Sending Docs Checklist For Tax Planning

The STP handles the data. These questions are about thinking, not paperwork. You do not need written answers- just come prepared to discuss. Like, really really prepared.

Keep in mind that tax projections and tax strategy often go hand in hand. All WCG advisory platforms include at least one tax strategy session plus an end of year strategy session, so these questions are relevant regardless.

• Capital Capacity. How much cash or borrowing capacity can you realistically deploy into a tax strategy without straining your lifestyle or core investments? Be honest here.
• Time Commitment. How much time can you or your spouse (or both) consistently commit to a strategy that requires active participation (hours per week or month), including documentation and oversight?
• Risk Tolerance. How would you describe your risk tolerance (conservative, moderate, or aggressive), both financially and from an IRS audit perspective? We ask this in the STP too, but here we go deeper.
• Income Volatility. Do you expect your income to increase, decrease, or fluctuate over the next few years, and how confident are you in that outlook?
• Strategy Awareness. Are there specific strategies you have heard about (STR loophole, cost segregation, oil & gas working interest, car washes, structured equipment leases, etc.) that you want to explore further or eliminate quickly? Any “bartender advice” worth pressure-testing? Feeling any tax deduction FOMO? Are you tired of your neighbors paying zero tax?
• Existing Strategies. Are there tax strategies you are already implementing that you want to revisit and stress-test, optimize, or expand?
• Liquidity vs Paper Loss Preference. Are you more interested in strategies that generate immediate cash flow, or are you comfortable with paper losses that reduce taxes today but require capital investment? Both? There is a phrase about cake and eating it too, right?
• Investment Horizon. What is your expected holding period for new investments? Short-term (1–3 years) or long-term (5–10+ years)? It likely depends, right? So what does it depend on?
• Decision Timeline. How quickly are you looking to implement a strategy? This tax year, next year, or just exploring options for now? Besides your spouse, what typical obstacles get in the way of your decision-making?

Keep in mind! Not every tax strategy needs to be a conversation starter at a cocktail party. Some of the most impactful moves are also the most straightforward such as donor advised funds, accountable plan reimbursements, the right vehicle deduction, putting your children to work in the business, timing a Roth conversion with a cost seg study, among other “let’s walk before we run” strategies. We always want to make sure the low-hanging fruit is picked before we start climbing trees.