Digital Transformation

Why The Right Strategic Planning is Important in your Digital Transformation Journey

Digital Transformation within your organization can occur and evolve in many ways, starting with very tactical reactionary changes with burning problems like data loss, error-prone manual processes, and time consuming “old school” efforts that get more difficult in the modern era (like trying use the “copier” and “send a fax”, etc.)  Remember, there are still plenty of people that perform their daily tasks that way for many reasons.

The other side of digital transformation is when organizations take a lot of time to plan out the approach and spend significant effort figuring out what they need, planning years down the road, interviewing, reviewing, discussing, gaining consensus, etc.  It’s hard for me to knock anyone who plans things out, so it’s difficult to be a critic here, however I will say this:  We have seen instances where paralysis occurs when you try to “boil the ocean” in your upfront efforts.  As someone who has seen hundreds of attempts at these with our customers, I’d like to think I’ve pulled a little wisdom out of the experiences and feedback.  I think it falls into these camps of the why elements to watch out for:

  1. You get so deep in planning that the plan becomes the project and there is so much investment that it’s hard to get your head out of it and get started on something meaningful without getting pulled back into the road map. Your time is spent in the plan, not the results.
  2. The participants required to make decisions, define guidelines, or modify policies that the plan depends on are either not positioned to execute, not ready, or not available.
  3. The changes being sought in the name of security or compliance may reduce the flexibility and ease of use of the platform / tools and therefore create friction with the end user community.
  4. The platform / tools / technology you are using have meaningful changes and updates by the time you get to the implementation. The capabilities have improved enough that you must revisit your intended implementation.
  5. Your employees have changed enough via new hires, attrition and their projects / goals have adjusted, that the requirements you intended to meet have moved enough to warrant revisiting your implementation goals.
  6. The strategic needs of the organization change – new strategic initiatives, business challenges, a number of top-down elements that make planning down to the tactical level difficult to maintain

I call it the moving targets that we face while trying to make a meaningful impact helping the business transform over a period of time.  These essential drivers are constantly in motion, and I think this ends up being one of the big reasons many digital transformation initiatives fail to meet their expectations.  Keep in mind that It’s only in recent times that these targets move so quickly due to the changing technology and business landscape.  The big waterfall project that worked 20 years ago is much less effective now.

You might think this is a good thing, we didn’t implement something that wouldn’t be valuable by the time we got to implementing it.  This is why we plan, gather requirements, think about the specifics of delivery, etc.  We avoided something that wouldn’t have helped us anyway.  I challenge that notion as old-school thinking.  My approach is actually more of a hybrid or meeting in the middle of the two extremes.  You need to plan, but don’t plan yourself beyond current understood needs. Create agility in delivery within your strategic planning.  Transformation occurs incrementally over time, not at the end of a project.

Second, don’t even refer to it as a plan, it’s a process.  It will never end because the moving targets never stop moving.  If you shorten your strategic cycles, you get smaller iterations of implementation that meet current understood needs BUT allow for feedback to incorporate into the process moving forward.  However, they can’t be so short as to essentially be one-off tactical responses with no cohesive thought behind the big picture.  You are going to help guide the process, and a guide has pretty good of where he or she is going but knows there are multiple roads to get there.

A wise man once told me:  “If you don’t know where you are going, any road will take you there”.  This is the reason why strategy and planning are still critical.

So, what does the right strategic plan look like?  With the usual disclaimers that every organization is different, your mileage may vary, etc., there are still some elements the make sense in every organization.  The following are elements of your strategic approach the need careful consideration:


Stakeholder ownership.  What are we doing, why are we doing it, and how will it help us increase our business objectives?  Where do we want to be?  A stakeholder driving the 30k foot view of what the organization is trying to achieve across the business as a whole.


Goals are the logical next step below the vision, let’s break them down into some discreet items so we know when we have completed the goal.  For example, one goal may be to “Increase our ability to securely collaborate with out external partners “because you know you are falling behind, wasting resources, or at risk for data security issues using your current methods for working with parties outside your organization on documents and data (customers, vendors, contractors, etc.)

