• Microsoft is offering buyouts to around 60,000 employees.
• Chris Williams, former Microsoft VP of HR, said waiting for a better offer may or may not backfire.
• He shared what employees who are offered a buyout should consider and what they may not realize.

Microsoft is offering buyout packages to some 60,000 employees, or more than 25% of the workforce. That's a huge number in any terms, and it sent a signal and shock wave through the industry this week.

I'm the former VP of HR for Microsoft, and although I've been away from the company for some time and have no insider information, having been on the inside at Microsoft and in the industry for 50 years, here is what Microsoft employees should be considering — and what they may not realize about taking a buyout offer.

Your buyout offer may or may not be the best offer you get

During a buyout, position, tenure, level, and other factors are taken into account for each bespoke offer. The offer is likely to include compensation, benefit continuation, and possibly some acceleration or continuation of equity vesting.

That said, Microsoft might not offer more generous buyouts than severance packages, but companies usually offer better terms to people who take a voluntary separation than people who get laid off. That is not only to induce employees to go voluntarily, but also because the costs to the company are less if these workers voluntarily leave. There is less legal risk, time, and expense. It's also simply easier for the company to manage.

If you're offered a buyout, I usually find it could be the best offer you'll get. If it's not, you could be settling for the same offer as someone in a layoff and miss out on collecting unemployment.

A buyout can force some very hard career choices

If you get a buyout offer, looking at your budget should be your next step. Does the offer provide you with enough to retire? Enough to support an extended job search? The buyout can be a good forcing function for some very hard career choices.

Spend time looking at your cash flows, and pay particular attention to benefits. For many, healthcare costs are a substantial part of their budget. Weighing the buyout offer against continued coverage is often a tipping point in the decision.

Also consider any equity vesting dates you may have. Compare when you might vest with and without the offer, as those dates can mean a significant change in your investments. Whether you should take the buyout is highly dependent on both the offer and your situation. If you had retirement anywhere in sight, this offer might be just the trigger you need to move on. Perhaps the best offer you'll ever see.

However, if you need to continue working, there's a great deal more to consider.

Taking a buyout can give you a head start in a tough job market

The tech industry job market has been rough for the last year or so, and shows all the signs of getting worse. If the buyout doesn't afford you the ability to retire, you should plan on an extended period of job searching, maybe six months or more. It's tough out there. Be prepared.

One thing to consider if you need to continue working is that taking the buyout might give you a short head start in the job market. Assuming Microsoft and others follow this up with more layoffs like they did the last time, the technical job market will be flooded with quality people. Of course, you can search for a job while you have one, but taking the buyout gives you time for a full-time job search.

In any case, if a job search is in your future, don't delay. This market shows no sign of getting better.

Finally, if you're offered a buyout, don't ignore it. It's a sign. I'd read it as a clear signal from the company about your value, at least from their perspective. You can bet on the odds, but if follow-up layoffs happen, I'd bet that those who declined the buyout are somewhere on that list.

Buyout or not, some things to do

This buyout is the latest signal of a broad realignment of the job market, at least in the tech sector. Even if you aren't offered it or don't think you're at risk of later layoffs, you'd be wise to keep all your options open.

Get your résumé up to date. Spend time honing it, emphasizing the clearest set of skills you can. When a market is contracting, the safest bet is having a particular skill someone is looking for. When times are tight, the generalist is often the first person let go.

Work with and expand your network. Have coffee or a Zoom chat with everyone you know. Peers in other companies, even other industries, are invaluable when things get tough. Especially when the world is changing, and predicting the next hot spot is so hard, having as many warm connections across industries is a huge asset.

Don't go asking for jobs as much as keep those connections alive. You never know when someone's manager will say, "We need someone like that." And your friend can say, "I know just the person."

Whether you are offered a buyout, or whether you decide to take it or not, having a network of people to connect with is your single biggest career asset.

What to do if you get a buyout offer

Budget first, and outreach next.

Carefully decide your near- and long-term financial future, and make the decision from hard facts. Then connect with people you know across industries, far and wide. Those connections will be excellent sounding boards and could well provide the path to your next role, or the friends you need in retirement.

