Understanding Employee Stock Options

More and more employee compensation plans include stock options. Options are a cost effective way for a company to share its success with employees, to recruit, motivate, and retain top-notch employees. The downside for the employee, is that options are difficult to understand and plan with. Typical questions one should ask include:

what are my options likely to be worth?
how are my options taxed?
what type of  options do I have (non-qualified? qualified/statutory/incentive/ISO)
when should I exercise my options? should I exercise them before an IPO? should I exercise them before they have vested? (yes you can do this and its sometimes a good idea)
how should I ensure proper diversification while still retaining significant upside

Our belief is that you can understand the way options works and how to go about making intelligent decisions -- if you want to and if you put in the time and effort to learn about how they work. The resources listed here and the talk given by Jon Rochlis at LISA 2000 are intended to help you come up to speed. Either so you can work out your own strategies or be better able to evaluate the skills and knowledge of a financial or tax advisor. Please note: nothing on this pages should be taken as specific advice related to your personal situation. Rather we only discuss the way options, investing, and taxation work. How they general rules apply to your situation is often complex. Consult your personal advisor before taking action.

Slides for Jon's LISA 2000 talk are available. Lisa2000.pdf

Books   

There are a few  books which describe the ins and outs of employee stock options. More and more seem to be coming out every day! Which are useful and which should you stay away from?

Consider Your Options: Get the Most from Your Equity Compensation, 2005 Edition by Kaye A. Thomas.

This is where I'd recommend starting. Kaye Thomas does an excellent job at describing the complex landscape of employee stock options. Despite a difficult and tedious subject Consider Your Options is quite well organized, readable, and comprehensive.  The authors run a very good web site devoted to the subject (www.fairmark.com). The site consists mostly excerpts from the book plus discussion groups, frequently answered by the authors.

What Consider Your Options  lacks, however, is a set of illustrative examples, or detailed discussions of strategies and how they might relative to your own personal situation. Think of it as a excellent description of the rules of the game and a great place to start.

Stock Options: An Authoritative Guide to Incentive and Nonqualified Stock Options (2nd edition) by Robert R. Pastore

Robert Pastore's thin but expensive book is excellent as well. But it is much harder to absorb. The organization and formatting make it difficult to get through. Unlike Consider Your Options, Pastore's book, isn't polished. But make no mistake about it Pastore knows his stuff and the data is all in here -- including primary source IRS rulings and details relating to insider restrictions. 

 If you're a techie you'll like his graphical description of option taxation. It helps make all of the  text about qualified vs. non-qualified options, bargain element taxation, basis, and Alternative Minimum Tax comprehensible.

This is the book to go for if you want to really get into it. But be careful not to get lost.

Pastore spends a significant amount of time walking through several case studies. This is, perhaps, the best part of the book. Not only do they help to explain the technical details, but they also serve to give one a framework to approach an analysis of what to do. The differential cash flow Internal Rate of Return analysis comparing Buy & Sell with Buy & Hold is excellent but quite involved. Read it several times and take it to heart. 

Other Books

We will add other books over time. In particular I have received requests for pointers to books which address the company point of view more than the employees. If you would like to be notified when we add more reviews or pointers send email.

For now, the box bellow contains Amazon's automatic take on what employee stock option books might be interesting:

Search for other books at Amazon.com

Use the search function below to see a list of all the books Amazon has relating to Stock Options. Note that this will match books from the company point of view (e.g. how to set up option plans) especially on the (mostly) unrelated topic of playing the stock market with puts, calls, and the like. Feel free to type in another string, and search on that - title, ISBN, author name, etc. should all work, too.

Tax Code

This is the actual tax code defining Incentive Stock Options (ISO) from www.findlaw.com: Laws: Cases and Codes : U.S. Code : Title 26 : Section 422. Remember this is only one portion of the tax code and you should not draw legal conclusions based on a layman's reading of a such a small portion. Yet you can see how understandable this section is. (Don't believe all code sections are similar).

