If you are sponsoring a digital transformation, you already know you have a lot on your plate.\u00a0 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.\u00a0\nEvery digital transformation effort will be faced with significant adversity, uncertainty and risks that could negatively change the trajectory of the effort.\u00a0 From my experience, these eight questions can be extremely useful in assessing the overall resiliency of the digital transformation effort.\u00a0 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.\n1. Is there a clear understanding of how benefits will be captured?\nUnderstanding these 3 details can play a significant role in streamlining the program governance process:\n\nKey business capabilities that are required to capture benefits\nWhich executives are on the hook to deliver benefits\nHow business process compliance will be enforced\n\nMaking sure the right people have enough intellectual runway to make big business decisions is critical to keeping the program on schedule.\n2. Has the PMO accounted for the influence of corporate programs beyond their control?\nThe saying \u201cfocus on what you can control\u201d applies most of the time; except for when you are managing the Program Management Office (PMO).\u00a0 Companies typically have several change programs in flight simultaneously.\u00a0 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.\n3. Does the program have a program\/resource contingency strategy?\nEstimates are just educated guesses.\u00a0 Almost by definition, the time that has been allocated in the plan is going to be wrong.\u00a0 What are the buffers that have been built into the plan?\u00a0 What are the triggers to initiate these buffers?\u00a0 If contingency involves working overtime or weekends, has this been clearly communicated to those involved?\n4. Are the resource demands beyond the project team control secured?\nOne of the most common \u201couts\u201d for a systems integrator on a fixed price contract is that the users were not ready to accept the system.\u00a0 The bottom line is that users can\u2019t be blamed if they don\u2019t know what is coming.\u00a0 PMO\u2019s should be collaborating with line management to secure resources for data preparation, testing, training, support, and implementation.\u00a0 PMO\u2019s should also be proactively engaging legacy application support teams to secure resources for the same demands.\n5. Is there a clear exit strategy for the system integrator?\nTwo things system integrators are motivated to do: look for new opportunities to penetrate the client\u2019s value stream and make themselves indispensable to your project team.\u00a0 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.\u00a0 If system integrators understand they can be easily replaced, clients will retain some leverage in annual contract renewal negotiations.\n6. Is there a pathway to capability advancement?\nIt is not too dramatic to infer that the benefits associated with a particular program can be doubled with some forward thinking.\u00a0 Ask questions like:\n\nHave plans been put in place to enable parts of the software that were deemed not necessary at the start of the program?\nIs it clear how the capabilities enabled for one part of the business will be extended to others?\nAre the techniques associated with program management and business transformation being perpetuated across other corporate programs?\n\n7. Is there a robust risk and issue management process in place?\nNumerous studies have shown that digital transformations are successful about 50% of the time.\u00a0 This high failure rate can be attributed to any number of causes.\u00a0 One significant failure point is the lack of engagement of the transformational leader in a robust and comprehensive program risk management process.\u00a0 Robust processes require the engagement of experienced practitioners with a well-developed situational awareness of digital transformational program efforts.\n8. How is the project team obtaining an outside perspective?\nIt is easy for project teams to fall prey to cognitive biases and blind spots.\u00a0 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.\u00a0 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.