Buyout on the Table? 5 Questions to Ask Before You Sign — and How to Hit the Job Market Ready

Microsoft recently offered voluntary buyouts to around 6,000 employees, and they're far from alone. When a big company dangled a check in front of workers, plenty of people took it without fully thinking through what comes next. If you're staring down a similar offer right now, slow down for just a minute.

Accepting a buyout can be a genuinely great move. It can also leave you scrambling if you haven't prepared. Here are the five questions worth answering before you sign anything, plus a practical game plan for getting your job search off the ground the moment you do.

1. What Does the Severance Package Actually Cover?

Read the fine print carefully. Severance pay is the headline number, but the real value is often in the details:

• How long does health insurance continue? COBRA is expensive. Know exactly when your employer coverage ends.
• Are unvested stock options or RSUs included? Sometimes a buyout accelerates vesting. Sometimes it doesn't.
• Is there a non-compete or non-disparagement clause? These can quietly limit where you can work next.
• What happens to your PTO balance? Some states require payout; others don't.

If the package is substantial, spending a few hundred dollars on an employment attorney to review it is almost always worth it.

2. How Long Will the Money Actually Last?

Be brutally honest here. Take your monthly expenses, divide the net severance by that number, and you have your real runway. The average job search runs three to six months, and that timeline stretches significantly in a market where thousands of people from the same industry are job hunting at the same time, which is exactly what happens after a wave of tech or corporate buyouts.

If your runway is shorter than your likely search, start looking before you sign. You can job search while still employed, and doing so puts you in a much stronger negotiating position.

3. Are You Eligible for Unemployment?

Voluntary buyouts are a gray area in most states. Many workers who accept them are still eligible for unemployment benefits because the alternative was often a layoff anyway. File promptly and let your state agency make the determination. Don't assume you're disqualified.

4. What Does Your Network Actually Know?

Most people believe their network is stronger than it is in practice. When did you last talk to your former colleagues, managers, or clients, not to ask for something, but just to stay connected? A buyout announcement is a legitimate reason to reach out. Something like, "I'm exploring what's next and would love to catch up," is not awkward. It's normal.

This matters because a huge percentage of jobs are filled through referrals before they ever hit a job board. The sooner you activate your network, the better.

5. Is Your Résumé Actually Ready?

This is where most people lose weeks they can't afford to lose. They update their résumé in a rush, send it out, and hear nothing back. Here's the uncomfortable truth: most résumés never reach a human. They're filtered out by Applicant Tracking Systems long before a recruiter sees them.

Before you send a single application, it's worth understanding how those systems actually read your résumé.

A quick pre-launch checklist:

• Fix your format first. Two-column layouts, text boxes, headers and footers, and tables all cause parsing errors in most ATS software. A clean single-column format is the safest bet.
• Check what gets extracted. ATS systems pull your name, contact info, job titles, dates, and skills into structured fields. If your formatting is off, any of those can get dropped or scrambled.
• Match your language to the job description. Skills keywords matter. If a job posting says "stakeholder management" and your résumé says "cross-functional collaboration," a keyword-matching system may not connect the two.
• Tailor your bullets, but don't fabricate. Rewriting a bullet to emphasize the part of your experience most relevant to a specific role is smart. Inventing experience is not. Keep it honest and specific.

Tools like the ATS scan and job-match scoring at Past the Bots can show you exactly what a parser sees when it reads your file and where the gaps are against a specific job description, which takes a lot of the guesswork out of the process.

The Bottom Line

A buyout offer can be the push you needed to find something better. But the people who come out ahead are the ones who treat the decision deliberately and hit the market prepared rather than reactive. Answer the five questions above, get your paperwork in order, and make sure your résumé is actually working for you before you send it anywhere.

You've got this.