Driving Digital Smarter and Faster - Because Everybody is a Technology Company

Driving Digital
I hope you will listen to my recently recorded podcast at AMA Edgewise on my book, Driving Digital: The Leader's Guide to Business Transformation Through Technology.

Link is below and here are some of my favorite quotes -
  • New entrants (startups) + consumer choice + availability of technology + falling price point => is driving digital transformation

  • CIOs "get it" - but many organizations (IT, Marketing, Sales, etc) are still learning digital practices.

  • Drop rank at the door. What will this company be 5-10 years from now without factoring in legacy and how you do things today?

  • You need to experiment. I don't call it fail fast. I call it learn quickly and adapt.

  • Understand your culture and capability. Are you an early mover, or are you better by learning from examples and finding niche opportunities to grow from?

  • Is there really something different between digital transformation and previous decades of transformation? What's really different is the aggregate of capabilities and that customers will switch brands and products easily.

continue reading "Driving Digital Smarter and Faster - Because Everybody is a Technology Company"

Driving Digital in the News!

Isaac Sacolick Driving Digital
Long time readers of Social, Agile, and Transformation know that I've recommended going on vacations to help clear the mind and having fun as a key tenet of your organization's culture. So before I sign off for some end-of-summer time off, I'd like to update you on the latest news around my book, Driving Digital: The Leader's Guide to Business Transformation Through Technology.

First, Driving Digital is now available at select bookstores and on Amazon in print, ebook, and audio formats. I'm pictured here with Driving Digital on the shelves at the Barnes and Noble at NYC's Union Square.

Second, there's been a number of articles written that reference Driving Digital -

"Driving Digital: The Leader’s Guide to Business Transformation through Technology by Isaac Sacolick is a timely, engaging, and practical roadmap to developing and implementing digital strategies. It shows how to make the culture of the organization more digital-friendly, generate growth through new digital channels, create digitally immersive and rewarding experiences for customers, develop new competitive advantages, and drive new operational efficiencies."- Gil Press
He goes on to say
"Sacolick’s book is a must-read for the business and technology executives managing the digital transformation of their organizations, whether they are CEOs, Chief Digital Officers, Chief Information Officers, Chief Technology Officers, Chief Marketing Officers or any manager, at any level, seeking guidance as to which digital tools and practices to deploy and how."- Gil Press

"Digital transformation impacts the entire organization. Technology and marketing teams need to operate as a collaborative digital organization driving leads to new products. Sales teams have to develop broader relationships and be well versed in how technologies embedded in products and services operate. Financial teams have to be more data driven to provide more frequent insights on how the business is functioning. 
We’re moving to a smarter and faster world. Those that are too slow transforming will be left way behind."- Isaac Sacolick
"When there is a shared understanding and a better alignment on priorities and process between the development and operations team, a more customer-centric devops culture emerges."- Isaac Sacolick
"The book is compellingly written, giving fresh insight into the role of technology officers."- Peter Krasilovsky 
  • Why Digital Transformation is my article on Medium speaks to why we need businesses with long histories of integrity to drive digital transformation
"Startups can challenge these businesses and some will disrupt them, but many long standing businesses can’t easily be replaced. These businesses have to modernize their customer experiences, leverage automation to improve quality and lower costs, and experiment with new business models. To accomplish this, these companies have to learn and borrow techniques developed at software companies"- Isaac Sacolick

CIO Insight Driving Digital

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Three Tips on Developing Successful Citizen Data Science Programs that Drive Transformation

Citizen data science or self-service BI programs are catching on with more businesses and enterprises of all sizes. More executives understand the importance of becoming a data-driven organization and are willing to break away from the mostly manual analytics performed in spreadsheets.

For those of you that have embarked on this journey, here are some key strategies to consider to ensure your efforts drive transformation:

  1. Prioritize dashboards and analytics that have strategic impact - It's very easy for citizen data science programs to fizzle out if they are perceived as just the next enterprise effort to leverage the newest dashboard or reporting technology. To avoid this fate, prioritize efforts around some of the more strategic areas of growth or operational risk in the enterprise especially if they are high on a data-driven executive's radar. Citizen data science programs need to be highly visible initiatives to garner sufficient support if they are going to succeed in transforming more departments to be data-driven.

