4 struggles every executive hides

 We often talk about leadership as power, influence, and impact.

But what most leaders don’t expect is how heavy it can feel at the top.

Behind the confident exterior, many executives are battling something far more personal:
pressure, isolation, and the constant demand to have answers, even when they don’t have any.

Beneath the surface of success lies an emotional cost that too few people talk about, and even fewer know how to manage.

In today’s edition, I'm diving into:

• The four emotional challenges even the most capable executives struggle with
• How these pressures affect decision-making, performance, and long-term growth
• And 3 proven approaches to prevent leadership from becoming an emotional burden

Let’s dive into the 4 emotional challenges:

1. The Loneliness Of Leadership

The higher you climb, the lonelier it gets.

Executives often find themselves without a trusted confidant who truly understands their challenges. They can’t openly discuss their deepest uncertainties with employees, board members or investors, who all may have their own agendas.

Consequently, without a trusted circle of peers, senior leaders carry the weight of responsibility alone. Decision-making becomes more insular, leading to blind spots or second-guessing.

The loneliness becomes worse over time, turning into a feeling of isolation, stress, decision fatigue and even burnout.

2. The Pressure To Always Have The Answer

At the executive level, uncertainty isn’t an option - at least, that’s the perception.

Leaders are expected to have solutions, even in the face of constantly evolving realities. This pressure creates a fear of vulnerability, making it difficult to admit when they don’t have a clear path forward.

Instead of opening up, many executives suffer in silence. They avoid tough conversations and push forward alone rather than seeking input that could lead to better outcomes.

They struggle to admit that they, in fact, don’t have all the answers.

3. The Lack Of Honest, Agenda-Free Feedback

Most feedback executives receive is filtered.

Employees are cautious about challenging authority or pointing out weaknesses. Board members and investors have financial interests, and even external advisors can bring their own biases.

Getting open, honest, valuable feedback is rare.

But feedback is the breakfast of champions. Without candid feedback from people who truly understand the complexity of leadership, executives live in a bubble of filtered communication and blurred realities.

And this results in the risk of making decisions based on incomplete or skewed information.

4. Fear Of Stagnation And Falling Behind

Since the beginning of this century, the business landscape has been experiencing a constant stream of crises and technological advancements.

In an era of AI, digital transformation and shifting consumer behaviors, the ability to adapt and innovate is a challenge.

And this makes many executives worry: Am I staying ahead, or am I becoming obsolete?

With constant performance pressures and reacting to yet another crisis, it has become increasingly difficult for executives to make space for themselves and their own growth. But without continuous development and learning, we fall behind, and leaders who fail to prioritize their own growth risk leading their companies into stagnation.

And by the time they realize this, it’s too late.

3 Steps to safely navigate these pressures

While these emotional struggles are common, they are not inevitable. The most effective executives proactively build structures of support, insight and accountability around themselves.

Here are three proven approaches to prevent leadership from becoming an emotional horror story:

1. Join A Peer-To-Peer Executive Group

One of the most effective ways to combat executive loneliness is by joining a high-caliber peer group.

Unlike traditional networking groups, these are small, curated circles of senior leaders who challenge each other’s thinking and act as a confidential sounding board. They provide a trusted environment for candid conversations about leadership struggles and offer agenda-free feedback, as peers have no stake in one another’s business.

At the same time, leaders experience valuable learning through exposure to different industries and new perspectives.

While premium networking groups often come with a significant price tag, remind yourself that you get what you pay for. However, there are more affordable options, like a personal board of advisors or working with an external Executive Co-Pilot.

2. Build An Inner Circle Of Trusted Advisors or use a Co-Pilot

Executives should be deliberate about who they turn to for insight.

Cultivating a personal board of advisors can be invaluable. It’s a mix of mentors, former executives and independent thinkers who provide diverse perspectives without the constraints of internal politics. Ideally, they encourage long-term strategic thinking, instead of short-term execution. The key is to choose advisors who are willing to challenge your thinking, not reinforce your existing beliefs.

