CC 2-28-2026
#1
Key Strategies for High
Functioning City
Councils and Staffs
Presentation
9999
Key Strategies
For High Functioning
City Councils & Staffs
City of Cupertino City Council/Staff
Workshop
February 28, 2026
Goals For This Session
• Refresh Key Concepts Regarding:
• Effective Governance
• Effective Council Working Relationships
• Effective Council/CM/Staff Working
Relationships
• Consider How These Concepts Can Be
Strengthened in Cupertino
Why Being a Council Member Isn’t Easy
• Challenging Issues
• Varied Opinions/Perspectives
• Group Decision Making
• Not a Group of Your Choosing
• Done in Public/Anyone Can Participate
Why Being a Council Member Isn’t Easy
• Media and Public Scrutiny (Social Media)
• Never Enough Resources
• Not Fully Appreciated for Your Time
Commitment
• Lack of Knowledge Regarding Your Role
• Less Patient/Understanding Public
Understanding You and Your “Teams”
• As Soon as You Get Elected You Become Members of Several Critical Teams:
Council
Council/CM
Council/CM/Staff
Council/CM/Staff/Commissions
Council/CM/Staff/Commissions/Public
• How Effectively These Teams Work Together Will Determine the Success of the Organization & Community
Why Is Effective Teamwork So Important?
Without A Strong/Effective Working Relationships:
• The Organization Will Not be Effective
• The Community Will Not Be Well Served
• Citizens Will Not Want to Serve
• You Will Not Be Able to Attract/Retain High
Quality Staff and Community Members
• It Will Not be an Enjoyable Experience
Teams
Succeed or Fail as a Group
• Is it Good or Is it Bad?
• Can Conflict Be Positive?
• Are Differing Ideas/Viewpoints “Conflict”?
• Can a Lack of Conflict Be Counterproductive?
• “Group Think”?
• No Challenge to Bad Ideas or Inappropriate
Conduct?
• Ethical Issues?
• Not Represent All Community Perspectives
• When Does Conflict Become Counterproductive?
TEAM CONFLICT
The Sources of Team Challenges
• Different Experiences & Backgrounds
• Different Policy Perspectives/Positions
• Varied Communication Styles/Failures in
Communication
• Lack of Clear & Consistent Expectations
• Varied Ways of Processing Information
• Personality Differences
• Differences in Handling Conflict
• Election Hangovers/Never Transitioning
• Role Conflict
• Lack of Trust
DIVERGENT VIEWS/OPINIONS: ACCEPTING DIFFERENCES
• Develop an Appreciation and Understanding Regarding Why It’s OK • Differences Are Not Usually a Result of:
• Dishonesty
• Lacking Values
• Intelligence
• Differences of Opinion are Normal and Should be Expected—Does it Reflect the Diversity of Opinion in Your Community?
• The Key Issue Is: How Does a Team Deal With Differences of Opinion? • Does It Devolve Into Personal Conflict? Does It Become About “Settling Scores”
Recognize That Differences of
Opinion is OK—And Often Desirable
It’s OK to Disagree
Not Appreciating the Difference Between
Campaigning & Governing
A Primary Area of Conflict
Accepting That There Can be Legitimate Different
Conclusions Reached From the Same Set of Facts
Understanding & Accepting Differences
Recognize Your Super-Power is Your Power of
Persuasion—Don’t Squander It
Your Ability to Persuade Requires:
• Trust
• Respect
Your Super-Power
TRUST: Start From a Position of Trust:
• If Start to Lose It, Confront the
Issues Causing the Loss
• Be Open to the Other Party Having
Good Intent
• Listen Thoughtfully
Nothing Works Without Trust
• Accept That You Will “Take the Heat”
• Your Job is to Make Tough Decisions That
Everyone Won’t Agree With—Embrace It!
• Exercise “Emotional Maturity” In Regard to
How You Respond
• When Under Pressure You Are at Risk of
Doing or Saying Things You Will Later Regret
Be Resilient
Key Indicator of City Organizational
Dysfunction: How Much Time, Money &
Focus are Devoted to “Inside City Hall”
Issues
Warning Sign
Key Questions
• What Do You and Your Fellow Council Members Need
From Each Other to be Successful?
• What Does the Council/Council Members Need From
the Manager and Staff to be Successful?
• What Does the Manager and Staff Need From the
Council/Council Members to Be Successful?
