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

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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, 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.

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5 Things CIO Should do this Summer

Take a step back - it's summer time. You may not be able to slow down, but you should have more opportunities to do things outside of the normal day to day and monthly grind. If you do, consider the following options -

  1. Unplug - My advice for CIO on taking summer vacations includes unplugging from email, learning something new, and setting priorities on your time. Consider using the time to catch up some reading. Later this summer, my book Driving Digital: The Leader's Guide to Business Transformation Through Technology will be available and there is also CIO Insight's list of summer books

  2. Develop a new business relationship - CIO leading transformation efforts need partners and collaborators to lead programs. Summer is good time to select someone new in the organization and develop a meaningful relationship. For example, if you haven't done this already, here are my tips on starting a killer relationship with the CMO.

  3. Have fun with your team - Transformation programs require a lot of hard stressful work and summer is a good point to bring fun back into the IT culture. My favorite department activity is to host a summer pot-luck picnic or barbecue.

  4. Schedule fall events - Before your Q4 calendar gets overfilled with meetings and tasks, consider scheduling some time out of the office to attend a conference. Here's my dashboard of upcoming events for CIO, CTO, Chief Digital Officers, and Chief Data Officers.

  5. Get hands on - If you have the time, nothing beats rolling up the sleeves to learn a new technology. At minimum, you'll get some insights on how the technology functions and what you can accomplish with limited time and training. You'll certainly get a better appreciation for your staff who often have to figure things out on their own. For example, here are some of my DevOps and cloud lessons after setting up a personal AWS environment.

Happy Summer!

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