If a whole personal board sounds a bit much, hire an external Co-Pilot.

This is a high-touch advisory relationship; essentially a strategic sounding board and trusted confidant for deep strategic thinking when stakes are high and timelines are tight. Make sure you don’t just hire an executive coach and instead go for a Co-Pilot who can blend executive sparring, strategic counsel, and leadership guidance to help you think deeper, act faster and lead smarter.

A good Co-Pilot challenges your assumptions, provides fresh perspectives, helps frame critical decisions, and prepares you for high-stakes meetings, especially around strategy, leadership, culture, and governance-related issues.

3. Commit To Executive-Level Learning And Reflection

One of the most overlooked approaches to combatting stagnation is dedicated time for learning and reflection. Many executives focus mainly on operational execution, leaving little room for deep thinking and growth.

Learning and reflection time ensures executives stay close to evolving leadership insights. It helps develop clearer, more confident leadership skills and reduces stress by providing structured time to step back and refocus. Whether through executive coaching, taking courses, reading, or offsite retreats, deliberate learning and reflection keeps executive leadership sharp.

I suggest focusing on skills that are non-negotiable for leaders, but are typically not part of a subject-matter focused career growth. A sales manager becomes a team leader and later VP of sales, often without having gone through proper education on strategy or leadership. And latest when leaders reach a level where the organization looks at them for direction and strategy, they realize they have a knowledge gap.

Final Thoughts

Leadership can at times feel lonely and overwhelming, but it doesn’t have to be that way.

The key is building a strong support system - one that includes trusted peers and opportunities for continuous growth. Engaging with the right people and making time for learning helps executives gain fresh perspectives, sharpen their decision-making and reduce stress.

How to Make the VP Title Catch Up With Your Work

 

One of my clients had a problem that sounds flattering until you are the one living it: Everyone treated her like a VP except the org chart. She was doing the work, but she didn’t get the title.   Rachel was a Senior Director, but she was already sitting in the same meetings as the VPs, making similar decisions, and carrying work with comparable scope.   Other executives trusted her judgment. She was included in strategic conversations. She had already demonstrated that she could operate at the next level.   So she assumed the title would eventually catch up. It didn’t.   Her company was already getting the benefit of her VP-level leadership. There was no automatic reason for them to redesign the role, find the budget, and make the title official.   The turning point was not another big win.   Rachel stopped waiting for senior leaders to connect the dots and “award” her the recognition.   She became more deliberate about communicating the business impact of her work. She built advocacy with other VPs and members of the C-suite. And she told them she wanted the VP role.   Eventually, she had a direct conversation with the CEO.   She explained that she was already operating at the next level, showed what she could accomplish with a broader mandate, and asked what needed to happen for the title to follow.   They agreed on a roadmap and a timeline. Just months later, she was promoted to VP.   Her performance made her qualified. Her promotion strategy made the decision possible.   Doing VP-Level Work and Creating a VP Promotion Are Two Different Jobs This might be where you get stuck. You take on broader scope, solve increasingly complex problems, and become the person everyone relies on when the stakes are high.   Then you assume the work will speak for itself. It rarely does.   Your company can benefit from your VP-level contribution for a long time without changing your title, authority, or compensation.   Your work is the evidence, but you still need to build the bridge between that evidence and a promotion decision. That is what no one tells you upfront.   Here’s the good news: following this strategy is how you turn all of your effort into a promotion without waiting in line.   Think of it like turning great ingredients into a five-star meal. You already have the raw material. The strategy makes it something senior leaders want to order.

