Diana L. Wollman’s practice focuses on complex international M&A and internal restructuring transactions, tax audits, tax investigations, and strategic audit preparation.

She repeatedly has been recognized for her leading role in the profession, including being named the “Lawyer of the Year” for New York tax litigation and controversy by Best Lawyers in 2013.

Diana joined Cleary Gottlieb in 2015 after serving as the Internal Revenue Service’s first Director of International Strategy for the agency’s Large Business & International Division, where she was responsible for developing and managing its international strategic program. Her work included improving how the IRS identifies and addresses significant international tax issues, manages and utilizes its institutional knowledge and data, and trains agents; she also worked to improve the collaboration and coordination between the audit division and the Office of Chief Counsel. She represented the IRS on several Organisation for Economic Co-operation and Development (OECD) working groups, including those focused on BEPS (the OECD’s base erosion and profit shifting project), the Forum on Harmful Tax Practices, and the Forum on Tax Administration.

Prior to her 2013 appointment to the IRS, Diana was a partner in the tax practice of another major international law firm, where she began her career as an associate in 1993. There she built a diverse practice that included federal and New York State tax controversies, complex cross-border transactions, fund and private equity work, and bankruptcy.

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Selected Activities

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  • Member, Executive Committee, New York State Bar Association’s Tax Section; Former Tax Section Chair (2013)
  • Fellow, American College of Tax Counsel
  • Member, The Tax Club (Harvard Club of New York)
  • Member, The Tax Review
  • Member, The Tax Forum
  • Former Adjunct Professor, Columbia Law School
  • Law Clerk to the Hon. Robert J. Kelleher of the U.S. District Court for the Central District of California, 1991-1992

Publications

Author or contributor to more than 30 written works on a host of tax issues. Highlights since 2008 include:

Formal Paper Presented at Seminar

  • The “Just Say No” Doctrine (The Tax Club, November 2008) 

Principal Author of the following New York State Bar Association Tax Section Reports

  • Report on the Partnership Audit Rules of the Bipartisan Budget Act of 2015 (May 2016)
  • Report On Qualified Intermediary And Related Withholding And Information Reporting Legislation Proposed By The Administration (September 2009)
  • Letter to House Committee on Ways & Means and Senate Committee on Finance on Recent and Proposed Statutory Changes to Tax Return Preparer Penalty Rules of Internal Revenue Code Section 6694 and Related Issues (January 2008)

Significant Contributor to the following New York State Bar Association Tax Section Reports

  • Report on Proposed Regulations Under Section 162(m)(6) (September 2013)
  • Report Suggesting Administrative Guidance Be Issued Addressing the Procedures for the Collection of Tax Liabilities Under New York State Law Section 174-B and Related Provisions (June 2013)
  • Report on Proposed Regulations Regarding the Tax Treatment of Noncompensatory Partnership Options (May 2013)
  • Report on Proposed Regulations Section 1.1411-10 (May 2013)
  • Report on the Proposed Regulations Under Section 1411 (May 2013)
  • Report on the Definitions of “FFI,” “Financial Account” and Related Terms in the Final FATCA Regulations (April 2013)
  • Report on Proposed Circular 230 Regulations (December 2012)
  • Report on Tax Opinions in Registered Offerings (April 2012)
  • Report on Application of Employment Taxes to Partners and on the Interaction of The Section 1401 Tax and the New Section 1411 (November 2011)
  • Possible Tax Relief for Disaster-Related Efforts (July 2011)
  • Report on Announcement 2010-9 (March 2010)

