Embracing new digital technologies, or just moving to the cloud in your work is almost mandatory. Just remember, if you don’t have real buy-in from the top, your odds of success are low. Here are some steps to consider.

Digital transformation is hard. Just trying to move to the cloud from legacy infrastructure can seem overwhelming if not impossible. Yes, there are technology hurdles (new “Tab A” won’t plug into old “Slot A”) but the real challenge arises from your institution’s people, processes and organization. Regardless of whether you are a for-profit enterprise, a non-profit, academia or government, the barriers to a better future are the same and they start at the top. Here are three things to watch out for.

First, “Is the Leader Committed to the Change?” Successful transformation only occurs if top leadership is solidly behind it. This can take many forms but direct advocacy and leadership is key. Often, given the demands on the leader, a trusted advisor or perhaps the heir apparent will lead the charge but the connection to the top dog and his/her support must be unambiguous.

Beware of the effort being narrowly defined as only a technical challenge that the IT department head should lead; or perhaps the head of HR for a new HRM SaaS; or the CMO for a new marketing automation system. There is nothing wrong with them leading the day-to-day, slogging through the trenches but if your “el supremo” does not personally, publicly own the effort – look out!

Next, “Does your Leader Know What They are Getting Into?” The odds are your leader is not deeply steeped in digital technologies or the cloud. There is a lot of hype in the marketplace and plenty of consultants pushing the transform or die message. There is no doubt that the head of your shop has been exposed to it and may have become one of the converted. But is that enough?

Take a look at Jeffery Immelt, formerly CEO of GE and Mark Fields, formerly CEO of Ford. Immelt spoke of the imperative to digitize the industrial world and Fields proclaimed that Ford was really in the mobility business, not just a carmaker. They seemed to have gotten the digital message but they were nonetheless booted out. These are smart people but they were undone by their lack of understanding about the speed of digital; risks of doing or not doing it; shortage of talent in the market; potential financial consequences of selected paths and of course, internal resistance.

You don’t need to be a Fortune 50 to get undone by these forces. They are permeating the entire competitive arena. If you are advising the top honcho, you need to make him/her aware of these factors in a structured manner that allows them to evaluate the trade-offs and at least make reasoned decisions rather than stumbling into a fail. This does not alone assure they’ll get it right but it will greatly improve the odds.

Last, “Is the Leader Engaged in Bringing the Effort to a Successful Conclusion?” Ok, so they own it and they know what they are getting into. It can’t stop there. The leader must be engaged in the on going process, otherwise – whoops! It starts at the beginning with the analysis just described above and extends to endorsement and adoption of the plan to get the work done and address the risks and issues.

The leader must also commit a regular chunk of their time to staying abreast of progress and participate in overcoming the bumps as they emerge. That does mean the leader needs to develop the recommended solutions – that’s what the program team is for – but it does mean maintaining his/her awareness and blessing the proposed approaches. Let’s face it with something this fundamental to the business, there are times you are going to need “air cover”.

This is the day-to-day manifestation of the leader’s ownership described in the first point. Red flags are: they are too busy to meet regularly on the topic, or they always seem to delegate it to someone else. Every culture has different processes and structure for managing the key programs. So, the exact method will vary but we all know when the chief is not interested.

For digital transformation to be successful the leader must own it, understand it and actively be engaged. Words to the wise: if you get swept up in one of these transformations where “numero uno” is not wholly on-board, run, do not walk to the nearest escape. Pretty simple isn’t it – yeah right!

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