Driving Digital Transformation from the bottom up: An interview with Isaac Sacolick

Driving Digital Transformation from the bottom up: An interview with Isaac Sacolick

‘Leading Digital Transformation’ is a weekly podcast series produced in collaboration between The Digital Transformation People and Rob Llewellyn digital transformation advisor and founder of CXO Transform.

During this series, Rob interviews experienced practitioners, authors and thought leaders whose stories and experiences provide valuable insights for digital transformation success.

In this episode, Rob is joined by Isaac Sacolick, author of the best selling book “Driving Digital: The Leader’s Guide to Business Transformation Through Technology”  in which he shares the lessons learned from multiple successful transformations to detail the ‘how to’ of digital transformation; from strategy, to alignment, achieving agility, organisation, talent, culture and more. Isaac is also Founder of StarCIO which helps businesses drive smarter, faster, and more innovative transformation programs by leveraging the data, analytics, software, automation, and emerging technologies. With this experience, it comes as no surprise to find that Isaac is a sought after keynote speaker and Contributing Editor to both InfoWorld and CIO Online.

“Bottoms-up” means that you have created an environment where you’re listening and you’re speaking to everybody in your organisation. You’re giving them the tools and practices whereby they have a voice in shaping the direction of where the company is going. That’s not to say that mission statements and goals and strategies aren’t important but it means they’re not written in stone and they are not divorced from the intelligence of the entire organisation.”

Listen here and read the full transcript below.


Rob Llewellyn [00:00:22] Isaac Sacolick is a start-up CTO turned transformational CIO turned digital guru, for StarCIO that guides organisations through transformation programs that deliver results. He’s the author of Amazon best-seller “Driving Digital“. He’s a keynote speaker and a contributing editor at CIO Info World and other well-known blogs on the subjects of agile and transformation. Let’s jump into the interview with Isaac. Isaac, welcome.

Isaac Sacolick [00:00:57] Hello, Rob.

Rob Llewellyn [00:00:59] Hey, Isaac, great to have you here and I want to talk to you about a bunch of things but before we do that, you’re the author of the bestselling book “Driving Digital”, which you came out with a couple of years ago. Can you just give us some insight as to what drove you to write that book?

Isaac Sacolick [00:01:18] You know, I’ve been writing and speaking through my whole career. One of the things I figured out when I was leading transformation programs and enterprises is they needed somebody out speaking and writing and really carrying the brand into the technology audience. So for a long time, I was writing and speaking and I did this event and it was, you know, How Should CIOs Respond to Digital Transformation? This was back in 2015 and the room doubled up in size and it was all Fortune 500 CIOs coming to it. And I just had this moment at that event saying, if I don’t write this book, I’m going to regret it. Somebody else will. And so I looked through all my materials and I came up with the outline that night. And the rest is history. You know, my objective was just to share my best practices. I had done technology as a CTO in start-ups and I had done being a transformational CIO and really leading data and technology and customer experience at a couple of companies in different industries. And so I just said, “look, I’m going to put my best practices into a book format into something that people can follow”. And so that was my objective. And I really didn’t know what the response would be, because clearly people have written about DevOps and have written about agile and product management but I don’t think anybody had stitched it together in the way that I did that says, you know, here’s why the transformation is affecting every business. Here’s why you have to start with agile to really get a real foundation in how the company is collaborating and how you’re experimenting and how do you build a program from the ground up from a company that maybe never had a strength in technology to one where technology and data and even customer experience needs to be a differentiator. So that was the notion of the book. And it’s been an incredible ride, as you said, Rob, it’s been a couple of years since it came out. And I still get feedback from readers. I still get asked to speak at conferences about it. So I’ve thoroughly enjoyed it. And yes, I am working on a follow-up book to it!

Rob Llewellyn [00:03:31] Isaac, you mentioned that you were speaking at a conference back in, I think you said, 2015. Now, the whole thing about digital transformation, it was a lot less spoken about four or five years ago than it is now, right?

