Phil Tomassini, State Government Department CIO

Interview Questions

1. What is your preferred structure for an IT department in an organization like yours in your industry? Why do you prefer that structure and why do you feel it serves the business?
Phil Tomassini’s vision of an IT organization is definitively clear. Phil prefers a consensus driven structure. In other words, he prefers a structure that is collaborative and allows the towers within the structure multiple checkpoints and mechanisms for their voice to be heard. The CIO in Phil’s preferred structure reports to the Chief Executive of the organization it supports, which in his case is the Secretary of the Department. He also supported a matrix organization into the State CIO, so that both department and state level IT objectives could be addressed. Tomassini insists IT needs to have a “seat at the table”, a phrase I heard time and time again from many leaders in the interview cycle. Tomassini believes that the IT structure should be custom made for the business, meaning that the org chart below the CIO is heavily influenced by the business it supports.

With that noted, he achieves his collaborative culture and strategic precision by creating multiple oversight teams. This is a centralized approach to standards, while allowing the structure to remain nimble. It resembled the quote “You make policy for direction and you manage by exception.” So, the oversight structures set the policies and the branch structures manage to the policies. This is a centralized structure through committee, and it works well within the state government environment. Tomassini prefers four structures including an IT Executive Committee, a Project Management Office, an Architecture Committee, and a Quality Committee. Each has their role in setting standards and project oversight.

Phil utilizes one additional method for flexibility and that is a vendor managed services team and staff augmentation mechanism to support the internal structure. This is a significant advantage to Phil in the state government environment, as it can often be difficult to approve internal headcount or secure project focused resources. By combining the capabilities of the committee oversight structure, with the fast procurement capability for staffing centric resources, Phil positions his IT group to respond to changing business needs.

The oversight structure also gives strategic clarity to the IT group. Oversight structure ensures projects succeeding based on common expectations and alignment with business. By combining business alignment with focused policies and common sense methodologies, Phil believes the structure is the best available structure for the industry within which he works.

2. What are the key areas / strategies / tenets you align with on every initiative to ensure it is aligned with the business?
First and foremost, Phil sets the department mission as objective #1. He opens his strategic plan with the department mission statement. He likes it to be the number one objective, and in that way he leads from the front and his teams see that business alignment is paramount. From there, he prefers to break the objectives out into eight core tenets, with at least 75% being directly from the business, and one to two being foundation level IT initiatives such as infrastructure upgrades or shared services tools to service more than one initiative. Some of the tenets included:
• Modernization,
• Workforce Development and Organizational Alignment,
• Improved customer experience.

He also noted “There always needs to be some IT focused objectives that will enable a department to service the business.”

3. What are the key indicators you see that repeat themselves through your successful business aligned initiatives?
Phil drives collaboration and consensus within his teams and his expectations are high that his teams execute that way with their business counterparts. Therefore, he likes to see productive and professional problem resolution within an initiative. When he sees this, he has confidence that it is business aligned. When he doesn’t, it is a red flag. A cooperative environment to him is a signal that satisfaction is high within the business.

4. How do you encourage your teams to stay invested in the business? How do you keep them business focused, and not technology focused?
Phil starts with making his group’s mission and vision statement identical to the overall business mission and vision statements. He also creates a key objectives roster annually and makes 75%of those objectives business focused. These objectives then become the summary level objectives to which team and even personal objectives will map.

He also employs hands-on tactics such as having IT team members work “on the floor” so to speak with the business. He sets the bar high by expecting IT to know the business (through hands-on experience) as the business knows it. This means shadowing the jobs they automate and seeing what the business people see daily. Finally, he does employ trainings for his people with a business focus. He believes in investing in his people.

