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Most tax planning happens too late. By the time year-end rolls around, options have narrowed, opportunities have passed and decisions become reactive instead of strategic.

This year, that approach could be especially costly.

Between rising costs, shifting policies and an unpredictable political landscape, midsized businesses need to build tax strategy into the rhythm of the year — not treat it as a December exercise. That means identifying planning windows in advance, aligning them with business decisions and giving your tax team the visibility and lead time they need to help you move with confidence.

To help you stay ahead, we’ve outlined six critical tax planning windows to watch — along with what to evaluate in each one.

1. Q1: Entity and structure review

Start the year by confirming your current business structure still supports your growth strategy. That includes evaluating whether your entity type aligns with your revenue model, ownership plans and tax efficiency goals. If you're considering a change — such as moving to or from an S corporation or partnership structure — Q1 is the ideal time to model impacts and implement before deadlines hit.

Also review any new or reorganized entities, especially if your business expanded across state lines or launched new products. These changes may affect your SALT exposure, apportionment strategy or eligibility for certain deductions.

Tip: Don’t forget to review ownership changes, control thresholds and passive activity exposure if you’ve brought on investors or partners.

2. Q2: Compensation and benefits strategy

 Mid-year is a powerful checkpoint for aligning your compensation design with your tax and talent strategy. Are bonuses, equity or deferred comp plans structured to deliver tax efficiency for both the business and your top performers? Are fringe benefits or expense policies triggering unexpected exposure?

With the job market still in flux, many companies are adjusting pay models or remote work policies — both of which carry tax implications, especially across jurisdictions.

Tip: If you're offering remote flexibility, this is the time to evaluate multi-state payroll and nexus risks before the second half of the year.

3. Summer: Tax credit and incentive timing

Don’t wait until Q4 to consider credits — especially for energy investments, R&D activity, or hiring-based programs. Most credits require proactive documentation and may be tied to spend that’s already happening in Q2 or Q3.

Many of Wipfli’s midsized clients are exploring Inflation Reduction Act and OBBB-related credits, including those tied to clean energy, fleet electrification and facility upgrades. Planning ahead lets you structure spending to qualify — and monetize — the credits.

Tip: Consider running a mid-year incentive assessment to uncover federal, state and local programs aligned with your capital plans.

4. Q3: Capital expenditure planning and depreciation strategy

 As you begin budgeting for the coming year, revisit capital expenditure plans — especially with interest rates still volatile. Understanding how depreciation strategies, Section 179 deductions or bonus depreciation can offset tax liability helps you evaluate projects more holistically.

This is also when tax and finance teams should align with operations to assess the timing of purchases, in-service dates and financing structure. Too often, capex decisions are made without full visibility into tax optimization levers.

Tip: Run side-by-side pro forma models that incorporate both traditional depreciation and any available credits, particularly in construction and manufacturing-heavy sectors.

5. Q4 kickoff: Tax provision modeling and tax liability forecasting

By early Q4, your team should be working with updated forecasts to project year-end tax liability. This allows for smart decisions around estimated payments, cash preservation or accelerated spending. It also gives you time to identify any surprises and implement clean-up strategies if needed.

If you’re expecting losses or reduced income, Q4 modeling can help identify carryback or carryforward opportunities — or determine if you should rethink planned deferrals or bonuses.

Tip: Don’t just look backward. Use provision modeling to project what Q1 could look like, especially if you have seasonal business dynamics.

6. Q4: Estate and gift planning moves

The OBBB made the $15 million lifetime gift and estate tax exemption permanent starting in 2026 — replacing the uncertainty of a TCJA sunset with a new planning baseline. That said, 2025 still presents a valuable opportunity to align estate strategies with evolving tax policy.

For high-net-worth individuals and business owners, this is the time to assess gifting strategies, trusts and entity structures in light of the new rules. If you previously modeled plans assuming a reversion to pre-2018 levels (~$7 million), it’s important to revisit those scenarios now.

Even without looming deadlines, estate moves often require time to structure, fund and finalize — so early action still creates an advantage.