Isaac Sacolick [00:03:45] Absolutely. In fact, you know, just before that conference, a Forbes writer had interviewed me and published an article, “What does a CIO have to know about digital transformation?” And I was taken aback by the title because I hadn’t heard it before. You know, I was plenty read and looked through all the magazines and the websites and hadn’t heard the term before. And so when I researched it, there was a couple of things I figured out. One was that I had really been doing transformation almost my entire career. I mean, my first SaaS company that I was a CTO of was helping newspapers go from print to digital. And that was back in 1995.  So you know, I really felt like I had a front-row seat to seeing how industries were being disrupted and transforming. And at the same time, you know, realised that my practices were mature for things, for companies that were looking to really get smarter with the technology and data that they were doing. And, you know, sort of the rest is history. I think what you see in the industry today is that depending on, you know, really how digitized your environment is, that’s how fast your industry has to go and what regulation and compliance exists in your industry, those are the drag forces that slow you down. So media, essentially a very digital industry, has had to move very fast. You know, banking, healthcare, a lot slower. But, you know, digital transformation’s happening to all industries and it’s affecting how businesses are operating.

Rob Llewellyn [00:05:16] So, Isaac, what’s your frame of reference around digital business and transformation?

Isaac Sacolick [00:05:22] Yeah. So, again, I’m going through my story a little bit. I did 10 years of being a CTO in start-ups and some of those were start-ups that were trying to disrupt and some of those were start-ups that were helping existing companies really move to a digital world. I’ll reference the start-up in newspapers. We had sixteen hundred newspapers running on a SaaS platform, basically the entire backbone of their websites back in ’95. We had 10 newspaper companies that invested in us. In 2001, when the bubble burst, many of you who bought print ads for real estate or cars or jobs, spending over a thousand to ten thousand dollars an ad, decided there was a better experience, a better response to doing it through a web experience for a fraction of that cost and the disruption that’s been happening in media has been carrying forward since then. So number one, you know, having the background in start-ups and really a focus on media which saw a transformation early, I then pivoted my career. This is back in 2007. I decided to take what I was doing in start-ups and bring it to the enterprise. I became a business unit CIO at McGraw-Hill, first at BusinessWeek magazine, then at a construction data company, and then, later on, I went on to work in a financial services market research company. So again, what was common about those three companies is somewhat being disrupted, their businesses losing market share, needing to think through a digital experience, needed to think through how to be smarter with data. And so I took three companies that didn’t have any kind of real semblance of a technology or a data capability and built both of those up and started the build up in terms of how to build digital customer experiences. My feeling around this is that status quo will kill existing businesses. Now that I run a consulting company, I work with lots of companies and when you look at how they’re servicing customers, how do they think about their product and services, what’s happening in their industries, who’s coming in and trying to disrupt what they’re doing, companies have to be much better at experimenting with new business models and thinking through whether they’re completely digital or completely physical, how to enable a product that transcends both boundaries. And what I see is that it requires a ton of change. It’s both culture, it’s changes in terms of priorities, it requires the leaders in the organisation to really express a vision in terms of where the company is likely to be over the next three, five, seven years, requires a lot more collaboration between the business teams, between data, between technologists. There’s a lot of opportunity to automate things with technology today, and there’s certainly a lot of things that need to happen to enable sales and marketing teams to be more data-driven. So that’s my vantage point from a nutshell.

Rob Llewellyn [00:08:27] You touched on a couple of key points there: culture, collaboration, vision, you know, as you go in and out of so many different organisations, Isaac, is there one common denominator which is really challenging these organisations?

