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September 25, 2019

Top Enterprise Transformation Lessons Learned

By IT Revolution
Ross Clanton at DOES19 London

This was an excerpt from a presentation by Ross Clanton, Executive Director, Technology Modernization, Formerly of Verizon.

Today I’m going to tell stories of failure, a bit like ‘DevOps confessionals.’

I am a transformation executive. I’ve been doing this for a while now at a bunch of different companies, and I’ve had a lot of different roles. It’s definitely broadened my perspective around what works and what doesn’t when you’re trying to drive change in organizations. 

The last six years I’ve led two large technology transformations at two fortune 50 companies, at Target and at Verizon. I’ve also been a pretty active member in the enterprise DevOps community. I collaborate with a lot of the different executives that are doing change in their different companies. A lot of people that are part of this community. I have done podcasts, white papers, etc. whatever I can do to give back to this community. It’s really important to me. Through this journey, I’ve gained a lot of experience on the key constraints that impact the effectiveness of transformation enterprises. 

Let’s start diving into some of these lessons learned

Driving DevOps transformation in large enterprises is extremely hard.

To achieve true success not only do you have to transform your technology practices, you often have to change your culture. That includes dealing with politics and complex leadership dynamics in companies. You often change your model and the structure for how work gets done — not just in IU, but also how IT interacts with the business. You have to reskill a lot of people in your workforce.

When you think about it, there are a lot of barriers to deal with. Why don’t we hear more stories about these challenges? Think about it, when you do a talk at a conference you probably need to get approval from an internal public relations or communications group. So then, when you go to them and share that the idea for a talk is about the massive failures — they’re not too excited about that. That’s why you don’t hear a lot of these stories. It’s really hard to come and share, so I’m going to share. 

This talk is going to get into real life examples from challenges that my colleagues and I have faced in driving change in complex enterprises. They are going to be based on firsthand experiences and through my direct collaboration with others in this community. I want to stress, none of these stories are attributed to a specific company. Don’t try to figure out who I’m talking about. We’re going to keep it a little bit obfuscated, but they are real examples and the names of the individuals have been changed to protect the innocent.

But before I dive into the stories, I want to talk about the types of failure that I’m going to discuss. 

There are many types of constraints that actually impact transformation success, but one theme that I think deserves particular focus and attention is failures and leadership — things like sponsorship, executive support, leadership behaviors. It’s a huge problem and it’s actually something that has come up a lot in my research. It also comes up in almost all of my direct experiences and my colleagues direct experiences. So, there are going to be a lot of examples of leadership constraints in this talk. Let’s see if you can pick them out.


Now let’s dive into the three stories

These will underscore many of these constraints.

It’s time to meet Jaxon, Isabella and Jayden, three fictional transformation change agents all working in different companies. 

First up is Jaxon.

Jaxon is a transformational executive that’s recently been promoted to the vice president of the digital portfolio in his company. He’s a strong believer and champion of lean and DevOps ways of working. He’s built a strong leadership team, made up of some of the best DevOps minds in his company and best leaders in the company. This company was also on the heels of a failed Agile transformation and this team felt there must be a better way. Over the next two years, Jaxon, his team and some close partners across the business and technology groups worked together to grow a better way of working.

Jaxon started by orienting his portfolio around DevOps ways of working, but he also focused on championing this across his executive peer group in the organization. He built a continuous improvement practice and actually used that to help teams even in other organizations adopt these practices. They initiated a talent development program modeled after one of the leaders on Jaxon’s team to improve talent across the organization and even had another leader on his team spend time helping middle management learn lean mindsets and ways of working. 

Beyond that Jaxon drove alignment with the executives on the one metric that mattered to that technology organization at that time, which was cycle time. Things were on a really good track. There’s clear executive focus and clear measures. Teams were starting to see better results. They were visualizing their value streams and they’re systematically removing the biggest constraints for each team, continuously improving cycle time. They even started to operate as more full-stack end-to-end teams similar to what you would see in a product model.

But, and there’s always a but, one day things changed. 

This company always had a fairly operationally minded CIO. They continued to face significant digital disruption in their industry and recognizing his own gaps, the CIO decided to hire a CTO from outside the organization to up their digital game. 