What Does The Council Need From the Staff? (Executive Team) • Complete & Accurate Information Regarding All Issues and Projects Brought Before Them
• Clear & Timely Information (No Surprises)
• Recommendations Based on Best Professional Judgement With Options
• Complete Policy Analysis (Including Implications of Decisions) • Projects/Policies in Alignment With Council Strategic Goals & Priorities
What Does The Council Need From the Staff? (Executive Team) • Accurate & Timely Information Regarding City Operations • Accurate & Timely Legal Support and Communication
• City Protocols & Procedures to Guide Decision-Making
and Communication
• Transparency (Records; Agendas; Communication)
• Reliable Records
• Clear & Timely Agendas and Minutes
What Does The Council Need From the Staff? (Executive Team) • Conduct City Business in a Neutral, Nonpartisan Manner • Provide Honest & Independent Professional Advice
• Willingness to be Frank with the Council Regarding the Feasibility/Legality/Appropriateness of a Proposal
What the Staff Needs From Council (Executive Team)
• Clear Direction (Policy Direction/Priorities)
• Realistic Prioritization/Recognition of Resource Limitations • Respect Staff’s Best Professional Judgement (Whether or Not You Chose to Follow It)
• Unified Goals/Strategic Alignment
• Constructive Feedback & Evaluation
• Trust
What the Staff Needs From Council (Executive Team)
• Professional Working Relationship/Environment
• Respecting the Difference Between Policy Making &
Implementation
• Adequate Resources to Meet Council & Community
Expectations
• Foster Trust & Collaboration With Staff
• Assure Adequate Legal Resources
• Support Established Procedures & Policies
What the Staff Needs From Council (Executive Team)
• Channel Communication Through the City Manager
• Refer Constituents to Staff Re Operational Issues
• Stick to Prioritized City Work Program
• Provide Questions re Agenda Items as Early as
Possible
• Try to Keep the Whole Community In Mind When
Making Decisions/Directing Staff
• Be Responsive When Staff Needs Feedback (Scheduling
Meetings, Etc.)
What the Staff Needs From Council (Executive Team)
• Respect for Legal & Procedural Requirements
• Support Realistic Workloads & Resources
• Support Policy & Procedure Manuals/Documents
and Promote Adherence
• Separate the Messenger From the Message
What Do Council Members Need
From Each Other? (KD)
• Respect for Different Perspectives and Opinions
• Effective Listening Skills
• Emotional Maturity
• Handling Conflict Respectfully
• Coming to Meetings Prepared/Do Homework
What Do Council Members Need
From Each Other? (KD)
• Treating the Public, the Staff and Other “Audiences”
With Respect
• Supporting Council/Board Decisions
• Dealing With Issues With Honesty
• Being Willing to “Move On” From Council/Board Votes
• Support Efficient Meetings
What Do Council Members Need
From the Manager and Staff? (KD)
• Establishing and Maintaining High Standards
for Work Performance
• Responsiveness to the Council and
Community Members
• Complete and Professional Staff Work
• Avoid Bringing Personal Value Judgments to
Recommendations
• Creativity and Innovation
• No Surprises
• Accountability
• Ethical Conduct/Integrity
• Straight and Complete Information
• Need for the Manager to be Politically
Astute, But Not Political
What Do Council Members Need From the Manager
and Staff? (KD)
What Do Council Members Need
From the Manager and Staff? (KD)
• Equal Communication/Information
• Respect for the Office
• Recognition of the Pressures Faced by
Elected Officials
• Good Customer Service/Community Member
Responsiveness & Follow-Up
• Keep Personal Opinions/Preferences in Check
What Do Council Members Need
From the Manager and Staff? (KD)
• Respect for the Policy Making Role of the Elected
Officials
• Long Term Planning Perspective
• Professional Competency
• Selection/Retention of High-Quality Staff
• Know When to Withdraw From the Discussion
What Do the Manager and Staff
Need From Council Members? (KD)
• Clear Communication and Feedback (Usually
Through the Manager)
• Tolerance for Mistakes/Imperfection—Focus on
Fixing the Problem, Not Blame
• Appreciation of the Difference Between
Professional/Technical Perspective vs. Community
Perspective
What Do the Manager and Staff
Need From Council Members? (KD)
• No Surprises/Blindsiding
• Avoid Jumping to Conclusions Regarding Community
Member Complaints
• Respectful Treatment
• Willingness to Set Priorities
• Ethical Conduct/Integrity
What Do the Manager and Staff
Need From Council Members? (KD)
• Don’t Attack the Messenger if You Don’t Agree With
the Message
