Michelle DiGruttolo

Michelle DiGruttolo

Shorewood City Council Candidate

Biographic information. Tell us about yourself.

As a candidate for Shorewood City Council, I bring over 25 years of leadership and service experience, combined with a deep passion for preserving the unique character of this community. After serving as an Army Intelligence Officer in the U.S. Army, where I specialized in national security, geopolitical risk analysis and strategic intelligence, I retired and chose Shorewood as my home due to its vibrant community and natural beauty. My military service has shaped my ability to solve complex problems, strategically plan in resource-constrained environments, and to transform poorly performing teams into high-performance organizations, skills that I am eager to apply to our local government.

I hold an MBA from the University of Virginia and a master’s in political science from the University of North Carolina, giving me a strong foundation in both business and public policy. These qualifications have been instrumental in my career, where I successfully built and led two geopolitical consulting practices, advising businesses on navigating complex global markets. I am currently the founder and principal consultant at Sage Raven Advisory, where I work with clients to mitigate risks and develop long-term strategies. This combination of business acumen and public service uniquely positions me to address the fiscal challenges facing Shorewood while maintaining a strong commitment to community values.

In addition to my professional and public service background, I am actively involved in the community as the treasurer of our local VFW and a member of the American Legion, where I support local youth leagues and community activities. These experiences have given me a deep understanding of the values that make Shorewood special, and I am committed to ensuring that our city remains a place where residents feel connected, supported, and proud to call home.

Describe the skills you have that will make you a good Shorewood councilmember.

- How have you demonstrated those skills in the past?

The skills and experience I bring to the Shorewood City Council are ideally suited to tackle the pressing issues facing our community. My 25 years of military leadership have given me the ability to create clear, strategic visions—something our city needs to align decisions, actions, and investments for a sustainable future. I have a proven track record of developing and executing mission-driven plans that synchronize resources across departments, which is crucial for updating Shorewood’s outdated strategic plan and ensuring our commissions and departments are working together with prioritized budgets and timelines.

I also understand the importance of transparency and accountability, skills I refined in both my military and consulting careers. I will bring fiscal discipline to the City Council by ensuring taxpayer dollars are spent wisely, with a clear rationale behind every decision. No more reckless spending without oversight. As a small business owner and consultant, I understand the importance of evaluating contracts and ensuring that city employees—not outside contractors—are empowered to lead and manage critical projects, holding all parties accountable for their performance and costs.

Finally, my background in geopolitical risk analysis gives me a unique perspective on understanding long-term risks and the need for resident-centered governance. I will work to end the trend of making decisions that benefit only a small percentage of residents. Instead, I will actively seek input from the entire community, ensuring that every project reflects the needs and priorities of all Shorewood citizens while stabilizing the city’s financial future. With my skills and experience, I am committed to delivering responsible, transparent, and effective leadership for our city.

If elected you will serve for 4 years. What do you see as the top 5 challenges or opportunities for the council to address during that time?

  1. Lack of an up-to-date comprehensive, synchronized, and vision-oriented strategic city plan that outlines our vision, mission, and values for the future of Shorewood. Shorewood faces several significant governance and financial challenges that demand immediate attention. The city currently operates without a clear vision or an up-to-date strategic plan to guide its decisions, actions, and investments. The lack of synchronization between the city’s commissions, departments, and budgets has led to inefficient spending and poorly prioritized projects. Additionally, the decision-making process of the City Council is opaque, offering little transparency to residents, and failing to solicit input or provide clear rationales for budgetary decisions.

  2. Unprioritized and irresponsible spending and insufficient bond oversight. Over the past few years, Shorewood has seen reckless spending and an unsustainable rise in debt, with over $23 million in bonding debt incurred in just 3.5 years—doubling the debt from previous councils. Critical decisions, such as contracting with outside firms like Bolton & Menk, have resulted in costly overruns and inefficient project management. The city has prioritized projects that benefit only a small percentage of residents, while ignoring the broader needs of the community. Residents deserve fiscal responsibility, transparency, and input in decision-making, but the current trajectory of unchecked spending and debt threatens the city’s future stability.

