Context: Charting career progressions is a fascinating endeavor. What are the motivating factors that inspire people to enter into specific fields of work?&nbsp;My Journey: How I transitioned from a Project Manager to a Scrum Master and now an Agile Coach.&nbsp;What Is Discussed: The pitfalls, humor, and ah-ha moments of each position.Take-Aways: I hope to inspire and encourage you on your path and demonstrate that you possess the ultimate authority and power to shape the future of your vocation.

How I Moved From A Project Manager To Scrum Master To Agile Coach

Charting career progressions is a fascinating endeavor. What are the motivating factors that inspire people to enter into specific fields of work? And how do they nurture, develop and progress? In…

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Charting career progressions is a fascinating endeavor. What are the motivating factors that inspire people to enter into specific fields of work? And how do they nurture, develop and progress? In this article, I welcome you on the evolutionary journey of how I transitioned from a Project Manager to a Scrum Master and now shifting into an Agile Coach career. We will look at the underlying reasons for the movement, the pitfalls, humor, and ah-ha moments that have propelled me forward. I hope to inspire and encourage you on your path and demonstrate that you possess the ultimate authority and power to shape the future of your vocation.

When I graduated from <a dir="ltr" href="https://carleton.ca/" rel="noopener nofollow">Carleton University </a>, located in Ottawa, Canada, in 1999, the tech boom was in full swing, and there was a feeling of immense progression and possibility. I and thousands of others ‘fell into’ the optimistic and exciting digital age despite having an Art History degree. Given I didn’t possess a shred of self-awareness in my early twenties, I was subconsciously drawn to creating order out of chaos. I believe most of these attributes came from growing up in an unstable home with addiction and divorce coupled with being an only child for most of my life. Taking on an empathetic leadership role and ‘making things right’ felt second nature. Through this lens, it is little wonder I became a Project Manager.

I spent the first fourteen years of my career in project management. Looking back, today, I half-jokingly smile and tell people I am a “reformed Project Manager.” What does this mean? First, let me say, there is absolutely nothing wrong with being a Project Manager. Sometimes the profession can be challenging, and you need to have tough skin dealing with multiple stakeholders, each with competing interests. One of the most difficult aspects of the role is communicating to clients when any of the three points along the triple constraint triangle are failing; poorly defined scope, unrealistic time management, and improper cost management.

Let’s return to my reformation. As I matured and deepened into the project management practice, I discovered that my style is much more loose and unstructured than a traditional Project Manager who utilizes the <a dir="ltr" href="https://www.pmi.org/certifications/project-management-pmp?utm_job_number=5&amp;utm_campaign_name=pmp_lead_generation&amp;utm_region_name=north_america&amp;utm_program_origin=planned_campaign&amp;utm_program_type=continuous_campaign&amp;utm_campaign_intent=acquisition&amp;utm_funnel_stage=lead_acquisition&amp;utm_initiative=certification&amp;utm_product=pmp&amp;utm_marketing_channel=paid_media&amp;utm_marketing_subchannel=search_ppc_nonbranded&amp;utm_start_date=05012015&amp;utm_end_date=12312030&amp;utm_source=google&amp;utm_custom_field_one=pmp_certification_north_america&amp;utm_custom_field_two=pmp_projectmanagementprofessionals&amp;utm_custom_field_three=457565480616&amp;utm_custom_field_four=project%20management%20professional%20certification&amp;utm_custom_field_five=e&amp;gclid=CjwKCAjwmv-DBhAMEiwA7xYrd-uD3vBg5d_xvMqMAdY8beKr77t-wRKXnuE-36Wpp93Z96VvaJS7_hoC3AkQAvD_BwE" rel="noopener nofollow">Project Management Professional (PMP) certification </a>as the foundation or framework of their approach. Don’t get me wrong, I tried hard to obtain my PMP — and even wrote the exam three times to be exact. With each try, I failed with epic proportions. Why?