Events

  • August 2022
    The Inflation Reduction Act’s Proposed New 15% Corporate Alternative Minimum Tax
  • January 2022
    PLI’s Taxation of Financial Products & Transactions 2022
  • June 2021
    2021 U.S. Tax Reform: The Changes Proposed and Their Relationship With Current OECD and EU Initiatives
  • May 2021
    2021 Tax Reform: The Substantive Changes Being Proposed
  • December 2020
    IFA USA International Tax Conference: “The Tax Cuts and Jobs Act – A Three-Year Review”
  • July 2020
    IIB’s 2020 Annual Tax Seminar
  • December 2019
    The BEAT Regulations Are Finally Out: Cleary Gottlieb Insights
  • September 2019
    73rd Annual Congress of the International Fiscal Association
  • June 2019
    NYU’s 11th Annual Tax Controversy Forum
  • June 2019
    New York State Bar Association Tax Section Spring Meeting 2019
  • April 2019
    19th Annual NYU/KPMG Tax Symposium
  • February 2019
    1st Annual UCI Law Tax Symposium
  • January 2019
    New York State Bar Association Tax Section Annual Meeting 2019
  • October 2018
    PLI’s Tax Strategies for Corporate Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations Restructurings 2018
  • July 2018
    International Tax Institute July Seminar
  • June 2018
    NYU’s 10th Annual Tax Controversy Forum
  • June 2018
    PLI’s Tax Planning for Domestic & Foreign Partnerships, LLCs, Joint Ventures & Other Strategic Alliances 2018
  • November 2017
    George Washington University Law School 30th Annual Institute on Current Issues in International Taxation
  • November 2017
    PLI’s Tax Strategies for Corporate Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations and Restructurings 2017
  • October 2017
    NYU’s 76th Institute on Federal Taxation, Federal Taxation on New Partnership Audit Rules: What You Need to Know and Do Now
  • July 2017
    NYSBA Tax Section Summer Meeting, Hot Topics in Partnership Taxation
  • April 2017
    The Tax Review, Kind-Of-Proposed Partnership Audit Regulation
  • March 2017
    Federal Bar Association’s 41st Annual Tax Law Conference
  • February 2017
    IFA USA 45th Annual Conference
  • January 2017
    ABA’s Section of Taxation Midyear Meeting 2017
  • November and December 2016
    PLI’s Tax Strategies for Corporate Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations & Restructurings Seminar, Exploring the Limits of the Evolving Economic Substance and Business Purpose Doctrines and Related Ethics Issues
  • May 2016
    Wall Street Tax Association Spring Tax Seminar 2016
  • March 2016
    Tax Analysts’ Opportunities and Challenges Conference
  • December 2015
    ABA’s 32nd Annual National Institute on Criminal Tax Fraud and 5th Annual National Institute on Tax Controversy
  • November 2015
    Columbia Business and Law Association’s Current Issues in Tax Law
  • June 2015
    Institute of International Bankers 2015 Annual Tax Seminar, Audit Controversy and the IRS Budget Crunch
  • June 2014
    New York University 6th Annual Tax Controversy Forum, LB&I – Focus on International
  • May 2014
    ABA Tax Section, Ethical Issues in International Transactions
  • March 2013
    ABA Tax Section/International Bar Association/Tax Executives Institute Second Annual International Tax Enforcement Conference, The Interaction of Policy & Law – How the Development of the Law and its Application is Changing
  • January 2014
    New York State Bar Association Tax Section Annual Meeting, Luncheon Speaker
  • December 2013
    GW/IRS 26th Annual Institute on Current Issues in International Taxation, What Will We Be Discussing at This Conference Twenty Years From Now?
  • July 2013
    International Fiscal Association USA Branch International Tax Seminar, The International Aspects of Section 1411
  • March 2013
    PLI Nuts & Bolts of Tax Penalties 2013 Conference, But It’s Not My Fault: Reasonable Cause
  • December 2012
    ABA Tax Link Live Teleconference, Avoiding Malpractice
  • November 2012
    Financial Institutions Tax Coalition Annual Conference, New York State Tax Reform: Implications for Article 32 Taxpayers
  • November 2012
    ABA Tax Section/International Bar Association/Tax Executives Institute First Annual International Tax Enforcement Conference, Special Issues Facing In-House Tax Practitioners
  • November 2012
    ABA Tax Section 23rd Annual Philadelphia Tax Conference, What Keeps Tax Directors Up At Night? Issues of Concern to In-house Tax Departments and Their Advisors
  • October 2012
    New York University 71st Institute on Federal Taxation, Crossing the Line: Real Life Ethical Issues in Tax Practice
  • October 2012
    PLI Tax Strategies for Corporate Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations and Restructurings 2012, Tax Directors Forum: What’s Keeping them Up at Night?
  • July 2012
    NYU Advanced Topics in International Taxation Summer Institute, Hot Ethical Issues in International Taxation
  • June 2012
    Institute of International Bankers Annual Tax Seminar, US Tax Legislative/ Regulatory Update
  • June 2012
    New York University 4th Annual Tax Controversy Forum, How Far Can You Go? Real Life Ethical Problems for Tax Practitioners
  • June 2012
    PLI Tax Planning for Domestic & Foreign Partnerships, LLCs, Joint Ventures, & Other Strategic Alliances 2012, Interesting Partnership Transactions of the Past Year
  • June 2012
    The Tax Forum, Ethics and Whistleblowing: Once Upon a Time There was a Big, Bad Whistleblower Who Said to the Tax Director “I am Going to Huff and Puff and Blow Your House Down!”
  • May 2012
    PLI Tax Planning for Domestic & Foreign Partnerships, LLCs, Joint Ventures, & Other Strategic Alliances 2012, Interesting Partnership Transactions of the Past Year
  • May 2012
    ABA Tax Section 2012 May Meeting, Avoiding Malpractice
  • April 2012