The BRIDGE Framework If you are already operating beyond your title, or if you want to be, use this six-part framework:   B: Benchmark the VP role Define what VP-level leadership actually means inside your company.   R: Reframe your work Translate responsibilities and achievements into executive-level business impact.   I: Illustrate the future value Show what the broader VP mandate would allow you to own, change, or accelerate.   D: Develop senior advocates Build support with the leaders whose opinions influence the decision.   G: Gain agreement on the path Get clear on the criteria, decision-makers, and realistic timeline.   E: Execute against the roadmap Keep building evidence, visibility, and advocacy until the decision is made.   The goal is not to create six separate steps. It is to build one clear story that senior leaders can understand, believe, and repeat.   1. Benchmark the VP Role in Your Company Before you say you are already operating at VP level, you need to know how your company defines it. Titles vary dramatically. A VP in one organization may have less responsibility than a Director somewhere else.   More work is not automatically higher-level work either.   You can manage a larger team, inherit more projects, and stay deeply involved in execution without demonstrating the judgment or organizational reach expected from a VP.   Start with three things: Scope: What business outcome, function, or strategic priority does a VP own? Decision-making: What tradeoffs, investments, and resource decisions are they trusted to make? Organizational reach: How far beyond their immediate team does their influence extend?   Use your company’s level guides or executive competencies if they exist. You can also study two or three current VPs. If your manager is at that level, compare the altitude of their role with yours.   A useful definition might sound like this: In our company, a VP owns an enterprise-level outcome, makes tradeoffs across several functions, owns budget and headcount decisions, contributes to SLT planning, and shapes the operating strategy rather than only executing it.   Now compare your current work with that mandate.   Where are you already operating at that level? Where do you still need more experience, authority, or exposure?   This is not an exercise in convincing yourself that everything you do is VP-level. It is an honest assessment of what is already true and what still needs to change.   Your output: Write a clear definition of VP-level leadership in your company. Then create two columns: what you are already demonstrating and what you still need to develop or make visible. You are not looking for 100% overlap, aim for 30-40% of your work being at or impacting the next level.   2. Reframe Your Work as Executive-Level Impact Most promotion cases read like annual performance reviews.   They list projects, responsibilities, and achievements: Launched a new program. Improved a process. Inherited another team. Delivered against the plan.   All useful. But a longer list of accomplishments does not automatically demonstrate executive readiness.   Senior leaders need to understand the pattern behind the work: What kind of problems are you trusted to solve? What judgment are you already exercising? What changes for the business because of your leadership?   Use this structure: Scope → Judgment → Business impact   What did you take ownership of? What important decision, tradeoff, or change did you lead? What happened for the business as a result?   For example: We completed the new customer onboarding program.   That explains the activity.   A stronger version is: I aligned product, sales, and customer success around a new onboarding model, which reduced friction for customers and created a more scalable path to enterprise adoption.   The second version shows cross-functional leadership, decision-making, and business value.   Same work. Different altitude.   This translation should not happen once, six weeks before your promotion conversation. It should show up in your executive updates, presentations, Slack conversations, one-on-ones, and the way you explain your recommendations.   Your promotion document should not be the first time senior leaders understand the value of your work. By then, the story should already feel familiar.   Your output: Practice communicating your impact in everyday situations. Then build an evidence bank with three to five examples using Scope → Judgment → Business impact.   3. Illustrate What the VP Role Will Unlock This is the step that surprised me the most when I was doing this work. I assumed my past experience is the way to prove myself for the future VP role.   It’s not.   Your future impact, once you are in the role, is what makes the promotion inevitable. Let me explain the logic behind it.   A promotion is a bet on future value, not a lifetime-achievement award.   Many leaders spend most of their promotion case documenting the past, then expect senior leadership to reach the obvious conclusion: I have already done all of this, so it is obvious I will succeed at the next level.   That argument asks senior leaders to trust something they can’t imagine.   A stronger case shows what you have done up until now, and what you will do once promoted.   What would move faster if you had the broader authority? What business outcome could you own more fully? What disconnected priorities could you bring under one strategy? What executive bottleneck could you remove? What capability does the company need that you could build?   For example: Over the past year, I have expanded my scope across customer acquisition, retention, and product adoption. Today, those areas sit across three teams with different priorities and no single owner for the full customer journey. In the VP role, I would own the end-to-end growth mandate, control the tradeoffs across budget, product priorities, and team resources, and be accountable for increasing net revenue retention from X% to Y%, worth $Z million in recurring revenue.   That is more than a request for recognition. It is a business case for the role.   It also creates healthy FOMO. Senior leaders can see what the organization may be leaving on the table by keeping your mandate fragmented or unnecessarily narrow.   Your output: Identify the three most important outcomes the broader VP mandate would allow you to own, improve, or accelerate.   4. Develop Senior-Level Advocates Your manager’s support matters. For a VP promotion, it is rarely the only support you need.   Senior-level promotions usually involve several people. Some approve the decision formally. Others influence the conversation before it ever reaches that stage.   