Why Digital Strategy Fails—And What To Do About It

Why Digital Strategy Fails—And What To Do About It

At every organization in the world, there is a strategic plan gathering dust on a shelf.

There is a whiteboard with a strategic brainstorm session with dried out ink that never fully erased—partly because no one can find the dry erase cleaning solution, but mostly because the drawings were left on the board too long before being erased, perhaps in hopes that it might one day be put into action. It’s a grim reminder of what could have been…

Strategy by itself is fun—it gets your creative juices flowing about how you can better serve your customers, how you can improve your product, how you can change the world.

Executing that strategy, however, can be challenging. When projects start late, are underfunded, or lack focus and follow-through from the team, the implementation of said strategy can become a massive, seemingly insurmountable frustration.

In the corporate world this is extremely commonplace. So common, in fact, that the causes of failed implementation are somewhat predictable.

Today, we’ll examine the reasons behind the gap from strategy to execution and provide some advice on how to get the ball rolling at your organization.

Why Strategy Fails In Action

Corporate strategy initiatives are the New Year resolutions of the business world.

After an energetic session at the corporate retreat, a strategic plan is formed, perhaps even written down. And three months later, the majority of these plans sit by the wayside. 

Why, though?

It’s different for every organization, but when it comes to execution failure, here are a few of the usual suspects.

The Team Has Trust Issues

If your company culture doesn’t foster innovation, or places a greater emphasis on individual achievement, you are going to have a huge problem. Large-scale strategic changes aren’t possible if employees aren’t willing to share data and insights.

Perhaps the greatest (or worst!) example of this happened at Microsoft just prior to the launch of the Apple iPhone. When Microsoft received word that Apple planned to unveil a device with society-changing potential, they set out to create a device that could compete. But despite access to thousands of engineers and nine-figure research and development budget, Microsoft couldn’t pull it off.

Why? Well, part of it may have had to do with the infamous “stack ranking” system they used to evaluate employees. Since employee performance was grade on a curve, somebody always had to be in the “poor” category, which meant no promotions or salary increases for that employee. Not much of an incentive to share your ideas companywide, is it? Perhaps that’s why Microsoft stopped using stack ranking to evaluate employee performance in 2013.

Failure To Lead By Example

Organizational change comes from the top. When a company is ready to move in a new direction based on a strategy, leadership needs to start executing right away. This means getting budgets approved, providing training, and not falling back into their old habits and routines. It also means not locking themselves up in strategic meetings for weeks – or months – while employees are left to wonder what's actually happening. Strategy sessions should be clearly communicated with departments and teams. And once planning is over, a clear action-based summary can help communicate the details of what went on

When employees see a leader changing her own day-to-day activities, they’ll know the new strategy is being put into action.

Lack Of Proper Technology And Tools

Part of a leader’s responsibility is to provide the proper tools and training for employees to be able to carry out the strategy.

Does your strategy involve a digital transformation? Then you had better provide ways for employees to handle their day-to-day processes digitally. For example, if your HR department is responsible for recruiting, onboarding, and paying contractors, they’re going to need digital HR tools (like HelloSign!) to be able to deliver.

Setting Up To Execute Strategy

So you have a desire to pursue a new strategic direction, and you even know the snags you might run into—so how can you set yourself up for success?


The first area you need to focus on is your team. For any chance at successful implementation, your team needs to be engaged, collaborative, and trusting of each other.

A few of ways to get your team off the bench and into the game are:

  • Involve them in the actual creation of the strategy
  • Connect day-to-day activity with the larger business goals
  • Plan your project communications in advance with updates, milestones, and acknowledgements

An engaged team with company policies and practices that encourage collaboration is the path to successful strategic plan execution.


Engagement is great—it’s the fuel that powers the ship. But your organization also needs direction, a true North to align all that energy with your strategy.

For the executive team, this happens naturally, as those individuals sat in on the strategy meeting. But how does that roll out to everyone at the organization? Mapping day-to-day activities with strategic goals is the best way to keep things top of mind and moving in the right direction.

There are lots of way to do this, but the simplest might be to have each employee sit down with his manager and list out his tasks, then associate which strategic goal each tasks contributes toward. If there’s an abundance of tasks that don’t contribute to the corporate strategy, consider working with that employee to figure out a good way to reallocate their time so it better supports the larger company goals.


Lastly, you need to be realistic. There will be plenty of things that don’t necessarily align with the new direction, but still need to get done nonetheless. Determine what percentage of these off-strategy tasks you can accept and still keep driving toward the goal before you make any drastic changes to schedules.

Execution isn’t more or less difficult than strategy, it’s just a different skill set. If you’re looking at a digital transformation at your organization, let the team at HelloSign help you execute on paperless processes via electronic signatures, faxes, automated workflows, or our API.

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