Isaac Sacolick [00:08:43] Yeah, I mean, look, any organisation I’ve walked in and I’ve worked with, small charities of 20 people with three and a half million in revenue and then billion-dollar Fortune 100s. And to some extent, every one of these organisation has silos based on how they were organised to fulfil the legacy businesses. And so when you come in and you speak about experiences for your customers online or you talk about how to leverage data across the organisation or, you know, what’s the team you’re going to put together that’s really going to think through whether it’s an enterprise application or a customer-facing application, anywhere you cut it, you’re going to be cross-cutting through that organisation in a way that is not aligned for how their legacy businesses are operating. And so the very first thing that you really need to do is think through an operating model that brings those groups together, that gets them to understand their vantage points, their priorities, how they think about things, how they work together, how they communicate. And I use agile practices as a backdrop to do that. And the reason is that you know, agile focuses teams on short term deliverables. You think in sprints, sprints are usually in two weeks duration. It promotes cross-collaboration by saying we’re going to put together a multidisciplinary team. It requires constant feedback loops so you can put something out up in front of an end-user or a  customer, get some feedback and reprioritise things. And today and nowadays what was different working with start-ups for me compared to working with institutions and larger companies is it requires some form of continuous planning, some way of taking all the feedback that’s coming in and saying “we need to use that feedback to our advantage to reprioritise, rethink what the experience needs to do, look at data and tell us what it’s doing. And that drives a new form of collaboration and it drives a new form of experimentation within the organisation.

Rob Llewellyn [00:10:53] Now, you touched on agile there, Isaac. Why are agile practices the heart of executing transformation programs?

Isaac Sacolick [00:11:00] So agile to me is, you know, you take a team, you are giving them a mission that you’ve outlined in a vision. And when I work with companies, my vision statements are one-pagers. They’re not 25-page decks. They’re not full blown up business plans. They’re answering about 10 different questions that are saying “you’re here to collaborate and work on this. This is the opportunity. This is the problem we’re solving, this is why we’re working on it. These are some of the constraints that we have to work with.” And you’re letting them self organise around that solution. But putting some practice controls in place, you’re saying “at the end of every sprint, we want to see some output from what you’ve completed.” So we call those demos. At the beginning of every sprint, we might ask you to do 10 things, but we’re going to let you decide of those 10 things, which of those do you think are things that work well together in terms of what you’re working on? How much work can you take on? Do you understand what’s being asked of you? And maybe one sprint, you’re taking on seven things, and the next sprint you’re taking on 12 things. So really giving you the ability to commit and tell us what you’re capable of doing. And then we’re putting some tools in place so that we can track our activities and get smarter about what we’re prioritising. You’ll hear those in terms of backlogs in boards and things that 10 years ago we were doing on whiteboards and stickies and today we’re doing through electronic boards. So to me, this is the operating model of the future, it’s how to take that team and be successful executing every couple of weeks. It’s how to take multiple teams and get them to collaborate, number one, by identifying how to create those teams so that they work largely independently, but then also to share feedback so that one team complements what the other team is doing. And then what you see a lot in my book and a lot of my writing, I write a blog called “Social, Agile and Transformation”. I write for CIO and for Info World. And a lot of what I write about is something called “continuous planning”. It’s the ability to not only focus what you’re delivering on every sprint, but actually to plan three, four or five sprints ahead of where you are so that there’s some visibility into the roadmap that you’re working on. So to me, this is the operating model for anything where the organisation is trying to do something different than what it’s doing today. And that’s the heart of transformation.

Rob Llewellyn [00:13:30] Isaac, we do see that organisations are prepared to embrace agile working practices. But, you know, it’s often easier said than done. What do you see as some of the major hurdles that some of these particularly large organisations need to overcome in order to fully embrace and benefit from agile practices?