Rachel’s case became stronger because other VPs and C-level executives had already seen her operate at the VP level, and heard from her directly, that she is pursuing that promotion.   They trusted her judgment. They understood her impact. When her name came up, the CEO was not hearing an ambitious proposal from one employee. He was hearing a case that other senior leaders already believed.   Your advocacy map should include three types of people: The process owner: Usually your manager or another leader responsible for initiating the promotion. The validators: Senior peers or cross-functional executives who can confirm that you already operate credibly at their level. The decision-maker or executive sponsor: Someone with enough influence to support the business case and move the decision forward. Could be your skip level manager or C-suite exec.   Do not wait until promotion season and ask someone to advocate for you out of nowhere. Advocacy is built through repeated exposure to how you think, decide, communicate, and lead.   Create opportunities for the right executives to see you work on meaningful problems. Bring them recommendations, not only updates. Ask for their perspective on strategic decisions. Build shared wins that allow them to experience your leadership directly.   By the time the formal conversation happens, your name should not feel like a new proposal. It should feel like the logical conclusion. I have a full guide to building executive sponsors here   Your output: Create a simple map showing who owns the process, who can validate your readiness, and who can influence the final decision.   5. Gain Agreement on the Promotion Path This is where many promotion conversations quietly die.   You tell your manager that you want to become a VP. They say you are doing an excellent job. They tell you that you are on the right path. You leave encouraged, but nothing has actually changed, and now you feel weird to bring it up again.   A compliment is not a promotion roadmap. A stronger conversation might sound like this: I am interested in moving into a VP role to continue growing my impact and helping the company [achieve goal]. Based on the scope I am already leading and the impact I have delivered, I believe I am operating at that level in several important areas. I would like to align on what still needs to be true, who needs to support the decision, and what a realistic timeline could look like.   You are not asking for a guarantee. You are asking the company, and your manager, to define the path.   By the end of the conversation, you should understand three things: What must be true: The remaining evidence, outcomes, or development required. Who must agree: The leaders involved in recommending, validating, and approving the promotion. When the decision can happen: The checkpoints and realistic decision window.   Inside Success Builders, I teach clients to begin the promotion conversation six to twelve months before they expect the promotion.   Senior-level decisions take time. The organization may need to consider compensation, budget, succession planning, organizational design, and the effect on other roles.   Rachel’s promotion took eight months after she raised the conversation directly.   That did not mean the strategy was failing. It meant there was finally a real process, with an actual decision at the end of it. Without it she might have waited three more years.   Your output: Document the agreed criteria, decision-makers, checkpoints, and target decision window. Check in with your manager every 2-3 months to make sure you and the process are on track.   6. Execute Against the Roadmap A promotion case is not a just a document you unveil during your annual review. It is a story you build over time.   Once you have a roadmap, your job is to keep producing the evidence and making it visible to the right people.   Each month, reinforce one important proof point, create one meaningful moment of senior-level exposure, and move one advocate closer to confidently supporting your case.   Then use your checkpoints to assess progress.   What has changed? What evidence is now stronger? Who has become more supportive? What remains unresolved? Has the company taken concrete action, or are you still receiving vague encouragement?   This matters because a roadmap should help you move toward a decision. It should not become a more sophisticated way to wait indefinitely.   If the company keeps changing the criteria, delaying the conversation, or benefiting from your expanded scope without creating a credible path, that is a sign to consider your options.   You may still decide to stay. But you should make that decision with your eyes open.   Your output: Create a monthly plan for the evidence you will build, the leaders who need exposure to it, and the checkpoints where you will reassess the path.   Your Six-Month BRIDGE Plan The exact timeline will depend on your company, but the work usually follows this sequence:   Months 1 and 2: Build the foundation Benchmark the VP mandate and create your evidence bank. You should know how your company defines the role, where you already meet the standard, and which gaps are real.   Months 2 through 4: Socialize the case Start communicating your impact and your desire to grow more deliberately. Develop the future mandate and create stronger exposure with potential advocates. The goal is for senior leaders to understand both what you are already doing and what the company gains by expanding your role.   Months 4 through 6: Formalize the path Raise the direct promotion conversation. Align on criteria, decision-makers, checkpoints, and timing. Then execute against the roadmap and keep testing whether the company is genuinely moving toward a decision. Some organizations might need more time than others. Don’t focus on the timeline, focus on the process.   Copy-and-Paste Template: Your VP Case in Five Sentences Use this as the foundation for a conversation with your manager or another senior leader: Over the past [time period], my scope has expanded from [previous scope] to [current responsibilities]. In that scope, I have led [important decisions or cross-functional work] and delivered [meaningful business outcomes that demonstrate VP level work]. Based on how our company defines VP-level leadership, I believe these examples already demonstrate [relevant scope, judgment, and organizational influence]. In the VP role, I would use the broader mandate to [future outcomes the role would unlock]. I would like to align on what still needs to be true, who needs to support the decision, and a realistic timeline for moving forward.   Do not deliver this word for word like a speech.   Use it to make sure your case includes the five things senior leaders need to understand: Your scope. Your impact. Your readiness. The future value. The decision path.

