Experience Report

The Transformation of a Transformation Agent: How becoming an Agile Coach Challenged Everything I Thought I Knew

About this Publication

In 2013, Envisage, a small, cool, start-up in upstate New York was beginning to grow its agile practices and was looking for some help. After a few years of working in Scrum as a Business Analyst and then a Scrum Master, I felt I was ready to share my passion for agility and begin my career as an Agile Coach. After a surprising and intense interview, I was hired to help the company transition to being a mostly flat agile organization that was empowered to make and act upon their decisions. This report tells my story of the 3 years that followed.


To this day, I see very few coaches in the agile coaching ranks. This isn’t a judgment but rather an observation that has been clarified over 10+ years working in Agile as a Manager, Business Analyst, Scrum Master, Product Owner, and Coach. I have worked with many talented consultants, mentors, trainers, and well-meaning change makers. Very few of them, however, are coaching in the way I now understand the stance and ‘moves’ consistent with the art. Coming up as a System Engineer and Business Analyst I was enamored with processes and methods for communicating a design, a product specification, or the flow of information between people and systems. I encountered Agile and Scrum about 10 years into my career and was immediately drawn to its humanistic engagement and its embrace of reality over hope. Agile felt like a huge deep breath of fresh air and I quickly became enamored with this new way of thinking and working. As soon as I started working on agile teams my desire to learn more was insatiable. If you were willing to listen, I was eager to share all the practices and methods I was spending nights and weekends reading up on. The early agile Coaches supporting my teams and me were incredibly effective in their ability to educate and mentor on roles, events, development practices, technologies, etc. The agile coach role was ubiquitous and I didn’t question the title or the intent. I just experienced them being helpful. My time at Envisage Information Systems forced to me to clarify ‘Coach’ for myself, those that hired me, and those that I supported. It was a thrilling, messy, painful, and important experience. I’ll start at the beginning.

2.     Background

In the late fall of 2013, I walked bleary eyed out to my car completely unsure of how the interview actually went. I sat there, as the heater overcame the Upstate New York November chill, with this odd feeling. It was an unusual combination of numb and perplexed. I wasn’t sure how to feel. Did I want this agile coach position with this cool little start-up?

The interview process was four rounds, two interviewers per round. All but the last interview in the same clean and not overly formal conference room. The first was with the CEO (Steff) and the head of Business Development. Steff sat across from me and told me the story of his company and where they were on their agile journey. A few months prior, on a Friday he declared, “Monday we will be Agile.” The organization was struggling to adapt to this new way of working and being. He wanted a flat organization that was largely supported by coaches. He abhorred a traditional organizational structure and wanted his company to put the client and the employees at the center. He laid out the challenges, and asked me if could help. I wasn’t grilled on my background, my certifications or my experience. He simply wanted to know if I could help and if so how. In the next two rounds of interviews, I asked most of the questions. The format was roughly, “Here’s what we have going on” and, “Can you help, and how?”

The last round was with the CIO and COO. This interview was in the COO’s office. The three of us sitting around a small table. The COO asked me, “How do you think you’ve done so far?” I said something along the lines of “Well, given what I’ve heard I think I can be helpful here. I think it’s going very well.” He gave me a long look and squinted a bit as if to communicate his disagreement with my assessment of the day’s conversations. I stuttered a bit, searched for a response and gave a generic response to his speak-volumes look. “Well, I suppose I could have asked better questions?” I was a bit confused on where this was going.

The CIO asked several pointed questions about my resume: “You seem to use the terms Leader and Manager interchangeably. Is there a difference?” Well there was, but up until that point I had not really considered the subtle and not so subtle differences. What I took from his line of questioning is that words matter, and so does intent. We wrapped up the interview stepping through a logic problem the CIO had presented to me. I crashed and burned on that one! He gently provided me an entry point to solving it. In retrospect, he wanted to get an idea of how I think and under some pressure. My assessment? My reptilian brain took over and I lost the ability to think critically.