During my tenure as a Project Manager, I worked alongside various PMs who either have or don’t have their certification. And from my perspective, the result was a mixed bag of marbles. Some non-certified Project Managers were just as good, if not better, than those who possessed the PMP. Above all else, experience matters more than a piece of paper. And it wasn’t until I studied, wrote, and failed the exam three times to understand the reason behind this phenomenon. People who pass the PMP exam are better at writing multiple-choice questions. Point blank.

And trust me, I was incredibly hard on myself with each flop. I felt stupid like there was something wrong with my intellect. However, with time and retroflection, I came to believe nothing was further from the truth. That Art History degree, with a focus on Medieval Studies , suddenly became quite valuable in the corporate realm. My time in university writing essays paid off because I learned vital critical thinking skills; to assess challenges from all angles and contrast differing opinions and ideas from social, geopolitical, economic, and religious backgrounds. I also learned the value of writing and communicating my perspective, even when it is unpopular. When I think back to the months I spent preparing for the PMP exam, no wonder I bombed. I had never written a multiple-choice test in my life, and there is zero room for interpretation.

After my fiasco with the PMP, I gave up after the third attempt. Besides, I kept landing contracts, and my career wasn’t dependent upon it. The PMP did reveal in me a push away, a resistance, if you will — from a complex framework that too often felt like a rigid, tight box, one that didn’t allow room to deviate from the process. As the years progressed and I refined my craft, toward the end of my project management career, I physically carried the following emotional weight inside my body:

<ul><li>The project management framework feels heavy, at times, burdensome. I often wanted to shout —why are we focusing so much on the process? Why can’t we do the work! </li><li>Over time I felt the project management lexicon or language to feel uninspiring. For example, the “risk registrar” evokes a complex ledger where one must adhere to the constraints of documenting challenges in a specific manner. All the time spent scribing the risks seems better allocated to fixing the root cause of the issue and removing the blocker. The red, green, yellow dashboards feel more like hamburger condiments, and the “Change Control Board” reminds me of an old episode of Star Trek when <a dir="ltr" href="https://en.wikipedia.org/wiki/Jean-Luc_Picard" rel="noopener nofollow">Captain Picard </a>meets <a dir="ltr" href="https://en.wikipedia.org/wiki/Borg" rel="noopener nofollow">The Borg </a>. That or a Medieval Executioner. Anything with the word “control” in it generally makes me nervous. </li><li>Timelines were always and forever wrong. I constantly padded 15–20% extra into the schedule in waterfall projects because people notoriously underestimated the time required to test and retest defects and bugs in a software initiative. </li><li>People can hide behind their work given deliverables live in a Gantt chart rather than on a visible board. I always struggled to see the reality of progress on a day-to-day level. And over time, I began to distrust vendors whose original estimates didn’t meet expectations. And sometimes, the vendor relationship was on shaky ground when their version of reality and mine were worlds apart. To sum it up, I often lacked an inner feeling of confidence in the plan, especially when dealing with third-party companies. </li><li>But most of all, the top-down approach of project management never suited my personality. I was happiest and in my element when collaborating in the trenches with developers, designers, and quality assurance people. </li><li>While I don’t miss the days of writing complex Gantt charts in Microsoft Project, I appreciate when a plan is created, followed, and iterated upon. And I also see a wealth of value in using the waterfall methodology for certain types of initiatives, like back-end infrastructure projects or construction, instead of product-oriented work, such as application feature customization. </li> </ul>

The underlying message here is, I was increasingly dissatisfied with the traditional waterfall approach, and on a subconscious level, my values didn’t always align with the methodology. I was ready and “primed” for change without possessing full awareness of my need to pivot. And it was through this lens; my “reformation” happened via a happy accident of being in the right place at the right time.

In 2015, I worked for the Canadian division of <a dir="ltr" href="https://www.rsagroup.ca/" rel="noopener nofollow">Royal and Sun Alliance </a>as a Senior Project Manager within their Digital pillar. At the time, we had an innovative Director who embraced an agile transformation and encouraged all PMs to attend a three-day Scrum Master training certification through <a dir="ltr" href="https://www.agilealliance.org/" rel="noopener nofollow">Agile Alliance </a>.

