows you are the best solution.   If the company is scaling fast, don’t just say you are are a great engineer. Say you “built systems that can double capacity without doubling headcount.” If they’re struggling with brand awareness, don’t say you “ran marketing campaigns.” Say you “helped a company in a similar stage go from unknown to category leader in one year.”   When you show up that way, people stop evaluating you as a candidate and start picturing you in the role.   The Reality of Changing Jobs to Level Up Everything I just shared with you helped me level up multiple times ,and yet… Some of you may still think “If I’ve never been a VP, no one will hire me as one.” But that’s just a limiting belief.   I’ve had multiple clients jump to Director and VP roles without ever holding the title before. One went from Director to VP in six months after reframing her story and showing she was already operating at that level. Plus, positioning herself as an expert in her industry. Another landed a Director offer during a promotion freeze because he learned how to connect his work to business outcomes and speak like a peer to executives.   They didn’t get lucky. They got intentional. They learned how to make companies see the value they already had.   You don’t need to wait two more years to “earn it.” You just need to show up as if you already have.

Your Next Steps If you’ve outgrown your company, don’t shrink yourself to fit it. Design your next step intentionally and make sure it reflects your potential, not just your current title. You don’t need to wait years for your next promotion. You can create it. Because once you stop waiting for permission to rise, that’s when the real growth begins.

How to Think Like an Executive

 

One of the most common pieces of feedback ambitious professionals get: “You just need to be more strategic.”   If you’ve ever heard that, you probably walked away wondering: Okay… but what does that even mean?   It sounds like a compliment and a critique at the same time. And because no one actually explains what “strategic” looks like, most people try to fix it by doing more of what they already do.   They create fancier presentations. They add more data. They make sure every bullet point is perfect. But that’s not what being strategic means.   It’s not about slides or polish. It’s about how you think, how you make decisions, and how you communicate your point of view.   Early in my career, I prided myself on being efficient. If something needed to get done, I was on it. Fast.   But one day, an SVP stopped me mid-update and asked: “That’s great, Maya… but why are we doing this?”   I froze.   I could tell you what we were doing, but I hadn’t thought deeply about why it mattered in the bigger picture. I was optimizing for speed, not impact. And in that moment, I realized that’s the difference between being a high performer and being a strategic leader.   So What Does “Be More Strategic” Actually Mean? When a manager says “you need to be more strategic,” they’re not asking for fancier decks or longer reports. They’re telling you they need to see that you can think like an executive not just execute.   Here’s what that means in practice: You understand the bigger picture — not just what you’re doing, but why it matters. You anticipate implications — how one decision affects other teams, customers, or priorities. You focus on leverage, not activity — choosing what moves the business forward. You communicate with a point of view — not just data, but a clear recommendation.   It’s not about knowing all the answers. It’s about showing that you can connect your work to business outcomes and make confident, informed decisions the way leaders do.   Here’s how to start doing that.

Step 1: Get the Context Before You Act Too often high performers jump straight into execution. Strategic thinkers start by understanding the landscape.   They want to know: What are the company’s top priorities? How does our team contribute to those goals? What’s happening in the market or industry that could impact us? What do my stakeholders actually care about?   Without that context, you’re operating in a vacuum. You can’t connect the dots if you don’t know what the dots are.   That’s why one of the best things you can do is run a stakeholder listening tour — short conversations with key leaders to understand their goals, priorities, and challenges.   You’ll be amazed at how much clarity you gain and how much more confidently you can make decisions that actually matter.   Step 2: Zoom Out and Connect the Dots Once you have context, you can elevate your perspective.   Most high performers are trained to think in terms of projects and deliverables. What’s due, who’s responsible, and how to get it done faster. But executives think in terms of systems and outcomes.   They can explain how today’s projects tie to tomorrow’s results. They can see how one decision affects another function. They anticipate risks and trade-offs before they happen. They stop thinking in tasks and start thinking in systems.   A simple habit that helps: before starting anything new, pause and ask: “How does this decision fit into the broader strategy, and what are the downstream effects?”   That single question instantly changes how you’re perceived: from someone who executes to someone who leads.   Step 3: Make a Call and Communicate a Point of View Here’s where many high achievers get stuck. They collect tons of information… and then stop short of an opinion. They share all the details but no direction. They think it’s safer to “let leadership decide.”   But strategy requires judgment. Executives don’t want a data dump — they want your perspective.   They want to know: What do you recommend? What options did you consider? What’s the trade-off you’d make and why?   That’s what shows you’re thinking at the next level. As one of my clients put it, “I stopped giving updates and started giving recommendations, and that’s when people began treating me like a peer, not a report.”   How to Show Strategic Thinking at Work Thinking strategically is one part of the equation. The other part is showing it through the way you communicate, plan, and prioritize. Here are 3 simple ways to do that every week:   1. Reframe Your Updates Around Outcomes Stop reporting activity. Start communicating impact.   Instead of: “We launched the campaign this week.” Try: “We launched the campaign to improve adoption by 15%, which ties directly to our Q4 growth goal.”   This shift helps people see that you understand the why, not just the what. (If you missed my newsletter on sending strategic weekly updates, you can get my exact formula here)   2. Ask Questions That Elevate the Conversation Strategic thinkers don’t just provide answers, they ask better questions. They zoom out and consider the long term instead of only considering the immediate response.   Try these zoom out questions in your next meeting: What does success look like from the exec team’s perspective? If we say yes to this, what are we saying no to? How does this align with our top company priorities? What’s the biggest risk if we don’t act? How will we measure success?   Every time you ask a question like that, you demonstrate altitude. You’re thinking like a business owner, not a task owner.   3. Align Proposals to Company Goals Before any planning session or pitch, review your company’s annual objectives or the CEO’s priorities.   Then ask yourself: How does what I’m proposing help achieve those goals?   When you frame your recommendations that way, you’re not just offering ideas — you’re offering strategy.

