Transformation & Change108

Building the Plane While Flying It

Building the Plane While Flying It.

Sangeeta Sastry

June 16, 2023


Organizations have the challenge of innovating and delivering new products/services and experiences, while continuing to invest and improve their current portfolios. Now, more than ever before, it is critical to design the organization (structural and cultural) purposefully to rise to the challenge. It feels like building a plane at 30,000 ft while flying it. How do you modernize your current organization, processes, and technologies while managing risks to its current operations?


Building the Plane While Flying It.(PDF)



About the Speaker(s)

Sangeeta Sastry
VP, Digital Transformation and NA Delivery, Thoughtworks

As a Digital Transformation and Agility leader, Sangeeta brings 20+ years of experience in coaching executives on designing fit-for-purpose organizations as they shift their paradigms in the digital era. Sangeeta counsels leadership teams as they transform their organizations to improve performance, organizational health, innovation, speed, and agility. Much of Sangeeta’s work focuses on helping large distributed organizations achieve transformational change with organizational design, leadership development, culture and change adoption, team effectiveness and capability building. She serves clients across several industries, including financial services, automotive, health/life sciences, and technology, having led transformations at PayPal, eBay, Salesforce, Cisco, and many other organizations.


Video Transcript


Thank you.

I'm not a poet, but a big fan of Game of Thrones for sure.

Hi, everyone.

Quick introduction for myself. I work for a company called Thoughtworks. It's a technology consulting firm. I lead their digital transformation practice as well as North America delivery for the West Market where I live, San Francisco.

Really quick recap how I got to the goddess point. I have a bachelor's in dance, choreography, and Sanskrit theater. I have a master's, an MBA in International Business and Marketing. I've worked my way through technology, grew up in Detroit, moved to San Francisco, worked for some big banks there, and then somehow hit my head, fell into the Agile pit, so to speak. I led PayPal's transformation back in 2012. So a couple of folks—Brent is nodding— that I worked with there. After that eBay, Salesforce for many years, Brent is nodding again. From there, this is where the story starts.

What I wanted to highlight of my experience at Salesforce is that I worked internally first initially, and then I was asked to join the customer success organization to lead Salesforce customers in their transformations. A lot of times it would be Agile transformation. So what do you need to do to design your organization, to prioritize, move from project to product and things like that, things we all know all too well. One of my large customers that I worked with was Cisco. This is a story about Cisco and the work that I did there prior to coming to Thoughtworks.

Has anybody ever seen a fig tree grow?


Okay, couple of people. All right.

You might recognize the straggler fig pattern.

It's a concept that Martin Fowler, who's the Chief Scientist at Thoughtworks introduced in terms of legacy modernization of software applications. Why I bring this up is that you saw the plane analogy on the first slide. We all talked about building planes or fixing planes in mid flight at 30,000 feet. There are three analogies I'm going to use. Two of them you've heard of so far. This is the third one.

Figs, the way they grow in tropical forests around the world, they germinate in a tree as a vine. The creeper grows, grows, grows downward and then takes its root and then eventually starts to take over the host tree. That's the progression that you see. Why this becomes important is there's a time that transformation happens where fig plant is taking over the host tree piece by piece, by piece. There's a very short period of time where they co-exist. There must be some agreement between the two. Then eventually, the host tree completely disappears. It is eliminated, and then stands the Fig tree. This is how figs grow.

This is the work that we did at Cisco, and here's how. Cisco has been going through a multi-layer transformation for, I would say, probably a decade.

New CEO came in, decided this was an existential crisis time. Cisco really needed to step up their technology game. They were being disrupted left and right. They really wanted to follow Adobe and Microsoft's successful examples of moving from hardware to software and then a recurring revenue business with services on top of that.

So how do they do it?

What is the playbook?

How do you build a successful SaaS software?

Wait, we work with Salesforce. Let's use Salesforce. Let's work with Mark Benioff and his team to see what are the parts and pieces they put in the organization to be able to do this successfully.

