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Tax Planning & Advisory
Forward-looking tax strategy integrated with business decisions. Entity structuring, transaction tax planning, and the year-round advisory work that reduces tax liability over multi-year horizons. Distinct from compliance in that it analyzes decisions before they are made, not after.
Situations that typically drive this conversation
A major business decision has tax implications that require analysis
Entity restructuring, sale, acquisition, or significant capital event introduces tax considerations that warrant forward-looking analysis before execution.
Current entity structure may not be optimal for current circumstances
Entity elections made at earlier stages — S election, LLC vs. C corporation, disregarded entity treatment — may not be optimal for current size, ownership, and strategic direction.
A transaction is contemplated or active
Sale, acquisition, merger, or capital raise requires structured tax analysis integrated with deal structure and negotiation.
A capital event is on the horizon
Anticipated capital events — IPO, sale, refinancing — warrant preparation and structuring work in the twelve-to-eighteen months preceding the event.
Year-round planning has not been integrated into tax compliance
Current tax relationship is compliance-only. Planning opportunities go unidentified because there is no advisory cadence.
What this service line delivers
Entity structure analysis and planning
Analysis and recommendation on legal entity structure, including C corporation versus pass-through elections, multi-entity architecture design, disregarded entity treatment, and the specific elections that affect long-term tax outcomes. Quantified analysis with projected after-tax impact.
Transaction tax planning
Pre-transaction planning for sales, acquisitions, reorganizations, and capital events. Structure recommendations that preserve after-tax value. Coordinated with legal counsel on transaction documents. Includes analysis of Section 338 elections, F reorganization structures, Section 1202 qualified small business stock analysis, and the transaction-specific elections available under current law.
Multi-year strategic tax planning
Tax planning across multi-year horizons covering expansion, investment, compensation structure, ownership transitions, and other decisions with durable tax consequences. Integrates with strategic planning cycles rather than operating as a separate workstream.
Estate and succession planning coordination
Tax analysis supporting estate planning, family business succession, and ownership transition. Coordinated with estate planning counsel on gifting strategies, trust structures, and valuation discounts.
Compensation and equity design
Tax analysis of compensation structures, equity plans, and incentive arrangements. Addresses both the business-entity tax implications and the individual-owner or employee implications. Coordinated design where both perspectives require integration.
Time horizons stack from annual to strategic
Effective tax planning operates across multiple horizons simultaneously. Annual execution happens within the context of multi-year positioning, which happens within strategic ownership decisions. Integration across all three is where value compounds.
What clients receive
Entity structure recommendation with supporting analysis
Transaction tax memorandum with projected outcomes
Multi-year planning roadmap
Implementation checklists and coordination with counsel
Compensation and equity design analysis
Documentation supporting positions taken
Questions clients ask before engaging
How does this differ from tax compliance?
Compliance produces accurate filings for prior-year activity within the rules as they applied to decisions already made. Planning analyzes future decisions before they are made, with the goal of optimizing their tax treatment while there is still flexibility. Both are required for sophisticated organizations — compliance without planning leaves value on the table; planning without compliance creates execution risk.
How is planning coordinated with legal counsel?
Transaction and structural planning routinely coordinate with legal counsel on documents, elections, and execution. Outlook operates as part of the advisory team with clearly delineated roles: we develop and document the tax positions; counsel drafts the legal instruments and provides attorney-client privileged advice; implementation is coordinated across both firms. The roles are complementary, not overlapping.
Can planning work be engaged without compliance?
Yes. Planning engagements can be stand-alone or combined with compliance. Many clients engage Outlook for specific planning initiatives — a transaction structure analysis, a capital event, an entity restructuring — while maintaining compliance relationships elsewhere. Others combine the two for integrated service.
What are some examples of planning that materially affects outcomes?
Section 338(h)(10) elections on qualifying stock sales, F reorganizations for pre-transaction restructuring, QSBS qualification under Section 1202 for founders and early investors, entity conversions between C corporation and pass-through treatment, Section 754 elections following partnership interest transfers, and state residency planning for high-income individuals contemplating relocation. Each of these can affect after-tax outcomes by millions of dollars in the right circumstances.
How is planning work documented?
All planning work is documented in memoranda that serve as both internal decision-support tools and defensive documentation for the positions taken. Documentation standards reflect the scrutiny the positions may face on examination — more rigorous documentation for positions that could be challenged, streamlined documentation for routine matters. The documentation is retained for statute of limitations periods to support audit defense if required.
Explore the Tax & Compliance practice
Discuss a tax planning engagement
A brief conversation is the fastest way to determine fit. We will listen to your situation and provide a candid view on how we can help.