Recently, I had the pleasure of joining Jan Hoppe on his Produktkraft podcast to discuss how product leadership evolves across different organisational sizes. We recorded the podcast in German, and I felt it could be worth summarising what we spoke about in English for this blog post. If you speak German I still suggest you listen to the podcast to get all the nuances of our 100+ minute conversation.

For our conversation, we explored the common threads and unique challenges of product leadership across organisations with 10, 100 and over 1000 employees - based on our personal experiences:

While I brought perspectives from enterprises and medium-sized organizations from my work as VP at XING (ca 2K employees), CPO at Facelift (ca 150 employees) and now as a product leadership consultant, Jan contributed valuable insights about product leadership in small organizations and startups, drawn from his extensive experience in early-stage companies. Together, we identified several success factors that shape product leadership effectiveness across organizational sizes.

Directional Clarity: Setting and Maintaining Course

One aspect is always true: Regardless of organization size, providing clear direction is fundamental to product leadership. This means establishing a coherent vision, strategy, and priorities that teams can align with and act upon.

In different org-sizes, the amount of contributors & stakeholders and their proximity to the actual product work influence the focus of product direction and how formal it’s articulated.

At XING, Martin Eriksson's Decision Stack mental model helped me and my colleagues better understand how different elements of product direction - such as Vision, Strategy, and Objectives - connect to form a cohesive direction. However, the challenges of directional clarity in a large organization are quite specific: we needed to involve many stakeholders in shaping and discussing the direction, from product directors to the supervisory board, requiring more formal documentation. While we were fortunate to have access to excellent internal specialists in areas like Analytics and User Research, one of our key challenges was keeping the process lean enough. With so much expertise available, we had to resist the temptation to strive for perfection and instead focus on maintaining momentum.

At Facelift, a medium-sized organization, we could be more pragmatic. While we still needed clear direction, we could use lighter-weight tools like Miro boards for strategy work and maintain more direct communication channels because all relevant parties were much more closely involved.

Jan shared that in small organizations, directional clarity often focuses more on immediate goals like finding product-market fit. While the long-term vision might be clear, the path to getting there needs to remain flexible as the company explores different opportunities. Thus, clarity matters more in the question of where to go, than in how to get there. Being clear about the need to discover how to get there, is the actual goal.

Organizational Setup: Structuring for Success

Every organization needs clear reporting lines, well-defined responsibilities, and effective collaboration mechanisms to leverage the available people and their competencies as much as possible.

As product organizations scale, roles become clearer cut and it becomes increasingly important to avoid silos through effective communication.

At XING, we implemented a cluster structure where Directors led groups of 4-7 PMs, focusing on related areas. This helped maintain focus while enabling cross-team collaboration. The challenge was keeping communication flowing effectively across multiple layers of hierarchy.

In my role at Facelift, I chose a different approach. All PMs reported directly to me - a deliberate choice to maintain a close connection with product work while avoiding unnecessary layers of management. This worked well for our size but required careful attention to scaling concerns.

Jan noted that in small organizations, formal hierarchies often exist only on paper. With teams of around ten people, everyone typically sits together and hierarchies are much more fluid. The challenge isn't organizational structure but rather ensuring everyone can contribute effectively while wearing multiple hats.

Situational Clarity & Decision Making: Moving forward

Clear decision-making processes and the ability to act effectively in different situations are crucial for any product organization. Teams need to understand who can make which decisions and how to move forward when faced with uncertainty or conflicts in order to move fast and effectively.

Depending on org size there are different challenges in balancing decision velocity with alignment. 

Large organizations typically require more conscious alignment procedures and a substantial part of a product leader’s time will be spent on internal alignment & decision preparation. In this context, clear priorities and product principles can significantly increase decision velocity.