• Clear Operating Policies/Respect for Those Policies
• Willingness to Make Tough Decisions/ Say “No”
• Openness to Creativity and Innovation
What Do the Manager and Staff
Need From Council Members? (KD)
• Provide Direction in Appropriate Ways
• Respect for Communication Protocols
• Service Quality Feedback Focused on the “What”
vs. the “How”
• Honesty/No Hidden Agendas
What Do the Manager and Staff
Need From Council Members? (KD)
• Respect for Form of Government/Different Roles &
Responsibilities
• Recognize (And Utilize) Professional Knowledge And
Experience
• Clear Policy Direction
• Support for Hiring Top Quality Staff
• Speaking With a Unified Voice
Six Attributes of Exceptional City
Councils
1. Develop a “Sense of Team”: Mayor/Council/City Manager
2. Recognizes/Respects Clear Roles and Responsibilities
3. Honor the Relationship With Staff and Each Other
Six Attributes of Exceptional City
Councils
4. Routinely Conduct Effective Meetings
5. Hold Themselves and the City Accountable
6. Practice Continuous Learning and Development
Your Legacy
• Your Time in Office is Short in Comparison
To The Time Frame of the City
• What You Accomplish is Important
• But You Will be Remembered As Much for,
If Not More, By How You Conduct Yourself:
• How You Treat Each Other
• How You Treat the Staff
• How You Treat the Public
Kevin C. Duggan
[email protected]
650-888-5850
CC 2-28-2026
#1
Strategic Planning
Presentation
City Council Retreat
City of Cupertino
Strategic Planning
Drew Corbett
2025 Priority Setting Workshop
2 March 2025 workshop to set priorities for the next two fiscal years (2025-26 through 2026-27)
Unanimous adoption of Strategic Vision Framework to guide decision-making and long-term planning
Six Council goals and three focus areas for review every two years; Council to reaffirm or revise
Creates framework for two-year City Work Program
3 Status Update – Related Initiatives
City Work Program
update in December
2025 – Modest updates
approved to CWP
2025-26 mid-year
budget update
scheduled for March 3,
2026
Capital Improvement
Program Update
scheduled for March 3,
2026
2026-27 operating
budget and 5-year CIP
development in
progress and on track
Present proposal for maintenance of the Strategic Vision Framework that:
● Establishes a consistent process and timeline
● Sets expectations for Council, staff, and community
● Aligns resources and status updates across the City Work Program, operating budget, and CIP
● Prioritizes staff time on service and project delivery Today’s Objective
Timeframe
Purpose and
Overview
Maintain Strategic Planning Framework
established in 2025 Priority Setting Workshop
Continue with goals and focus areas
affirmed or revised every two years
Two-year City Work Program developed in
conjunction, as are operating budget and
CIP
Ensures process continuity across election
cycles but does not preclude adjustments
Timeframe, Purpose
and Overview
Target Timeframe and Major Deliverables
Begin implementation of Year 2
City Work Program initiatives
July 2026
Provide mid-cycle (end of Year 1)
update on City Work Program
Sep/Oct 2026
Query Councilmembers on
initiatives for upcoming priority
setting cycle
Nov/Dec 2026
Annual new Mayor and Council
orientation session
December 2026
Target Timeframe and Major Deliverables
Staff consolidates
priorities and
develops high-
level resource
estimates
Jan/Feb 2027
Mid-year operating
budget and City
Work Program
updates
Feb/Mar 2027
Preliminary review
of upcoming 5-
year CIP
Feb/Mar 2027
Bi-annual Council
priority setting
workshop
March 2027
Study session to
introduce
proposed
operating budget
April 2027
Study session on
substantially
complete 5-year
CIP
May 2027
Delivery of
operating budget
and Council
approval of new
City Work Program
May 2027
Public hearings and
budget adoption
June 2027
Target Timeline and Major Deliverables
Begin
implementation
new City Work
Program
July 2027
Provide close out
report on prior City
Work Program
Sep/Oct 2027
CIP update to
Council
November 2027
Annual New Mayor
and Council
orientation
December 2027
Mid-year budget
and City Work
Program update;
preview of CIP
Feb/Mar 2028
Introduction of
proposed operating
budget
April 2028
Delivery of
operating budget
and CIP
May 2028
Public hearing and
budget adoption
June 2028
1. Does Council want to retain the Strategic
Vision Framework adopted in March 2025?
2. Are there adjustments Council wants to make
to the core elements of the framework?
3. Does Council have feedback on the proposed
timeline in support of the framework?
Next steps:
● Amend framework and timeline based on
Council feedback
● Return to Council for formal approval
Council Feedback
and Next Steps