&
Blues
For small business owners
The Bookkeeping Blues
Aligning expectations and improving communication with your bookkeeper.
Presented by Monica Colgan · April 3, 2026
Monica Colgan.
Founder & Principal Consultant, Launch Industries
- M.S. in Organization Development — Central Washington University
- M.A. in Administration of Justice — University of Alaska
- B.A. in Law & Justice — Central Washington University
- 20+ years of business operations & management experience
- Personal bookkeeping journey — learned from the ground up
- QuickBooks certified
- Practical, hands-on expertise with small business bookkeeping
Who is Launch Industries?
A Seattle-based small business consulting firm — a one-stop resource for entrepreneurs and nonprofits seeking practical, hands-on support.
Bookkeeping specialists, payroll & HR specialists, and business operations consultants who simplify operations, manage payroll, maintain compliance, and implement time-saving systems.
The right support transforms a business — freeing owners to focus on strategy, growth, and community. Launch Industries empowers small businesses to operate with confidence and clarity.
Class objectives.
- 01Understand the bookkeeper's role — why misalignment happens and what bookkeepers actually do.
- 02Explore other financial roles — know who does what across your financial team.
- 03Identify service gaps — spot issues and assess their root causes.
- 04Set clear goals & align deliverables — match bookkeeping outputs to your business needs.
- 05Provide feedback & improve communication — constructive, consistent, actionable.
- 06Evaluate & adjust — know when to reset expectations or seek alternatives.
The business owner's financial role.
The leader and visionary for the company's financial operations.
Set Goals
Define financial priorities and KPIs.
Monitor Reports
Review financial data regularly.
Allocate Resources
Tools, staff, financial processes.
Ensure Compliance
Legal accountability for the business.
Make Decisions
Pricing, hiring, investments.
Understanding your bookkeeper's role.
- Day-to-day financial record keeping
- Categorize income and expenses
- Reconcile bank & credit card accounts
- Maintain accurate financial records
- Verify report accuracy
- Compliance with tax & regulatory requirements
- Monitor A/R and A/P
- Support decision-making with updated data
- Investigate transaction issues, correct P&L & Balance Sheet
- Bookkeepers are accountants — they're not
- They handle strategy — they focus on data
- They do all financial functions well — training is often limited
- They file all your taxes — many DO file Excise (DOR, City)
- They handle payroll taxes — usually your payroll provider (Gusto, ADP)
- They file your federal income taxes — most do not
Payroll Administrator.
Focuses on payroll processing and compliance.
- 01Process paychecks — including taxes, benefits & deductions.
- 02Ensure compliance with payroll laws.
- 03Handle employee tax forms — W-2, 1099.
- 04Maintain payroll records and resolve inquiries.
- 05Coordinate with HR for onboarding & pay adjustments.
Controller & CFO.
Oversees bookkeeping and accounting.
- Ensure financial accuracy and compliance
- Review and approve financial reports
- Monitor internal controls and processes
- Manage the bookkeeper and accountant
Develops and oversees overall financial strategy.
- Analyze financial risks and opportunities
- Manage funding, investments & financial planning
- Guide business growth through financial leadership
Tax Preparers.
Tax prep can be one generalist or split between specialists. Some practitioners cover both excise and income taxes; others focus on just one. Know which your preparer handles.
Files state and local excise taxes.
- Prepare and file state excise/sales tax returns
- Prepare and file city excise/B&O tax returns
Prepares and files federal taxes.
- Federal business returns (Form 1120, 1120S, 1065, or Schedule C)
- Personal federal returns (Form 1040)
- Identify deductions and credits to minimize liability
- Advise on quarterly estimated tax payments
Financial Advisor & Auditor.
Investments, retirement, wealth.
- Personal and business financial planning
- Retirement accounts, insurance, investments
- Long-term wealth strategies
- Examples: Edward Jones, TD Ameritrade
Audits for accuracy and compliance.
- Examine financial records for discrepancies
- Ensure compliance with regulations and policies
- Recommend improvements to financial processes
- Prepare audit reports
Why misalignment happens — the root of the bookkeeping blues.
Unclear Expectations
Neither party has defined what success looks like from the start.
Service Gaps
Errors, delays, or missing information erode trust over time.
Communication Breakdowns
Infrequent or unclear communication leaves issues unresolved.
Unrealistic Expectations
Both parties may expect more than the agreed scope allows.
Identifying service gaps.
- Reports are late or inaccurate
- Lack of proactive communication
- Inconsistent categorization of expenses
How to spot them: review past deliverables; compare outcomes to expectations.
- 01Lack of clarity around roles.
- 02Lack of clear expectations.
- 03Lack of written financial procedures.