  2. The job isn't done when you've delivered the dashboard - Dashboards, like any other tools or applications only deliver business value when they are used in business process and stakeholders agree to sunset legacy methods. In many cases, that means using your dashboards and foregoing the use of spreadsheets or performing other manual analysis. So before moving onto the next dashboards, citizen data scientists have to consider approaches to gain user adoption of their dashboards. This is far less trivial than it sounds especially when users demand that dashboards implement improvements a, b, and c before they start using them or inform you that they will continue to leverage legacy practices even when these dashboards are done. Citizen data scientists should plan to spend significant time with end users to illustrate how to use dashboards and analytics when performing specific business processes. 

  3. Create visual standards and establish a Center of Excellence (COE) - Self service BI tools are designed to help citizen data scientists to rapidly prototype and deliver new analytical dashboards. So, it's very easy for even a small group to push out many dashboards very quickly without considering the impact on users when dashboards are published without functional or visual standards. BI programs need to start with some basic visual standards, get agreement on their importance, and grow them over time.

Driving Digital
My newly published book, Driving Digital: The Leader's Guide to Business Transformation Through Technology has a full chapter dedicated to best practices on citizen data science programs.

continue reading "Three Tips on Developing Successful Citizen Data Science Programs that Drive Transformation"

How to Rapidly Plan Digital Products and bring Amazing MVPs to Market Smarter and Faster

When it comes to planning new digital products, I find many organizations fall into one of two camps.

"Analysis Paralysis" Camp - These organizations are slow to endorse new product ideas. They send sponsors and product managers back for more and more market research, industry analysis, financial forecasting, and other activities to build up organizational confidence that they are embarking on a low risk, high reward journey. 

"Serial Initiator" Camp - This camp is just the opposite. They float many ideas around and rarely say no to them. Their stakeholders scramble and often compete for marketing, technology and other resources to bring their products to market resulting in many products that don't follow standards or best practices. They then compete with sales leaders to be top of mind when presenting new products to clients. 

These are not ideal ways to manage product pipelines or to drive a digital, innovative culture. 

What is a Product Pipeline?

StarCIO Product Pipeline

Product pipelines are similar to marketing funnels to manage leads or sales pipelines to manage deals. In a product pipeline, organizations start off with a lot of half baked ideas. As more discussion, research, and experimentation is completed around the idea, the product's target customers, value proposition, competitive factors, strategic requirements, and feasibility become better understood. This planning process - whether ad hoc or highly structured - ends up helping stakeholders define key artifacts such as product visions, journey maps, go-to-market strategies, technology architecture, and financial projections.

Unfortunately, many organizations don't define what's expected in their product development process. More specifically, they don't define what decision making criteria is used in making product investments. The culture of the organization often dictates what happens next. Conservative organizations often fall into the Analysis Paralysis camp and stakeholders are left guessing what to focus on and at what level of detail to get backing, approvals, or investment. More aggressive Serial Initiator organizations are likely to start working on lots of ideas skipping many of the disciplines that lead to amazing MVPs.

Rapidly Planning Digital Products

I share a big secret on how to rapidly plan digital products in my book, Driving Digital: The Leaders's Guide to Business Transformation Through Technology

Driving Digital
Organizations that have invested in product management may have standards on artifacts needed for product approvals. What should the vision statement look like? How much market validation is required? What level of detail is required in financial projections? They may also define formal stage gates in their product development pipeline such as what artifacts and approvals are required to tap into budgets available for research or prototyping.

All important stuff and really good when you have experienced product managers that need formal guidance on what is expected of them. 


It's not necessarily sufficient especially if you have potential innovators or intrapreneurs that don't have all the training and skills of a product manager. Formal definitions of artifacts and pipelines define a target end state and don't always blaze an easy path for idea generators and influencers to develop a product.

My approach focuses on answering questions. Similar to how data scientists should be asking questions to find insights from data, innovators need to ask and answer key questions around the market, segments, personas, competitive factors, regulation, and other topics to drive smarter and faster from ideas to minimally sufficient plans that can fold into an agile development process.