On the 90-minute drive home, when my brain slowed down, I decided I wanted this job but I wasn’t entirely sure why. Two weeks later I received a compelling offer that I accepted. Looking back, the interview laid out my learning journey over my three-year tenure at Envisage. What is it to lead? How do I get the upper hand on my amygdala when pressure mounts? Can I look at myself and the way I show up more critically? What is it to be a coach and to coach? Over the next three years I engaged in a learning journey that challenged everything I thought I knew and understood about being a ‘good’ employee.

My experience at Envisage fundamentally changed who I am, how I think and what I believe in.

3.     My Story

3.1        Year 1—Learning

On my first day I felt special. I was the second agile coach to join the company and the teams were excited. “Oh, you’re the expert!” “You can fix all of my problems.” “Can you join our sprint planning and tell us what we are doing wrong?” After a few weeks and some false starts with teams and leaders I felt a deepening insecurity. At this point in my career I only had a couple of years of Agile and Scrum under my belt. Having barely gotten going, I felt as if I had already started to exhaust the knowledge that I had.

I had already explained (“coached?”) Agile and Scrum to the senior leaders a few times now, and while they seemed to understand what I was saying, when it came to execution, I saw nothing really change. The way leaders “showed up” was not congruent with how they spoke. One of my first projects was to implement a delivery model using feature and component teams. My approach to working though this problem was to schedule working sessions with the leadership to design the model and gain alignment on the design. The first working session, 2 hours, was slow going but we were making progress. The next day I got a ‘dressing down’ from the COO, basically telling me we didn’t have time for all of this conversation, our clients were waiting!

Same goes for the teams. Countless conversations and “coaching” around scrum events, agile mindset, et al., but the tone from the teams was more or less “Yeah, yeah…but that’s not going to work like that here. It can’t! We have to deliver!” If they didn’t say it, their eye rolls told me plenty.

Furthermore, people were coming to me for all kinds of things:

“Can you tell the CIO ‘…?’”

“Can you coach me on ‘…’.”

“Team such and such is generating too many defects.”

“We need to build out job descriptions for all of the agile roles.”

“We need a class on this and that.”

“The teams aren’t meeting their sprint commitments; I need you to fix that.”

“What’s a coach? What do you do anyway?”

In no time I was lost and feeling like I was letting everyone down on a certain level. I felt terrible. For the first time in my career I didn’t know what I was supposed to do or how I was supposed to do it.

We hired a couple more agile coaches over the next year…and the challenges only got more acute.

Leaders were looking for managers to fix performance issues and get the teams on track.

Teams were looking for support in buffeting the incessant pressure from the leadership as well as work through local team issues. The primary issue was that leadership was making commitments to clients not informed by the team’s capability to deliver.

Here I was, a ‘silent leader’ in the organization unable to really help anyone in a meaningful way.

In that first year, the coaches and I would talk with Steff about the challenges we were facing in meeting what could at times feel like competing demands: Support individuals and teams, and deliver to the client. Steff always made himself available to us and reassured us that we were doing what he wanted. He recognized that all of us were on our own journey and he believed, in time, we would achieve his vision. Ultimately, he wanted a company of whole-hearted and authentic employees that cared for each other and that company with each employee “on the right seat on the right bus.” Stay the course!

3.2        Year 2—Growing

I committed myself to figuring out how to be more effective in my role and to bring some clarity to the organization. My first challenge was to help people understand what an agile coach even was. I researched every corner of the agile body of knowledge for crisp and useful definitions of the role of an agile coach. I was disheartened to find there was very little to be found. I did discover that coaching is a discipline all to itself, agnostic of agile. Much of what I had experienced agile Coaches doing, and what I was emulating, had little in common with actual coaching.

There are a few working definitions of coaching. Coaching as defined by the ICF (International Coach Federation) [ICF] is a very specific kind of relationship:

“Partnering with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential.”