Isaac Sacolick [00:13:50] Yeah, it’s a great question. You know, I’m going to start with the product management function and this notion of product ownership. If you look at agile, it only specifies two high-level roles  – a product owner that’s effectively learning the experience of the customer and is setting high-level priorities and expressing the high-level user story requirements. And the second is the team, right, the team that’s executing on it. And so, you know, organisations, some don’t have people that are skilled at product ownership. Some of product management is looked at funnelling all the wishes and wants and needs from stakeholders and funnelling them into a group that executes on them. That’s not really what product management is all about, which is more about figuring out where you can make impact, what are the drivers of the business, where our experiences going to make an impact, where then users and drive value, what types of data and analytics are really required which are action-oriented. And that means making priorities based on outcome and impact and not based on a long list of things from the CEO down to salespeople, to marketing, in terms of everything that they want to get done. That’s a feature list and we know that a lot of features get built and invested in and don’t get used. It’s because they’re misaligned with business value and value props to the end-users. So, you know, I think the first thing is this entire product management function is lacking in many organisations, even when it’s there, there’s a lot to be learned by how technology companies operate and the collaboration between business (and I.T. in particular) in coming up with solutions. So if a product comes in and says, I want to build this design with this experience and sometimes even specifying how the technology has to operate, they’re really missing an opportunity to get what technologists can do with platforms that they’re versatile in, that they’ve already built some core competencies in and look for smarter and faster ways to actually do things with technology. So I think there’s a collaboration there that’s still stuck in how legacy companies have operated where business specified and technology implemented. I think the third thing that’s really important to call out when you work with leadership, particularly at the C-level, you still have CFOs that for what they need to be successful, they’re still looking for three, six, twelve-month and three year horizon plans that at the very nature of agile, they don’t really fit, right? You can’t ask an agile team “what are you going to deliver for me over the next 12 to 18 months?” But you can approximate it and you can get there by putting continuous planning and estimating and other forecasting tools in place, by putting vision statements in and building that kind of data resource from the ground up. It just takes time to mature to that. You also have to work with the CEO differently, right? The CEO is sometimes used to (particularly in medium-sized companies or where founders are involved), they’re used to being the ones who really understand the vision and fully understand where the market is going. And their roles need to change. They need to be better listeners. They need to solicit feedback from their sales and marketing and technologists in terms of what they’re hearing from customers and what they’re seeing in the market. And then they have to guide them with their data that they have, with their analytics and with their intuition. So that’s, you know, three big changes just off the bat that have to be in place as agile teams are trying to mature and really execute off a new game plan.

Rob Llewellyn [00:17:41] Now, Isaac, you’ve written a lot of posts about bottoms-up transformation. Firstly, what do you mean by bottoms-up transformation? And can you give us some examples to bring that concept to life a little bit?

Isaac Sacolick [00:17:54] Yeah. So, “bottoms-up” basically means that you have created an environment where you’re listening and you’re speaking to everybody in your organisation. You’re giving them tools and you’re giving them practices whereby they have a voice and shaping the direction of where the company is going. And so it’s not to say that mission statements and goals and strategies aren’t important, because organisation need guardrails. They need starting points. They need to be built off of pre-existing wisdom. But it means they’re not written in stone and they are not divorced from the intelligence of the entire organisation. So I’m going to share with you a few examples. A bunch of years ago, I was working with a marketing group and marketing groups typically have the opportunity to use lots of different tools out there, either to run campaigns or to learn from customers or prospects or to control their brand. And before there was a lot of integrated platforms, there really wasn’t a good way for a marketer to pull data from, you know, a web analytics tool from the CRM, from the ERP in terms of what customers were spending, maybe from a few different social tools that they were using, from their email marketing tool and answer a very basic question. What’s working? Where should I invest in my time? Where should I spend? What segments should I go after? And so before all the integration became a little bit more mainstream over the last few years, I had a very simple recipe. I gave those marketers Tableau. I gave them training in terms of how to become data driven around it. I provided data governance so that they understood what data they were working with and how to integrate it. I helped them understand how to ask questions and used data visualisation to get answers to their questions. And within six months, that group was in front of the whole company in a town hall, sharing with them how to use data to drive decision making. And that small investment became the backbone in terms of how other operating groups were using data and analytics and a tool that really enabled business users to be more effective with analytics, to go out and use the analysts to drive their decision making. So that’s an example of  “bottoms-up” in analytics. I do a lot of workshops with teams that are starting to think through how to apply DevOps in their organisation. And these are not start-ups. These are institutions. The one I’m thinking about is a university. They knew they wanted to deploy things more frequently. They wanted to automate more. But they really didn’t see the connection between those KPIs and those goals with some of the platforms and the tools that they were doing. So we did a workshop. We came up with a bunch of success criteria. We came up with two different places to do a POC and then they used that POC and places where they had success to take their little experiment in one small area of the university and to scale and talk about it with other elements and other groups in their university to see what is going to be their DevOps strategy, how are they going to implement CICD pipelines, where to start from, what platforms to use and how to implement it in a consistent way. A third area is I work with a charity called Charity Navigator. You can look them up. They do ratings of charities. They collect metrics on 24 metrics. They come down with two KPIs, a financial and a Governance KPI, and they ultimately help donors understand how their charities are making use of their funds. And so a lot of what we’re doing there is evolving their ratings, how do we make it smarter, more efficient, scale to handle lots of more charities, smarter to handle new modernised metrics. And we’ve put together a slew of low code platforms there. So not only are technologists developing technology there, but analysts are developing dashboards. They’re building applications and workflows so that they can be self-sufficient in terms of how they’re operating. So these are all examples of whereas before if I looked at these three problems ten years ago, most of those would’ve been services that I.T. were providing. Right? I’d build BEI reports out for them. I build applications out for them. I was totally in control of the data centre and spending 60, 70 per cent of my time run costs because things weren’t automated. And now I’m putting a lot of controls and tools and practices in the hands of the team and doing it in such a way that when they’re having success and when they’re finding insights, those can bubble up to the executive levels.

