Most employees view resigning from a job to be rather simple: just let your Manager and HR know you’ll be leaving your job, and when. Years ago it was that simple. Today, a “safe” resignation requires greater strategic precaution; and any failure to act strategically when resigning can result in career calamity. It’s always your choice: you can be careful or be careless; in either case, you’ll live with the results.

1. Above all else, how certain are you that you really want or need to leave your job? At work and elsewhere, setbacks, depression, disappointment and disillusionment can each blind us to the many and substantial blessings and opportunities we enjoy “where” we are. At other times, the grass on the other side of the fence seems far greener than it really is.

Perhaps worst is leaving a job because you’ve concluded that you will never receive recognition or rewards when, in fact, you’ve never clearly or resolutely requested them. There are few regrets more upsetting than “I wish I never left that situation without giving it a better chance.”

2. You may not have the “freedom” to leave your job. While no employer can force you to remain in their employ, there are a surprising number of reasons you may not be “free” to leave your job, including (a) an offer letter or employment contract you signed committing you to a defined but unfinished duration of employment, and (b) so-called “garden-leave” agreements by which you agreed to give lengthy resignation notice, perhaps as much as six months.

Can an employer “force” you to remain? No, but your employer is entitled to both (a) sue you for any damages resulting from your leaving early, and (b) notify your next employer that you cannot start work there for a period of time, or face a lawsuit for facilitating your breach of contract. That could result in your resignation from your former job, as well as termination from your next job. I’ve seen it happen many times.

3. You’ll almost surely lose critical documents, data and contact information if you don’t have a workplace “Go File.” Public Safety experts advise people to always have on hand at home a “Go Bag” of necessities just in case of an unexpected necessary or forced exit. It should contain such necessary items as (a) prescription medications, (b) cash currency, (c) copies of important legal papers, and (d) a one-week supply of protein bars.

For parallel reasons, we recommend you assemble and keep at home a workplace “Go File,” to be available if you’re unexpectedly locked out of your workplace or its computer. It should contain, as examples, (a) copies of all personal information in your computer or office, (b) offer letter, employment agreement, stock option plan and non-compete agreement, (c) emails that confirm your right to yet-unpaid compensation, and valuable benefits and promises, (d) your “portfolio material,” that is, samples of your exemplary work product, and the like.

Uncertain if something is a trade secret, proprietary or confidential? It is best to print it out, keep a copy and later get an attorney’s opinion, as it is easier to later destroy such material than it is to somehow re-create it.

It’s a good idea to start a workplace “Go File” today, and supplement it as necessary by printing out and taking home new items, especially if you are considering a departure.

4. Don’t ignore critical “strategic financial timing.” How difficult would it be to delay your departure date? As an example, if you waited just one or two more months to resign, might you in the interim earn (a) valuable vesting of unvested equity or deferred compensation, (b) bonuses or commissions soon to become payable, (c) freedom from having to repay sign-on bonus, relocation expenses or education outlays, (d) reach anniversaries of employment upon which you would be awarded special entitlements, such as enhanced retirement or separation benefits, lifetime privileges or discounts, perhaps even free college tuition for your children?

In our practice, these precautions are “standard fare”: in recent months, one client held off her resignation submission by just three weeks, thereby avoiding repayment of a $50,000 sign-on bonus; another client’s careful adjustment to his resignation timing by a scant two days enabled one-third of his unvested RSU’s to vest. And annual bonuses? No client of our firm resigns before their annual bonus check clears the bank . . . unless their next employer has agreed, in writing, to “make them whole.” And, anything they leave “on the table” is a subject of serious “make whole” discussions with their next employer, too.

5. If resignation timing is inflexible, consider compelling rationales to mitigate financial losses that result from resignation. In certain circumstances, financial losses are inevitable. But, adroit executives nonetheless seek ways to limit or even eliminate those losses. Some of the means to mitigation include (a) requesting that your next employer “make you whole” by granting you equivalent deferred awards and unpaid bonuses, (b) requesting that your employer accelerate payments and benefits in consideration of your assurance of future transition assistance, even (c) very careful, and perhaps creative, review of the specific language of applicable documents.

For example, your loss, forfeiture or repayment obligations might come into effect only upon your “voluntary” departure, and circumstances may exist upon with which to posit that your departure is not truly “voluntary.” Seasoned negotiators know well that “If you don’t ask, you’re unlikely to get.”

6. Finalize and sign your next employment offer letter or agreement before you resign. Without doubt, if there is one wisest pre-resignation precaution you MUST take, it’s that you don’t want to resign before your next employment is as clear, signed and without unmet conditions, to the degree possible. Otherwise, you could find yourself without either (a) your prior job or (b) your next job. No result could be worse.

While you can never make 100% certain your next job will become a reality, you should do everything in your power to make sure there are as few hitches as possible. Any written confirmation of terms should include such things as your start date, your title, your responsibilities, your compensation, your benefits, your reporting structure, and the location of your office. Get rid of as many of the “if’s, but’s and maybe’s” as you can before you sign.

7. Have an experienced Executive Employment Attorney Review Your Documents, Your Facts and Circumstances, Your Analysis and Your Presumptions. In employment matters, it’s always preferable to keep attorneys – even mention of attorneys — out of discussions, and for as long as possible. That said, having an experienced employment attorney review your steps, your decisions, and the presumptions upon which they are based, can only help. In addition, having an attorney on “stand-by,” ready to act to prevent conflict or achieve prompt finality, is the definition of prudence.

In this newsletter, we’ve addressed the Seven Strategic Precautions Before Resigning. In future “Sklover Executive Risk and Reward” Newsletters, we will address Strategic Precautions to take both When Resigning, and, thereafter, After Resigning.