When significant digital transformation projects fail, it’s not uncommon to see executives lose their jobs (just look at what happened to John Linwood, CTO of The BBC, in 2014 when the Digital Media Initiative failed). Disaster stories such as Linwood’s can make digital transformation a sensitive subject for the C-suite; but VPs and directors should be prepared to push these executives to move beyond business models that don’t support digitization.

Following these three best practices to selling your executives on digital transformation can help mitigate the risks of initiating change—for you and your executive team.

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Know What Your Executives Care About—Start with the End in Mind

It’s no secret that financials are top of mind for any executive listening to a presentation that involves making an investment. No matter what you present or how you present it, the executive team will turn straight to the financials page and work backwards to determine how the plan will fit into the organization and its overall digital budget. 


That’s why you need to start your presentation planning with the end in mind. To do this, ensure that you can explain the following to the executives:

When you understand these endpoints of the digital transformation conversation, you can start working backwards to develop your messaging.

Download our latest free white paper, The Pillars of a Successful Digital Transformation Strategy, for a more detailed understanding of what it will take to truly adapt to the era of digitization.

Solicit Feedback from Your Colleagues

There’s power in numbers, both in terms of the ROI numbers you present and the number of colleagues you can get on board with your plan. It might seem as if digital transformation is mainly concerned with implementing technology creatively to carve out new market value—but you’ll need leaders from many different aspects of your organization to make a lasting impact in the minds of executives.

The challenge with soliciting feedback from the rest of the organization is that digital transformation means something different for every key department. For a deeper understanding of how to inspire your colleagues, see what we’ve already written about the 6 key departments in a digital transformation. 

Be Willing to Start Small with Digital Transformation

Large companies accustomed to the status quo will only see high risk if you present a digital transformation plan that wants to do too much too quickly. Don’t try to boil the ocean with your initial strategy—introduce digital transformation methodically with the same “try fast, iterate fast, fail quick, and stop” ideology we’ve discussed in the past.

Download our latest digital transformation white paper, The Pillars of a Successful Digital Transformation Strategy, for a more detailed understanding of what it will take to truly adapt to the era of digitization.

Consider these Four options for introducing digital transformation slowly:

  • The center for digital excellence: Establishing a variation of Texas A&M’s center for digital excellence as presented by CIO Mark Stone gives you the opportunity to start the digital transformation discussion throughout your organization before making an initial investment that might cause executives to pause for concern.
  • Wedge digital transformation into an overarching process: Find one of your current processes to wedge a small digital project into before initiating a dedicated project. Even if it’s an existing customer experience process, when you can prove quick impact on the top or bottom line with digital transformation, executives will be far more likely to get on board with your long-term plan.
  • Digitize your internal tools to prove effectiveness: Think about how you can make your organization more efficient or make processes more transparent with digital solutions to prove that digital transformation can make a difference before introducing the idea of cannibalization. For example, implementing SaaS platforms such as BetterWorks for objective alignment or Slack for communications can change the way employees work and think about digital transformation. Once an executive team has embraced the value internally, it will be easier for them to grasp the value of a more holistic initiative.
  • Don’t be afraid to compete against your own business: Competing against yourself by cannibalizing your own business can be a great way to succeed with digital transformation—but this might seem too risky to C-level executives who don’t want to sacrifice a cash cow. Just remember, if you don’t attack the market in new ways, someone else will. Making smaller bets on these initiatives will allow executives to see that the cash cow is (mostly) safe.

An Old Adage for a New Era in Business

The old adage, “you can lead a horse to water, but you can’t make it drink” rings true when it comes to presenting digital transformation to your executives. No matter how important digital transformation is to the survival of your organization, the executive presentation is all about proving the ends justify the means—with as little risk as possible.

Starting with the end in mind, soliciting feedback from colleagues, and starting with small projects are three keys to getting executives on board with digital transformation. However, there are more concrete details to cover once you get them interested.


Download the Pillars of a Successful Digital Transformation Strategy White Paper

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