5. How do you maximize awareness of IT successfully servicing the business? Up, down and laterally?
Phil uses group events to get the word out on success. He holds Semi-Annual All Hands meetings. His most recent meeting was fully dedicated to sharing success stories and getting the teams invested in the successes. He shows a short poem at the beginning of this meeting. I had the opportunity to sit in the meeting, and there was an atmosphere of recognition and acknowledgement. The poem went like this:
“As I see it…..
Stop and smell the flowers.
Some things we get to do only once, and we rush by them and miss the moment that will never be repeated.
There are people in our life that we’ll be too busy for; stop and give them your attention.
We are rushing from here to there and miss so many things that if we stopped for a moment those things could bring a ray of sunshine to our lives.
In our haste we miss many magical moments, that if we stopped to see them they can make a big difference in our life.
Our trip on this planet is very short; invest your life in creating a life of fulfillment. Put things in perspective and don’t spend your life worrying, find solutions and move on.
Take the time to smell the flowers along the way, cherish your moments, your family and friends and be thankful for the things that you have attracted into your life.”

The tone was that successes have certainly not “finished the job,” but rather they are steps along the way. Phil brings business people into the meeting to celebrate the successes, and often they will be the ones presenting.

Phil augments these group events with quarterly newsletters that includes a CIO Section which focuses on successes as well as upcoming initiatives. He also provides an email newsflash announcement which serves as a regular bulletin board highlighting successes.

Finally, Phil provides mechanisms for his entire IT team to report successes for review and publication. He established a special email address that team members can use to send a note about the success. It is almost like a general suggestion box, only it is used for providing success stories, not suggestions.

6. What are the most common barriers to business alignment you have faced repeatedly?
Phil noted that one of the frequent barriers he sees is that many people feel that change and alignment can only be accomplished through significant financial investment. He takes the approach that every day, if his team makes their routine decisions with a business alignment in mind, change can come without spending one extra dollar. His point: financial constraints are not obstacles to change. Change can happen within the current scope of duties. Change does not always cost more.

Another obstacle was not knowing expectations. Therefore, he heavily emphasizes a clear strategic planning process (see the answer to #8).

Finally, he notes that, many times, IT doesn’t assume the role of innovator. He encourages his teams to stay current and think out of the box.

7. If you had to highlight things that you learned from life lessons, what would they be?
At his current position, Phil did not have initiatives that he would say were failures. He was not complimenting himself by stating this. Rather, he noted he relied on experience to make impending failures and turn them into “close calls.” Most notably, he relied on the experience of working with the business to execute even if it ventured off what the original plan had predicted. It was reminiscent of the saying “Don’t work hardest to make the perfect plan. Rather, work your hardest to make your plan perfect.” The point was you have to adapt to challenging situations. He put at the top of the list that the business should be consulted at every step of the way. Relationship and communication builds alignment. His primary message: “Learn, pivot, and succeed through the lesson. Never give up.”

8. Do you have any best practices or tricks of the trade that help you see when technology is being proposed for technology sake?
Phil supports using a formal and rigorous process to flush out initiatives that may be being proposed simply for technology sake. He noted a tool specifically as one he personally likes (Decision Lens). This tool forces a strategic planning process that brings everything back to business objectives. These objectives are then modeled and all initiatives are scored for how they support the objectives. The scores reveal the initiatives that are most business aligned, simply because the formula is made up only of already agreed upon business objectives. One caveat to this process is that he doesn’t support that the score alone is the final determinant. He supports a “veto” step where the executive sponsor has the opportunity to override the output of the process and personally disapprove. He encourages this to ensure the human element and personal investment of the sponsor are always present.

Another practice Phil supports is to eliminate shadow IT. He likes all projects in the open. This way he ensures there is no “hidden money” to fund “shadow IT.” His strategic planning process is his main instrument to achieve that goal.

9. 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?
Phil took the approach of noting a story where he was the one proposing a technology that turned out to be a technology for technology sake. He noted he had come up with an idea for a mobile application. He was personally convinced it would have value for the business so he started preliminary planning for the initiative. His instincts told him to check with the business so he set a meeting with each and every business owner that would be affected. What he learned surprised him. Each and every business owner told him the idea was not the right one, He said that each of them had a different suggestion, and their suggestions were all the same. So, he changed the priority of the initiative, implemented the idea, and ended up attaining ROI within the first year. The lesson: consult and listen to the business. Ideas in a microscope are dangerous and often wrong.

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