8 questions to evaluate the resiliency of a digital transformation program

How to help your program team bounce back from challenges they'll encounter along the way.

Navigating a field of uncertainty and doubt questions

If you are sponsoring a digital transformation, you already know you have a lot on your plate.  Before you dive head first into project timelines, budgets, and issue review meetings, I recommend you take a few minutes to think through this digital transformation resiliency evaluation. 

Every digital transformation effort will be faced with significant adversity, uncertainty and risks that could negatively change the trajectory of the effort.  From my experience, these eight questions can be extremely useful in assessing the overall resiliency of the digital transformation effort.  Putting in place tactics to answer these questions in an affirmative manner will help the program team bounce back from program challenges as they are presented.

1. Is there a clear understanding of how benefits will be captured?

Understanding these 3 details can play a significant role in streamlining the program governance process:

  • Key business capabilities that are required to capture benefits
  • Which executives are on the hook to deliver benefits
  • How business process compliance will be enforced

Making sure the right people have enough intellectual runway to make big business decisions is critical to keeping the program on schedule.

2. Has the PMO accounted for the influence of corporate programs beyond their control?

The saying “focus on what you can control” applies most of the time; except for when you are managing the Program Management Office (PMO).  Companies typically have several change programs in flight simultaneously.  If there is not a corporate PMO that is managing the interaction between these programs, then the responsibility falls on each of the individual programs to understand and manage potential interactions.

3. Does the program have a program/resource contingency strategy?

Estimates are just educated guesses.  Almost by definition, the time that has been allocated in the plan is going to be wrong.  What are the buffers that have been built into the plan?  What are the triggers to initiate these buffers?  If contingency involves working overtime or weekends, has this been clearly communicated to those involved?

4. Are the resource demands beyond the project team control secured?

One of the most common “outs” for a systems integrator on a fixed price contract is that the users were not ready to accept the system.  The bottom line is that users can’t be blamed if they don’t know what is coming.  PMO’s should be collaborating with line management to secure resources for data preparation, testing, training, support, and implementation.  PMO’s should also be proactively engaging legacy application support teams to secure resources for the same demands.

5. Is there a clear exit strategy for the system integrator?

Two things system integrators are motivated to do: look for new opportunities to penetrate the client’s value stream and make themselves indispensable to your project team.  To balance the scales, digital transformation leads need to keep an eye on knowledge transfer plan execution as well as maintaining a plan to keep switching costs low.  If system integrators understand they can be easily replaced, clients will retain some leverage in annual contract renewal negotiations.

6. Is there a pathway to capability advancement?

It is not too dramatic to infer that the benefits associated with a particular program can be doubled with some forward thinking.  Ask questions like:

  • Have plans been put in place to enable parts of the software that were deemed not necessary at the start of the program?
  • Is it clear how the capabilities enabled for one part of the business will be extended to others?
  • Are the techniques associated with program management and business transformation being perpetuated across other corporate programs?

7. Is there a robust risk and issue management process in place?

Numerous studies have shown that digital transformations are successful about 50% of the time.  This high failure rate can be attributed to any number of causes.  One significant failure point is the lack of engagement of the transformational leader in a robust and comprehensive program risk management process.  Robust processes require the engagement of experienced practitioners with a well-developed situational awareness of digital transformational program efforts.

8. How is the project team obtaining an outside perspective?

It is easy for project teams to fall prey to cognitive biases and blind spots.  Even the most experienced project teams can lose sight of, or unconsciously ignore the warning signals of, a project that could potentially go off the rails.  Having an independent fresh set of eyes review your program to identify blind spots and assist the team in understanding how they can mitigate risks might just be the best investment you can make to secure successful delivery of your program.

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