Your path to a leadership role doesn’t start with you.

A realization that changed my career trajectory.

Sponsored by Sidebar, peer-to-peer professional development platform.

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You want to be in a leadership role someday, so you’re making a plan. You’ve got your trajectory lined up, you’re stacking your wins, you’re running down your path.

If this sounds familiar, let me offer you a tip that changed everything for me: the road to leadership is actually not about you.

You probably know this about the destination: As any experienced leader can tell you, the journey from Individual Contributor to manager to executive is a gradual progression away from focusing on your own impact. You increasingly move toward considering the impact of your team, your department, your entire organization.

But as it turns out, the journey to leadership itself is also a group project. So as you’re plotting your course, here are the essential characters to consider:

1. The Role Model - Study the success of others.

2. The Boss - Get your manager onboard.

3. The Guides - Build a personal Advisory Board.

4. The Replacement - Always be succession planning.

5. [Bonus Character → Keeping reading to see who it is]

The Role Model - Study the success of others.

The corporate world is a bizarre place, filled with superficial hierarchies, politics that resemble schoolyard squabbles, invisible glass ceilings, and 'team collaborations' that are much like assembling IKEA furniture without instructions.

Navigating this minefield is one of the first places it becomes obvious that going it alone isn’t a good idea.

Current leaders at your company have not only deciphered the cryptic manual of corporate survival but have also become experts at it. So why try to crack the code from scratch? Study these people instead. Observe how they ask questions, what they invest their time in, and how they navigate the daily dose of politics.

When I was advancing in my career, I aspired to be like my amazing manager, Selina Tobacowalla. She blew me away during every meeting: she always had all the bases covered, had considered all paths, posed the most thoughtful questions, and even had answers for all the questions. How could she possibly be so on top of things? I eventually figured out that before going into a meeting, she would think through all possible objections and suggestions related to the project and address them beforehand. This made meetings efficient, eliminated the need for follow-ups, and allowed her to consistently walk away having gotten her way. I have since adopted this strategy as my own.

So do try out other leaders’ tactics. If one feels right, adopt it; if not, discard it.

The Boss - Get your manager onboard.

When I was an analyst at SurveyMonkey, I dreamed of advancing to a managerial role. Feeling stuck in my current position, I got a managerial job offer from Electronic Arts. Proudly, I presented this to my manager as evidence of my achievements. He looked at me, puzzled, and said point-blank, 'Why didn't you tell me you wanted to be a manager? You could achieve that here in the next six months. Why gamble on a new place when you can succeed here?'

His question took me aback. Why hadn't I told him I wanted to be a manager? I had simply assumed he would know, which was a significant oversight on my part. It's crucial to communicate your aspirations to your manager so they can support your journey. (Thank you, Brent Chudoba, for being so supportive and patient with me.) Let them know where you want to go and how quickly you aim to get there. Keep revisiting this conversation every 3-6 months to check on your progress.

Trying to figure out how to engage them in this process? Don’t just ask, 'How do I get there?' This isn't the most effective strategy. You understand your strengths, aspirations, and capabilities better than anyone else. Asking such a broad question risks receiving a generic answer based on your manager's personal experiences, which may not align with your unique journey.

Instead, consider asking, 'What defines excellence in that role?' This will help you understand the benchmarks for success. Armed with that insight, assess the gap between your current position and your desired role. Draft a progression plan based on this self-assessment, and then present it to your manager. This proactive approach not only showcases your initiative but also ensures a tailored path forward.

The Guides - Build a personal Advisory Board.

I'm not a fan of the term 'mentors.' It's overused and often comes with inflated expectations. Instead, I advocate for assembling a personal Advisory Board. This 'board' is essentially a group of people you trust implicitly to provide advice on all elements of your career: comp negotiations, new role selection, co-worker issues, career mid-life crisis, etc. These advisors can be friends, family members, bosses, colleagues, or just people you admire in your industry.

Here's how to build your own personal Advisory Board:

1. Select individuals you trust and who genuinely understand you: Just because they’re smart, doesn’t mean their advice will be relevant. Choose individuals that get you and where you’re trying to go. You’re going to them when you’re second guessing yourself, so you don’t want to have to second guess them!

2. Include people who think differently from you: Getting a lot of “Ooo, great idea, Elena” every time I consider a new path would be fun, but not very helpful. Not only do you want people who are willing to disagree with you, you need people from various perspectives. Ideally, try to find some individuals with different personalities, strengths, and industry/role backgrounds.

3. Set up a schedule: My board doesn’t actually gather together (although it would be fun if they did!), but having a consistent cadence of check-ins guarantees that I stay in touch and get feedback. It’s funny how often I don’t think I have anything to report, but then realize that there’s a lot to catch a “board member” up on!

4. Be open to their advice: This may seem obvious, but if you’re not willing to listen to your board, they can’t help you. You don’t have to do exactly what they say, but if they’re pushing you to reconsider something, at least spend the time to understand why.

5. Take actionable steps based on their worthwhile recommendations: All this guidance doesn’t mean anything if you’re not moving forward. Build the muscle of putting your board’s wisdom into practice.

My own board is a diverse mix, including my husband, former bosses, ex-colleagues, and even a few folks who used to report to me. Despite their differences, each member has a deep understanding of who I am.