- 04Lack of consistent communication.
Defining success with your bookkeeper.
Use SMART Goals — Specific, Measurable, Achievable, Relevant, Timely. Clear goals = smoother bookkeeping & better decisions.
Weekly A/P Reports
Every Monday by 12PM.
Cash Flow Updates
Every Friday by 12PM.
Monthly Categorization
All transactions done by the 10th for the prior month.
Monthly P&L Review
Meet the 3rd week of every month.
Books Closed
By the 15th of each month for the prior month.
Quarterly Finance Meeting
Owner, bookkeeper & accountant together.
Bringing goals and services together.
Turn objectives into actionable deliverables. Ask why each goal matters, then define the specific tasks that fulfill it.
Goal: "Maintain updated financial records"
Why it matters:
- Make informed financial decisions
- Stay loan-ready at all times
- Give your accountant a shot at on-time taxes
Track progress and accountability.
Task management software like ClickUp or Asana turns deliverables into trackable, accountable work.
Developing feedback for your bookkeeper.
Be Specific
State the issue clearly and define the expected change.
Be Consistent
Hold monthly finance meetings — scheduled in advance, with pre-set agendas, follow-up task lists, and your own follow-through.
Miscategorization
"Google transactions should be categorized as Software in the chart of accounts, not Advertising."
Scenario: late reports.
"We have already established that we need the books closed by the 10th."
"I haven't been receiving any 'final monthly finances' report."
"I need this reliably and regularly for our finance meeting with our accountant and our board of directors, which takes place the first week of every month."
"It is stressful for me when I go into that meeting without confidence that our finances are done."
"Plus, I rely on it to make financial decisions such as whether I can afford to hire another person or take on a new software expense."
"Can you please add a reminder to your calendar to send me these on time?"
Key principle: Be direct about the impact on your business — not just the missed task.
Scenario: missed tax deadline.
"As you know, our DOR report is due by the 25th of each month."
"I looked at our filing, which was completed late, and see part of the fee I paid was a $650 penalty for filing late."
"I am taking some responsibility because I should be checking in with you if I don't see a confirmation of filing on time, but I also don't want to micro-manage you."
"Thus, I expect that if you are responsible for tax filings, you will complete them on time, consistently, and if you have an issue, you will come to me before the deadlines so I can help troubleshoot and avoid penalties."
"If this happens again, I want to be transparent and let you know that I will start looking for a new bookkeeper."
Key principle: Acknowledge shared responsibility while setting a clear, firm boundary.
Building stronger communication channels.
Schedule Regular Check-Ins
Weekly, monthly, or quarterly depending on size and transaction volume — keep both parties aligned and issues from compounding.
Use Clear Updates
Concise emails or messages — no ambiguity about what's needed or when.
Provide Agendas
Written outlines for every meeting ensure productive, focused conversations.
Use the Right Tools
Shared platforms like ClickUp or Asana, plus shared calendars for deadlines.
What's "reasonable" — both sides.
It depends on your agreements with your bookkeeper…
- Operate within the agreed scope of work
- Operate with integrity:
-
- Do what they said they'd do, when they said they'd do it
- Communicate proactively when something is in the way
- Let you know when they spot issues
- Tell you when they lack the skill or knowledge
- Communicate expectations — don't assume; state your needs clearly and in writing
- Provide timely feedback — don't let issues fester; address them promptly and constructively
- Operate with integrity:
-
- Do what you said you'd do, when you said you'd do it
- Look at their work and flag issues
- Ask for help when you don't understand the reports
Minimum knowledge every business owner needs.
To spot issues, you need to know your accounting software well enough to check the work.
Bank vs. Register Balances
Notice when bank balances don't match the register in your software.
Last Reconciliation Date
Know how to see when an account was last reconciled.
Read Key Reports
P&L / Income Statement and Balance Sheet / Statement of Financial Position.
A/P and A/R
Know how to view your Accounts Payable and Accounts Receivable at any time.
Chart of Accounts
Recognize misclassifications (e.g., expense vs. COGS).
When to adjust or seek alternatives.
Reset, don't replace.
- New business needs or shifting priorities
- Limited resources or scope of work
Time to move on.
- Repeated errors or missed deadlines
- Lack of responsiveness
- Misalignment on values or goals
- Cost factors
Key takeaways.
- 01Know your bookkeeper's role — and your own.
- 02Set SMART goals and align deliverables to your business needs.
- 03Feedback is key! Communicate consistently, specifically, and with integrity.
- 04Know when to adjust expectations — or seek alternatives.
Independent Contractors & Employees: Navigating the Differences
12:00–12:50pm · Virtual via Zoom · FREE · Register at launchindustries.biz