I worked as a customer success organization person with my team, two of whom are here actually, Heidi Ling and Dr Lillia Lund whom you heard yesterday. We worked with Cisco on… If you know anything about Cisco, it's grown through acquisition. It's more like the Indonesian archipelago. It's a bunch of islands that work independently, but you can club them together as one company. But what the new CEO wanted to change was that he wanted one Cisco, one definition of a Cisco customer, one life cycle journey for a Cisco customer, and experiences that are layered based on that journey.

From Salesforce professional services and customer success, we helped Cisco unify that single life cycle journey, that single definition and taxonomy of who a customer is, what their experiences should be in that journey, and we use that to build their SaaS software, which would become the front door to Cisco.

Every single Cisco customer, enterprise customer is treated the same. You log into CX Cloud, it's a portal, you see everything you need. You can ask for help, you can interact, you get support. There are levels of support and all kinds of things. It was a very bold aspirational vision. It was great in 2019 when that was rolled out as a vision. When we started out, once having built that customer lifecycle journey for CX Cloud, when we looked at how do we build an engineering organization to build that SaaS application, we ended up with about a team of 2,000 engineers who had never used cloud technology, whose code looked like it was from the '90s still, and who were entrenched in waterfall processes. A lot of missing capabilities for a SaaS software organization. My team, called transformation readiness, had the charter of not only building a plane, a separate plane at 30,000 feet, but also transferring all the passengers safely onto the new plane at 30,000 feet.

Then I want you to take this ride with me. We started in February 2020. A couple of weeks after we started, we were in a pandemic and we were locked down. Imagine being on a flight path. You have six hours or six months actually to do this work. That's your time. That's all the gas you have available on the flight. You are quarantined in different parts of the plane, so you cannot see anybody, you cannot meet anybody in person. You have to build a completely virtual environment and a virtual team. Lucky for us, Cisco owns Webex, so that was helpful. Then there was a host of other tools that we discovered, which was also helpful. We only had six months to deliver. Again, nobody knew Cloud, nobody had done this before, and we had a team of eight people that were chartered with this.

It was great.

So headwinds that we encountered.

We had an Instapot leadership team.

Anyone know what that is?

Have you used an Instapot?

You put your ingredients in, you turn it on, you walk away, you come back, maybe 10 minutes later to check on it. It's not a crock pot. You don't leave it for six hours, because we only had six hours total. The Instapot leadership team, we kicked off with a bang. It was great, and then we went into lockdown, and then it was just like, "Let me know when that's done." They were not in front of everybody modeling the behaviors that we wanted to see in the organization. So that was one. It was great.

Making change stick.

How do we differentiate all the different types of transformations that Cisco has undergone over many decades from this one. The leaders were not on the same page. They were not even in the same book, and that was hard. Aligning was a continuous activity. It was not a one-time thing. Culture, obviously, eats strategy for breakfast, lunch, maybe dinner for a few months at a time.

The question that we constantly got asked, "We are a great place to work. There's nothing wrong with our culture. Why are you here to change it?"

Then we would smile, nod and say, "Because your COO, your CXO and your CEO want to do different things, which means we have to do it in a different way, which means eventually culture will change and adapt, but nobody's telling you what to do right now, especially in a Zoom meeting where you can drop off." And disciplined execution. What that really meant is, at the time, it was heavy waterfall. Even then, people would say, we don't have a planning process. We just deliver and then hope that it works. And if it doesn't, we start all over again. I mean, what's the big deal? It was quite a challenging time, to say the least. The tailwinds, on the other hand, were really helpful.

When we showed up as a Salesforce team, as consultants, it was great because we could look around and say, "Hey, how's the water?" And they'd look around and say, "What's water?" It's the fish talking to other fish. As consultants, we have the luxury of asking questions and people will actually answer. However, when we were employees of the company, which we were asked to be to lead the transformation, we didn't have that luxury. You have to figure out a way that people can do the things you need them to do but want to do them on their own.

