How to Tackle Big Complex Digital Problems

As our process strengthened, and our capacity in digital has grown, we began experimenting and then implementing more strategic and repeatable methods.

Our progression and maturity in digital and strategy through the years has been quite natural. As our process strengthened, and our capacity in digital has grown, we began experimenting and then implementing more strategic and repeatable methods.

Our work takes us deep into organizations, where we are exposed to all the complexities of cohesively and strategically growing a large organization. The more time we spend working internally with organizations, the more we recognize there is a huge spectrum of both digital literacy, and digital maturity within industries and organizations of all sizes. With this variability, digital transformation can become increasingly complex.

Simply setting out to work on a digital project is often not enough to drive organizational change, and any product developed with this mentality increases risk and lowers success rates. Strategy needs to be continuously nurtured.

Some simple things to remember on your journey

Over the last year we have been revising our methodologies and exploring new techniques. Most importantly, we have been learning some of the more emotional side of the process. Here are a few things that we always try to remember, and remind our stakeholders. We have a laundry list, but these are our favourites that tend to resonate most.

  • Ideas are never fully formed: A project is like a ball of yarn in the early stages. Spend the time upfront untangling the yarn before you start; it’s hard to knit something when you’re constantly focussed on untangling your ball of yarn.
  • Uncertainty: Get comfortable with it. Rules change, and sometimes things can feel like a moving target. It’s important to move fast, trust the process. Stay focussed, and learn to recognize distractions before you get pulled into the new shiny thing.
  • Brand ecosystem: Always consider brand and strategy before any project, where does this fit in your brand ecosystem? Does this project or product reinforce or extend your brands mission/vision? Is it a sub-brand, or part of the primary brand?
  • Myths: “If you build it they will come” does not exist. Start thinking about year 2 before you even begin. You will need to be thinking long term commitment, and consider how you will remain agile.

With every initial step into the world of digital or innovation, there is an inherent level of risk. Through years of doing what we do and building/revising our process, we have learned that managing risk is a big part of the process. Risk is deeply connected to complexity, and where you position the complexity in your process defines where your risk will be. This graph should help with this concept.

We like our complexity to be worked out at the early stages of a product when pivots and rethinks are cheap. Thinking back to the ball of yarn analogy executing without a strategy carries over that level of risk into every detail of the project.

Developers spend 50% of their time fixing issues which could have been avoided

As marketers, brand stewards, and innovators, we should all be spending the time upfront to unpack the layers of complexity and be very clear in our goals, execution, KPI’s and support of a project over its lifetime.

Following this method, the risk of failure is significantly lowered as you move along the process. Today we are sharing some introductory insights to process that we have discovered along our own journey.

Fixing a problem in development costs 10 times as much as fixing it in design, and 100 times as much if you're trying to fix the problem in a product that's already been release.

The Level Set

No matter the type of project this level of analysis will typically take the form of a half-day workshop involving key stakeholders. The following five sections cover the high-level stages we go through during our workshops. The stages have evolved to bridge the gaps between design, technology, people.

Workshop Kick-off

Setting the stage for a successful workshop is an art in itself. I won’t spend too much time in this piece because it deserves its own post.

We design the workshop to be an open world to explore. The most important part of this stage is to begin defining the direction, understanding the current state, identifying weaknesses, and making an action plan. This process is designed to facilitate exposure to ideas, and to reveal blindspots. In the end there may be some additional synthesis required, but it’s about what you discover on the journey.

Business Model

As you move through the process you will begin to define the business (and new business if its a rev generating project), short term, future states, and capabilities in detail. Defining the business helps in a few ways.

  • It maps overall strategic initiatives and goals of an organization to project outcomes.
  • It helps to define audiences and stakeholders that can be engaged during the design phase.
  • Helps to identify future opportunities for innovation and revenue.
  • Helps to identify neighbouring opportunities to build in support (data use, sales support)

If the project is a new revenue source, defining that business model is obviously very important and helps to start planning out workflows that will inform CX, and UX/I. This is where stakeholders come into play. But more importantly, it is helpful to ask the project leadership the following questions—as a pulse check on assumptions. Whether an assumption is correct or not, doesn’t matter.

  • What are your decision makers spoken & unspoken needs?
  • What are they asking for? (very useful for service based businesses)
  • What tools do your salespeople use? (helps create opportunities to drive sales through the project)
  • What is your promise as an organization?

Organizational Structure

Irrespective of your size, there are plenty of stakeholders that are directly, or indirectly involved. This stage will help you build a map of support structures, advisors, partners, and the workflows that connect them all. Most obviously this helps to understand the hierarchy for reporting, and collaboration, but it also gives insights into how the organization operates—in theory.

Simply defining roles and those involved will save tonnes of complexity down the road when it comes to feedback and approvals. A simple example is your IT team. Some organizations have IT professionals that handle migration and hosting while smaller organizations may not have dedicated IT staff. Simply understanding this early in the process defines the expectations and, and the future needs with respect to support and implementation.

  • Define every role and title of people involved present and not present
  • Define approval process and who is involved at what level
  • Describe your internal culture
  • What level of involvement with senior leadership seek on this project

Your Tools

From web design, product design, branding, and experiential design; all require different approaches. Objectively look at the tools you have at your disposal. Be careful with a one size fits all mentality with your tools. Design research is a toolkit, not a process—and although we said earlier to trust the process, you need to be willing to “go off book” when necessary.

This stage is all about defining goals, direction, and mapping out all other support structures that might be needed. Below are some strategies and tools you might use if you’re going through this process.

  • Use a feedback grid to categorize your ideas if you’re building off of something new.
  • Card sorting is a method to help participants categorize ideas.
  • SWOT Analysis captures the strengths, weaknesses, opportunities, and threats as perceived by the organization.
  • Map out your product as a business, or in the business. Marketing is your landing page, finance is your selling page. What is needed and how do they connect?
  • Map strategic objectives of the organization, and determine how this project supports them?

Process and Expectations

As stated in the title this stage typically covers two areas for us. Defining approvals and the entire approval process. Rules of engagement (ie. how do we work together). Setting expectations up front and early in documents that we have already created and hand out help to define the relationship and what is expected from all parties involved. This could be on an organizational level or individual contributor level. If you are defining “rules” as you go, you are increasing the level of complexity and risk.


Technology is inherently complex and scales depending on the complexity of the project. Risk mitigation is part of the process and understanding where and how risk shows its ugly head can really help in defining, planning, and delivering a successful project.

This a snapshot of how we work. You don’t need to be working on some big hair goal in order to use a structured strategic approach to thinking holistically before embarking on any project digital or not.

I hope it will help at the very least elicit some thoughts on how to build a more structured approach to your processes.

Our Team

Meet the Author

Marcello Gortana
Executive Director

Working with business leaders to leverage design and technology to make change within their organizations.

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