Rob Llewellyn [00:22:54] Now, you just mentioned some of the things that you do with some organisations, you’re the president of StarCIO. How do you sum up the way in which you help companies drive smarter, faster, more innovative transformation programs?

Isaac Sacolick [00:23:09] Yeah, it’s a great question. You know, I generally work with companies that start realising, you know, whether they call it transformation or not, they start recognising that they have to improve their customer experience, that they have to get smarter with data. And more importantly, technology has to be more than just a check-the-box. It needs to even be more than a core competency, but they have to find ways to use technology as a differentiator. What I found working as a CIO and now from my clients, is big-budget technology companies, the ones that you read about in all the websites and magazines that get the notoriety in terms of what are they doing on the cloud and how many teams are running agile with and how they’re experimenting with AI and IoT.  You know, their game plan, their talent, their practices, the types of platforms they can use, they’re very, very different than what mainstream, small/medium businesses and even enterprises that are lagging in technology, data and experience, these are things that are very different than what they can use. So, you know, our company really focuses on companies that want to play catch up and start leapfrogging and build their core competency. We do that by starting what I call a “rapid assessment”. These are not eight-week million-dollar assessments, these are relatively simple things to execute on. They’re very important to baseline the organisation in terms of how they’re performing, what are their goals and aspirations. How are they using data today? What are some of the platforms that are legacy and which platforms can they invest in? We then do a lot of workshops. Our workshops are there to bring members of a company together, some leadership, some high performers, some just individual contributors together that we think can actually drive organisational change. There’s always a mix of business data and technology. We do workshops and agile planning. We do them in DevOps and product management for leadership. We do it in transformation leadership. And then we also do one for becoming a data-driven organisation, so four different types of workshops that we do that really start the basis of the operating model that’s different. Now, what we do that’s very different than other organisations is we do not put out frameworks. Frameworks come across as rigid. We want organisations to really build what their capabilities are and what their processes are in their governances from their vantage point, from their priorities, so that they can execute on their priorities while they’re learning a new operating model from their culture and governance, because they’re all starting from a starting point, they’ll all have to mature and change those things. So what we give them is a set of toolkits for them to go rebuild their practices. And so all in all, just to share an example, I know I’m working with one client. They’re working with about 30 different agile teams. They’ve rolled out planning practices. And just this week, they’ve been going through the practice of how do we share roles and responsibilities on an agile team in a way that works for our organisation. So they started out with one of my guides that defined what a product manager does, what a product owner does, who a tech lead is, and how does a QA lead work and what is a delivery lead? And they basically redefined them for their organisation based on my starting point. So that’s the workshops and those are the guides that we put out; we’re there to be advisory, to provide advisory in some cases, run transformation programs, in other cases just be the advisor to the leadership group. And then we take on a lot of special projects, places where the team feels they need somebody from the outside to run a program and we’ll run projects with them.  We’re starting to put some tools out with that. I’m excited that in 2020 we’ll have a set of Driving Digital StarCIO tools. And again, all of these things when we put them together, they’re really about organisations that have not had success with experience, data and technology and we’re really teaching them how to rebuild their operating platform to be smarter, faster, better and innovative.

