The Resilient Organization

Bridging the Gap Between Founder-Mode and Manager-Mode

Effective leadership in today's dynamic business environment requires a nuanced understanding of both founder-mode and manager-mode. As organizations grow and face constant change, leaders must adapt their strategies, balancing the visionary drive of founders with the structural support of skilled managers. By viewing these modes as complementary rather than contradictory, and by fostering ownership and accountability at every level, companies can build resilient, adaptable organizations capable of thriving in all conditions. The key lies in recognizing that change is constant. The role of leadership is to guide and empower teams to navigate change effectively, regardless of the company's size or stage.

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It's interesting that many founders don't believe in the value of hiring managers. This perspective is also held by many individual contributors at large organizations when they don't fully understand the job of managers.

The key lies in recognizing that change is constant, and that the role of leadership is to guide and empower teams to navigate this change effectively, regardless of the company's size or stage.

I'm oversimplifying here, but one huge aspect of the job is to manage change. Managers introduce processes, structure, and other mechanisms to help scale and place people where they complement others and best work collaboratively and bring different ideas together.

Before finding product-market fit (PMF), I fully agree with the sentiment that very early-stage startups don't need managers. To move quickly, a team of senior, like-minded individuals is the most optimal. No time is spent on coming to an agreement.

Alternatively, in a growing organization, it's important to bring more individuals together, which comes with benefits and drawbacks. More people means more diversity and perspective — that leads to a better-rounded product. It also leads to disagreements, miscommunication, and inefficiencies.

There's a popular quote that many believe in: "Hard times reveal true friends." Let's extrapolate this and apply it to leadership: Challenging periods showcase managerial excellence.

What defines Challenging Times in business?

"Challenging times" are periods of significant change—whether positive or negative. These periods can include:

1. A startup finding Product-Market Fit (PMF) and experiencing rapid growth.

2. A company losing market share and running out of funding.

3. A toxic work environment requiring drastic correction.

4. A new startup chasing idea after idea for PMF in vain.

Have you heard of the wartime vs. peacetime CEO concept? While I appreciate the illustrative and metaphorical adjectives, this simplifies the lifetime of a company as being binary: Good times and bad times, with bad times situated at the bottom half of Maslow's hierarchy of needs. In bad times, survival is of utmost importance; hence, there's no time to focus on anything else like building a strong team culture. As the most basic needs are met and the company stabilizes, this era is described as "peacetime."

Indeed, the set of problems a company faces at different times of its lifecycle are different. A strong and effective leader needs to learn how to navigate and adapt through all phases of a company's life. One of my core principles is to Be Adaptable.

Adaptability applies everywhere. Similar to why it's not a good idea to over-engineer a system, a good leader needs to find the best process, decisions, and management style for each period of a company's lifecycle. What worked at a small company most likely will not work at a medium-sized company. What worked at one small company may not even work at a different small company. What worked for your team last quarter might even need to be reassessed and modified to meet your team's needs this quarter.

It's not that individual contributors can't adapt their processes, communication, and direction alignment without the help of managers. It's more due to the lack of time. With the limitation of 24 hours in a day, how does one divide their time between solving hard technical problems and understanding the psychology and motivation behind every individual, aligning their motivations and incentives, and effectively collaborating together to achieve a common goal?

Why or not and?

In Paul Graham's Founder Mode, he illustrates "two different ways to run a company: founder mode and manager mode... The way managers are taught to run companies seems to be like modular design in the sense that you treat subtrees of the org chart as black boxes."

I'd like to offer a more collaborative perspective to organizational design. I agree with the modular design with trees and sub-orgs. However, each subtree is not a black box; instead, every layer is a complementary job focused on solving different problems. Ownership and accountability are required at every level.

As I reflect more on founder-mode vs. manager-mode, they no longer feel contradictory to me. Instead, they feel complementary, and one cannot succeed without the help of another.

Founder-mode: ownership & driving the team toward a shared goal

Manager-mode: evolving the organization with the goal of keeping up efficiency to the rapid rate of change

The "CEO" owns company direction in the next year. A "Head of" manager owns and represents their function. They operate at a longer-time horizon, let's say a year in advance. They change their organization to be able to efficiently reach that goal. The next layer of subtree managers owns managing change that happens throughout the year and is held accountable on a quarterly basis. The next layer manages month to month, or various features of the product, and so on and so forth, down to the leaf nodes — the front-line teams. These team nodes can focus on executing and building their targeted products without worrying too much about how to piece everything together.

When I first imagined this tree, I marked the leaf nodes as "individual contributors." But when thinking about software engineers, there are a plethora of trade-offs to consider when considering solutions, i.e., short term vs. long term, usability vs. scalability.

Individual contributors are then part of the tree alongside management at the various levels. Some think about the longer-term sustainability of the design. Others launch prototypes to test market hunger.

With this understanding of how the tree levels complement each other, it's not so much "macro-manage or micro-manage the black-box sub-tree." The job of a manager becomes: manage change at your level of responsibility and hold your subtree organizations responsible for taking ownership of their purview and meeting their targets.

As engineering and product leaders, embracing both founder-mode and manager-mode thinking is crucial for navigating the constant change in our industry. By fostering ownership at every level and adapting your leadership style to the needs of your growing organization, you can build resilient teams capable of thriving in any business climate. Remember, true leadership isn't about adhering to a single mode—it's about having the flexibility to shift between visionary thinking and structured management as your company evolves.

To develop this adaptive leadership style

1. Regularly assess your organization's current needs and challenges.

2. Cultivate a diverse skill set that spans both visionary and managerial competencies.

3. Encourage open communication and collaboration across all levels of your organization.

4. Remain open to feedback and be willing to adjust your approach as circumstances change.

By mastering the art of adaptive leadership, we will be better equipped to guide a team through inevitable challenges and emerge stronger on the other side.

In the ever-evolving landscape of technology and business, effective engineering and product leadership requires a dynamic approach that combines the visionary drive of founder-mode thinking with the structured support of manager-mode operations. By fostering ownership at every level of the organization, adapting leadership styles to meet changing needs, and viewing founder and manager modes as complementary forces, leaders can build resilient teams capable of navigating both turbulent and prosperous times.

It’s crucial to cultivate adaptability, encourage open communication, and consistently reassess and refine organizational structures and processes to meet the challenges of today while preparing for the opportunities of tomorrow.