My particular coach training program, Presence-Based Coaching [PBC], defines coaching as:

“….that part of a relationship in which one person is primarily dedicated to serving the long-term development of effectiveness and self-generation in the other.”

Coaching is not about fixing people or fixing teams. People don’t need fixing. Yet, we were routinely told “go coach that team,” whether they wanted coaching or not. Coaches believe those they coach are whole and capable of developing and implementing solutions that address their challenges. This belief system fit way better with mine.

All of the coaches read and worked through the book Co-Active Coaching by Henry and Karen Kimsey-House [Kimsey-House] and began to implement some of the strategies therein. We found that the more we just listened and remained curious and stopped trying to lead with solutions and our own ideas, teams often discovered potential solutions/experiments to try all on their own. Coaching became about the relationship and not the action or what I knew. One has to have the desire to be coached and be accountable to the outcomes. Coaching is not a hammer.

Furthermore, I started to understand that my story played into all of this. I had been trained for over 15 years in the corporate world to have the answers. Most organizations reward the heroes, those with all the ideas/answers. Tracking my career, I took great pride in doing the research, getting the certification and being the expert. It felt good to be acknowledged for being smart and ‘in-the-know.’ My ego was being propped up by ‘being right’ or clever. The identity I had manufactured over a 15-year career was not wired as of yet for coaching. For coaching to be effective I had to pay attention to my own desire to solve and fix. My ego needed to be smaller. Much smaller in fact. I needed to rewire my brain, my whole being really, to be at peace with being in service and to not have it be all about me. This required daily attention to stay present and mindful of how I was showing up.

I began a renewed commitment to a daily practice of journaling, meditation and gratitude. I say renewed, because years before I had been more diligent. As with many things, life, career and commitments took priority over my own well-being. About 5 years prior to Envisage I had moved from Southern California to upstate NY. The move was principally about getting closer to family. We took on new jobs, bought our first home and had our first child in tow. Shortly before we moved I began working with a life-coach to help me develop strategies to navigate all of this change and upheaval. To say I hadn’t handled the move well would be a massive understatement. Much of the work with my coach was about being able to stay in the present moment without dwelling on the past or becoming anxious about what may or may not happen in the future.

At Envisage, my identity felt attacked almost on a daily basis. I was struggling to find ways to be helpful. I was trying to be a better coach and keep myself emotionally balanced. Many days I didn’t even want to go into work? The daily practices, over time, began to help.

My Practice:

  • Wake early and journal for 15-30 minutes. The prompts were always different but usually involved some reflection on the prior day and an intention for the current day. I was only writing for me, so no editing or being careful with words. I just let the pen move and kept it moving until I felt complete.
  • The Intention—How do I want to be today? I learned that I could choose how I showed up. “Today I will be patient.” “Today I will generate feelings of appreciation for everyone I come in contact with.” “Today, I will be aware of my desire to solve.
  • Sitting Practice—Anywhere from 5-15 minutes of just sitting comfortably, alert and focused on my breath. Invariably, the thoughts would come and I would do my best to bring my focus back to my breath.

As a consequence of my practices I was beginning to raise my EQ—EQ being emotional quotient. The more I got tuned into my internal wiring and tendencies, the better I became at identifying the emotional cues in others. Also, I could regulate my emotions by being increasingly aware of the fight or flight instinct kicking in when a conversation got particularly heated or when the entire building felt like it was vibrating. I could catch myself, acknowledge the feeling and make a choice. It became increasingly clear to me that there is great power in presence and intention. I became able to stand in the middle of tense and emotionally charged conversations and respond calmly and in possession of all of my innate resourcefulness. On more than one occasion a senior leader would interpret my calmness as a lack of passion or commitment to the company. More than once I said, “If we are all swept up in the event, how can we think clearly about what is happening around us and rationally consider options?” I was a bit surprised at being misunderstood in this way. I discovered that I could be perceived similarly in my personal life—dispassionate or uncaring. Around this time, there were also some particularly trying personal challenges at play and I found my new sense of centeredness to be incredibly valuable there, too, if occasionally misinterpreted.

