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Woody Hobbs

Woody Hobbs

Woody Hobbs is an experienced executive who has served as CEO of several information technology companies and also as a CIO who has innovated new models. Woody and his team drove success via a new business model, key acquisitions, and industry-leading R&D. Woody is a Managing Director at Palmares Advisors. An executive advisor to CEO’s. Board Member. M&A and funding advisor for tech and tech enabled companies.

Palmares Advisors is a Merger and Acquisition Advisory Firm focused on helping technology companies with strategic exits and funding. We bring an unique operational experience focus to this process.

—————Guest Article—————–

Dwight Eisenhower once said, “In preparing for battle, I have always found that plans are useless, but planning is indispensable.” This quote is one of the best aphorisms a business owner can have.


Think about your current business plan for a moment. With unpredictable market shifts, competition, project failure and other plan-changing events, how likely is it that the future events developed will turn out exactly as you expected? This unpredictability is what makes product roadmaps so valuable.

An effective roadmap should highlight the greatest risks that may arise and provide you with alternative directions. This allows your company to forge ahead regardless of what the future holds. This is even true for major changes to a plan, or pivots, allowing decisions to be made much faster and more effectively than if you were to start from a blank sheet of paper.

There are several types of roadmaps for several different areas of business including:

  • Product
  • Project
  • Expansion of an organization

For the purpose of this article, we’ll focus on product roadmaps.

Roadmaps can diagram the plan for one or more products, showing the evolution of each product’s major features or attributes displayed along a timeline. The timeline indicates when a new set of features or attributes will be delivered. Each major node on the timeline may be called a model, release, version or similar name.

To illustrate what we mean, let’s look at the Apple iPhone™ evolution represented by our version of its product roadmap. Each major iPhone model and its release date are shown across the top of the diagram. The left hand column arrays the major features or feature sets that are important to the customer. For each model or release, major changes in the features are indicated.

The iPhone roadmap is an example of a useful framework for discussion with senior executives and the board of directors who need to understand and approve the company’s plans, programs, and investments. It highlights key priorities such as the importance of the iPhone’s video and imaging capabilities as well as the major investment Apple made in these capabilities. In this context, the roadmap can enhance strategic planning discussions about a variety of topics such as:

  • Risks of missing the delivery date of the next release.
  • Cost and development schedule of planned features.
  • Feature set of the next model that will attract customers and increase competitive advantage against rivals.
  • Strategic partners who need to synchronize their product plans and releases with yours.

To enable a useful conversation, the level of detail should fit the audience and the purpose of the discussion. Roadmap developers need to restrain their desire to add more information. Too much detail can easily confuse the roadmap’s audience and takes discussions to a micro level, which consumes valuable time and isn’t very useful in making high-level decisions.

Many companies plan to deliver a new design or a new package of features every quarter. A roadmap showing the changes that will take place each quarter over the coming year or two may be useful. On the other hand, a quarterly timeline will be too detailed and not very useful for a board of directors who only meet quarterly.

In summary, roadmaps are very useful high-level planning tools to communicate with senior management and boards in order to keep everyone in an organization on the same page. You should reduce or increase the time frame and level of detail shown to different levels and functions within your organization. As your planning skills improve, it is useful to be more inclusive and give the entire organization a clearer view of the future. This is certain to improve morale and will also improve results. We all like to know where we’re going and to understand when and why changes are made.

In the next article of this series, we will discuss applying the principles of product road mapping in order to plan many other kinds of key programs and initiatives.