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Startup Leadership Transition


This article marks my first drill-down into topics related to building a modern business culture. Adopting the principles outlined in the Agile Manifesto has been spotty at best. The industry of “Agile Transformations” is so fraught that it may just be taking Agility down with it.


Nonetheless, there are ideas that will endure. One such idea is the notion of empowering every employee to their fullest potential. This idea is antithetical to the traditional command-and-control organizational architectures most of us have known. Due to this fact, many leaders are unfamiliar with how to operate within a modern leadership structure.


Note that I am using the word “modern” here because I don’t have an established label for what it means. The term “servant leader” has been used in Agile circles, but the term fails to capture several important parts of a leader’s role in the organization. From my own reading and experience, great leaders have ALWAYS understood the principles of modern leadership. They just weren’t common.


First, let’s unpack the qualities of a modern leader. Then, we’ll go back and look at why we often fail to get the type of leaders we want in our organizations. Here are some qualities shared by all great leaders:


  1. Visionary

  2. Excellent communication skills

  3. Humility (they have an ego but recognize they need to keep it in check)

  4. Empathy (they actually care about all the people around them)

  5. Builder of trust

  6. Eliminator of fear

  7. Curious

  8. Delegator

  9. Driven to Excellence


There is so much to say about each of these that I will not do so here. I will be writing a separate article about each of these attributes. Each one carries a “why” and a “what it looks like” story that needs to be told. I have written about these topics in other contexts, but I will write about it more specifically about startup/growth company leadership.


Why A Transition?

Not all startups need leaders to transition to a new way of operating. Some startups launch with leadership principles and practices in place to take them forward into rapid scaling. Most don’t, and for good reason. Let’s deconstruct a typical startup.


There are many scenarios for the birth of a startup. The most common by far is when one to three people have an idea. That idea typically either fills a perceived gap of availability in the marketplace or offers a better way to fill a need already being addressed. In either case, the founder(s) believe they can execute their vision successfully.

In most cases, they will need to perform at an unsustainable level for longer than most people can endure. This is why so many startups fail. It takes extreme perseverance and force of will to be successful. Because of these qualities, coupled with the fact that the team is small and the vision remains mostly intangible at first, founders must assert themselves in everything that happens.


It is the perfect environment for command-and-control leadership. Venture funders look for these qualities in the leaders they back. They know that without the grit and determination required to push people beyond the brink of collapse, they will probably fail. In fact, these attributes work so well at first that it’s hard to know when to stop using them.


There is no hard number, but eventually, the success of the initial idea carries a startup into a growth phase that threatens the original leadership approach. Founders can only spread themselves so thin before people are forced to make decisions on their own in order to maintain continuity. Additionally, relationships and subcultures form that are out of reach of the founders.


These changes may be subtle at first, but eventually, they begin to shape the culture. Founders who don’t make the transition at this stage will gradually lose control as they continue to focus on the same things they did in the beginning despite the organization’s increasing complexity.


A2Agile has come to recognize the need for something we call “Intentional Culture.” This is a way to get in front of these changing demands and build an organization that can scale rapidly while maintaining the magic that spawned it. Stay tuned for more details.


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