A lot more in Chapter 6 of Driving Digital
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Five Questions Transformational Leaders and PMOs Should Address When Driving Digital

Let's consider the modern Project Management Office or PMO and what transformational leaders need from this function when driving digital transformation programs.

The Role of the PMO Before Transformation

In many organizations, the PMO is synonymous with bureaucracy and administration since many focus on tracking projects, managing budgets, defining project management standards, and overseeing risk mitigation. These responsibilities are often misaligned with executives that centralized PMOs expecting that they would drive execution. Centralizing a "one throat to choke" responsible for project execution is often ill suited for today's projects that are more agile, involve resources across multiple departments, and often require support from vendors and partners.

Plan, Collaborate, Deliver
Regarding project administrative, today, many needs can be streamlined as much of the tracking, reporting and risk mitigation functions are more delivered in today's agile tools. For example, burndown charts and other status reports are readily accessible to leaders, managers, and team participants when teams are committed to updating these tools with some regularity.

Now for larger organizations, there should be a leading group that creates the governance and standards for managing agile initiatives, but this doesn't necessarily have to be done by a centralized PMO. It can be a center of excellence comprised of members from multiple teams that not only defines these standards but also addresses the practices and culture of the teams to become more data driven and follow best practices.

What Transformational Leaders Need from a PMO

So this begs the question of whether the PMO is an obsolete organizational function. I'm not here to answer that question because every organization is different and some will benefit from centralizing this function.

But whether you have a PMO or elect to delegate their responsibilities across multiple leaders, there are some key new responsibilities for the PMO in organizations that are driving digital transformation. Here are my five key questions a PMO and transformation leaders need to master when driving digital transformation

  1. What's minimally required to plan a new initiative? - Many organizations are adopting agile to manage their transformation initiatives, but that doesn't mean that a new initiative can begin without some upfront planning. Plan too much and you can miss the market but plan too little and you can flood teams and resources with too many initiatives that are ill defined. Can the PMO help define and mentor business leaders on achieving "just enough" planning? What role should the PMO take on to promote agile thinking, ensure the user experience is well defined, or to drive MVPs

  2. What mentorship or training is needed to balance the portfolio? - Is the portfolio of initiatives oversubscribed with certain types of projects? Many enterprises have portfolios stocked with compliance, regulatory, or operationally driven initiatives while younger companies may overcommit to initiatives that they believe are revenue generating. Can the PMO successfully steer the ship by mentoring leaders that may have underserved needs?

  3. Where are there communication gaps and how can they be addressed efficiently? - No matter what tools are being used, there is a greater need in transformation programs to communicate to a growing list of stakeholders and participants. What's the best way to communicate to change agents, executives, other leaders, and laggards to ensure that the transformation program grows with minimal change resistance? What methods will be leveraged to handle detractors?

  4. Where are there organizational blocks that require new processes? - Transformation initiatives often requires organizations to run smarter and faster in many areas such as developing applications, producing analytics, modifying operational procedures, marketing to prospects, or selling new capabilities. Can the PMO forecast where a department will need a new or modified practice that aligns with the transformation goals? Just as important, can the PMO call out an organizational sacred cow and bring leaders to the table to think differently?

  5. Driving Digital
  6. What skills will be in demand and what are new options to fulfill them? It's easy to proclaim that you are going to do things differently - maybe Marketing will be more data driven, IT more agile, Sales more process driven, Ops more cloud driven - but a key question is whether the organization has the right mix of partners, talent, training, and practices to successfully transition. Can the PMO assess skills and recommend training programs, mentoring options and new partners that can ensure a successful transition?
Lots of questions with some answers but I do have some good news. My book, Driving Digital: The Leader's Guide to Business Transformation Through Technology has a whole chapter dedicated to modernizing the PMO and why this function is critical in large transformation programs.

Have more questions that need answering?

continue reading "Five Questions Transformational Leaders and PMOs Should Address When Driving Digital"

Three Agile Management Practices for Driving Digital Transformation

When I joined Businessweek ten years ago to lead their digital technology team, I was very surprised that they wanted to develop their own proprietary web applications. Could a magazine owned by a publisher mature a software development practice and deliver new customer experiences?

