6 Ways to Get Your Board on Board with Digital Transformation

While cost efficiencies are important milestones, the real value of digital transformation lies in long-term innovation. Here’s how you can get some mileage by making your case.

Guest Commentary, Guest Commentary

January 13, 2020

4 Min Read
Image: Pixabay

For companies not born in the cloud, digital transformation drives competitive gains. In our work with companies that aren’t true digital natives, we consistently see a common theme. Regardless of the scale, size or goal of a digital transformation initiative, they are always more complex than expected. Digital transformation will never be linear -- it’s an agile progression that is constantly evolving. But with constant evolution comes constant feedback, and that feedback coupled with transparency, context, supporters and direction can become your greatest supporter in getting, and keeping, your board of directors on board with digital transformation.

So, you have a framework for a digital transformation project. You’ve identified the expected capital investment costs. Now, how do you approach the board for their sign off? Below are six key considerations for getting your board of directors aligned with your digital transformation efforts, and the inherent complexities that will surface.

1. Build supporters

While ultimately you want all board members in support, it’s critical to have two or three advocates at the outset of your effort to sell a digital transformation project. Understand the unique perspectives of board members: Which of them has a background that includes these types of initiatives or brings experience with digitally native companies? Sell your vision to them first and cultivate their support by seeking their input on development and road mapping. This helps to foster a sense of ownership and can create champions for the project during the inevitable pauses, setbacks or hurdles. Seek out board members with differing backgrounds, perspectives and priorities to recognize and understand multiple stakeholders’ views on the project. Use this understanding to balance priorities, build a project road map and establish the project need together.

2. Paint the picture from the outside in

Mapping your digital transformation project to market needs shows the business case for investment and reinforces the value of the initiative. Moving digital transformation from a buzz word to an actionable initiative with practical outcomes isn’t easy but applying market and industry intel can help reinforce the project’s purpose and place in your company’s future. It’s important that your board understands the project’s need both internally and externally. Reporting in the context of the broader market and industry can also support greater flexibility and help sell potential shifts in direction. Seek out market industry analysis or research at the outset of plan development.

3. Develop a clear project roadmap

By creating a high-level overview of the digital transformation project, projected outcome and achievements can help set expectations. It’s essential that the project road map discloses any anticipated challenges or elements that are likely to fail to help the board understand progress and expect setbacks. When it comes to digital transformations, setbacks are inevitable -- don’t expect the transformation to progress flawlessly.

4. Be transparent

Along with sharing the project roadmap, prep your board for your project by providing pre-read materials ahead of kickoff. These materials should illustrate previous digital transformation efforts, what’s worked, what hasn’t (and why) and key learnings. It’s ok to admit flaws or past failures -- they’ll be some of your greatest tools in this project’s success. It’s essential to not only be transparent, but to also create an environment of transparency to communicate fluidly about the status of your project.

5. Fail first to succeed

As you go through the stages of your digital transformation project, remind yourself and your team of one thing: It’s normal to have setbacks. It’s no secret that many digital transformations ultimately fail -- accept failures and use setbacks as an opportunity to evaluate, assess and pivot if necessary. Also, be comfortable with failing quickly -- acknowledge when something isn’t working rather than increase investment in that piece of the project.

6. Report to the board early and often

Digital transformation projects will undeniably draw eyes from every corner of the organization, especially from the board. Quarterly updates won’t satisfy their interest. Successful digital transformation projects share significant evidence points in real-time to illustrate the ongoing value of the project.

With boards focused on quick and tangible returns, digital transformation isn’t an easy feat. And, while cost efficiencies are important milestones, the real value of digital transformation lies in long-term innovation. Selling digital transformation to the board is important but keeping the board on board with digital transformation is the real battle. Evolve with failures, remain transparent, rely on your supporters and continue mapping to the project’s purpose to empower the project’s success. 


As Iron Mountain’s CTO and lead of its Global Technology Organization, Fidelma Russo provides the leadership, vision and roadmap for how technology can further strengthen the company’s current and future product offerings, service delivery and overall business. Her previous roles include leading Dell EMC’s Enterprise Storage and Software Solutions team and serving as COO of Sepaton/HDS as well as executive holding positions with HP, Sun Microsystems/Oracle and others. She holds two US patents and serves on the board of SBA Communications.

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Guest Commentary

Guest Commentary

The InformationWeek community brings together IT practitioners and industry experts with IT advice, education, and opinions. We strive to highlight technology executives and subject matter experts and use their knowledge and experiences to help our audience of IT professionals in a meaningful way. We publish Guest Commentaries from IT practitioners, industry analysts, technology evangelists, and researchers in the field. We are focusing on four main topics: cloud computing; DevOps; data and analytics; and IT leadership and career development. We aim to offer objective, practical advice to our audience on those topics from people who have deep experience in these topics and know the ropes. Guest Commentaries must be vendor neutral. We don't publish articles that promote the writer's company or product.

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