This CTO was a self-proclaimed ‘DevOps expert’ who was ushered in to kick the company into a higher gear. Very quickly they started undoing the changes of the previous two years, moving the organization back to a functionally siloed model, all in the name of increased efficiency. Within a few short months, two years of progress was nearly wiped out. Jaxon and change agents across the company revolted and challenged this new direction. Unfortunately though, realizing that they were in a difficult spot, they all eventually decided to leave the organization over the following months and they’ve all moved on to be awesome DevOps leaders in other companies. 

Now, that’s kind of a sad story, I think, but it had a good outcome for some of the individuals.

Let’s talk about another story — Isabella.

This company was looking to modernize their technology practices, build an engineering culture and improve time to value of their technology delivery. Isabella was leading this initiative reporting to the CTO. Alongside a close band of leaders, she was working hard to drive change across this very large complex company. The CIO at this company was excited about these changes and even set a vision for IT to be an investment center and a destination for top talent. It was a bold aspiration and it served as inspiration for the technology transformation. While the messaging was set at the top, a few key issues quickly became apparent. First, the business was still largely viewing IT as a cost center. They had a history of piling up a lot of demand for IT in the form of predefined requirements and expecting IT to just line up and deliver.

Additionally, there was a lot of business executives across the organization, with all their own agendas. In the name of customer service, IT would constantly shift and re-prioritize their work managing their day-to-day by escalation. 

This company had also been attempting an Agile transformation for many years without success due to many of these same issues. Beyond that, the behaviors of middle management didn’t change. Those leaders still tended to operate command and control with a focus on execution at all costs and continued to tell all their teams what they could and couldn’t do, putting constant pressure to over commit on delivery. As a result, these teams didn’t have space to learn, they weren’t empowered to innovate and improve and additionally the quality and delivery was not improving in this organization. The business was getting very frustrated with IT’s capabilities and they thought IT was a black box with no transparency.

In recognizing this problem, Isabella began experimenting with some teams and having success. She suggested moving to a product model, effectively bringing the business and IT closer together. The CIO liked this idea and attempted to pitch it to the other business executives, but at that point IT lacked credibility with the business and there wasn’t strong business sponsorship to pursue. 

Around this time, a new chief executive took up with this company. They immediately asserted that IT was too expensive. This resulted in an increased focus on IT being a cost center. While the CIO never changed their vision of being an investment center and destination for talent, they started embarking on an outsourcing strategy for IT. This created an even bigger problem because now leadership actions were not matching words. Teams lost trust in management, the organization remained relatively fixed in a legacy model with subpar performance. It also, was very sad.

Finally, here’s the third story — Jayden.

Jayden had worked in this company for quite some time and witnessed the systemic dysfunction building the technology organization over many years. Years before this company had transformed into a COBIT based model around plan, build, and run, they’d built a whole bunch of centers of excellence and they outsource many of their engineering activities. 

Over time, the performance and the cost of the company actually got worse. This coupled with increased disruption in their industry, created a ripe environment for change. Jayden led the charge to start championing DevOps as a new and better way. At that time the biggest constraint in the overall value stream for this company was infrastructure delivery. It took nearly 200 days to get web application environments for development projects.

Jayden pushed to make these problems transparent and to drive improvements. While he was making good progress on his automation initiatives, he recognized that the operating model was a major hindrance due to all the siloing, so he made a case to change that. 

Knowing this, he designed a product in a DevOps inspired operating model, optimizing the infrastructure organization for agility and better integrating it with the development teams. While he was working really hard to influence this, it faced a lot of resistance from the infrastructure executives which can be expected because it’s a pretty big shift from how they were operating.

After two months of no change, he decided to try a different approach and he started socializing the model with the development executives to show them how it benefited them. As expected they were pretty excited about these changes and they actually worked with Jayden to put outside pressure on the infrastructure executives to make the model happen.

As a result, he actually broadened his role to have more impact across the overall technology transformation. I would actually say that this situation could serve as an initial lesson on how to navigate leadership challenges, but over the next two years they had a lot of success on their transformation. 

It changed the operating model that changed the culture. The teams were delivering more value, faster than they ever were before. But one day this company suddenly hit a rough patch. They were having a lot of increased stability suddenly and they were putting a lot of pressure on the VP of operations. One day someone caused a major outage due to a router misconfiguration and had widespread impact across the whole company. When they investigated it was determined that the change was made without a change request. And even though this wasn’t malicious, the VP decided to make an example out of this person so that others would be more disciplined with their changes.

As a result, the individual is exited from the company and the event was actually publicized across the technology organization. Even against Jayden’s advice as to the impacts on the morale and the culture of the company, there was a revolt within the engineering community. How could management claim that we’re a culture that embraces failure and focuses on learning, but they take actions like this?