    The Graduate Tax Program at New York Law School Workshop on Tax Lawyering, Standards of Practice: The Factual Basis for Tax Opinions in Registered Offerings
  • April 2012
    Penn State Law and New York City Bar Association’s 9th Annual Institute on the Tax Aspects of Mergers and Acquisitions, Cocktail Chatter: Sexy Ethical Issues You Will Want to Chatter About at Your Next Cocktail Party
  • April 2012
    International Tax Institute, Cocktail Chatter: Six Sexy Ethical Issues You Will Want to Chatter About at Your Next International Cocktail Party
  • March 2012
    ABA Tax Section CLE Teleconference, Circular 230 Discipline and Sanctions: How Worried Should We Be
  • January 2012
    PLI Taxation of Financial Products and Transactions 2012, Getting Out the Guidance: LB&I Takes Over
  • December 2011
    GW/IRS 24th Annual Institute on Current Issues in International Taxation, Ethical Issues in International Tax Practice
  • December 2011
    The Tax Review, The Work Product Doctrine
  • December 2011
    Philadelphia Bar Association Tax Section Annual Meeting, Tax Opinions: What Should Be In Them and Not in Them to Get Penalty Protection
  • December 2011
    PLI Tax Strategies for Corporate Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations and Restructurings Tax Strategies 2011, Tax Director Forum What’s Keeping Them Up at Night
  • November 2011
    The Tax Club, The Newly-Revised Circular 230: Why You (Yes, You!) Should Care
  • November 2011
    PLI Tax Strategies for Corporate Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations and Restructurings Tax Strategies 2011, Tax Director Forum What’s Keeping Them Up at Night
  • November 2011
    ABA Tax Section 22nd Annual Philadelphia Tax Conference, What Keeps Tax Directors Up at Night
  • November 2011
    Life Insurance Council of New York’s Annual Tax Conference, Ethical Issues in International Tax Practice
  • November 2011
    The Clearing House 1st Annual Business Meeting & Conference, The Limits of the Attorney-Client Privilege and the Work Product Doctrine
  • November 2011
    Financial Institutions Tax Coalition Annual Meeting, New York State Tax Reform
  • October 2011
    PLI Tax Strategies for Corporate Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations and Restructurings Tax Strategies 2011, Tax Director Forum What’s Keeping Them Up at Night
  • October 2011
    New York University 70th Institute on Federal Taxation, Ethical & Penalty Issues in Tax Practice
  • July 2011
    NYU Summer Institute: Advanced International Taxation Program, Interesting & Fun Treaty Issues
  • July 2011
    Wall Street Journal Video (interview), Erosion of Privilege for Tax Advisers
  • June 2011
    Institute of International Bankers 2011 Annual Tax Seminar, Global Tax Gaps, Transparency and Compliance
  • June 2011
    The Tax Review, Work Product Doctrine
  • June 2011
    New York University 3rd Annual Tax Controversy Forum, Kovel Privilege
  • May 2011
    PLI Tax Planning for Domestic & Foreign Partnerships, LLCs, Joint Ventures & Other Strategic Alliances 2011, Interesting Partnership Transactions of the Past Year
  • May 2011
    ABA Tax Section 2011 May Meeting, Debate: That the Standards for Tax Return Positions of Section 10.34 Should Conform in All Respects to the Standards Prescribed by IRC Section 6694
  • April 2011
    Penn State Law and New York City Bar Association’s 8th Annual Institute on the Tax Aspects of Mergers and Acquisitions, Ethical Issues in Tax Practice
  • March 2011
    11th Annual NYU/KPMG Tax Lecture Series, Uncertain Tax Positions and IRS Access to Tax Accrual Workpapers
  • March 2011
    11th Annual NYU/KPMG Tax Lecture Series, Debate: FATCA Was An Appropriate Response to the Problem
  • February 2011
    2011 International Fiscal Association USA Branch Annual Tax Conference, What Corporate Tax Directors Are Spending Time on Now
  • December 2010
    PLI Tax Strategies for Corporate Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations and Restructurings Tax Strategies 2010, Hindsight is 20-20: What the Tax Covenants Should Have Said?
  • October 2010
    ABA 21st Annual Philadelphia Tax Conference, Tax Director Forum: What’s Keeping Them Up at Night?
  • October 2010
    ABA 21st Annual Philadelphia Tax Conference, State and Local Meets International
  • October 2010
    New York University 70th Institute on Federal Taxation, Ethical & Penalty Issues for Estate Tax Practitioners
  • August 2010
    Philadelphia Bar Association, Codification of Economic Substance, FIN48 Revisited, Disclosure of Uncertain Tax Positions
  • July 2010
    New York University Summer Institute, Advanced International Taxation, IRS Schedule UTP: Some Things A Responsible Ethical Practitioner Should Know
  • July 2010
    NYSBA Tax Section Summer Meeting, New York State Corporate Tax Reform: A Handful of the Most Interesting Aspects
  • June 2010
    New York University 2nd Annual Tax Controversy Forum, Reporting Uncertain Tax Positions
  • June 2010
    ALI-ABA Executive Compensation: Strategy, Decision, and Implementation, How To Preserve Attorney Client Privilege and Work Product Protection”
  • May 2010
    The Tax Review, More Transparency about the IRS’s “Transparency Announcement”: Schedule UTP and Its Implications
  • May 2010
    ABA Tax Section 2010 May Meeting, What Are The Decisions That Determine Which Positions Will Be Reported on Your Schedule UTP: Are These Determinations As Clear-Cut as the IRS Thinks?
  • April 2010
    Penn State Law and New York City Bar Association’s 7th Annual Institute on the Tax Aspects of Mergers and Acquisitions, Ethical Issues in Tax Practice
  • February 2010
    Practising Law Institute Webinar, IRS’s New Proposal for Reporting “Uncertain Tax Positions”: What Announcement 2010-09 Says and What It Does Not Say”