5 Things CIO Should Do in First 100 Days of Leading Digital Transformation

I am now one year into my third CIO role where digital transformation was a top priority. It's hard enough to jump into an organization as a new CIO and make an impact in year one and much harder to either lead or be a team member in a transformation program.

Bu that's exactly what I've been tasked to do, and my last several posts come from insights across all three organizations. My post on What Digital Practices Are Needed for Digital Transformation should give CIO and leaders a sense of when specific skills are needed. I've also posted on selecting platforms for digital transformation, and a bit on how to kickoff discussions on digital transformation.


First 100 Days In A New CIO Job


If you're in year one into your role as a CIO or technology executive, this post is for you. It will give you a sense of some of the things you have to look for and change in your first year in order to either lead or be an executive in a transformation program. In fact, chances are you'll have to do some of this in the first 100 days if you're hired with digital transformation as an expectation or stated goal.


The key to year one is a balance of execution (agile), finding efficient ways to learn the keys to the business, developing new talent, challenging the financial status quo, and evolving to a data driven organization. Here are the details:

  1. Find the Agile On Ramp - Even organizations that are already practicing agile, there's a maturity, consistency and culture that needs to be cultivated over time and experience. As I've said in previous posts, agile is a key practice to enable transformation. If the organization isn't practicing agile, then look for teams and projects to develop a beach head practice. If they are practicing agile, then look for teams that are leading in execution and see how to best utilize their skills and their experiences. 

  2. Don't "Learn the business", Develop Relationships - In my experience, it can be difficult to learn all the nuances of a business especially if it has different product lines and customer segments. I find it more beneficial to develop relationships with key customer facing people in the organization and learn the business through their experiences. The key is to find the "right" people - those that are very open to sharing information, or will take you on a customer call, or have ideas that challenge the status quo and may have innovative ideas that can translate to new products and services.

  3. Find the hidden talent - Transformation often requires a steep increase in the number of initiatives and projects being run in parallel. To pull this off, the CIO needs to find individuals with talent and leadership qualities that with mentoring can take on new responsibilities. This means getting to know the organization below the leadership level. Who can you rely on to be the next product owner, technical lead, or business analyst if you want to accelerate new programs?

  4. Review the financials - The hardest part of transformation programs is getting executive buy in, identifying financial returns for investment, and finding funding sources for programs. The CIO has to review with the Finance team IT spend and spending across the firm for places to reduce costs or shift spending to fund transformation projects. Don't expect to find a full business case or ROI just from cost savings, your objective in the earlier days is to find sufficient funding to get the transformation program started.

  5. Identify Underutilized Data - Many organizations collect a lot more data than they can analyze and use for decision making. Review what tools and data finance, marketing, and operations teams are utilizing and identify gaps - data they should be collecting or already have and need to leverage. Then consider developing a self-service BI program as a method to increase the analytics and data science capabilities of the organization. You'll need the data for later rounds of transformation and you'll need the organization to be more data driven in order to succeed in a digital business world.
This is on top of some good advice for CIO in their first 100 days from Gartner, McKinsey, CIO, and other sources.

By the way, this assumes that the CEO and the Board 'get' the digital disruption and the need for digital transformation. If they don't, you have some work cut out ahead of all this to get them understanding the digital trade winds and new ways to think about the business.

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