Your Next Steps If your company already trusts you with VP-level work, do not assume the title will eventually catch up. Start building the decision now.   Use the BRIDGE framework to define the role, make your impact visible, show what the company gains, build the right advocacy, and agree on a real path forward.

Read The Room: 3 Traps to Avoid in Executive Meetings

 

“Are you sure that’s the right direction?” I was presenting my yearly marketing strategy to the leadership team. I had done the research. I had benchmarks. I could explain exactly why I had chosen that direction.   So when they started questioning it, I did what many smart, well-prepared leaders do. I defended the work.   I walked them through the research. I explained my rationale. I added more evidence to prove I had made the right call.   Except that was not what they were really asking.   I was new to the company. They did not know me well enough to trust my judgment yet. They were not asking whether I had done my homework. They wanted to know whether I believed in the strategy enough to lead it.   They needed conviction. I gave them more data. I answered the question and completely missed the room.   That is the tricky thing about executive meetings. What is being said and what is actually happening are not always the same.   A question about the numbers might really be about risk. A challenge to your recommendation might be a test of your confidence. Someone pushing back on the plan may be protecting their budget, their team, or another priority you did not know existed.   Reading the room is your ability to recognize what is happening beneath the surface and respond to that, rather than simply delivering what you prepared.   This is why the best leaders often seem so good at thinking on their feet.   It can look like they always have the right answer ready. Usually, they don’t. They simply understand the people in the room, the dynamics shaping the conversation, and the question that is really being asked. That context helps them react faster when the conversation changes.   So, if you have ever found yourself stuck in a meeting because the discussion moved somewhere you did not expect, or you struggled to figure out what to say without a prepared answer, this newsletter is for you.   Let’s look at the three biggest traps leaders fall into during executive meetings, and what to do instead.