If there is one thing I learned from writing the PMP exam multiple times — a certification does not guarantee any measure of success in the role. The same ideology exists for Scrum certifications. Instead, the certificate is a badge you can display on LinkedIn — and that’s it. Experience in the trenches matters more than a row of acronyms after a name. And now that I’ve been a Scrum Master for eight years, here are the critical lessons learned.

What I appreciate about the role of the Scrum Master is the responsibility to help cultivate an agile mindset within the team I serve. And this is especially so when working alongside a diverse, multi-cultural group aspiring to improve their practice.

In my experience working with Fortune 500 start-ups, when I see “agile mindset” or “servant leadership” written on a job posting, the statements feel reduced to buzz words. The work environment may not have the right structures in place to support the transformation. First, let’s return to the original definition of an agile mindset from the founding fathers of agile:

Responding to change over following a plan — <a dir="ltr" href="https://agilemanifesto.org/" rel="noopener nofollow">Agile Manifesto </a>

When I think about possessing an agile mindset, I believe this entails shifting behaviors, breaking down barriers to improve collaboration, becoming client-centric, or being client-obsessed to deliver value. And these aspirations are challenging to strive for or cocreate, especially when working in an organization that doesn’t acknowledge or measure what client success looks like.

A Scrum Master can gently remove the buzz words and through mentoring, teaching, and coaching the team to focus on micro, iterative changes that, with duration, equal substantial shifts in mindsets. In metaphorical terms, consider the drip of tiny raindrops, that over time fill a rain barrel. Scrum Mastery is a long game and requires an incredible amount of patience and persistence to see the change through.

For example, in my current role, we talk a lot about moving away from being an “order-taker” to becoming an “order-maker.” What does this mean for someone who possesses an agile mindset? We must shift our Product Owners and Business Analysts away from accepting all software enhancements or change requests from the business simply because of a demand to be an equal partner and facilitate the value definition process. When feature requests align to organizational strategy and include a business case, everyone focuses on the highest priority work allowing the most significant value to be delivered. Through these changes, we can eliminate the noise and reposition everyone towards a north star.

Rome wasn’t built on a Saturday afternoon, and the switch from order taker to order maker is a long and windy road. People need to feel empowered to use their voice and change how work enters the system in the upfront pipeline, which is not an easy feat, especially when people are comfortable in their current way of being.

When the agile manifesto calls for “people over process,” I feel a sense of confidence I am home , in the right place cultivating relationships with my colleagues — partnering, collaborating and serving. An over-engineered process stifles creativity and prevents people from making the valuable contribution of failure, leading to deeper insights. And let’s face it, people are the driving force behind successful processes.

One area I continue to focus on in my career is bridging the gap between people and processes. What do I mean by that? For example, when we have issues with a software release, our retrospectives are laser-focused on root cause analysis to discover what went wrong and how we can quickly pivot into a new way of being. The entire team is a part of the co-creation of new processes, and we iteratively refine together; this way, everyone has a voice at the table, and shared ownership occurs across the board.

When I first joined the investment company I currently work for, in the first three months, I made a mistake and inadvertently backtracked on my commitment as a “servant leader.” Our objective was to showcase achievements to Executives within the agile transformational context. However, on the call, I spoke on behalf of the group the entire time rather than sharing ownership. What was I thinking?

Reflecting, at that moment, I wasn’t operating in a place of self-awareness. And even a well seasoned Scrum Master like myself can make mistakes. From my experience and observation, the minute I disengage with myself is precisely the time when I default into a reactive state with the people I serve. Active and intentional presence is a critical personal requirement with both Scrum Mastery and Coaching and deepens the relationship between all parties.

What was the outcome of the Executive presentation? When a Senior Manager reminded me of the importance of a more collaborative demonstration of our team’s capabilities, I could not have agreed more and felt grateful for our conversation. From that moment on, I ensure everyone has a chance to speak and is an active participant in all our sessions.

