Tax,
Corporate,
Alternative Dispute Resolution
Jan. 16, 2026
Mediating executive termination disputes
Executive terminations carry unique risks for both companies and individuals, but a skilled mediator can help parties navigate tax strategies, restrictive covenants and creative solutions to reach confidential resolutions that protect business interests while securing favorable outcomes for departing executives.
Mark S. Zemelman
Neutral
Signature Resolution
Mark Zemelman is a neutral with Signature Resolution who previously served as General Counsel for Kaiser Foundation Health Plan, Inc.
The involuntary termination of a
corporate executive, particularly where the executive believes that the
termination is wrongful, involves risks for the company and the individual that
differ from typical non-voluntary employee separations. The company's risk is
that the executive may possess intimate knowledge of the company's business
strategy, competitive weaknesses and sensitive information that it would like
to keep from competitors, regulators and the public. The executive's risk is
that a formal termination or public dispute could impair his or her ability to
obtain subsequent employment.
Both parties thus have an interest in
a quick and confidential resolution. Their respective goals, however, may make
this difficult. The executive typically wants a substantial amount of money,
structured in a tax-advantageous manner, with no strings. The company may want
"strings" to assure that its confidential information is not revealed, its best
people are not poached, and its reputation is not injured.
A mediator with experience in such
situations can help the parties reach a win-win resolution through
consideration of a range of creative options. The following hypothetical
provides an illustration of this. A
In 2020, Janet Jones was hired as a
senior vice president by Acme Electric, a regulated public utility, to create a
non-regulated consulting function to advise companies regarding energy
strategy. In 2025, Acme's lawyers realized that it could not provide
non-regulated services, and Acme decided to spin this function out as a
separate subsidiary, terminating Janet's role in the process. The company has
offered Janet a package involving a "cliff" payment structure: Six months of
additional regular pay, plus her earned long-term incentive pay, will be issued
to her within 60 days after termination.
Janet believes she is the scapegoat
for a legal error and she considers the severance
package to be inadequate. She has hired a plaintiff's lawyer to represent her;
the company has responded by hiring a litigation firm. The parties have chosen
a mediator well-versed in both employment law and the tax implications of
various executive termination scenarios.
The mediation process
For a mediation of this type, the
starting point for the mediator will be, as early as possible, to (1) talk with
the respective attorneys to understand the emotional and business factors that
will need to be considered; (2) review the documents that are central to the
mediation, including the executive's employment agreement, trade
secret/confidentiality agreements, the offered severance agreement, and
relevant company policies; (3) determine whether the mediation should be
structured as a set of meetings, rather than a single mediation, and the order
of issues to be addressed; and (4) determine whether, in addition to the
parties' representatives, other experts might be helpful.
In standard employment cases, tax
considerations are often left to the end of the negotiation. When the
termination involves a highly paid executive, however, the opposite applies
because it will take time for the company's HR personnel and the executive's
accountant to evaluate the range of alternatives. Moreover, the process of
evaluating tax implications typically is cooperative; early evaluation can help
set a constructive tone for resolution of the other issues.
Settlement: Tax strategies
In the best-case scenario, the
company's severance policy has already been designed to provide severance
packages with tax-favorable designs. This is not, however, the case with Janet.
In her case, with guidance from tax, investment and benefits experts, Acme and
Janet may consider the following non-comprehensive list of tax strategies:
Structured settlement. A structured
settlement enables the company to make a one-time settlement payment that is
booked in the present year while offering the executive the tax benefit of
receiving settlement payments over a period of years. With a structured
settlement, Acme would assign the obligation to make future periodic settlement
payments, typically to a highly rated life insurance company. Structured
settlements can be customized to meet the executive's goals, e.g., paid through
a fixed or indexed annuity. If the parties wish to pursue this option, they can
retain a firm that specializes in developing structured settlements.
Salary continuation agreement. For
tax purposes, a severance paid in installments post-termination generally is
treated as wages in the year paid. For executives, post-termination payments of
12 months to two years are not uncommon, and longer periods are possible with
careful structuring. The parties will want to assure that a salary continuation
agreement is not deemed a "deferred compensation" arrangement under Section 409A of the
Internal Revenue Code.