Rob Llewellyn [00:27:31] Now, I want to pull you out of the organisation to somewhere else where I know you spent quite a bit of time and that’s on stage. When I look at some of the keynotes that you deliver upon, Isaac, you talk about data driven organisations, artificial intelligence, agile and DevOps. But you’ve got one keynote which is called Digital Leadership 2025. Can you share some of the insights on what you speak about in that? I’m fascinated by the title, actually. Can you tell us about that?

Isaac Sacolick [00:27:58] Yeah. I mean, remember the book I started writing in 2015 and it published in 2017. So here we are on 2020. And it’s been very exciting to see some of the things that I know our practices that are key to transformation, they’ve been recognised as elements that many organisations are implementing. So a lot of the Leadership 2025 program is about what leaders have to think about to be successful over the next five years. And so a lot of what I talk about is some of the things we’ve already covered. How do you invoke bottoms-up change? What does that mean? How do you implement it? Who are the types of people that you have to work with? There’s some very specific messages I give to leaders about working with the board and working with their executive team, how to change the status quo, how to work when you start leading transformation programs and everybody is gunning at you, because of the changes that you’re trying to implement, that’s impacting their philosophies, their mindsets. I just wrote an article that published yesterday on how to manage the blow-up meeting, the meeting that goes awry because you’ve really impacted somebody’s thinking and, you know, how do you use that to actually get a breakthrough moment? So I do a lot on the culture of working with the leadership team, the culture of working with people across the organisation. Then I talk about certain practices that I think will become the key ones over the next five years, things that I think every organisation point to somewhere in their horizon invest in. So becoming a more real time enterprise, so using data and analytics to look at things on an hourly and daily basis, taking data governance and going beyond just becoming compliant and securing your data to what I call proactive data governance, which is, you know, how to improve data quality and create master data sources and data catalogues so that more people in the organisation can be successful using analytics and then set up the foundation to actually experiment with A.I.. And then again, back to agile, going beyond agile mechanics and agile basics and getting away from this notion of scaling agile. And really helping organisations with agile cultures and mindsets, how to hire for agile and how to really do continuous planning so that you can bridge the gap between the two-week sprints that people are executing on and the six to 18-month horizon that your business needs in terms of where the organisation is going.

Rob Llewellyn [00:30:40] Isaac, before we started recording, you and I were talking about how time runs away with you, particularly when you’re on stage. And it’s done exactly that with us. We’ve run out of time. Some fascinating insights. But before we go, can you please tell our audience where they can go and learn more about some of these concepts that you’ve been sharing with us today?

Isaac Sacolick [00:31:02] Yeah, I mean, the first place I would go is come to my blog, “Social, agile and Transformation”. That’s Blogs.StarCIO.com. If you want to follow all my writing, I have a newsletter that you can sign up for that’s Driving-digital.com, that will get you to a page where you can sign up for the newsletter. I answer all questions that come to me on Twitter. My handle is @NYIke and you know you can find me there if you really want to have a correspondence. And I love getting feedback for my book. It’s still selling well. It’s still very relevant. And you can find that one on Amazon. It’s called “Driving Digital“.

Rob Llewellyn [00:31:45] Terrific and we’ll put links to all of those in the show notes. Isaac, thank you so much for your time.

Isaac Sacolick [00:31:51] Absolutely, Rob, really appreciate it. Love your program and look forward to hearing and speaking with your audience.

Announcer: [00:31:58] We hope you enjoyed this episode of “Leading Digital Transformation” with Rob Llewellyn and The Digital Transformation People. Visit www.thedigitaltransformationpeople.com to secure the knowledge, talent and services you need for digital transformation success. To continue your journey as a certified transformation professional, visit www.RobLlewellyn.com. Be sure to subscribe to the podcast and follow us on Twitter @TheDigitalTP and @RobertLlewellyn

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