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Executive Coaches and Experienced CAOs

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Executive Coaches

In early 2013 OMAA issued an RFP for Executive Coaching Services. Executives Coaching is a facilitative one-to-one, mutually designed relationship between a professional coach and a manager who has a powerful position in the organization. The coaching is contracted for the benefit of the client who is accountable for highly complex decisions with wide scope of impact on the organization and industry as a whole. The focus of the coaching is to assist the client in achieving a mutually identified set of goals to improve his or her professional performance and personal satisfaction - with the intent ot improve the effectiveness of the client's organization. OMAA Members are encouraged to consider the benefits of working with a qualified Executive Coach for personal skills enhancement, or that of their Staff. As a result of the OMAA RFP, five Executive Coaching firms have been selected as having an understanding of municipal government and with experience working with CAOS and/or their senior management teams.

Please Note: While these firms met the criteria of the RFP issued by OMAA, the association has no direct experience with any noted Executive Coach. In turn, OMAA provides no warranties or guarantees. It is the responsibility of the client to enter into their own agreement with an Executive Coach and to oversee performance.

 Cynthia Calluori / Cynthia Calluori & Associates

Cynthia Calluori

Cynthia Calluori & Associates Inc. is a leadership and coaching consultancy that provides professional services to organizations and individuals seeking to improve their effectiveness and rise to new heights. We work closely with clients to develop tailor made solutions that meet their needs. Our work includes the delivery of leadership focussed consulting, coaching and training solutions designed to unlock the maximum potential of untapped knowledge capital. Our coaches establish a relationship based on trust, collaboration, and integrity, which focuses on the needs and growth of the individual in a context which has high performance expectations. We partner with our clients to create strategies for personal and organizational growth, with a focus on performance. Our clients are individuals and teams in both public and private sectors. Cynthia Calluori founded and is the principal coach for Cynthia Calluori & Associates Inc.

 Sid Ridgley / Simul 


Sid RidgelyWe're very good at assisting you to "simultaneously look through the microscope and telescope" in preparing you for higher levels of leadership impact. The truth is, as a leader you need to be successful today (microscope) while you adapt and flex to be successful again tomorrow - in a changed world (telescope). Our executive coaching is about developing people, not fixing people. You'll receive both strategic and pragmatic guidance about how to improve your skills, competencies, attitude, style and brand. We have diagnostic tools and models that have been helping 2,500+ municipal/regional leaders since 2000. You will benefit from our expertise in leadership development, organization culture change, customer satisfaction, team building, and strategic planning. We're experts in helping you assess and decide on the transitions and transformation that increase the impact value of "you" in the workplace. Call us when unlocking the true executive in you, is important.

 Ben Cornell / Ward & Uptigrove 


Ben CornellWard & Uptigrove is a large accounting firm in Listowel Ontario, that also provides consulting services in HR, IT and Wealth Management. It is owned by seven partners and has a staff of approximately 50. Ward and Uptigrove provides services primarily in Southern Ontario. The Consulting and Human Resources (HR) practice was started in 2000 to provide HR services to municipal clients in southern Ontario. Our clients typically do not have their own HR Manager. Over the years, we have developed various HR services and expertise in the municipal sector including: CAO coaching, Council code of conduct, pay equity compliance, market checks, municipal organization review and restructuring, performance management (particularly CAO reviews-proprietary program), senior recruiting (particularly CAOs) job evaluations (proprietary system), job descriptions, pay administration, HR policy manuals, terminations and many other services typically provided by HR managers. We ensure the HR strategies developed and implemented tie into the overall municipal strategic plan. The HR consulting practice has four professionals.

 Randy Brooks / Wilson Brooks


Randy BrooksIn our WilsonBrooks practice, Marc Wilson and I provide a range of services to clients in both public and private sectors. In addition, for over ten years, we have worked with various municipalities, including executive coaching with CAOs, Commissioners, Directors, managers and supervisors.

What We Do: Coaching, Consulting, Facilitation, and Research

  • Coaching: Individual leaders, intact teams
  • Consulting on Strategy, Organization Design, and Change
  • Facilitation of Learning Sessions: leadership and team development, strategy, planning, leading change organization design, project start-ups, after-action reviews.
  • Research: New concepts and practices.

