This Isn't Working How I Thought it Would: Rethinking your Digital Transformation

The more I talk to executives about their digital transformation efforts, the more I clearly see that the most common source of friction hindering their progress isn’t about the technical aspects of the work at all. It’s all about the people involved and the impact to the organization.

Digital transformation is the integration of technology in every aspect of the business, with the ultimate goal of improving the value to the customer. Once transformation starts to gain momentum within an organization, it can be a lot of change to absorb all at once. This creates significant pressure on the culture and risk to the operations of the enterprise.  As that pressure mounts, more than one leader has expressed that they simply do not feel equipped to see the next phase of their transformation through. That's where things usually stall out.

In plain terms, this sounds like:

We’re doing agile development but no one outside of IT understands what that means, so it's not spreading the way I think it should.

I have people in product management roles, but I’m not sure I (or they) really understand what their job is.

We're trying to turn our Project Managers and P&L owners into product managers, but I'm starting to see that might not be the best path forward.

I’m all for transformation, but why can’t anyone tell me what we’re going to need for budget next year? Or really just what we're going to build next year?

When are we going to be done?

As an executive in the product space, I knew that the bulk of my job wasn't about the products in my portfolio, as much as it was about making sure that my product teams had the tools they needed to operate at their highest possible function. And in most cases what was needed was new frameworks and ways of working across the enterprise. I turned to my organizational effectiveness tool belt on a daily basis.

As a consultant and fractional leader in product innovation and digital transformation, the work is really no different. It's about understanding the unique internal points of friction and helping my clients see that there's no magic bullet that will fast track their transformation. While there are many paths forward, the optimal path likely involves setting (and re-setting) the vision for HOW the organization should get work done, not just what they need to work on. Areas of inquiry might include:

• How should teams be evaluated and trained in order to accelerate the evolution to the new normal?
• Where and when do operational processes and collaboration pathways need to be refactored?
• Where should expectations about common business cycles be reset to give teams the freedom to work on the most valuable things while also keeping finance and sales from having a heart attack every time the roadmap is reprioritized?
• When do teams need space to innovate, and when are constraints actually needed to ensure that innovation moves the business forward in a meaningful manner?

These are the key questions that executives are grappling with across industries. While there are examples and templates for new ways of working that come from outside the organization, the more powerful answer is that simple organizational design changes paired with agile and product management principles can yield tremendous upside for adding speed and effectiveness to digital transformation efforts.

Remember that digital transformation is, by definition, a whole-organization activity, and so changes to ways of working in the new normal won't be siloed to just the product and technology teams. These changes will ripple across every unit of the company, and the more transparent and upfront leaders are about facilitating these changes and pairing them with an Agile or product-focused approach, the more speed, momentum, and stickiness the digital transformation will achieve.