So how do you kindle that desire?

You figure out what motivates them in the first place.

Is it rewards?

Is it values, alignment to values?

Is it an ecosystem of support for each of those stakeholder constituencies that you start to see and group together?

Or is it something else altogether?

Is it training and an email saying, "We're going to be Agile next week. Here's your two-hour training, go watch it on Zoom. It's a recording. Put it to your Netflix queue and good luck." Or is it more than that?

Alignment, as I said, was a continuous activity. The strategy and execution plans were reflective of the organizational culture. This is an important point because if you think about a stodgy, old bureaucratic organization, this was one when we started, but it was really trying hard to move. So how do we get it to move? We tell them movement in any direction is progress, so just keep moving. By the time they start moving, you change to the next thing, and you change to the next thing.

We started out with, let's make sure everybody understands what Agile is. We at least have the same taxonomy. We're using the same words to mean the same things. Okay, so now we're in teams, we've designed the organization.

Next step, "Hey, what's everybody going to work on?" Portfolio. We need a portfolio. What are the things that we are doing? Those things, are they long lived? We need a roadmap.

Every time they start getting used to something, we would change and say... And it's not changed just for the sake of change. It's the next evolutionary step that makes logical sense to add on. Once we started into this moving from annual delivery cycle to a quarterly, and then a biweekly delivery cycle. When I say delivery, it means actual release into production as well, building those capabilities was very important, but also recognizing that we had no way of discovering in the beginning how much work needed to be done. Adding continuous discovery, which Heidi Ling was leading, and managing this entire chain of activities through change management, which Lillia Lund was leading. I had an amazing team.

Every time we did that, people would get disgruntled and get shaken up and we'd say, "No, calm down, calm down. This is just the next step. We're going to take you through it." I had a team of eight coaches, including Heidi and Lillia. We really helped the 2,000 person organization learn to move together in unison, building that engine mid flight through a pandemic while you're quarantined on Webex at 30,000 feet, and transferring all the passengers to the new plane. It was amazing.

Yes, we had six hours or six months to do it. But given the pandemic, we took a couple more months, so 8 months, 2,000 people, 8 coaches. How we did that is the Strangler Fig pattern. We applied that.

Every time you want to do something, you want to modernize a process, a business process, or a technology process, or a component, or a unit, or anything, you isolate it, you modernize it, you let it co-exist for a very short period of time, and then say you're done and you eliminate the old way.

Over the course of the year of 2020, we launched CX Cloud successfully. We onboarded over 100 customers in two months, which was an amazing feat. Everything that we built, we called as part of a CX Agility framework, which was then rolled out to the rest of Cisco as One X Agility framework, one experience, one Cisco. We were the pilot child, which is an amazing feeling.

Even when I connect with our former colleagues at Cisco, I see 1 X prioritized everywhere. It's amazing to see that the work that we did is still there, it's still thriving, and many, many people are working with it.

So coming back to the mountain, because we love climbing the mountain. When we started working with Cisco as part of Salesforce, we started with this analogy. It is ideal that you start with, "Here's my summit. I know where I'm climbing to, that's my North Star. I have a map or a Waze app." If you have network up there, all you Everest base campers can correct me. I have some tools, I have an ice pick, I have a stick, I know when to use what, I know where to go for help and what to do, and I'm off on my way. I have a backpack, a tent, and I have my stuff. Yes, you need all of those things, but you need to have the mindset, the muscles, structural and cultural muscles, the motivation, and the endurance to be able to climb. While this is an ideal scenario, it doesn't always work this way. It's not always this easy, and it's not always the thing that you go somewhere to do. Because even though we started out with this approach, we ended up with a plane that had a six-hour flight path that could be easily grounded at any time. It almost was because of the pandemic, but we still continued and we did the work pretty successfully.

If you go to Cisco… Is it you will see it. It's an amazing feat that this little team transformation readiness achieved.

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