Your Next Steps “Be more strategic” isn’t vague feedback it’s a roadmap for leadership.   It means: Stop reacting, start understanding. Stop reporting, start interpreting. Stop summarizing, start leading.   When you combine context, big-picture thinking, and a clear point of view, you stop being seen as the doer… and start being trusted as the decision-maker.   So, before your next update or meeting, pause and ask yourself: “Do I have the full context? Am I connecting the dots? Am I making a call?”   That’s how you start thinking like an executive — and more importantly, how you start being seen as one.

The 60-Second Intro That Instantly Positions You Like a VP

 

The VP-Level Intro: 4-Part Formula Want to create your own introduction to shape perception? Use this in meetings, offsites, interviews, and exec roundtables.   1. Start with basics Name + title. Calm, steady, two beats.    2. Add strategic context Explain the business value you drive (not your task list). → “I lead our digital operations team to automate revenue-critical workflows across product, marketing, and sales.”    3. Show one outcome Pick a result that signals scale, impact, or velocity. → “Last quarter our rev-ops overhaul cut sales cycle time by 18%.”   4. (Optional) Add a one-liner of personality A light touch makes you memorable—without turning it into a TED Talk.  → “I’m leading our finance transformation… aka ‘spreadsheet therapy.’”   The 60-Second Script (Steal This) Copy, personalize, and practice: “I’m [Name], [Title] at [Company]. I [lead/own] [scope] to [business outcome]. In [timeframe], we [proof: metric/result]. This quarter we’re focused on [next strategic priority]. [Optional personality line].”   Examples across functions Product: “I’m Priya, Director of Product at Dogdash. I lead our collaboration suite to accelerate cross-team delivery. In the last two releases, we increased active teams by 22%. This quarter we’re simplifying enterprise onboarding to cut time-to-value in half.” Engineering: “I’m Marco, Senior Eng Manager at Shoplist. I own checkout performance. Over six months we reduced p95 latency by 31%, unlocking +7% conversion. Now we’re rolling out edge rendering globally.” Operations: “I’m Lina, Head of BizOps at Datalane. I centralize forecasting and planning to improve capital efficiency. Our new model cut variance by 40%. Next up: automating quarterly scenario planning.”   Pick the Right Proof Point Your metric should be: Business-relevant: Revenue, margin, retention, adoption, cycle time, cost to serve, incident rate not vanity metrics. Time-bound: “In Q2” or “over the last six months.” Directional: Up or down and by how much. At your altitude: Team-level if you lead a team; portfolio-level if you lead a function.   If you can’t share a number (NDA, early project), use concrete proxies: “launched across three regions,” “adopted by top 10 enterprise customers,” “cut approval steps from 7 to 3.”   Won’t This Sound Like Bragging? Only if you deliver it like you’re campaigning for Best Actor. Stating outcomes is not bragging, it’s leadership. You’re giving people the information they need to place you correctly. Keep the balance: Credit the team (“my team,” “with our partners”). Own the result (don’t hide behind “we” to avoid accountability). Stay fact-based (numbers, timeframes, outcomes).   If people don’t understand the value you bring, they won’t think of you when it’s time to promote someone. The most effective executives do the work and ensure the right people understand the impact.