Best used: Now through Q4

Tip: Coordinate with an estate planning attorney, CFO, tax advisor.

7. Final stretch: Pre-close strategy alignment

As your fiscal year end approaches, take a final sweep through your tax position — not just for compliance but for alignment. Are you accelerating income or deferring expenses? Are there owner distributions or charitable giving strategies that should be finalized? Are you capturing all available deductions?

This is also the right time to ensure your tax strategy is coordinated across departments. Sales, operations, legal and HR all make decisions that can have year-end tax impact — so alignment is key.

Tip: Create a simple cross-functional checklist to track decisions across the org in the final 30–45 days of the year.

Planning is your edge in uncertain times

Every year brings tax changes, but 2025 feels especially unsettled. With the OBBB Act solidifying key provisions and the 2026 TCJA sunset on the horizon, now is the time to act strategically. That’s why this checklist focuses on planning windows — not just technical rules.

If you use these six windows to guide your internal cadence, you’ll not only reduce surprises — you’ll empower your business to move faster, make better decisions and stay strategically aligned.

How Wipfli can help

We help midsized businesses build tax strategies that support agility, growth and resilience. Whether you're expanding, reorganizing or simply want more predictability, our advisors work with you to:

• Identify and time planning windows tied to your goals.
• Evaluate entity, compensation and capital structure for tax efficiency.
• Model scenarios and forecast tax impact across the year.
• Align tax strategy with cross-functional business decisions.

A smart tax strategy doesn’t start in December. Learn more about our strategic tax services.

Across finance, tax and operations, our teams are helping clients navigate uncertainty by planning for the upside, managing the downside and building agility. See how.

Your 2025 tax planning checklist

6 strategic windows to reduce risk, stay agile and align tax with business decisions

Q1: Reassess structure

Start the year with a foundational check:

• Does your current entity structure (S corporation, partnership, etc.) still support your revenue and ownership model?
• Have you made any reorganizations, mergers or acquisitions that require tax treatment updates?
• Are you entering new states or markets that trigger additional SALT exposure or registration?

Best used: January-February

Coordinate with: Legal, finance, strategy

Q2: Align compensation and workforce planning

Mid-year is the moment to catch misalignment before it compounds:

• Are executive bonuses or deferred comp structured for tax efficiency?
• Is your remote or hybrid workforce triggering new payroll or nexus exposure?
• Are fringe benefits or reimbursements causing unexpected tax risk?

Best used: March-May

Coordinate with: HR, payroll, legal, finance

Q2-Q3: Map credits and incentives to planned activity

Timing matters for credits — especially under the Inflation Reduction Act:

• Are you planning capital projects (e.g., solar, EV, HVAC, facility upgrades) that could qualify for federal or state credits?
• Do your vendors meet prevailing wage or domestic content standards?
• Have you reviewed R&D activity, new hires or geographic expansions for additional incentives?

Best used: May-August

Coordinate with: Tax, operations, external vendors

Q3: Build depreciation and capex into tax strategy

Before finalizing your 2026 budget:

• Are you maximizing bonus depreciation or Section 179?
• Are planned purchases timed to maximize tax benefit in 2025?
• Are you modeling capex decisions based on both operational and tax return impact?

Best used: August-September

Coordinate with: Finance, ops, tax

Early Q4: Model year-end position

With updated forecasts in hand:

• Have you modeled estimated year-end tax liability using current performance?
• Are you reviewing options to accelerate expenses or defer income?
• Are you aligning Q4 tax moves with your broader financial strategy?

Best used: October

Coordinate with: Finance, executive team, tax

Final 30-45 days: Pre-close alignment

Use the last stretch to clean up and align decisions across the org:

• Are owner draws, bonuses and charitable giving plans finalized with tax impact in mind?
• Are vendor payments and contract timing optimized for deduction eligibility?
• Are departments following a consistent year-end checklist to reduce friction and surprise liabilities?

Best used: November-December

Coordinate with: Tax, finance, HR, ops

Want help applying this to your business?

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