Nonqualified deferred compensation
plan. If Janet already participates in the company's deferred
compensation plan, she may be able to elect to defer all or part of the payment
to a future tax year. Any modification of a nonqualified deferred compensation
plan must be reviewed for compliance with Section 409A.
Health benefits.
Continuation of health benefits generally is not taxable to the executive.
Subsidization of a COBRA plan may also be excluded from Janet's taxable income.
Equity-related payouts.
Depending on the company's stock plans and Janet's participation in them, the
year in which payment is recognized can be shifted through mechanisms such as
accelerated vesting, equity buyouts, incentive stock options (ISOs),
non-qualified stock options (NQSOs) and restricted stock units (RSUs). For
example, it may be possible for Acme to move the exercise date of Janet's
vested stock options and/or move the date on which her RSUs are to be paid to
later dates. Again, expert assistance is essential in order
to avoid legal barriers or adverse tax consequences; for example,
converting a cash severance to equity after termination generally is not
permitted.
Charitable trusts.
Let's say that Janet expects substantial future income and the various tax
strategies discussed above are not meaningful to her. The settlement could
provide that Acme will put funds into a charitable trust or donor-advised fund
directed by Janet.
Other settlement terms and
restrictions
The parties' respective counsel will
come prepared to argue about Janet's contention that she was treated unfairly.
Resolution of this issue may be much easier if the company is able to achieve
its non-monetary objectives in exchange for paying more money to Janet. A
mediator who is experienced with executive terminations may be able to identify
terms that will facilitate such resolution.
The company may, for example, want
the following provisions in the settlement agreement if the executive is not
already bound by prior agreements: (1) a non-compete clause to prevent Janet
from using her energy expertise to help an Acme competitor; (2) a
non-solicitation clause to preclude her from helping another company poach
Acme's top performers; (3) a non-disparagement clause preventing Janet from
criticizing Acme or its executives; (4) a confidentiality clause precluding her
from using Acme's confidential information or trade secrets; and, (5) given the
regulatory issue that led to the spinoff, a provision that prohibits Janet from
disclosing the issue or encouraging others to sue Acme and requires her to
cooperate with the company in the event of an investigation or litigation.
The challenge is that, even if Janet
is willing to agree to some or all of these
restrictions for more money, certain restrictions will be void on public policy
grounds in some states and will only pass muster in other states if they are
drawn narrowly. For example, a non-compete clause is likely to be void in
California, even for an executive like Janet, but a tightly drawn non-compete
(limited in time, geography and activity) may be lawful in some other states if
there is a legitimate business interest and substantial consideration for the
clause.
Non-solicitation agreements can run
afoul of antitrust, unfair competition and labor laws if they are viewed as
limiting other employees from obtaining better work. Precluding Janet from
informing government agencies of regulatory violations would run afoul of
public policy, and the law is clear that a settlement agreement cannot prohibit
Janet from filing a False Claims Act case with respect to claims that Acme has
submitted to the government. A limitation on encouraging others to sue also may
be deemed invalid. Because of the complexity of the law regarding such
"strings," the mediator may want to encourage the parties to have appropriate
legal experts design the desired provisions.
Creative solutions
An expert mediator will understand
the legal implications of the parties' choices and, when appropriate, will help
them achieve their objectives through creative solutions. In California, for
example, even though non-compete clauses generally are prohibited, Acme may be
able to achieve its objective through a carefully tailored confidentiality and
trade secret provision, a customer non-solicitation provision tied to trade
secrets, a narrow employee non-solicitation clause, and a mutual
non-disparagement provision.
With proper guidance, Acme may also
be able to create a strong incentive for Janet not to violate settlement
restrictions by tying her right to certain severance payments to her compliance
with the agreement. If Janet is willing to do this, she will want the agreement
to provide that the company cannot unilaterally declare a breach, i.e., a
dispute resolution process must be invoked. The company could even consider a
positive incentive for Janet not to injure Acme's new subsidiary by granting
her a non-qualified stock option in the new subsidiary; for Janet, this may be
a tax-favorable means of addressing a portion of the monetary settlement.
Conclusion
This article should demonstrate the
plethora of options available to facilitate settlement of executive termination
disputes. A high level of expertise is needed to assure that the final
agreement is appropriate from both a legal and tax perspective. A skilled
mediator will understand how to use these options responsibly and creatively in order to help the parties reach an agreement that
achieves their respective objectives.
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