You will develop and nurture these goals over time, they will change, adapt, and move around in order of priority if you continue your ongoing strategic planning correctly.  Build, maintain, and continue to challenge your list of goals.


Sometimes this gets lost in the vision and goals, but the end-users are where all the magic happens.  If one of your goals is external collaboration using Teams, then this is where you meet and discuss how to implement this in a way to hits the target.  The daily interaction and usability of your implementation is pivotal, you are doing all of this provide value for your users.  Continue to discuss, document, and deliberate on how to make their lives better as you achieve these goals.  Be flexible, jamming a solution onto someone is rarely the answer.  Be prepared to adapt and modify “post go-live” based on lessons learned in production.  You need to know needs to be configured to provide value for their specific use cases.

Holistic View

When you understand the targets at multiple levels, you start to see how it all fits together.  This is one of the most difficult items to visualize if you don’t undertake some strategic initiatives.  Seeing all the initiatives across the wider audience will give you great opportunity to identify both gaps and opportunities to get economies of scale and additional solutions that help tie your goals into the whole vision.  See the forest, not just the trees.

Road Map

One of the most critical elements of strategic planning is your road map.  All this really entails is a time-based visual diagram representing when you plan to start & complete various initiatives you have defined via your goals & needs.  This map does a lot of good things:  It holds you accountable for getting things done, even if it’s not perfect.  It provides visibility to the end users making requests, so they understand why their needs are or are not the top priority.  People get to see when certain initiatives will impact and be available for them.  It makes you do some architectural work so you can define and understand dependencies.  Example:  You can’t hit the goal defined above if you haven’t built a governance plan for Teams yet?  No external sharing without governance / guidance / security property setup, right?  This includes your organization as part of the process.

Small Projects to implement

The road map helps define the small chunks of discernable work that allow you to hit the goals.  This is where the true project planning work is done.  Resources, timelines, tasks, etc.  If I am a project manager or subject matter expert, the road map helps me understand in advance where my skills and time will be needed to help achieve the goals.

Insight & Visibility

Communicating the efforts using the methodology above gives a lot of transparency to everyone in your organization.  That is a good thing.  It helps ensure everyone is aligned with your approach and timing.  It also allows them to ask questions and get on your list of people to talk to about needs and ideation.  It helps ensure they are a value asset to the success – you are not doing this TO them, you are doing this FOR them with their input.


If you can only take one thing from this list to remember, I have to admit this is it — I believe the highest chance of failure for true digital transformation is to treat it like a project and not and ongoing evolution.  Instead, digital transformation can be organized as an on-going program made up of small projects.

For your transformation process to continue, you absolutely must revisit your goals, road map, and the moving targets on a regular basis.  This is how you prevent getting out of alignment and straying too far down a path that is no longer valid.  The good news is this is the easiest part if you are committed to it, the hard part is the commitment.

Why is it so easy?  Because all the elements you work on the beginning simply get revisited on a regular cadence.  It’s like going to the gym – I sat on the couch for most of 2020 during the pandemic and gained a bunch of weight.  Going back to the gym was very difficult to build the routine and work up to a decent amount of exercise, but after I got back into some reasonable shape, going regularly becomes less painful and it’s somewhat predictable.  When you build your recurring mechanisms to reviewing feedback, talking to end users, adjusting your goals, road map, associated projects accordingly, and communicating it to the end users becomes easy and anticipated.

User Experience

My final words will be to remember your users are the name of the game. To get momentum they need to be kept at the forefront, solicited for effective feedback, and supported with training and skilled helpdesk personnel that truly understand how to solve their issues.  Getting user adoption and true engagement will allow the ongoing efforts take on real momentum.  Get feedback, incorporate it, design for it, implement it, train/support it, and do it all over again at a pace your team and organization can sustain and you will look back and say “wow, look at all the positive change we facilitated”.

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