Ultimately, this did not have the intended consequences the VP was striving for. Some of the top engineering talent in the company actually resented management for this and it played a role in some leaving over the next few months.

Now, let’s discuss some of the leadership lessons learned 

I’d equate most of these constraints to the following four categories:

  1. Lacking strong C-level sponsorship for the transformation. 
  2. Executive behaviors that are contradicting cultural aspirations. 
  3. The frozen middle. I’ll talk about this more, but it’s a term I’ve grown to enjoy, to talk about how to help the middle management change. 
  4. Technology transformation that’s disconnected from business strategy. 

First, lacking strong C-level sponsorships for the transformation. 

As we saw in the stories with Isabella and Jaxon, this type of change is too significant to drive across the organization without top-level support. Without the C-level leaders championing, the resistors will start to undermine the change in your organization. You can build momentum bottoms up, but it’s only going to go so far. 

This risk also exists when new senior leaders join the company. Without understanding what the modern trends are in technology, they may tend to rely on what helped them be successful in the past, which is exactly what happened with Jaxon, with his new CTO.

With C-level sponsorship and business and executive buy in, you can actually counteract these things. It’s less likely that you’re going to hire new executives that don’t align with the new ways of working. And even if you do, you’re better positioned to deal with any regressions they try to put into your environment. 

Secondly, executive behaviors contradicting cultural aspirations. 

As we saw in Jayden story, this can be a very difficult problem to solve. What tends to happen in these situations is executives communicate new aspirations that they want for the organization, such as, ‘we’re looking to empower teams to make more decisions’ or ‘we need to start embracing failures so that we can improve learning.’

However, the behaviors of these executives don’t always change to support these new aspirations. And some examples of that include making technology decisions without engaging their engineers, or as we saw in Jayden’s story, the witch hunts that result from failure, like looking for someone to blame or over committing delivery and then having your teams do these death march releases to get stuff delivered, leaving no room for learning.

This can derail change in an organization because employees don’t typically listen to what the executives say. They watch what they do and when what they do and what they say are out of sync it creates a huge problem. The best way to address this is to get transformational leaders in place in these organizations. 

Now, obviously, it’s hard to do wholesale and you’re probably not going to change leadership overnight, so you need to invest in your leaders. You need to coach them and help them understand what some of those new behaviors are and help guide those behaviors so that they’re modeling the way for the organization. It’s also beneficial to define what the new leadership expectations and behaviors are for the organization as well. 

Third, the frozen middle. 

My feeling about middle management has changed a lot over the past six years. I used to be really negative and I felt like they were these really strong active resistors, and they’re just going to fight change. What I grew to appreciate over time was that it’s ultimately a really hard level to be at. For one, you’re dealing with the operational needs of your teams everyday, you’re managing up to the executives above you. You’ve got to manage down, as well. You’re buried day-in and day-out and then now you’re suddenly expected to learn all these new things and help your teams change how they’re working. 

What I think is more important is you need to invest in these people and help them learn how their roles are changing, how this change adds value to the organization and adds value to them. What can they do to thrive and be successful as this change happens as well? Pay attention to this group and work with them. When you start on these changes, focus on the people that want to change and start small, build momentum with those people and you’ll pivot some of the later adopters.

I will say though, even after your best efforts, some people are not going to get on board. Some of the laggards aren’t going to turn over, and the key is to build enough momentum in your change so the others realize that they need to make a decision to get on board or leave. Some will leave and that’s quite okay.

Finally, technology transformation that’s disconnected from business strategy

Often enterprises just focus on the technology organization when they’re doing these transformations. And by doing this, they’re actually not tackling the complicated problem of aligning with the business. This can create huge problems when you’re looking to scale things like your operating model because you’re not tackling bigger challenges such as prioritization, funding, and roles across the organization. You won’t be able to be successful if the business isn’t engaged, and you’re not going to be able to get them engaged if you can’t frame your transformation in the context of how it helps their business strategy.

Spend the time early on to understand the business strategy and understand how your transformation is going to help accelerate business agility. Get business leaders on board with the change. And I will say if IT is pursuing transformation because it’s a cool thing to do and they see other people doing it, you’re going to fail. You’ve got to align it with the business. 


Now, let’s make a new narrative. 

We explored these lessons learned. I now have a new narratives for Jaxon, Isabella and Jayden. 