How to make your role more strategic

 

15 Practical Ways to Make Your Role More Strategic You can’t show up one day and say “I don’t want to be in the weeds anymore” and expect to immediately be given strategic responsibilities (I wish it worked that way). Making your role and your value more strategic is a process that starts with you proving you can think like a leader. And the more you do it, the easier it will become to offload tactical work, to secure more headcount, and step into a more senior role.   Here’s how you can get started:   How You Think (Strategic Mindset in Action) 1. Ask “why” before you start. Don’t accept tasks at face value. When your manager asks you to deliver X, respond with: “Got it — and can you share how this ties to our bigger priorities?” That context allows you to frame updates strategically later or delegate work that isn’t critical.   2. Turn updates into executive-level briefs. Instead of: “The project is 60% done,” try: Progress: “We’re on track to launch next week.” Risk: “There’s a resource gap that could delay testing.” Recommendation: “I propose we shift timeline A to stay aligned with Q4 goals.”     3. Bring one new insight to every meeting. Start preparing for meetings instead of trying to wing it. Connect the dots before you get in the room and share a pattern you’ve spotted, an opportunity, a problem or risk: “Across three teams, adoption stalls at the same point. Here’s what that might mean.”     4. Flag risks early and offer options. Executives hate surprises. The minute you know something is wrong or risky send a note and offer solutions: “If X slips, Y is at risk. Two options: add resources or adjust scope.” You’re not just flagging — you’re problem-solving.     5. Translate tasks into outcomes. Finished a deck? Don’t just say “Slides are ready.” Say: “The deck is ready — it will help our VP make the case for funding in the board meeting.” Always connect to business impact. BONUS: And document them.   How You Show Up (Visibility in Action) 1. Ask to join planning sessions. Don’t wait for an invite. Ask to join strategic meetings even as a spectator. Say: “I’d love to share frontline insights as you shape the annual roadmap.” Even listening in signals you’re thinking at the next level.     2. Use the language of impact, upside, and risk. Replace task talk with business framing: Impact: “This will reduce churn by 3%.” Upside: “Faster onboarding means quicker revenue recognition.” Risk: “Delayed testing could push launch past quarter-end.”     3. Volunteer to present at an all-hands. Don’t wait for an opportunity - ask for it. You can co-present with a team member or even your boss. You can represent you’re team’s efforts, or present your part in a cross functional project. Either way, get a spot, and share the problem, solution and impact. “Our team’s work saved 200 hours this quarter, freeing sales to focus on closing deals.”     4. Submit one process improvement proposal. Think of the last time you complained something isn’t working well, thinking you could do it better or have a better process. Now go do that. Pick a recurring pain point, write a one-page suggestion, and tie it to a business goal. Share your proposal and ask for the support or resources to execute. Example: “If we automate reporting, we’ll free 5 hours per manager per week, accelerating decision-making.”     5. Start sharing executive briefs with your manager. Before the next leadership sync, hand your manager a 3-bullet overview (status, risks, recommendation). They’ll start seeing you as a thought partner, not just a task owner.   How You Lead (Influence in Action) 1. Ask stakeholders what success looks like. In your next kickoff, ask: “What does success look like from your perspective?” Then tailor updates to show how you’re delivering that version of success. By the way, you don’t have to wait for quarterly planning or kick off. You can initiate a “listening tour” anytime to align on priorities and needs.     2. Work in public, not in silos. Don’t wait for the project to end to send updates. Share drafts and early thinking with stakeholders as a way to align and get buy-in: “Here’s the first version — what would make this most valuable for you?” Now they’re invested in your success.     3. Automate or delegate one recurring task. Free yourself from the busywork trap. Use the time to attend higher-level conversations strategy reviews, roadmap discussions, or skip-level 1:1s. You may think delegating is punishment but it’s a gift. You are empowering your direct reports to do work you were doing just 5 minutes ago. They now get to do next level work.     4. Shape the meeting agenda. Don’t just show up and hope for the best. Bring up the topics you want to discuss. Propose an addition: “Can we spend 10 minutes on how this initiative affects next quarter’s revenue priorities?” That one question elevates you from executor to strategist.     5. Circulate a trend brief once a month. Pull three insights (customer, market, or competitor) and share with your team: “Here’s what I’m seeing and what it could mean for us.” That’s how you build thought leadership.

Your Next Steps Strategy isn’t something you wait for. It’s something you practice.   Every executive you know started tactically but they made the leap by showing up differently. They didn’t wait for permission. They turned everyday interactions into proof points of their strategic value.   You can too.   Pick one of the 15 and try it this week. Don’t overthink it - just start.