The first time I was handed a confidential separation agreement, it was full of things I didn't realize I could get. I was clearly getting fired — by surprise — and thought I was supposed to feel grateful for whatever they were offering. I assumed the number on the page was the number — sign here, done.

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What I didn't yet understand was that most employment in the US is "at will." That gives an employer wide latitude to let you go for almost any reason, without owing you anything beyond a small list of legal obligations: earned commissions, accrued PTO in some states, and the like.

What they're actually worried about is you suing them — for discrimination, for wrongful termination, for something else entirely. The separation agreement is the tool for that: money and other consideration, offered in exchange for you waiving your right to sue. It might re-cast a termination as a "mutual separation agreement and general release" but the whole transaction is about closing the legal door once and for all. And that's exactly why there's often room to negotiate — the number they put in front of you isn't a fixed cost, it's an opening offer in a negotiation they'd rather you didn't realize was happening.
 

As my career developed into one where I was on the other side of the table, I learned that the offer in front of you is not automatically their best and final offer - even when it's an offer being made to multiple employees at the same time. It's often just the first number someone put on paper, and it's worth checking.

As a senior executive, the offer letter and employment agreement I signed on day one already spell out the severance I'll receive on my final day (potentially with variations that depend on the path we took to get there). But I know from experience that even those agreements often still leave room for just a little bit more change.

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Here are some common things worth asking about — not all of these will be on the table every time, but none of them are unreasonable to ask for:

• Severance amount and structure. Whether it's paid as a lump sum or salary continuation may affect what your technical "last day of employment" is - which has implications for when your health care coverage ends, whether it's eligible for 401k match, and more. Also, check whether the number itself has any room to move. 

• Timing of payments. Especially near year-end, when it lands can matter as much as how much. Receiving a payment in December versus January can shift your income tax bracket for that payment — particularly if you don't expect to earn much for a while afterward — and can affect 401(k) matching and total annual earnings calculations, since those often reset on the calendar year.

• Health insurance. Extended employer-paid coverage beyond what's initially offered, or help covering COBRA premiums for a few additional months. People's needs aren't one-size fits all, and you may decide that something other than cash is important for you. An employer may be happy to pay two more months of premiums to help your spouse finish their last round of chemotherapy, even as the regular paychecks come to an end today.

• Equity. Continued or accelerated vesting, or an extended window to exercise options you've already earned.

• Bonus and PTO. Prorated bonus for time worked this period, and payout of any unused PTO.

• Notice period or pay in lieu of notice. Extra weeks of pay in exchange for an earlier last day, or vice versa, depending on what you need.

• Outplacement services. Career coaching or job-search support, sometimes fully paid for by the company.

• References and characterization of departure. A written reference letter, or agreement on what will be said (or not said) to future employers who call to verify employment.

• Non-compete and non-solicit terms. Whether the scope or length of any restrictive covenants can be narrowed.

• Equipment. Whether you can keep your laptop, phone, or other equipment rather than returning it.
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Beyond the list itself:

• Take the time they're implicitly telling you not to take. They want your signature quickly, in part to limit their own legal exposure. But you're already being let go — a few more days to actually read the document and think it through rarely changes their calculus, and it might change yours. After all, they're already firing you - what else can they do to you for taking some more time before signing?

• Get the layoff-versus-resignation distinction straight before you sign anything. How your departure is characterized can directly affect your eligibility for unemployment benefits. If there's any ambiguity in the language, that's worth clarifying.

• Read it with fresh eyes, or someone else's. This is a legal document written by people whose job is to protect the company, not you. If you can afford even a short consultation with an employment attorney before signing, it's often worth it — particularly if there's anything in the document you don't fully understand. Many will offer you a free consultation, charging only a portion of any increase they're able to negotiate on your behalf.
   

When I was given that confidential separation agreement, it was just a severance package and an NDA. I spent years wondering what I'd done wrong — a nagging doubt that persisted through multiple, successful C-level roles and exits at companies that valued exactly what I brought to the table. You may never fully know why you're being separated, and that's not something you can negotiate your way into learning. The agreement in front of you, though, often can.