The 3 biggest traps in executive meetings Trap #1: Sticking to the script after the conversation has moved on You came prepared to give an update. Three minutes into the meeting, the executives start asking about risk, resources, or the impact on another part of the business.   Instead of following the new conversation, you keep pulling everyone back to the presentation. You explain the next slide. You add the context you had planned to share. You try to complete the story in the order you prepared it.   The problem is not the quality of your material. The problem is that it is no longer the conversation the room needs to have.   Executive meetings move quickly. A status update can become a strategy discussion. A request for approval can turn into a debate about priorities. A tactical question can expose a much larger business concern.   Your job is to recognize when that shift happens.   Ask yourself: What is the room trying to understand now? Are they still gathering information, or are they evaluating options? Are they questioning the plan, or are they worried about the risk behind it? What decision are they trying to make?   Then adapt.   You might say: “It sounds like the bigger concern is the risk to the launch timeline. Would it be more useful if I focused there?”   That does not make you look unprepared. It shows that you understand the purpose of the meeting.   Your job is not to finish the presentation. Your job is to help the room move the conversation forward.   Executive meeting trap #2: Answering the question instead of hearing the concern When the leadership team questioned my marketing strategy, I heard: “Did you do enough research?”   So I answered with research.   What they were really asking was: “Do you believe this is the right direction?”   Those questions require very different answers.   This happens all the time in executive meetings.   “How confident are we in this forecast?” could be a request for more information. It could also mean: How much risk are we taking? What happens if you are wrong? Do you stand behind this recommendation? Should I trust your judgment?   When you only respond to the literal question, you can end up giving a long, detailed answer that still does not address what the executive needs to know.   A better answer in my strategy meeting would have sounded more like: “Yes. I looked at the benchmarks and considered the alternatives, and I believe this is the right direction for us. Here is why.”   The evidence still matters. But it supports the recommendation and conviction, it doesn’t replace it.   The next time you get a challenging question, pause before you start explaining.   Ask yourself: What are they trying to understand about the decision, the risk, or my judgment? Then answer that question first.   Executive meeting trap #3: Preparing for the content, but not the people A lot of leaders believe the secret to performing well in an executive meeting is having every possible answer prepared. So they anticipate objections. They add backup slides. They memorize more data. They spend hours trying to predict every question that could come their way.   Preparation matters. But you will never anticipate everything.   The strongest executives are not walking into every meeting with all the answers. They are walking in with a strong understanding of what matters to the people in the room.   They know their leaders’ goals. They understand where resources are competing. They recognize the power dynamics. They know who owns the decision, who influences it, and who may have something to lose.   That context makes it much easier to understand where a question is coming from and respond well, even when you did not prepare for it.   Before an important meeting, ask: Who will be in the room? What is each person trying to accomplish? What pressure are they under? What might they be trying to protect? Who has the authority to decide? Who has influence, even if they are not the most senior person there?   You may be proposing a project that requires resources from another leader’s team. They may agree with the idea and still resist the recommendation because they cannot afford to take on more work.   You may think you are debating the strength of your idea when the real issue is ownership, timing, or political risk.   When you understand those dynamics, you do not need a perfect answer for every possible question. You have enough context to understand where people are coming from and make better decisions in the moment.   This is what thinking on your feet at the executive level looks like. You do not need to know everything. You need to know what matters, and to whom.   The ROOM framework for executive meetings Before and during your next executive meeting, use this check:   R: Real question What are they actually trying to understand?   O: Outcome What decision or progress does this meeting need to produce?   O: Others Who is in the room, and what matters to each person?   M: Move What is the most useful thing I can say or do next? (Not what you planed for)   You can use these four questions when you prepare, and return to them anytime the conversation starts moving in an unexpected direction.

Your Next Steps Before your next executive meeting, create a one-page room map.   Write down: The outcome the meeting needs (not the order) The two or three people whose support matters most What each person wants, fears, or may resist The hard question you expect them to ask   Then, during the meeting, stop trying to prove how prepared you are.   Listen for what the room needs from you now. Because executive presence is not having the perfect answer ready.   It is understanding what is happening and knowing how to respond.

