From Scorekeeper
to Strategist
Four live working sessions for accounting firm leaders making practical decisions about services, team capacity, client relationships, technology, AI and repeatable delivery.
Program details
Thanksgiving week: no live session on November 26.
What to expect
Each session combines concise facilitator instruction with practical frameworks, individual exercises, discussion and peer input.
Participants use information from their own firm as the basis for the work. This may include:
- a current service list
- team roles and recurring responsibilities
- a working client list
- the firm's technology stack
- an AI tool or vendor under consideration
- a process that needs to be documented
The program does not prescribe one operating model for every firm. It provides a structured way to evaluate choices, apply relevant frameworks and identify practical next actions.
Participants control what firm or client information they share. Sensitive or confidential information should not be entered into workshop tools unless the firm has approved their privacy and security.
By the end of the series, you'll be able to
Classify current services using the Four Quadrants and evaluate them using the Traffic Light framework.
Prioritize services to stop, outsource, automate or focus on.
Map recurring work to the team roles best positioned to own it.
Evaluate client relationships using value, effort and strategic-fit criteria.
Assess technology applications using defined selection, integration and cost criteria.
Apply an AI vendor due-diligence framework before using a tool with firm or client information.
Distinguish policies, procedures, workflows and tasks, and draft a procedure that can be peer-tested.
Reserve your seat
Registration includes all four live, 90-minute working sessions, participant exercises and 6 CPE credits, subject to the published attendance requirements.
Complete four-session series · Thursdays, 2:00–3:30 pm ET · Nov 5, 12, 19 & Dec 3, 2026
Register for the SeriesThe four sessions
Foundation and Service Portfolio
Participants begin by assessing the services their firm currently provides. The Four Quadrants framework distinguishes Operator, Steward, Catalyst and Strategist work, while the Traffic Light exercise identifies services that energize the participant, may belong elsewhere or should be reconsidered. The $100K Question then asks participants to design a service mix without allowing current revenue constraints to determine every choice. The session concludes with a specific 30-day service commitment and an accountability check-in.
- Distinguish between Operator, Steward, Catalyst and Strategist services.
- Apply the Traffic Light framework to a current service portfolio.
- Use the $100K Question to prioritize services and articulate a draft statement of unique value.
- An inventory of the services your firm currently provides
- A Traffic Light assessment of those services
- Stop, Outsource, Automate and Focus decisions
- A 30-day service commitment
- A marked service inventory
- A prioritized set of service decisions
- A draft unique-value statement and one dated next action
People — Team and Clients
This session examines who performs the work and which clients receive the firm's capacity. Participants use the 52-Card Team Pickup to sort recurring responsibilities across four functions: Business Owner/Strategist, Administration, Business Analyst and Technical. They then evaluate actual client relationships using the Gold, Silver, Bronze and Fire framework and a Value versus Effort matrix. The exercises help participants identify work sitting in the wrong role, consider which role could release capacity and distinguish relationships to grow, change or reconsider.
- Distinguish the four functions within a scalable advisory team.
- Map recurring work to the role that should own it.
- Evaluate client relationships using value and effort and identify a potential area of specialization.
- Current team responsibilities and recurring tasks
- The role that could release capacity next
- A portfolio assessment using five to 20 current clients
- Potential advisory relationships, wrong-fit clients and vertical patterns
- An initial work-and-role map
- A client portfolio map
- Named team and client actions for the next 30 days
Technology and AI
Participants evaluate technology as an enabler of consistent service delivery rather than a collection of disconnected applications. The Little Black Dress approach focuses the firm on four to six core applications, supported by the 80/20 principle and six app-selection criteria. Participants cost a sample advisory technology stack and examine integration and document-retrieval considerations. The second half distinguishes generative and agentic AI and introduces governance, human review and vendor due diligence before AI is used with client work or data.
- Apply the Little Black Dress, 80/20 and app-selection frameworks to technology decisions.
- Evaluate the categories, integration requirements and cost of an advisory technology stack.