How We Work: We help clients to:

  • Take stock of how they're doing as an individual, a team, or an organization
  • Identify what works well, what to change, and how
  • Carry out change

Our criteria for successful coaching:

  • Personal, compelling reasons for the client to develop. Identifiable desired outcomes.
  • Establishing a clear path to the objectives with progress measures.
  • Boss' involvement; and touching base periodically with the boss, in tandem with the client.
  • Regular contact among the coach, client and boss.
  • Personality fit between client and coach

 Neville Knowles / Knowles Leadership Group


Neville KnowlesMunicipally Neville has coached CAO/CM's, GM's, Fire Chiefs, Deputy Chiefs, Directors in all Divisional fields and many managers. He's worked in London, Hamilton, Halton Region, Burlington, Sarnia, Chatham-Kent, Halton Hills, Belleville, Fort Erie, Huntsville, Perth County, Stratford, Town of Kawartha Lakes and the Town of Scugog. His coaching services have been engage by between 175 and 200 leaders within the sector to date. Further he has experience providing leadership coaching to Mayor's and Councilors.

Neville received his training in Executive Coaching from the Coaches Training Institute (CTI) of San Rafael, California, which is recognized by the International Coaching Federation. He's a graduate of CTI's yearlong Leadership Development program, a member of the International Coaching Federation and the London Chamber of Commerce.

Experienced CAOs

The following OMAA Members have years of hands on CAO experience and have provided an outline of their skills and areas of interest - which may be a fit for you and/or your organization.

 Michael Boggs


Michael BoggsServices available by telephone, internet or in- person including problem-solving/team-building/performance-management initiatives.

Financial/Performance Management - financial plans to meet council`s goals/objectives; tools to measure progress/results; evaluate performance from perspectives of efficiency/ effectiveness/community impact. 

Human Resources - policies/practices; negotiating employment contracts; succession planning.

Strategic/Operational Plans - planning for the future based on the mission/vision/values of council and public to provide effective/efficient services; evaluating services and service-levels; and reporting the results of operations to council/public. 

Mentoring - meet with senior staff to discuss contract/ expectations/performance; discuss organizations expectations; recommend training to meet expectations or alternative courses of action; and recommend management team-building.

 Dave Cash


Dave CashDavid is President of Cash & Associates Inc., a management consulting company he started, after retiring from over 30 years in municipal government in Ontario. He provides professional advice to his clients, with a particular emphasis on Economic Development; Urban Planning; Municipal Policy and Strategy; Organizational and Service Delivery Reviews.Recent projects have included developing specialized training workshops for Senior Management Teams; providing advice on municipal collaboration (York Region Northern Six); site location studies; planning policy reviews and executive searches. Interim CAO services can also be provided.

 Tim Dobbie


Tim DobbieTim Dobbie served as City Manager in the City of Burlington from 1995 to 2007. For the past six years, Tim has operated his own consulting company - Tim L. Dobbie Consulting Ltd. Tim's work includes organizational reviews for municipalities, staff/council relations, service delivery reviews and very importantly, mentoring of Chief Administrative Officers and City Managers for municipalities. In the past Tim has mentored City Managers in Parry Sound, Stratford, Hamilton, Brant County, London and the Township of Centre Wellington just to name a few. Tim would be happy to provide you with a proposal for mentoring for your specific needs.

 John Fleming


John Fleming"It's lonely at the top."Never more true than in local government, with all its transparency, conflict, fiscal constraint and dramatically changing access by the public to both information and public attention. "Coaching" can be a vital support; whether it be aimed at growth and development of newly appointed CAOs; the struggle to find better, more creative solutions to daunting problems; addressing difficult interpersonal relationships with Council and management; or simply surviving the constant attacks that today's transparent world brings to the CAO, with no other place to turn.There are many coaching firms and individuals "out there." Few of those bring a deep understanding of the truly unique challenges of senior management in the public sector, simply because they have not experienced it, firsthand. John Fleming Occasional Consulting is the sole practice of a seasoned professional who worked a lifetime in the public sector world, as a CAO, as a Deputy Minister, as the head of a national not-for-profit charitable organization, and now as a very active member of several Boards of Directors. John understands the challenges CAOs face, and their resulting needs.

 Mike Trojan


Mike TrojanMike Trojan retired as CAO of Niagara Region in 2013 after a career in Municipal Government of 35 years, serving at both the regional and local tiers.Mike recently completed a seven month interim management/consulting assignment as Vice-President Administrative Services with Niagara College. For more information on Mike's background and accomplishments please view the attached biography.Mike is now affiliated with StraNexus Inc. , a full service management advisory firm specializing in Industrial Engineering, Strategic Planning, program Management and Corporate Training.Contact Mike to find out more about how the unique Apprenticeship Program offered by StraNexus can improve services and reduce costs by applying Industrial Engineering techniques to streamline processes and/ or increase taxpayer value.

 Ron Shaw

Ron ShawRon Shaw recently retired from 35 years of public service including 30 years as a chief administrative officer in just two municipalities.  Ron can bring passion and experience to help with municipal organization reviews, targeted recruitment, policy development and project management.  His experience in leading a progressive single tier municipality can be translated into providing insight and guidance in a variety of municipal issues.  Ron is also available to just talk over what is going on.