Joe Pleasant, CIO, Healthcare

Interview Questions


  1. What is your preferred structure for an I/T department in an organization like yours in your industry? Why do you prefer that structure and why do you feel it serves the business?

Joe started in on this question by addressing the role technology plays in advancing the business.  He emphasized that technology has profound impact on how a business positions and succeeds in the market.  Therefore, his preferred model reflects that paradigm.

First and foremost, Joe believes that the CIO (I/T) needs to report into the leader who is strategic and active in the business.  He noted the CEO first, but only if they are active in the business.  He did state the COO is a good option too, if they are engaged in the strategy[1].  A leader with a combined focus is best in Joe’s opinion.  He was emphatic that the I/T leader needs to be a part of the strategic planning and operational vision and not an afterthought (a byproduct of models that don’t give the CIO direct access).

When asked how the structure should look below the CIO, Joe focused immediately on the development arm of I/T.  His opinion is that the development organization needs to report into the CIO, but that capability must align to the business and be embedded with the business.  Joe also centralizes the core I/T functions, “the utility stuff” as he put it.  This would include technology operations, infrastructure, help desk and other below the strategic radar functions that have high impact.

In healthcare, security is an acute need, therefore Joe also emphasizes a relationship with the security function within the structure.  He elaborated by noting that he has seen security report into technology and to a compliance office.  His preference was that it reports into a compliance office[2] and that the Chief Information Security Officer has dotted line responsibility to I/T.

Joe prefers for each line of business to have their specific direction and strategic objectives.  In his opinion, I/T is most successful when that level of granularity and clarity is accessible with the plan.  Joe assigns lead people to be the interfaces into the business.  The business lead and the I/T business relationship manager work very closely.  Both are held accountable to the business results.  Joe creates business alignment teams that monitor and collaborate on project portfolio groups aligned with the business line or business function.  For example, in Joe’s business he may have a team for the pharmacy business line or the supply chain business function.  They are focused on that line’s initiatives.

Joe is a strong proponent of quality governance.  Therefore, he endorses having a portfolio governance team that reports into the COO and an architecture group that reports into the CIO.  All progress is reported to this joint team.

Joe’s preference is to have a three year strategic plan that is formulated starting with the board of directors stating imperatives.  Once the imperatives are established through cooperation with the executive team (that includes the CIO) they are socialized and initiatives are identified to meet the goals.  The initiatives that are chosen as best are then analyzed to determine measurements of success and to prioritize it.

Joe prefers to have a dedicated I/T strategic plan for technology initiative that are below the strategic radar, but are very substantial.  He also envisions significant I/T content in the business strategic plan where technology enables it.


  1. What are the key areas / strategies / tenets you align with on every initiative to ensure it is aligned with the business?

Joe rolls out the objectives to his teams in a specific way.  He first ensures there is line of sight for the board to measure success.  Once this is established be breaks down the objectives into team objectives that are traceable back to the overall corporate objectives.  These departmental goals have line of sight as well to the strategic imperative.  “Everyone has to understand how that goal they have on their goal sheet lines up with the overall goal,” he said.

Joe also prefers to ensure that every initiative is aligned to making the quality of life better for the community.  This sounds like a broad statement, however, Joe has seen it applied successfully.  In fact, in his current organization, they have metrics to track the quality of life in communities they serve, even though they are being contracted by the healthcare organizations in those communities.  This submission to accountability on a metric where they are one degree of separation from being in total control is a testament to true objective driven focus.  So, Joe’s organization tracks how well his organization’s client perform against direct competitors in common communities on quality and cost.

  1. What are the key indicators you see that repeat themselves through your successful business aligned initiatives?

Joe looks for collaboration and communication on an initiative to give him a sense it is strategically aligned.

Joe also noted that not having the business feel like they are being driven by technology is another indicator of alignment.  His point is that the business needs to feel like they have crafted the solution, and are not only being forced into what the solution offers.  In reality, Joe noted that often times the real innovator in an organization is the technology being acquired.  “I think a lot of times the innovation spark is provided by the technology itself, and no one person can take credit.  However, I would not want the business to think that (implying he prefers when they feel it originated from them),” he said.

  1. How do you encourage your teams to stay invested in the business? How do you keep them business focused, and not technology focused?

First and foremost I/T’s compensation is directly connected to the business.  Joe prefers at least 10% of his team’s compensation be directly tied to business outcomes.  This gives all I/T line of sight to the business goals and keeps them invested.  Other tactics include shadowing of the business and joint meetings with the business.  Finally Joe prefers to publish the I/T strategic plan to I/T so that the entire team understands the goals.


  1. How do you maximize awareness of I/T successfully servicing the business? Up, down and laterally?

Joe uses a scorecard measurement approach to showing value.  This is a transparency based philosophy that uses performance to form perception.  Joe also mentioned the governance scorecards specifically and broke things down from the “utility side” and the “development side.”


  1. What are the most common barriers to business alignment you have faced repeatedly?

Joe sees that traditionally I/T’s business knowledge lags behind their “tech” knowledge.  This is natural in his opinion, but still has to be managed.

Second barrier Joe sees commonly is that financial resources are always short of the desires of the business.  It invites a constant scrutiny on all purchases or expenditures.  The solution to this is to create a culture that educates the business, but does it in a way that is never condescending.

The final barrier is change management awareness.  He noted that many in business want impact without the need for change.  They expect the technology to just magically make things more efficient, without changing anything in the process.

  1. If you had to highlight things that you learned from life lessons, what would they be?

Joe’s life experiences flowed directly from the last part of his answer to #6.  He noted that he has lived through the pain of implementing systems where the business did not have commitment to change.  He said it inevitably results in heavy customizations, so much so that the forecasted ROI is never achieved, because I/T ends up making the new system do exactly what the old system did.  He noted that today, he will not implement a technology until the business shows commitment to the change needed.  He was that adamant.  “I’ve been through it so many times I stand firm in my policy not to implement any solutions until the business commits to best practice driven organizational change management.  It is the right stance for the overall success of the organization,” he said.  “If the criteria (for the success of an initiative) is that the business is happy, then sometimes being happy is the wrong dream,” he said.

  1. & 9. Do you have any best practices or tricks of the trade that help you see when technology is being proposed for technology sake?  Do you have any real life stories where you saw a decision moving towards technology for technology sake and you were able to refocus the decision on the business?  How did you do this?  What were the results?

“When you are in the business long enough you can sniff that (tech for tech sake) out pretty quickly,” Joe said.  Joe noted that people are pushing ideas all the time, “but only about 5% will stick.”  The way Joe prefers technology to be scrutinized is by using organization proven formulas that are known to the business.  These evaluations are conducted at the architecture governance level.  They include metrics such as size of cost, benefit to the business, capital expenditure, ROI, resource consumption, and whether it is in the technology plan.  All ideas go through these filters without exception, and by stating a process that enforces a policy the subjective opinion is removed from the equation.

[1] Joe later on mentioned that the COO is his most preferred option.

[2] Joe’s perspective was in total alignment with the security professionals we interviewed. His opinion showed a professional humility in that he was willing to note that a technology affected function was best suited to report outside of his purview.

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