  3. No consistent mechanism for soliciting and incorporating resident input or feedback. One of the key issues facing Shorewood today is the lack of a transparent and accessible process for gathering input, feedback, and ideas from our residents. The current system is fragmented, difficult to navigate, and fails to represent the diverse voices in our community. Decisions about resources, projects, and investments often seem disconnected from the real needs and priorities of Shorewood residents, with no clear guiding principles to drive them.

  4. Lack of Contractor Accountability and City Oversight into Outside Contracting. The lack of contractor accountability in Shorewood has led to multiple mismanaged projects that have cost the city and its residents significant funds. One glaring example is the Manor Road mill and overlay project, where engineering consultants, Bolton & Menk, failed to properly survey the boundary, leaving the project 150 feet short of the Deephaven border. Now, Shorewood is paying an additional $21,000 to cover the costs, while Bolton & Menk continues to bill the city for their failed work. Similarly, the Eureka Road North project was initially over-engineered, and it was only through the persistence of local residents that the city was able to save $1.3 million in unnecessary construction. Other projects, such as Birch Bluff, Strawberry Lane, and Shorewood Oaks, have suffered from extravagant spending, poor oversight, and inadequate inspections. Despite these costly mistakes, the city chose to extend Bolton & Menk’s contract for another three years instead of hiring a full-time engineer. Taxpayers deserve better fiscal responsibility, transparent project planning, and genuine oversight from the City Council to prevent these wasteful practices from continuing.

  5. Lack of a cohesive, synchronized and updated strategic plan for its parks and green spaces. The current plan is outdated and not aligned with the city’s budget priorities, leading to uncoordinated, ad hoc park improvements that fail to address the evolving concerns and priorities of our residents. It also lacks alignment with the city’s overall strategic plan, leading to confusion, fragmented budgeting, and resource allocation that doesn’t match the needs of our community. As a result, park projects are often out of sync with what our residents want and deserve. One example is the city’s “Bee Safe” policy, which is confusing to residents, staff, and park commissioners. This disorganized approach to park management and environmental sustainability is unacceptable and calls for immediate reform. The city needs a comprehensive, transparent plan that aligns its resources with the needs of all residents, stabilizes its finances, and brings accountability to how decisions are made.

What policies would you propose to address your priorities? Be specific.

