Why your Scrum Master might be your next CEO

Scott Weiner
Dec 26, 2019 · 9 min read

There are articles about “How to be a good scrum master,” or “Why you don’t need a Scrum Master,” or “Top Scrum Master anti-patterns.” Most of the focus is on what is wrong with Scrum Masters or how Scrum is being practiced. But, have you ever seen what a great Scrum Master is capable of? Do you even know what a Great Scrum Master looks like?

To set the context, let’s consider why Great Scrum Masters are well-suited for executive leadership by looking at some of the organizational factors that challenge teams in companies that strive to become more agile, more able to compete in the market and truly satisfy their customers. Then let’s contrast that with the qualities of a Great Scrum Master.

External factors challenging the team

Great Scrum Masters are not merely members of a Scrum team, they are creatures of the enterprise. Great Scrum Masters recognize that the “easiest” part of their job is to enable a team to run Scrum events with little fanfare and to facilitate productive retrospectives on what has been accomplished. The real challenges to the teams they support are the external factors, often considered out of a mere Scrum team member’s control. Consider the following examples of organizational challenges:

  • Lack of direct and frequent interaction with the customer — Limiting the connection to customers reduces any chance at a real understanding of what it takes to satisfy customers. Still, most companies put many layers between their customers and the people solving problems on their behalf. Worse the customer is often not the point of too many conversations, too much time is spent worrying about politics and technology. Too much time is spent on “what” and “how” and not enough on “why.”
  • Strategic intent and outcome alignment — If leadership has conflicting priorities or the team’s work is not aligned to strategic intent, then the value of the team is not optimal and may result in bad overall organizational performance. Teams end up focusing on producing output instead of real outcomes to justify their practices.
  • Funding and governance — As long as organizations continue to fund and empower silos of competencies or fixed project teams, instead of value streams and adjusting to changing priorities, there will never be a real sense of agility throughout the organization. For example, as long as the development team stays busy just to retain headcount the focus will never truly be on the customer or highest priority or real agility. Agile will continue to just be words on a poster and practiced in the bowels of the organization where no one benefits in ways that will keep the company from being overtaken by competitors one day.
  • Organizational design and structure — Companies that treat individuals as swappable components, moving them from team to team never really get the benefits of flow and predictability and trust the comes with team stability. Organizations that keep expertise segmented in departments that resemble fiefdoms, forcing each department (or tribe) to optimize for themselves instead of considering the whole lose any chance of real collaboration, trust or efficiency. These are examples of how companies fail to see their self-inflicted wounds because for generations, “that’s just the way it’s always been.” We know that stable, cross-functional teams are enabling higher performance. Yet so many companies resist these significant restructuring changes. As one coach speculated with me, “Maybe it’s because counting lines of code is easier than measuring trust and teamwork?”

Like oxygen, our culture is all around us and no company is posting “remember to breath” on their walls.

  • Lack of Inspirational Leadership — Too many Agile teams suffer from leadership that believes in the teams being agile as long as the leaders don’t need to change or model new behaviors. The lack of self-awareness, curiosity, emotional intelligence, or the unwillingness by leaders to be coached is a major factor in why so many companies simply don’t have cultures that support real enterprise agility. To support agility, leaders must lead by example and be agents of inspiration and focus, doing far more listening than talking and far less directing than empowering.
  • Failure avoidance cultures — If leaders want truly innovative organizations they need to do more than reward success, they need to celebrate the learning that comes from failure. This can’t just be lip service at some “all-hands” meeting, it needs to be in the way promotions occur, in the way they communicate with one another and yes, part of the culture. If people are afraid of losing their spot because of an error they won’t take risks.
  • Culture conflicts — What strong Scrum Masters know is that their culture is not found on their websites or walls. Like oxygen, our culture is all around us and no company is posting “remember to breath” on their walls. Whatever is posted is at best aspirational and more likely hypocritical because people aren’t leaving or bored or demotivated or afraid because of what is written under Values on the company website. When you recognize the culture, in reality, is not supporting your goals, then you can address the cause.

Research suggests 84% of transformations fail in part because of these factors.

Research suggests 84% of transformation efforts fail and these factors are some of the reasons. Yet, with all their experience and success in life legions of good executives struggle every day and many are unaware of how these factors are impeding the potential of their organization. If you look around you may see some or all of these factors holding your organization back.

Leadership is a major factor in agility impediments

In case after case, an unwillingness to change or lack of self-awareness by leadership drives many of the other issues. It makes sense if you think about it. A typical executive is a successful person. They got where they are following certain behaviors and patterns. Those strategies served them well when the building was more obvious, more direct — do the work, reap the rewards.

It’s about being the fastest… to adapt

Today, we need risk-takers, innovators who love our customers at all levels of the company, because it is no longer about being the biggest, it’s about being the most responsive to customers’ needs. Agility is about being fast but not in a straight line. It’s about listening and responding to what you learn quickly. For a large organization to be nimble enough to fund a good idea fast they need a great degree of psychological safety and clarity of purpose and they need to be inspired enough to take the necessary risks to overcome challenges. When they have this and the distractions are reduced they can achieve a state of collaborative flow where great things are accomplished.