U.S. Code as of: 01/22/02
Section 422. Incentive stock options
    
    (a) In general
      Section 421(a) shall apply with respect to the transfer of a
    share of stock to an individual pursuant to his exercise of an
    incentive stock option if -
        (1) no disposition of such share is made by him within 2 years
      from the date of the granting of the option nor within 1 year
      after the transfer of such share to him, and
        (2) at all times during the period beginning on the date of the
      granting of the option and ending on the day 3 months before the
      date of such exercise, such individual was an employee of either
      the corporation granting such option, a parent or subsidiary
      corporation of such corporation, or a corporation or a parent or
      subsidiary corporation of such corporation issuing or assuming a
      stock option in a transaction to which section 424(a) applies.
    (b) Incentive stock option
      For purposes of this part, the term ''incentive stock option''
    means an option granted to an individual for any reason connected
    with his employment by a corporation, if granted by the employer
    corporation or its parent or subsidiary corporation, to purchase
    stock of any of such corporations, but only if -
        (1) the option is granted pursuant to a plan which includes the
      aggregate number of shares which may be issued under options and
      the employees (or class of employees) eligible to receive
      options, and which is approved by the stockholders of the
      granting corporation within 12 months before or after the date
      such plan is adopted;
        (2) such option is granted within 10 years from the date such
      plan is adopted, or the date such plan is approved by the
      stockholders, whichever is earlier;
        (3) such option by its terms is not exercisable after the
      expiration of 10 years from the date such option is granted;
        (4) the option price is not less than the fair market value of
      the stock at the time such option is granted;
        (5) such option by its terms is not transferable by such
      individual otherwise than by will or the laws of descent and
      distribution, and is exercisable, during his lifetime, only by
      him; and
        (6) such individual, at the time the option is granted, does
      not own stock possessing more than 10 percent of the total
      combined voting power of all classes of stock of the employer
      corporation or of its parent or subsidiary corporation.
    Such term shall not include any option if (as of the time the
    option is granted) the terms of such option provide that it will
    not be treated as an incentive stock option.
    (c) Special rules
      (1) Good faith efforts to value of stock
        If a share of stock is transferred pursuant to the exercise by
      an individual of an option which would fail to qualify as an
      incentive stock option under subsection (b) because there was a
      failure in an attempt, made in good faith, to meet the
      requirement of subsection (b)(4), the requirement of subsection
      (b)(4) shall be considered to have been met.  To the extent
      provided in regulations by the Secretary, a similar rule shall
      apply for purposes of subsection (d).
      (2) Certain disqualifying dispositions where amount realized is
          less than value at exercise
        If -
          (A) an individual who has acquired a share of stock by the
        exercise of an incentive stock option makes a disposition of
        such share within either of the periods described in subsection
        (a)(1), and
          (B) such disposition is a sale or exchange with respect to
        which a loss (if sustained) would be recognized to such
        individual,
      then the amount which is includible in the gross income of such
      individual, and the amount which is deductible from the income of
      his employer corporation, as compensation attributable to the
      exercise of such option shall not exceed the excess (if any) of
      the amount realized on such sale or exchange over the adjusted
      basis of such share.
      (3) Certain transfers by insolvent individuals
        If an insolvent individual holds a share of stock acquired
      pursuant to his exercise of an incentive stock option, and if
      such share is transferred to a trustee, receiver, or other
      similar fiduciary in any proceeding under title 11 or any other
      similar insolvency proceeding, neither such transfer, nor any
      other transfer of such share for the benefit of his creditors in
      such proceeding, shall constitute a disposition of such share for
      purposes of subsection (a)(1).
      (4) Permissible provisions
        An option which meets the requirements of subsection (b) shall
      be treated as an incentive stock option even if -
          (A) the employee may pay for the stock with stock of the
        corporation granting the option,
          (B) the employee has a right to receive property at the time
        of exercise of the option, or
          (C) the option is subject to any condition not inconsistent
        with the provisions of subsection (b).
      Subparagraph (B) shall apply to a transfer of property (other
      than cash) only if section 83 applies to the property so
      transferred.
      (5) 10-percent shareholder rule
        Subsection (b)(6) shall not apply if at the time such option is
      granted the option price is at least 110 percent of the fair
      market value of the stock subject to the option and such option
      by its terms is not exercisable after the expiration of 5 years
      from the date such option is granted.
      (6) Special rule when disabled
        For purposes of subsection (a)(2), in the case of an employee
      who is disabled (within the meaning of section 22(e)(3)), the
      3-month period of subsection (a)(2) shall be 1 year.
      (7) Fair market value
        For purposes of this section, the fair market value of stock
      shall be determined without regard to any restriction other than
      a restriction which, by its terms, will never lapse.
    (d) $100,000 per year limitation
      (1) In general
        To the extent that the aggregate fair market value of stock
      with respect to which incentive stock options (determined without
      regard to this subsection) are exercisable for the 1st time by
      any individual during any calendar year (under all plans of the
      individual's employer corporation and its parent and subsidiary
      corporations) exceeds $100,000, such options shall be treated as
      options which are not incentive stock options.
      (2) Ordering rule
        Paragraph (1) shall be applied by taking options into account
      in the order in which they were granted.
      (3) Determination of fair market value
        For purposes of paragraph (1), the fair market value of any
      stock shall be determined as of the time the option with respect
      to such stock is granted.

Web Sites

The people who wrote Consider Your Options have a very good web site. It has many excerpts from the book plus discussion groups, frequently answered by the authors.

Send mail to with questions or comments about this web site.
Copyright © 2000 The Rochlis Group, Inc.
Last modified: 09 December 2000 except for minor non-substantive changes on 09 November 2005