Use this action roadmap to guide executive client discussions throughout the year.
Q1
January
Inventory outstanding grants and awards by type, issue date, quantity, vesting status, and option expiration date
Evaluate options, RSUs, and/or RSAs scheduled to vest and expected to be awarded this year
Confirm company blackout periods and trading windows
Review the existing Rule 10b5-1 plan to confirm scheduled trades and consider executing a new plan
Locate and analyze SEC Form 4 filings from the prior year
Analyze the most recent proxy statement for changes to the executive compensation plan and perquisites
Important dates
15: Q4 prior-year estimated income tax payments due
February
Calculate company concentration percentage and devise a diversification strategy, if needed
Calculate taxation of awards subject to be awarded or vest during the year
Determine whether to make a Section 83(b) election for restricted stock awards that vest in the future
March
Plan for the annual bonus against immediate, short-term, mid-term, and long-term goals
Evaluate liquidity and any need for lending services (mortgage, securities-based lines, etc.)
Q2
April
Confirm the form and amount of annual awards — most grants are made in February or March — and model the impact on the wealth plan and asset sufficiency
Important dates
15: Q1 estimated income tax payments due
17: Last day to make a prior-year IRA contribution
18: Individual tax returns due for the prior tax year
May
Review all estate plan documents
Analyze insurance policies (property and casualty, liability, health, disability, life) for adequate coverage
Perform a mid-year wealth plan review: confirm retirement contributions are on track and run an income tax projection to ensure proper payment through withholding or quarterly payments
June
Locate and analyze Form 4 filings for the current year
Important dates
15: Individual filing date for U.S. residents abroad
15: Q2 estimated income tax payments due
30: Deadline to elect to defer a bonus that qualifies as performance-based compensation
Q3
July
Analyze GRATs that may hold appreciated company stock
August
As kids or grandkids prepare for back to school, evaluate funding education through a Coverdell ESA and/or 529 plan
September
Important dates
15: Q3 estimated income tax payments due
Q4
October
During open enrollment, review health insurance coverage and other employer benefits
Evaluate whether to donate appreciated stock
Year-end tax planning: analyze whether to defer compensation earned next year, run a current income tax liability projection, and prepare an AMT projection
Important dates
17: Individual tax return due if a six-month extension was requested
November
Confirm retirement contributions are on track
Locate and analyze Form 4 filings for the current year
Analyze charitable giving goals and whether to donate appreciated stock or make other tax-deductible gifts
Calculate company concentration percentage and whether to dispose of stock
Consider tax-loss harvesting to potentially lower tax liability and better position the portfolio
December
Important dates
31: Deadline to elect to defer compensation earned in the following calendar year
31: Last day to contribute to charity for a tax deduction
31: Last day for 401(k) contributions
Educational content from advisingEquity. Dates reflect typical filing deadlines — confirm current-year dates before acting.
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