So why consider Scrum Masters for a CEO role?

Let’s consider the qualities of a great Scrum Master.

  1. They are Servant Leaders — This means they have strong empathy and self-awareness, they thrive on enabling others and see rewards through the success of the team. They typically have a strong moral code and value system that helps guide them and keep them focused on purpose while also inspiring others to model similar behaviors and attitudes. Most of all they see everyone as their customer and they seek to delight their customers, not by giving in to their every whim, but by empowering and enabling them and holding them to high expectations as well.
  2. They are natural collaborators — A Scrum Master’s first function is the facilitation of collaboration. They live for it. They also have an abundance of curiosity about all things social, psychological and technical. They use their curiosity to develop trust with their teams and other organizations they intend to collaborate with.
  3. They embody agility — Great Scrum Masters see everything as an experiment, unfixed, always measuring and testing and asking “why?” They do this because they model the behavior they expect from everyone in the organization, always using data to challenge norms that are not helpful, never satisfied with “that’s just the way it is.”
  4. They are strategic — A great Scrum Master is not interested in doing things for the sake of routine. They are looking for optimal results to satisfy the larger needs of the team and the organization. They are relentlessly focused on a higher purpose.
  5. They are evangelists — By the definition of Scrum Master in the Scrum Guide, Scrum Masters serve the organization by “Leading and coaching the organization in its Scrum adoption.”
  6. They are change agents — Also described in the Scrum Guide, Scrum Masters are “causing change that increases the productivity of the Scrum Team;” that includes external changes necessary to improve the team as well.
  7. They see the big picture — Too often Scrum Masters are thought of as meeting facilitators. Great Scrum Masters have deep insight and great foresight. They consider not just where their team is, but where it is going. They can establish trust with team members and still engage management to address concerns too. In this way, they don’t see organizational issues as us vs. them. They see them as opportunities for all of us to improve.
  8. They create safe environments — A leader that allows fear to drive the organization may be successful. Tell your salespeople they will lose their jobs if they don’t beat the sales quota and they may sell harder. However, these same leaders consistently do poorly at winning with innovation and change. Scrum Masters know their team is better served when everyone feels safe. Many studies such as the one at Google have shown the impact psychological safety has on team performance.
  9. They are transformational leaders — The manager that focuses on measuring productivity or uses money to drive motivation is typically a transactional leader. These types of leaders often do well in fixed, regimented environments and are often effective with short-term goals. However, for an environment where people are motivated to take risks and learn and collaborate towards shared larger goals, a transformational style is more helpful. Many of the failed transformations suffered from too much transactional and autocratic leadership styles. Transformational leaders inspire and create a sense of safety.
  10. They are coaches and mentors — Scrum Masters are all about sharing knowledge. They want to help others and they want to be a trusted role model for others as well. They are great contributors to the culture around them.

What do you look for in a CEO?

So if you could have a CEO that was passionate about delighting customers, knew how to inspire others, was immensely curious and thrived on collaboration, embodied agility and focused on strategic intent, saw the big picture and understood how organizational design affected each team, embraced change and helping others learn to embrace it, had the qualities of a transformational leader that could empower others to succeed and above all lived to share knowledge and purpose with everyone they met, enabling a stronger and more resilient and safe culture — would that be the type of CEO you would want in your organization?


I wrote this because I often hear how Scrum Masters struggle with career pathing options. They feel taking on multiple teams or new titles like “Agile coach” are the caps on their profession. I wanted to reflect on just how far this role could take someone great at it. Not all Scrum Masters are “great” but they all are working on the skills described in this article so maybe your scrum master isn’t ready for the responsibility but maybe you can help them get there?

The other motivation is that too often I hear that Scrum Masters can easily take on two, three or more teams and be effective because “the team is mature.” or “the team is small.” This thinking completely ignores the real work of the Scrum Master which is to encourage all aspects of the organization to support their team. This means addressing compensation models that reward individual contributors over collaboration or siloed departments who defend their internal optimizations at the expense of delivering valuable outcomes to customers and many of the other strategic challenges like the ones mentioned in the article.

In other words, the role, when run correctly is incredibly important. You don’t have to even have a scrum team to have someone with these characteristics make a difference in your organization. So does every Scrum Master need to be worthy of being your CEO? Of course not but aren’t the skills they are developing valuable and worthy of any CEO of an agile organization to aspire to?

Did I miss any critical attributes of a Great Scrum Master? Are there other major organizational challenges you want to mention? How does your organization value Agile roles, not just the Scrum Master?

I’d love to hear your thoughts on these subjects.

Thanks to Tanner Wortham

Scott Weiner

Written by

Organizational Transformation Practice Manager, NeuEon, Inc. www.neueon.com

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