At XING, we faced another interesting challenge: despite having experienced PMs, decisions sometimes stalled because team members were hesitant to escalate conflicts, wanting to maintain good relationships with colleagues. To address this, we created what we called an "Escalation Manifesto." This document emphasized that joint escalation - where conflicting parties come together to seek resolution - was not only acceptable but encouraged. The key was reframing escalation from a negative action to a natural part of decision-making in a complex organization.

Mid-sized organizations are typically able to maintain more direct decision-making processes. 

In our conversation, we noticed that the main challenge in these organizations is the stretch between remaining flexible enough while still bringing a grown organization along. This can be a crucial learning field for founders who learned to lead the org when it was still much smaller and have to establish new managerial muscles as the organization grows.

Jan shared that in small organizations, decision-making tends to be more immediate and organic. With everyone typically in the same room or virtual space, decisions can be made quickly with full context. The challenge isn't about process but rather about making good decisions with limited data and experience.

Role Clarity: Understanding Responsibilities and Expectations

People need to understand what's expected of them and how their role contributes to the organization's success. This includes clarity about their decision-making authority and how they should interact with others. All of this is important to avoid disappointments and unnecessary interpersonal friction.

The bigger your org, the more important it becomes to provide consistency about roles

In the large organization context at XING, we found it essential to work with competency profiles that clearly outlined expectations for different levels (Mid-level PM, Senior PM, etc.). These profiles helped create transparency about growth paths and made it easier to have meaningful development conversations. They also helped maintain consistency across different parts of the organization.

At Facelift, we took a more flexible approach to roles while still maintaining clear expectations. Without the multiple layers of hierarchy present in larger organizations, we focused more on expanding responsibilities horizontally - giving people opportunities to grow by taking on new challenges rather than moving up a predetermined ladder.

Jan noted that in startups, roles often exist more on paper than in practice. While someone might have a specific title, everyone needs to be ready to do whatever is needed for the company's success. The challenge is maintaining some role clarity while embracing this necessary flexibility.

Developing People: Growing Product Talent

Supporting the growth and development of product people is a core responsibility of product leadership because it’s in the organization’s interest that PMs are capable and motivated to do good work and deal with the responsibilities of the role. This includes providing learning opportunities, feedback & coaching, and career development paths.

No matter what size your organization is, it will be important that you as a product leader have clear standards for what you consider good and important for a PM in the context of that organization. I find it helpful to create your own, context-specific version of Petra Wille’s PM Wheel, compare your assessment of your PMs with their self-assessment and use this as a starting point for constant coaching.

The larger your organization, the more conscious you need to be about creating learning opportunities and about the overall seniority mix in your team

Apart from the individual coaching you can provide as a leader, larger organizations also offer great opportunities to learn from each other, because there will likely be a larger variety of backgrounds and experiences to learn from: Some PM colleagues may be able to share good practices in product analytics whereas others may be able to share ideation techniques. 

I’m a strong believer in internal communities of practice to create such learning opportunities and at the same time help to connect PMs across the org to avoid the risk of silos. Back at XING, I helped implement and run the internal Community of Practice for many years. My former colleague Jennifer Michelmann shared her experiences in this blog post.

Apart from dedicated learning opportunities, larger organizations also offer more opportunities for developing people through internal shifts. Don’t get me wrong: I’m not talking about simply pushing people around and I am 100% aware of the benefits of stable teams and of PMs who embrace topics for a longer time. Still, for a PMs development, it will be beneficial if they don’t remain in the same role for more than 2-3 three years. This is why me and my colleagues at some point started encouraging internal mobility, recognizing that PMs who experienced different parts of the business often developed broader perspectives and stronger skills. As a people manager, this means that you may need to encourage your best people to leave your team because it’s in their interest and in the company’s interest.

In my role at Facelift, development had to take different forms. Without the ability to offer traditional upward career moves or many suitable slots to shift, we focused on creating growth through expanded responsibilities and deeper expertise in specific areas. This required more creativity in how we thought about career development, but it also led to some very strong product people who developed deep domain expertise.