The step by step framework to position yourself for VP roles

The VP Positioning Strategy That Landed Me Two Offers Step 1: Decide what kind of VP you want to become I did not begin with my LinkedIn profile. I began by defining the role.   I knew I wanted to become a VP of Marketing inside a startup. That gave me a much more useful question: What would make a startup CEO trust me to lead their marketing organization?   Which capabilities would matter most? What gaps would make them hesitate? Who would need to know me before one of those roles became available?   That answers would have been different if I wanted to lead product marketing inside a global enterprise or run a mature demand generation organization.   “I want to become a VP” is not specific enough to guide your decisions. You need to understand the environment you want to lead in, the business problems you want to own, and the expectations senior leaders will have of someone at that level.   The clearer the destination, the easier it becomes to work backward.   Step 2: Find the sharp edge of your experience My experience was broad, but broad experience alone was not going to make my value explicit.   I decided product marketing would become the sharp edge of my positioning. It was close to revenue, and one of two main marketing disciplines that generate the most VPs.   I was not abandoning the rest of my background or pretending I had spent my entire career in one specialty. Product marketing became the part of my experience that led the story. It gave people a clear way to understand why I was valuable.   This is where a lot of senior leaders struggle.   You have spent years developing a wide range of capabilities, so when someone asks what you bring to the table, you try to include all of them. You describe yourself as a strategic, cross-functional leader who drives transformation, builds high-performing teams and delivers results.   All true.   Also true of thousands of other leaders.   You do not need to erase the breadth of your experience. You need to decide which part should lead.   What is the clearest reason a senior executive would pull you into an important conversation?   Which business problem are you unusually well equipped to solve? What part of your experience is most relevant to the VP role you want?   For me, it was competitive go to market motions. I knew how to find the right customers at scale. That meant that every marketing tactic that came after that was 10x more effective. And that was something CEOs wanted.   That is the sharp edge of your positioning.   Step 3: Learn how your market thinks and talks Once I chose product marketing, I went deep. For almost a year, I regularly listened to six or seven podcasts focused on product marketing.   I learned who the respected experts were, which ideas were shaping the field, what companies were struggling with, and how the strongest leaders explained their impact.   I also joined the Product Marketing Alliance because I wanted to be around people who were already operating in that world.   I paid attention to the terminology they used, the problems they prioritized, and the trends executives considered valuable enough to invest in.   I was not simply learning more about product marketing. I was studying the executive conversation and what VPs in particular were focused on.   You can have excellent experience and still struggle to position it if you do not understand how senior leaders value that experience.   Your work may be strategic, but if you describe it through tasks and deliverables, people may still see you as tactical.   Strong positioning requires you to understand what matters to the leaders making decisions: What problems are becoming more urgent? What results are executives accountable for? Where is the business investing? What separates solid functional leadership from executive-level judgment?   The deeper I went, the easier it became to connect my experience to the issues senior leaders already had on their minds.   Step 4: Reverse-engineer the people already doing the job At the same time, I began reaching out to senior marketing leaders on LinkedIn, especially VPs who had come from product marketing backgrounds. I wanted to understand how they had positioned themselves.   Which experiences did they emphasize? How did they describe their work? What helped them move from functional leadership into an executive role? What patterns could I see across their careers?   I documented everything I learned and gradually built a playbook for the day I became a VP. This was networking, but it was also market research.   You can apply the same strategy to your field.   Find leaders at the VP level who have a similar background and reach out. Ask for an opportunity to learn about their journey as you are designing your next move.   Pay attention to how they communicate, which problems they own, who relies on their judgment, and what evidence made senior leaders believe they were ready.   Do not copy their career. Look for the decision criteria hiding inside it. Start applying it in your day to day.   Step 5: Build proof before you need the title Joining the Product Marketing Alliance eventually created an opportunity I could not have planned.   