I started to share the work I was doing on myself, and interest grew with the company. I began offering short classes on Emotional Intelligence and Mindfulness to executives and team members. At the start of the class I would share the story of my California to New York move and my first foray into mindfulness practices. We eventually incorporated concepts of mindfulness and presence into our new employee orientation! At one particular all company meeting we invited each employee to participate in a mindful listening exercise—listening to someone without asking a question or interrupting, just practicing listening deeply. How often do we give the gift of our total and complete attention?

If you asked Steff how things were going about two years into my tenure, you’d get a very mixed response. We had been acquired by a large financial institution but remained a wholly owned subsidiary. He was doing everything he could to bring about the culture he envisioned and his support in the coaches never wavered. We were, though, struggling to meet the needs of our parent company and this was causing a lot of angst within Envisage. Again, we faced headlong the desire to support each and every employee and integrate our delivery with a much larger entity.

3.3        Year 3—Shifting

It wasn’t enough to say we were a flat, transparent organization that valued all the gifts everyone possessed. Just saying ‘we are agile’ wasn’t enough to bring everyone along and live in alignment with the values and principles. It was easy to say as much when things were going well. Envisage had to find a way to be true to our good intentions when things got hard.

Poll one hundred employees about our values and you’d get one hundred different answers and some lucky guesses. The lucky guesses more often than not were overused and trite and about ‘respect’ or ‘integrity.’ What company doesn’t want to demonstrate respect and integrity? These qualities, while important, don’t make us any different. We knew Envisage was special. We had to capture the feeling in words.

Over a 3-month period, led by my coach peer Sarah, the company values were re-written, socialized and discussed whenever and wherever possible. We put them in everyone’s faces and invited conversation and reflection at team meetings and all hands discussion. The entire company made a commitment to live and uphold the values. For real!

Here they are:

Own Your Story

Challenge Everything

Be Bold and Take a Chance

Be Real, for Real

Listen Deeply, Share freely

Jump in and Help

Invest in the Whole Person

Leggo Your Ego

We scrapped the generic 360, performance-based evaluation for one that centered on the values. I would evaluate myself, as would three to five other employees. The new 360 invited quiet reflection and deep consideration of how we each showed up:

Which 3 values do I exemplify and why?

Which 3 values to I need to work on and why?

There are three values I remain intentional about to this day. “Own your Story,” “Be Real, For Real,” and “Leggo my Ego.” To really be seen and show up without the burden of maintaining some persona or maintaining the identity that is informed by one’s ego can be frightening and requires more than a little bit of vulnerability. Our invitation to everyone in the company: If you choose to, Envisage can be a place where you can explore who you really are in an environment where it’s safe to do so. I learned that we have the best chance of being our best selves when we are whole-heartedly supported, not just in words but also action.

Our next task was to put in a structure where each and every employee had the support and partnership, they desired with the goal of being able to Invest in the Whole Person. Steff wanted everyone to be able explore any and all possible outcomes, whether they be within the company or not. We also wanted development conversations to be free of concerns regarding bias, performance or compensation. These tenets brought about the structure we called the Care and Feeding program.

First, we had to identify those individuals within the company that had a strong desire to be in service; to partner with empathy and Jump In and Help another employee. We put a call out to the organization and 30 people raised their hands! That’s about 10% of the company. The Care and Feeding Partners included some of CxOs, Development Leads, Project Managers, Scrum Masters, Product Owners and Coaches. Our cohort was a true cross-section of the organization.

We invited all 30 to a two-day off-site. There were a few objectives for the off-site.