Jan's experience shows that in small organizations, development often happens through direct exposure to all aspects of the business which is why it’s beneficial if people already have some experience. While formal development programs aren't feasible, the intense learning that comes from wearing multiple hats can accelerate growth for those who can handle it.

Ensuring Success: Measuring and Achieving Results

Product leadership must ultimately drive successful outcomes. However, success needs to be defined and measured appropriately for the organization's context and stage to be actionable and tangible. More importantly, we need to be conscious of how the available capacities are best invested.

At XING, ensuring success required attention to both measurement and resource allocation. While we had access to sophisticated analytics, I learned that the ability to measure many things could sometimes work against us. This became particularly crucial when we noticed teams optimizing for local maxima - improving their specific metrics while possibly missing bigger opportunities elsewhere.
I learned that as a product leader in a large organization, ensuring success isn't just about tracking the right metrics; it's about having the courage to make difficult changes in service of broader company goals. We had to be willing to make tough decisions about where we invested our resources. Even when teams were working well and hitting their metrics, we sometimes needed to reallocate people and resources to areas with greater potential impact. This was often unpopular - nobody wants to break up a well-functioning team - but it was necessary for overall company success.

In mid-sized organizations, the approach to success metrics needs to be well-balanced: Clear enough to guide decisions, sophisticated enough to inform strategy, but simple enough to maintain with limited resources. It makes sense to focus on metrics that indicate product-market fit and customer satisfaction, particularly important in the B2B SaaS context we were in at Facelift. Being very conscious about which parts of the product to invest in - and which areas to sunset to focus capacities - was an important challenge for me and our CTO.

Jan shared that in small organizations, particularly startups, success metrics often need to be more fundamental: qualitative feedback from early customers, basic product usage data, and ultimately survival metrics like runway and cash flow. He emphasized that at this stage, trying to implement too sophisticated a measurement system can be counterproductive because it can obfuscate the view of what should be right in front of everyone's eyes.

Clear Communication: Making Impact Through Effective Dialogue

Clear communication is essential for product leadership effectiveness because communication is how you bring people along (or not). What I've learned over the years is that clarity isn't just about being articulate - it's about ensuring understanding across different audiences and contexts.

We need to adjust communication to context, provide clear framing and keep the focus

One of my key learnings at XING came from a UX colleague who told me, "Arne, you think you're speaking at eye level with us, but you're not - you're still our boss." This helped me understand that in large organizations, every communication happens in the context of organizational structure, no matter how informal you try to be. We needed to be very conscious about:

- How we framed feedback and suggestions

- When and how we shared strategic information

- How we ensured consistent messaging across different levels

- The balance between transparency and appropriate timing of communication

At Facelift, communication had different challenges. With fewer layers, messages didn't have to travel as far, but we needed to be extremely clear about context. I learned to be explicit about whether I was sharing a decisive direction or just thinking out loud, as even casual comments from leadership can be interpreted as mandates.

Jan's experience with small organizations revealed a different dynamic: with everyone typically in the same physical or virtual space, formal communication structures matter less than the ability to maintain a clear, ongoing dialogue about priorities and challenges. The challenge isn't getting messages across organizational layers but rather ensuring that the constant flow of communication remains focused and productive.

Conclusion: The Art of Adaptation

Through our conversation, it became clear that while the fundamental principles of product leadership remain constant across organization sizes, their implementation needs careful adaptation to context. Success comes not from rigidly applying best practices, but from understanding your specific situation and adjusting your approach accordingly.

What works for a thousand-person organization won't necessarily work for a startup, and what works for a medium-sized company might be too rigid for a small team or too informal for an enterprise. The art of product leadership lies in understanding these differences while maintaining focus on the core principles that drive product success.

As I continue my work as a Product Leadership Sidekick, helping organizations navigate these challenges, I'm constantly reminded that there's no one-size-fits-all solution. The key is to understand the principles deeply enough to adapt them effectively to each unique context. If you'd like to discuss product leadership challenges in your organization, feel free to get in touch.*