The answer was yes - and as it turns out - many other companies are investing in their software development practices as part of their digital transformation programs. In many cases, the investment is driven by businesses needing to improve customer experiences with mobile and other capabilities. In other situations, businesses are looking to automate processes, become more data driven, or enable a strategic advantage with new capabilities in IoT, blockchain or artificial intelligence.

Whatever the driver, these IT departments are trying to operate like software companies and are highly likely to be establishing agile practices central to their transformation.

Teams, standups, demos, retrospectives, story writing, backlog grooming, sprint planning and other practices and tools follow. But are agile rituals sufficient to enable an agile culture or help drive transformation?

To enable transformation and enable an agile culture, organizations should consider the addition of the following  practices -

Aligning Product Management to Agile Delivery

A very common issue facing organizations looking to invest in application development occurs when agile is only applied to the delivery team (technologists) while product management participates only in tactical ways. They'll show up to to sprint planning to make sure their priorities are aligned and then to demos to review the deliverables. That may be the extent of the interaction. Now I've posted on the 20 bad behaviors of product owners and how to handle difficult product owners from many experiences working with product owners that don't fully align with agile practices. I've also suggested the 10 practices of strong product owners which center around market needs, collaborative behaviors, and being data driven.

The most common source of misalignment falls into two categories.

Some product owners propose solutions instead of defining the problem, aligning with personas, and articulating acceptance criteria. Their stories read, "Build me X that does Y" instead of "Enable user persona A to achieve B because it helps them address C if the solution can D, E, and F". No development teams prefer being told what to do instead of being engaged on what problem they are being asked to solve, for whom, for what benefit, and with what constraints.

The second misalignment occurs when product owners, often feeling the pressure from stakeholders, commit to specific deliverables and a delivery schedule without consulting the development team. The result boxes in the team (including the product manager) into a fixed timeline and fixed scope release cycle that may be difficult or impossible to achieve. Forecasting release schedules and scope must be solved collaboratively with an agile planning process which I will review in the next section.

But before we get there, the most troubling misalignment is when a product owner (or owners) have both issues. They commit to business schedules and then send marching orders to their delivery teams. Organizations that find these behaviors acceptable will never achieve an agile culture and will struggle to transform. In my experience, these divisions are not a "business IT alignment" issue, but speak to a larger leadership and cultural issue with how business leaders and business teams work with technologists.

What does alignment entail? Here are some suggestions

  • Developing roadmaps together (next section) 
  • Establishing brainstorming sessions so that business and tech leaders can collaborate on solutions
  • Documenting responsibilities by role
  • Enabling tech leaders to visit customers 
  • Aligning on usage metrics, other business value measures, and delivery metrics
  • Celebrating the wins

Estimating and Developing Delivery Roadmaps

Business doesn't operate on a sprint to sprint schedule or as a continuous delivery stream of product improvements. To enable Sales and Marketing to reach customers with new or enhanced products, or to enable business teams to plan process changes with the delivery of new internal technology capabilities, some semblance of a roadmap is required to enable business planning. Business leads are simply asking, "Roughly what are you developing and approximately when will you deliver it", a question that product owners struggle answering and development teams difficulty resolving.

Developing roadmaps and agile planning is a large subject of my book, Driving Digital: The Leader's Guide to Business Transformation Through Technology. In the book, I provide guidelines on establishing an agile planning process, defining roles and responsibilities in planning, developing estimates that can aid in defining MVPs, and establishing release roadmaps.

Want some background? See my previous posts on the 1-week agile planning sprint and on developing a release management strategy.

Leveraging DevOps and Enabling Developers to Continue to Innovate

Let's say you are successful with agile delivery and your teams have put out their initial products or applications. Maybe they've even released major and minor enhancements to these applications over a period of time. So here's my question
Are your development teams innovating and improving the product, or are they buried in technical debt, spend significant time supporting their cloud environments, or are largely performing support functions like defect fixing or implementing upgrades?
You can certainly measure this in your agile tool by tagging stories and tasks appropriately. If you haven't done this diligently, I highly recommend it as the results might surprise you. In my experience, the longer a development team works together on an application, the more likely they are taking on support related tasks and executing less innovation.