The older and hopefully wiser I become in my professional career, the quieter I am. Why? When we’re so focused on speaking and ensuring a heard voice, there is less space allocated for active listening. What am I listening for? Here are the main areas:

<ul><li>What are the needs and desires of the team? </li><li>What are my assumptions, judgments, and biases? And what can I set aside? </li><li>Listen to the words spoken and the silence in between. </li><li>Listen to the tone, rhythm, flow of conversation. </li><li>Listen on multi-levels; team, program, and organization. What are the unique sounds and silences? What is the language used by the organization? What does this information tell me about the maturity level of each level? How can I best meet each group where they are at? </li> </ul>

When we stop and listen, the world has a larger scope, and from my perspective, I can better understand the actual dynamics occurring in the entire multi-tiered system; team, program, and enterprise.

Now, eight years into the Scrum Master role, I have faced the pitfalls and organizational impediments while finding opportunities to coach team members, managers, and others along the way. Now, I have my sight set in a broader scope. While I continue to focus my attention on the team, I am also expanding my reach and listening to the system at the program and enterprise levels. Much of the beautiful transformational teamwork can be leveraged and scaled upward. Within the elevation, the following quote from <a dir="ltr" href="https://hbr.org/2019/01/to-improve-your-team-first-work-on-yourself" rel="noopener nofollow">Harvard Business Review </a>comes to mind:

To improve teamwork, I need to improve myself.

In keeping the concept in mind and practice, I remember how the responsibility of the Scrum Master and Agile Coach is to develop an agile mindset in their organizations. Even the techniques used to support and facilitate teams are similar. And as I mentioned above, the difference between the roles lies in the scope. While transitioning to the responsibilities of an Agile Coach, let’s explore how my experience is shaping up.

My experience in shifting from a Scrum Master to an Agile Coach is unearthing an essential factor; and one that continues to stay top of mind. While a critical skill set of an Agile Coach is to possess a deep understanding of multiple agile methodologies, I am frequently noticing:

<ul><li>Agile Coaches must listen to the system and seek out indicators or signals which highlight whether a team is working within the boundaries of the right framework for their needs. For example, if a Coach is skilled with Scaled Agile Framework (SAFe), the knowledge possessed does not give a Coach the right to implement the framework in an organization when the approach might not be the right fit. As Coaches, we need to check our bias and provide the right level of service in our servitude . I mention SAFe because I often see frameworks implemented without addressing the real underlying organizational challenges (be it culture, reporting lines, structure, people) disrupting the first place. </li><li>The second challenge I see with Agile Coaching is, at times, the intense focus on the implementation of frameworks without enough attention paid to establishing personal relationships. Strong affiliations take consistency and trust across the vertical and horizontal lines of the organization. Given my dual role as a psychotherapist in training, I am far more interested in co-creating a relational foundation before diving into frameworks. If you build a house and it remains empty, who is it serving? Maybe the ants eat into the wood? A team that works effectively together is far more likely to succeed when they trust the Coach is guiding them into new, unfamiliar territory. </li> </ul>

A Coach may have a ton of domain knowledge in specific areas; however, if the individual lacks self-awareness, people, and communication skills, promoting agile practices across the organization diminishes greatly. Above all else, a Coach should always be working on improving themself. As <a dir="ltr" href="https://www.lyssaadkins.com/" rel="noopener nofollow">Lyssa Adkins </a>accurately describes in her book <a dir="ltr" href="https://www.amazon.com/gp/product/0321637704/ref=as_li_tl?ie=UTF8&amp;camp=1789&amp;creative=9325&amp;creativeASIN=0321637704&amp;linkCode=as2&amp;tag=cricketwing-20&amp;linkId=c7200799cf6324a7c1dd22873cb3af41" rel="noopener nofollow">Coaching Agile Teams </a>:

They are exploring every facet of who they are in the quest to become fully integrated and complete human beings. Agile Coaching helps in both these areas: produces products that matter in the real world and add meaning to people’s lives.

Trust is built over time; by showing up each day and being consistent through allowing failure, being curious about others, and acknowledging that life is messy and things will not go as expected. Once trust forms along the vertical and horizontal lines, the easier it is to have those tough conversations to promote and deepen agility practices across the organization.