A few weeks before one of their events, they reached out and asked whether I could deliver a keynote. Someone may have canceled. I did not have a ready-made presentation, and I was scared shitless.   I said yes.   I knew the opportunity could help establish credibility in the exact space I wanted to own. (Side note: you don’t have to wait to get invited. You can reach out and pitch yourself)   The keynote was recorded, and I shared the video on LinkedIn. That one piece of visible proof started creating opportunities. CEOs and senior executives reached out to ask whether I offered consulting.   As I did more product marketing work as a consultant, my positioning became more credible.   At the time, I was already working on a project with Google, but it wasn’t giving me enough of the go to market exposure I needed. So I put together a plan to expend my scope and pitched it. They said yes, and I strengthened the exact reputation I was building, while doing meaningful work.   The keynote created public proof. The consulting work created operating proof. Together, they changed the story I could tell, and that changed how people saw me.   This is the part you cannot solve with a better LinkedIn headline. You need evidence.   Inside your company, that might mean taking ownership of a strategic initiative, expanding the scope of a project, advising another function, presenting to senior leaders, or solving a problem that normally sits one level above you.   Externally, it could mean speaking, publishing, consulting, advising, or contributing to an industry community.   Your positioning becomes believable when people can see you doing the work, not just talking about it. And no, this isn’t a quick fix. It’s a process that builds reputation, but when it finally falls into place you get to reap the rewards for the rest of your career.   Step 6: Build relationships that multiply your visibility By the time I was ready to pursue a VP title, my positioning was already working. My network had seen my expertise develop. I had speaking experience, consulting projects and stronger examples that supported the story I wanted senior leaders to believe.   Then I became more deliberate about who needed to know me.   It’s easy to think that if you just update your LinkedIn opportunities will magically come, but we’re not here to play the ego game. Waiting is not a strategy. If you want visibility - you need to create it.   Because I wanted to lead marketing inside a startup, I reached out to partners in venture capital firms.   One VC relationship could potentially open doors to multiple companies. An investor recommendation would also carry more weight with a startup CEO than a cold application.   By that point, I was not asking anyone to imagine whether I could operate at the VP level.   I had evidence that I already was. And (and this is an important one) after dozens of networking conversations with senior leaders, I also had the confidence to tell my story. That made it easier for senior leaders to recommend me, and those conversations eventually led to two VP offers.   The same principle applies internally.   You need relationships with people who influence opportunities. That might be your skip-level leader, a respected cross-functional executive, a business-unit leader, or someone who regularly participates in talent conversations.   Positioning becomes much more powerful when the right people can see it and repeat it when you are not in the room. Your job is to make it easier for them to see and advocate for you.   VP positioning starts before the opportunity appears The process of positioning myself for those two VP offers I landed? It took about a year because I started from zero right after moving to a new city and with no network to support me.   You might need 90 days if you have a good baseline, but the bottom line is that it’s not something you do over weekend.   You do not build VP positioning during the final weeks before a promotion decision. You build it through the strategy you follow and the choices you make long before that conversation happens.   Your resume and LinkedIn profile should reflect that strategy. But they are not the strategy.   I’m sorry I can’t give you a quick fix, but what I can offer is this: your brand and your positioning is one of the things no one can take away from you. Once you build them, they will continue to serve you and future proof your career.

Your Next Steps: The VP Positioning Playbook If you want to get started, follow the these six moves to build your plan:   Target: Define the VP role and business environment you want.   Sharpen: Choose the part of your experience that should lead your story.   Immerse: Learn the priorities, language and trends shaping that space.   Study: Reverse-engineer the leaders already trusted at that level.   Prove: Create visible evidence that you can solve VP-level problems.   Multiply: Build relationships with leaders who can help your reputation travel.   Your goal is not to tell people you are ready for VP. It is to make the evidence strong enough that they reach that conclusion themselves.