Jaxon, Isabella, and Jayden were all connected through the DevOps enterprise community. They’re part of this dynamic learning community. They recognize that the challenges they would face in growing momentum in their organizations were significant. They all started collaborating on a strategy. Seeing how Jayden was already having a lot of success given the levels of executive sponsorship and buy in from his organization, Isabella and Jaxon made it a top priority to make the case for change in their own organizations.

They both identified the disruptive factors and new threats emerging from more nimble digital competitors in their industries. They also did deeper internal assessments of their environment, understanding the constraints in their value streams. They ran things like Dora assessments to measure the current operating environment of their value streams or even talking to their business partners and their customers to understand what their pain points were with technology. 

Additionally, they were armed with product transformation guidance from IT Revolution books and papers that are helping guide people on these transformations. They could see that the key was to expand from purely a DevOps transformation to a product transformation, which would actually do more to pull the business and IT alignment into scope.

Each of them framed a case for change, anchoring on outcomes and data from The State of DevOps Report that they used to help their executives understand how the business and technology performance could be improved through this change. Having secured sponsorship in the C-suite, they also took this opportunity to align their executives on what was needed from them to effectively model this change in the organization. 

Here’s some of the actions that they took:

  • They defined a new set of expected leadership behaviors and incentives, emphasizing things like empowerment, responsibility, learning, orientation and collaboration. 
  • They rolled out training through immersive workshops. These leaders could then learn these behaviors in the context of how their teams were working. 
  • They invested in leadership coaching to guide these leadership behaviors and actions and ensure the executives are modeling them for the organization. 
  • They identified role model leaders and invested in transforming their teams first and then they held them up as a beacon of success to the rest of the organization, showering them with praise and recognition.
  • Finally, they brought in external leaders from outside of the organization that were driving these transformations in their own companies, and they had them talk to their middle management and their executives, helping them understand what their learnings were and how they were having success. 

After solving these problems, they were well on their way to transformation success. 

So, what happened to each of them? 

First, after aligning the CIO and the business executives on the transformation, Jaxon was promoted to that open CTO role. This positioned him to quickly build off the success he’d started and expand the transformation focus more broadly across the organization. 

Isabella built a strong coalition of the willing with other business executives and helped re-imagine the operating model for how business and IT would work in her company. She partnered with these business leaders to make the case for how their project to product transformation would improve the business strategy from both the speed and cost perspective. After receiving support from the C-Suite, they decided to start small with a single line of business. It’s really the best way to drive transformation. You can’t go all in from day one. They used their success from that small start with the one line of business to build momentum for change across the rest of the company.

As for Jayden, he was able to push his company further into an optimized state. The business was no longer putting pressure on a VP of operations for stability. Those challenges were now funneled directly to the engineering and product leaders who put emphasis on prioritizing quality and tech debt for their products.

The majority of the changes were now fully automated for the organization and the leaders were well coached on treating failures as learning opportunities and never miss an opportunity to continuously improve their products when an unplanned failure occurred.


To close, I have some of my advice to you

The one thing I love about the DevOps Enterprise Summit is that I feel like I’m in a community of my peers.

We have shared experiences and there’s a clear theme in that we’re all driving change inside of our organizations. What are some of the things that you can do to lead transformation and drive change? 

  • Embrace it. Embrace change. You need to be resilient and adaptable. You have to help other people work through their own change journey. 
  • Connect within this community. This is a very powerful community. Help each other. I owe so much of my career success to the advice I’ve gotten from others in this community. 
  • Get involved. Offer your expertise. You’ll be surprised how many people are willing to help you too. 
  • Find champions both within the business and IT. Build your support network because you’re going to need these people when you’re going through these changes.
  • Establish a clear North star. You need to inspire your teams and your partners for what the future could look like, and give people something to aspire to. 
  • Use your outside voice. I’ve said this a lot in previous conferences, you need to be vocal not only in your company but externally in the community as well. You have to be bold and willing to challenge the conventional ways that work has happened. 
  • You have to empower your teams. The only way to truly transform is to build high performing teams and enable them. That’s what it boils down to in every organization. 
  • Finally, walk the talk. You must demonstrate the type of transformative leadership that’s required to help teams thrive in these modern operating models.

This was an excerpt from a presentation by Ross Clanton, Executive Director, Technology Modernization, Formerly of Verizon.

You can watch the video of the presentation, which was originally delivered at the 2019 DevOps Enterprise Summit in London.

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