What I appreciate most about agile coaching is the wealth of experience and experimentation I bring into the practice from other areas of my life.

For example, in the winter, I am a downhill ski instructor. And believe it or not, there are definite parallels between the two practices. One such concept is the ability to “fail fast, fail often.” In downhill skiing, each run down a hill or mountain presents a unique challenge and opportunity. The terrain is constantly changing with new weather patterns, skiers shaping the snow, ice patches unfolding, or in the spring, the grass begins to emerge from underneath. How a skier responds to the ever-present shifts in the environment will shape the outcome of the run. Perhaps a skier will accidentally hit a protruding rock and do a face plant. I’ve been there! The point is to assess the situation, and if no injuries are present, rise and repeat the action of skiing down the vertical once again.

In the software delivery world, we can contrast downhill skiing to creating a proof of concept. An Agile Coach encourages experimentation and allows room for failure; while creating the space for individuals, teams, and programs to learn from mistakes while rising to the challenge for another kick at the can. Sometimes it takes more than one try to find a solution that solves the client’s challenge, and providing the ability to keep trying is what matters most.

And finally, Gestalt psychotherapy is a positive, life-changing career I am embarking upon in parallel, one that deepens the practice of coaching. Here are some of the ways Gestalt therapy inspires and informs how I approach coaching each day:

<ul><li>In working with challenging people from all walks of life, I have developed the capacity to ‘hold in’ longer than ever before and have patience with different processes. During agile transformations, some people shift their mindset faster than others. And for those who work at a slower, more methodical pace, it is my role as a Coach to meet them where they are and support individuals, teams, and Executives during periods of stuckness as well as in those ah-ha moments. </li><li>Gestalt psychotherapy is rooted in mindfulness. When I encounter a stressful situation or find myself in a heated discussion, my default is to focus on breathwork. When fresh oxygen flows through the body, my heart rate decreases, and I can think and feel more clearly. And when I remain calm, the stillness is felt in the space and helps diffuse conflict situations. </li><li>The ability to sense and develop intuition is a part of the Gestalt learning process. When I take time to listen and observe people and the system; I am opening the space to read a room; to sense where tension exists; where it doesn’t, and everything in between. Reading a room informs me what type of situation I am entering into and how to engage. </li><li>One of the cornerstones of Gestalt theory is the concept of “Here and Now.” Rather than reliving the past and remaining stuck in history, I look at how prior events impact today, where we are in this very moment. When in a coaching conversation, I find myself asking clients what is coming up for them right now and keeping the issue in the present tense. By focusing on the here and now, we can consider possibilities for change. </li><li>Life is messy. And this is not a Gestalt psychotherapy fact. I frequently see that people are doing the best they can under challenging circumstances with the tools they have. An Agile Coach helps the organization find the right tools and determines the proper stance (facilitate, mentor, guide, coach) to approach the messiness and support the change process. </li> </ul>

In Gestalt psychotherapy, we talk about “the process.” The same idea applies in Agile Coaching. Everything is a process of discovery, learning, and a lifelong commitment for the betterment of self to show up to support others — no matter the vertical or horizontal team, program, or enterprise.

Twenty years ago, if someone told me I would be a psychotherapist and an Agile Coach, I wouldn’t believe a word of it. Life has an exciting way of twisting and turning and forming new paths. I wouldn’t trade my project management days for the world and believe “the work” formed a solid foundation in preparation to move into becoming a Scrum Master, a career better suited to my personality. Time in the trenches has taught me many valuable lessons; patience, self-reflection leading to personal change, and a continued thirst for knowledge to better myself and support those I serve.

Agile Coaching is a natural progression and one I am embracing as the transition unfolds. I wake up excited each day to partner with clients and impact their path toward adopting broader agility practices and delivering value to our clients. While my journey has been two decades in the making, I feel the road is just getting started in many ways. I hope you are inspired and know you also have a unique and exciting direction; all you need to do is take the first step in your journey.

More like this:

What A Journey: From Project Manager To Scrum Master, Transitioning To Agile Coach

How I Moved From A Project Manager To Scrum Master To Agile Coach

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