Creating this trusted circle didn't happen overnight; it took me a decade to assemble my board. I picked carefully, focusing on those I deeply respected and trusted. Now, I can reach out to any one of them at any moment for their valuable perspective. They have been my go-to advisors at every critical juncture in my career—from negotiating salaries and selecting the next role to navigating infuriating politics within the company.

So why is having a personal Advisory Board crucial for career growth? This group acts as a diversified portfolio of perspectives and experiences, enabling you to make well-rounded decisions. While one mentor can offer limited viewpoints based on their own experiences, a board brings a multi-faceted approach to problem-solving. They can challenge you, support you, and offer insights you might not have considered, making you more resilient and adaptable in your career.

So, forget the notion of having just one mentor. Build your own ‘Personal Board of Directors’ instead.

Pro Tip: Not sure how to get started assembling your board?

Don’t wait a decade like me and checkout the approach Sidebar is taking instead. At Sidebar, senior leaders are matched with 6-8 highly-vetted, private, supportive peer groups to lean on for unbiased opinions, diverse perspectives, and raw feedback. They meet every two weeks and are guided every step of the way by world-class programming and expert facilitation, supporting you as you take on more responsibility, strive for faster promotions, and bigger impact. Sidebar is a paid community and you must apply.

The Replacement - Always be succession planning.

Planning for your succession is a critical yet often overlooked aspect of career growth. While it might seem counterintuitive to focus on who will take over your job, doing so has several key benefits. Doing succession planning for yourself will:

1. Open up new opportunities: If you've prepared someone to take over your current role, it's much easier for *you* to move on to new opportunities. Your managers are more likely to consider you for new roles if they know that your current responsibilities can be smoothly transferred.

2. Showcase your leadership qualities: Succession planning showcases your ability to mentor, manage, and prepare other employees for leadership roles. These qualities are attractive to higher-ups and can mark you as someone who’s ready for more significant responsibilities.

3. Help with scaling *you*: Often, you'll find that your role evolves to include more responsibilities than initially intended. Having capable team members who can take over some of your earlier tasks allows you to scale yourself effectively, focus on more strategic activities, and thus become more crucial to your organization.

4. Build your influence: When you actively help others grow, you're not just building successors; you're also building allies and expanding your professional network. These relationships can be invaluable as you progress in your career.

By actively planning ahead like this, you make it easier for the organization to give you more room to grow. It's a win-win scenario that benefits your career and ensures the continued smooth operation of your team or department.

[Bonus Character!] You - Lock on to what matters. Be flexible with the rest.

Okay, this article is about the impact of others on your journey, but there is one element where it’s particularly important to be true to yourself: What do you actually want? 

What part of having a leadership role appeals to you? For me, the opportunity to have a larger impact on organizations, to work strategically, to mentor and grow those around me, and (yes, naturally) get paid well were the things that drove me to the top of the corporate pyramid. What I eventually realized, though, is that working as a soloprenuer gives me those things, without some of the downsides that made traditional leadership roles unsustainable for me. 

Understanding the things I actually wanted from being a leader allowed me to hold the line on those objectives, while remaining flexible on the rest. For instance, I began my career as an analyst, but my dreams soared much higher—I aspired to become the CEO of a company. Initially, I expected to take the CPO (Chief Product Officer) route to reach that position. Who would have thought I’d end up working in Growth—a field that didn't even exist when I started as an analyst. And building a solopreneur business? I couldn't be happier with this unexpected turn.

Here's why pivoting is so important: careers are rarely linear, and the business landscape is always changing. New fields emerge, old ones evolve, and sometimes the skillset you've developed can be more valuable elsewhere. Pivoting allows you to adapt to these changes and find a path that not only suits your talents but may also bring you more happiness.

In my journey, when I was looking to move beyond analytics, I was eager and open to any opportunities that came my way. The first opportunity that presented itself was the chance to start a product marketing function from scratch. I seized it without hesitation. It turns out, I was a terrible product marketer—which became clear when the first product marketing hire I made significantly outperformed me. But then an opportunity to create a growth team surfaced, and it was a match made in heaven.

By being open to pivots, I was able to test different waters, assess my skills and interests, and eventually land in a role that felt tailor-made for me. Keep your eyes on the prize that matters to you—but if you lock yourself into a single path without room for adjustment, you might miss out on a role where you could not only excel but also find true happiness.

Conclusion: If you want to grow far, grow together.

So, there you have it. If you actually want to get yourself to the leadership level, you have to start looking to others. Remember these characters, along the way:

1. The Role Model - Study the success of others.

2. The Boss - Get your manager onboard.

3. The Guides - Build a personal Advisory Board.

4. The Replacement - Always be succession planning.

5. [Bonus Character] You - Lock on to what matters. Be flexible with the rest.

If you’re just starting this process and that seems like a lot, I have good news: All of this other-focused stuff will help you after you reach leadership, too. In fact, it might be even more important at that point. As I said at the top: Taking responsibility for others is one of the most important components of the role, and as you have more pressure to achieve results, you’ll need guidance and support more than ever. As I’ve said: leadership has a dark side that people don’t talk about. In fact, I ended up deciding that traditional, full-time leadership wasn’t for me.

But whatever your path: You’ll be more successful if you don’t try to navigate it alone!

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Edited with the help of Jonathan Yagel, storytelling magician.

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