  1. Comprehensive Strategic Planning Policy.
  • Policy Proposal. Draft and implement a new strategic plan that includes a clearly articulated vision and mission for Shorewood. The City Council should develop this plan with resident input and prioritize long-term sustainability, aligning departmental goals with available resources.
    • Implementation. Create a citywide task force to gather input from residents, city commissions, and departments. The task force will develop a timeline-based plan with budget allocations tied to clearly defined priorities.
    • Benefits. Synchronizes efforts across departments (Parks, Planning, Engineering), ensures budgets are aligned with needs, and creates a clear roadmap for future investments.
  1. Fiscal Accountability, Budget Transparency and Debt Management.
  • Policy Proposal 1. Ensure quarterly public budget reports provide detailed information about spending, budget priorities, and the rationale for key projects. Require metrics to evaluate success and make these reports easily accessible to all residents and include an opportunity for public feedback.
    • Implementation. Develop a budget oversight committee comprised of council members, finance professionals, and residents to review spending regularly and provide recommendations.
    • Benefits. Increases transparency, fosters community trust, and ensures fiscal decisions are aligned with Shorewood’s broader needs.
  • Policy Proposal 2. Implement a debt management policy that requires any new bonding to be tied to specific projects with clearly defined public benefits. Residents, in conjunction with the budget oversight committee will have the opportunity to review new bonding, and the staff will provide information for residents about the benefits and tradeoffs of each bond proposal.
    • Implementation. Establish a cap on annual bonding and require a public referendum for any bond that exceeds a certain threshold. Provide a clear articulation of the reasons for debt accumulation and its long-term impact on residents.
    • Benefits. Stabilizes Shorewood’s financial future, ensures debt is incurred responsibly, and prevents excessive burden on taxpayers.
  1. Resident-Centered Project Prioritization.
  • Policy Proposal. Establish a resident input policy that requires public consultations before approving any major project to ensure that projects benefit a majority of residents, not just a small subset.
    • Implementation. Host community forums/town halls (in-person AND online) and provide online surveys to gather feedback on proposed projects, prioritizing those with broad public support.
    • Benefits. Engages residents in the decision-making process, ensures public funds are spent on projects that reflect community needs, and avoids unnecessary expenditures on projects that lack public backing.
  1. Contractor Accountability and City Staff Roles in Contracting.
  • Policy Proposal. Introduce a contractor accountability policy that limits the use of outside contractors. City staff will lead all major projects, and seek advice, not oversight from contractors.
    • Implementation. Conduct a cost-benefit analysis of contractor use and develop a plan to hire full-time city engineers or professionals to reduce dependence on outside firms.
    • Benefits. Reduces excessive contractor spending, increases accountability for project outcomes, and ensures long-term cost savings by building internal capacity.
  1. Update the Parks and Green Spaces Strategic Plan.
  • Policy Proposal. Review, update, and adopt a comprehensive parks and green spaces strategic plan that aligns with the city’s budget priorities and focuses on sustainable, long-term planning. This plan will ensure that park improvement projects are not carried out on an ad hoc basis, but instead are part of a coordinated strategy that reflects the community’s environmental goals.
    • Implementation. Work with the Parks Commission, environmental experts, and residents to update the current plan and ensure it includes:
      • A coordinated and synchronized timeline for park improvements.
      • Budget allocations tied to specific projects.
      • Alignment with environmental standards to maintain the city’s status as a bee-safe city.
    • Environmental Commitment. Reinforce the city’s commitment to bee-safe practices by ensuring that the integrated pest management plan adheres to non-toxic, eco-friendly alternatives and follows the rules necessary for bee-safe certification.
    • Benefits. This policy will provide a clear, coordinated vision for the future of Shorewood’s parks and green spaces, reduce the influence of individual biases in decision-making, and prevent the haphazard implementation of projects. It will also demonstrate a serious commitment to environmental sustainability and align the city’s green space initiatives with its budgetary priorities.

You are asking to represent the citizens of Shorewood and if elected, will be one of the public faces of the city. How would you describe the top 3 things about Shorewood that makes it a great place to live?

Shorewood is a truly special place to live for several reasons. First, its natural beauty and abundant green spaces make it a haven for outdoor enthusiasts and families who value access to parks, trails, and lakes. Shorewood’s commitment to preserving its natural environment offers a perfect balance between suburban living and nature. Second, Shorewood is a close-knit community where neighbors care for one another, and residents are actively engaged in community events, local initiatives, and supporting small businesses. This sense of community fosters a strong feeling of belonging. Lastly, Shorewood offers excellent amenities and quality of life, from its well-maintained public spaces to its proximity to both nature and urban centers, providing residents with the best of both worlds.

What sets you apart from the other candidates?

What sets me apart from the other candidates is my deep commitment to servant leadership, which has been the driving force throughout my 25 years of military service. During my career as an Army Intelligence Officer, I learned to lead by putting others first, ensuring to prioritize the mission and the needs of the entire stakeholder community This dedication to service is reflected in my volunteer work within Shorewood, where I have had the privilege of serving on the Park Commission. Through this role, I have gained valuable insight into the city’s environmental and community needs, while also working to preserve and protect our parks and green spaces. Additionally, my volunteer work at the local VFW and my involvement with the American Legion further demonstrate my commitment to giving back to the community. These experiences have not only allowed me to integrate myself into Shorewood’s fabric but have also strengthened my resolve to serve this city with integrity, transparency, and accountability. I am running to ensure that every resident’s voice is heard and that we work together to build a brighter future for Shorewood.

Candidate website: https://michelleforcouncil.com

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