- Assess an AI vendor using data, security, contractual, oversight and audit-trail criteria.
- The direction of your firm's core technology stack
- A costed technology-stack exercise
- An assessment of one AI vendor or tool
- A narrow AI pilot or governance next step
- An initial core-stack direction
- A completed sample technology-stack cost assessment
- A Go, Conditional or No-Go AI vendor assessment
- A defined next step for AI evaluation or governance
Application Week
Thanksgiving week — no live session on November 26. The program pauses for Thanksgiving week. Participants may use this interval to complete unfinished worksheets, test one decision with a colleague and identify questions to bring to the final session.
Procedures and Playbooks
The final session focuses on making important work clear, repeatable and less dependent on one person's memory. Participants distinguish workflows from tasks and policies from procedures before applying the Seven Rules for Procedures. They cost a procedure-supporting technology stack and draft both the policy context and ordered steps for a month-end reconciliation procedure. A peer-review exercise tests whether someone who did not write the procedure could use it without additional explanation.
- Distinguish workflows, tasks, policies and procedures.
- Apply the Seven Rules for Procedures and identify the information a usable procedure requires.
- Draft and peer-test a month-end reconciliation procedure.
- The tools required to support procedure management
- A sample procedure technology stack
- The policy and procedural steps for a month-end reconciliation
- A peer-review gap assessment
- A 48-hour documentation commitment
- A costed sample procedure technology stack
- A draft policy and month-end reconciliation procedure
- A list of gaps identified through peer review
- A named procedure or procedure owner for immediate follow-up
What you'll leave with
Depending on the information brought to the sessions and the time required for each exercise, participants can expect to leave with:
- a service inventory assessed through the Four Quadrants and Traffic Light frameworks
- a prioritized Stop, Outsource, Automate and Focus decision set
- a draft statement of unique value
- an initial teamwork-and-role map
- a client portfolio assessment
- an initial direction for a focused core technology stack
- a completed sample technology cost assessment
- an AI vendor due-diligence assessment
- a draft policy and month-end reconciliation procedure
- peer-review feedback on the procedure
- dated 48-hour and 30-day implementation commitments
These are working artifacts and initial decisions. They are not a completed CAS practice, comprehensive firm strategy, finished AI governance program or fully implemented procedure system.
Prerequisites & advance preparation
Suggested advance preparation: no formal written prework is currently specified. To obtain the greatest practical value, participants should have access to:
- their current service list
- a summary of team roles and recurring responsibilities
- a working list of five to 20 clients
- their current technology applications
- one AI tool or vendor they are considering
- one process that would benefit from clearer documentation
Suggested participants — the series is designed for:
- accounting firm owners and managing partners
- partners responsible for firm direction or service delivery
- CAS, CAAS and advisory practice leaders
- practice managers and operations leaders
- senior leaders responsible for capacity, client strategy, technology or process improvement
Facilitators
Penny Breslin
Penny Breslin is an accounting industry leader, entrepreneur and co-author of It's Not Just the Numbers. As the founder of MoneyPenny, she has helped accounting firms build capacity, strengthen their operations and create better client experiences through outsourced accounting, tax and back-office support. Penny also co-hosts the It's Not Just the Numbers podcast, where she explores the people, technology and ideas shaping the future of the accounting profession.
Damien Greathead
Damien Greathead is an accounting technology and growth leader with more than 17 years of experience helping accounting firms and software businesses grow. He has held senior roles with Intuit, Dext and Ignition and is the co-author of It's Not Just the Numbers. Damien also co-hosts the podcast of the same name, where he explores the people, technology and ideas shaping the future of the accounting profession.
About the Sponsor
The CPA Trendlines Academy (Thomas Advisors LLC d/b/a), #170718, is registered with the National Association of State Boards of Accountancy (NASBA) as a sponsor of continuing professional education on the National Registry of CPE Sponsors. State boards of accountancy have final authority on the acceptance of individual courses for CPE credit. Complaints regarding registered sponsors may be submitted to the National Registry of CPE Sponsors via its website at nasbaregistry.org.