  1. Cover some of the administrative and logistical needs. Employees would be able to self-select their preferred Care and Feeding Partner. Eek! What if no one picks me?! Each Care and Feeding partner could support a maximum of 10 employees and we had to ensure that a Care and Feeding partner relationship was separate from another relationship—an example being a Scrum Master supporting a team member on the same team.
  2. Getting everyone on the same page as to what it meant to be just a partner in development. This partnership was not about correcting employee behavior or improving delivery. It was about serving the whole person. The agenda was the employee’s. When the agenda is the employee’s or client’s, ICF would say we have one of the necessary ingredients for a coaching relationship.
  3. This might be most important objective: You can’t be fully present and available to the employees you support if you aren’t doing your own deep work.

I was the facilitator for most of the 2nd day of the off-site and it was my opportunity to share the learning and growth I’d experienced over the previous two years with Envisage. I was going to allow myself to be seen more fully than ever before. I felt as if I had come such along way in those two years. Already a very different person than when I entered the company.

A dear coach friend of mind, Sarah, a couple of weeks prior had been coaching me a bit on what I really wanted to get across in my session. I had felt timid and insecure about going headlong into mindfulness and presence with this group. What if it didn’t land? At one point she paused and looked at me with very caring eyes. After some space she says…gently: “Are you playing small?” The words landed with impact and gravity. I was. I knew I was. I needed to Be Bold and Take a Chance. There was no other option.

The night before my session I could barely sleep. I did my best to remain calm and centered, but my mind raced with all the ways the session could go sideways. I intended to invite the group to meditate, to listen deeply to one another, to really consider their individual stories to be open to the idea that we all had room to grow. The session and messages were intensely personal to me.

By the time morning arrived I felt oddly calm. I possessed a sort of tired energy after I had not slept all that well. I felt focused. I felt ready.

I started the session with the primary message. We have to do our own deep work to be fully available to our partners. We have to be careful not to allow our stories, our egos to influence the direction of employee conversation. We had to be careful not to imbue our sensibilities onto those we coached. This takes intention and practice. After covering the objectives for the day, I guided a short mediation that ended with the gentle ding of meditation cymbals. I looked out and saw 30 employees of all levels following their breath, breathing deeply and doing their best to be still. When the bells rang, they all gently opened their eyes and looked up at me. No judgment just relaxed smiles and calm. I was being seen as the one that invited a deepening. It felt wonderful.

Our first activity was called “How are you for Real.” In this activity we talked about how often we respond automatically to the prompt “How are you?” How often do we stop and truly consider how we are? And even more, what would our engagement be like if we did so? So, in turn, each person came to the front of the room to share how they were, for real. The energy was alive and engaged. Everyone sharing how they were after a moment to consider the question. “Sleepy but ready for the day.” “Skeptical whether this program can work.” “Wondering if I am right for this role.” Then we got to Jim. Jim was probably the funniest guy at Envisage. So, he shared how he was, but it was clearly a joke. The whole room knew it. I said, “That’s funny Jim. But I’d really like to know how are you are, for real” Jim then shared his truth. One of his dearest friends had died the day before in a motorcycle accident. Tears welled in his eyes and he quickly walked out of the room. Jim was the last to share, except for me. We all had tears in our eyes as everyone look to the front of the room, to me. Then someone asked. “How are you for real?”

I had never felt so vulnerable. I took a breath. I felt my feet on the floor and the space that I was in. I said: “We were not prepared for Jim’s answer. But the truth is, we bring so much more of ourselves to work than our skills and our title. The things we shared this morning, that Jim shared, that’s real. To care for one another is to be available for whatever may come from the conversation. Let’s go find our friend Jim and make sure he is okay.”

The rest of the day we explored the dimensions of Emotional Intelligence. We practiced listening at all levels as described by Co-Active Coaching; our internal voice, the words and body language of the person we are speaking with as well the environment and energy in the space we occupy. We shared our learning edge with one another and provided generous and constructive feedback regarding the development opportunities we observed in each other. We journaled at breaks. We took moments to be still, feel our feet on the floor and be present. We created a community of vulnerable, caring leaders that were committed to their own growth and the growth of others.