There are a couple of things leadership can do at this point, but the most important one is related to how much the team spends on supporting the application in the cloud and automating the CI/CD pipeline. If the team is spending a lot of time on these activities, then it may be time to make sure that there is the right separation of duties and handoffs with a DevOps team. IMHO, one reason developers should now own DevOps is that it is a significant responsibility and diverts their attentions from improving applications and innovating.

Why These Agile Practices Drive Digital Transformation

  • Aligning product management drives productivity around the most important customer opportunities
  • Developing delivery roadmaps builds confidence of business leaders that need to support investing in transformation programs
  • Leveraging DevOps is a step to break off support related activities so that top developers can continue innovating

continue reading "Three Agile Management Practices for Driving Digital Transformation"

Why YOU Should be Driving Digital!

On August 24th, my book Driving Digital: The Leader's Guide to Business Transformation Through Technology will be available!

You probably guessed that I would eventually author a book. The book covers some of the themes that I've covered here on Social, Agile, and Transformation including agile management, DevOps, architecture, portfolio management, data science, product management, and organizational culture. But unlike a blog, it provides a sequence that explains why these practices are important in implementing transform, what specific practices to mature, and how to go about leading them in your organization.

Why Driving Digital?

Driving Digital
Driving Digital:
The Leader's Guide to
Business Transformation
Through Technology
This journey began a few years ago when I was interviewed by Gil Press for an article that he would later title, 5 Things To Do When You Lead a Digital Transformation. At the time, I had just started hearing about digital transformation and quickly realized it's something that I had been working on almost my entire career starting with the newspaper SaaS company that I joined in the late '90s. 
My career took me to be CIO at several different organizations that were facing disruption and required evolving the product set to address new market needs. What I learned is that organizations require a fundamentally new set of practices and capabilities to drive digital and enable a smarter and faster business transformation.

These topics are covered in the book's chapters - 
  1. The Transformation Imperative
  2. Agile Transformational Practices
  3. Technical Foundations for Transformation
  4. Agile Portfolio Management
  5. Transforming to a Data-Driven Organization
  6. Driving Revenue Through Digital Products
  7. Driving Digital: Smarter and Faster
Why digital? Here's what happened to newspapers, here's what industries are most likely to be disrupted by digital and here's why digital business capabilities can cause industry disruption. Most businesses require a digital strategy and plan to rebuild their digital businesses or face some form level of disruption.  

My book takes you on a "bottoms up" journey, starting with fundamental agile transformational practices and ending with more strategic capabilities like digital strategy, product development, product marketing and organizational culture.

Why YOU should be Driving Digital!

Digital transformation requires leadership at all levels. If you're the CEO, you need to embrace a strategy and realign the leadership team. If you're a CIO, CTO, or CDO (Digital or Data), you have a large number of practices to enable that drive transformation. If you're the CMO, you need new ways to prioritize customer segments and to experiment with digital marketing to reach them.

But digital transformation is not just about C-level leadership!

If you're a developer, you should understand how to improve agile practices so that thecan align with digital strategy and execute product roadmaps. If you're a data scientist you should be establishing practices that enable a data driven organization. If you were an engineer in the data center and now overseeing cloud infrastructure, you have to be enabling DevOps practices to automate and scale. If you're a product manager, you have to help connect digital strategy to product roadmaps and deliver product enhancements that wow customers. If you are a marketer, an operations manager, or a financial analyst - all your practices are likely to have growing importance but changing practices and technologies as digital becomes a more significant business driver.

What's Next in Driving Digital

It doesn't end with the book. Over the next several weeks on this blog, I'll be sharing new insights on DevOps, CIO leadership, and many other topics introduced in the book. I'll be speaking on many topics this fall, and sharing new insights on my blog at CIO.com, Driving Digital Transformation.

I hope to hear from you on your thoughts and questions! - find me as @NYIke, sign up for the digital transformation newsletter, or contact StarCIO.

continue reading "Why YOU Should be Driving Digital!"