At the end of the day, I looked once again at 30 humans in meditation. I thought to myself, this is Envisage.

4.     What we learned

The day I arrived I knew I had entered a special place. Over my three years with the company we never stopped trying to bring into the light the culture we believed in and knew was possible to create. Steff certainly knew it was possible and never lost sight of it. He never wavered in his belief and commitment. We took what was a feeling and turned it into words. The values brought the idea of Envisage to life. For me, the promise of Envisage culminated with the Care and Feeding program.

‘Envisage’ means to contemplate or conceive of as a possibility. Steff saw a future where each employee could be the best version of themselves and do work that was both deeply satisfying and beneficial to our customers. Ultimately, though, I think Steff wanted a company of employees that took care of one another and treated each other as human beings. A company that spoke the truth and was out from under the weight of a traditional hierarchy. I think we achieved that. More so, I think all of us that experienced Envisage are more fully realized.

The gravitational pull of a much larger institution eventually proved to be too great for Envisage. So, I left Envisage after about three years a very different person and professional. I’d become so much clearer on my values. Dedicated to the art of coaching and convinced more than ever that a transformation of an organization requires personal transformation. It requires being willing to look at ourselves deeply. Scars and all. It requires caring more about others than ourselves, whether it be the customer or the employees. I believe companies have a collective Ego and it needs to be small as well as that of its leadership, wherever they may reside in the corporate structure. I was able to help others to embrace coaching, adopt daily practices and look at themselves more deeply by doing that work myself. I led others to this place not by telling or explaining but by doing and demonstrating. This is what it is to lead.

Thank you Steff. I am better person for having worked for you. I’m sure I’m not alone in that feeling.

It’s now been four years since I left Envisage. I continue to learn and grow my practices and have continued the journey I started while at Envisage. I am now in the process of becoming an ICR credentialed Coach. In 2019, I completed an ICF accredited coach training program [PBC] and am currently coaching inside organizations as an independent. I coach in and outside the context of Agile and provide leadership, career and life coaching.

My daily practices continue to this day, though like many of us, I fall off and get going again. In the process of writing this paper, I was reminded again and again of why these practices are so important. To be my best for others I must attend to my ongoing development and presence. A very important mentor in my coaching said, “You can’t take someone on a journey you have not been on yourself.” Now, that doesn’t mean I can’t coach a leader who wants to be a CEO someday, because I myself have not been a CEO. What I do believe it means is that if we are to invite our clients to engage in a process of self-discovery and sense-making then as a coach I need to have done the same and remain committed to my own journey.

Our work is never done.

5.     Acknowledgements

There are so many I want to acknowledge. My first life coach Vida Weinstein who opened my eyes to the power of presence and mindfulness. To the entire Envisage family, with a special callout to my fellow coaches—JB, Cathie, Todd, Dave and Laura. Steff, for the opportunity to be a part of your vision and for all the growth that resulted from the experience. Darren and Nikola for challenging me to stand behind my words. Rob for music and support! Leigh and Evan for your counsel, support and perspective. My dear friend Sarah, I can hardly articulate sufficient words to communicate my deep gratitude and appreciation for you. Rebecca, my patient and supportive experience report shepherd. To the entire agile and coaching communities that challenge and motivate me endlessly to be a better coach, agilist and human being. Most importantly, my wife and children, who provide me the daily reminder of why I want to be a better human.


[Coactive] Coactive Training Institute. Website: https://coactive.com/

[ICF] International Coach Federation. Website: coachfederation.org

[Kimsey-House] K. Kinsey-House et al. Co-Active Coaching, Fourth Edition: The proven framework for transformative conversations at work and in life. Nicholas-Brealey. 2018

[PBC] Presence-Based Coaching. Website: presencebasedcoaching.com

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