When contacted about this story, a Microsoft spokesperson pointed Business Insider to its statement on the official Microsoft Blog, which read in part, "Today, we're introducing a new Voluntary Exit Offer (VEO) to eligible employees within participating organizations." They added that "the VEO is similar to a standard severance offer, which varies by market. The offer includes payment based on completed service and base pay, as well as career transition services, which includes career coaching and job search assistance."

• Dropbox co-CEO Ashraf Alkarmi announced layoffs of roughly 200 workers.
• Alkarmi said the cloud-based storage company is profitable but needs to make "hard choices."
• You can read his full email to employees below.

Dropbox is dropping the layoffs hammer.

Dropbox co-CEO Ashraf Alkarmi announced on Wednesday that the cloud-based storage company is laying off roughly 9% of its global workforce.

"Today, we're making difficult choices about where we invest and how we organize Dropbox to achieve the product and growth priorities that will matter most for our long-term strategy," Alkarmi wrote in an email to workers that the company posted publicly.

Alkarmi said Dropbox is eliminating roughly 200 roles across its across Engineering, Product, Design, and G&A team. The company, Alkarmi wrote, is profitable but needs to make "hard choices" about where it spends its money.

"Delivering on that strategy requires concentrating our resources on the priorities that will have the greatest potential for customer impact and growth," he wrote.

As part of the changes, Alkarmi also announced that chief technology officer Ali Dasdan will be stepping down.

Read the full email

Hi everyone,

Today, we're making difficult choices about where we invest and how we organize Dropbox to achieve the product and growth priorities that will matter most for our long-term strategy. As part of these changes, we've made the decision to eliminate about 200 roles across Engineering, Product, Design, and G&A teams (approximately 9% of our global workforce). For most impacted Dropboxers, today will be their last day.

S-team and I take full ownership of this decision and recognize that these colleagues have made meaningful contributions to Dropbox, our products, our customers, and our teams. Our first priority today is to treat every person affected with the care and respect they deserve.

Changes to Senior Leadership

I also want to share that Ali Dasdan has decided to move on from Dropbox. During his time here, Ali led and strengthened many of the technical capabilities we'll rely on as we move into the next phase of our transformation. I'm grateful for his leadership, his partnership, and the foundation he and the team have put in place. Ali's last day is November 18th, and he'll be focused on ensuring a smooth transition through next month. We wish him all the best in what comes next.

Why we're making these changes

Our business is profitable, and we've built real momentum this year. Our two-year strategy sets a clear direction for growth: solving more of our customers' critical workflows; reaching more of our chosen customers, including larger companies; and bringing our technology to new markets.

Delivering on that strategy requires concentrating our resources on the priorities that will have the greatest potential for customer impact and growth.

That means making hard choices about where we invest, how we're organized, and what work we simplify, scale back, or stop. Those choices include the difficult decision to reduce the size of our team.

How we'll prioritize going forward

In order to be successful, we can't take the same work and spread it across fewer people. We'll streamline teams and concentrate support and resources against product areas that have the highest impact on our customers and Dropbox as a business.

Taking care of impacted employees

To those leaving Dropbox, we're committed to supporting you through this transition. Departing Dropboxers are eligible for a severance package in line with the following:

Severance, equity, and transition support:

Sixteen weeks of pay beginning today, plus one additional week for each completed year at Dropbox. International packages will reflect local practices and legal requirements

Q4 equity vesting

For employees on the Corporate Bonus plan, a prorated lump-sum payment based on their 2026 bonus target

Immigration support for impacted visa holders

Healthcare and well-being:

U.S. employees will receive six months of COBRA subsidy, if elected and eligible

Modern Health access will continue through the end of the separation month to support mental well-being, with extension options detailed in severance packages

Payment for eligible current and approved upcoming paid leaves, including medical and family leave

Additional support:

Devices: Impacted employees will be eligible to keep (1) Dropbox laptop, (1) mobile device if assigned, and all existing desktop peripherals

Job placement: Job placement services and career coaching will be available at no cost

What comes next

Right now, our focus is on the colleagues who are leaving Dropbox. Please give them the space and support they need.

And to everyone leaving Dropbox: thank you. Your work to build our capabilities, serve our customers, and contribute to our culture has been deeply meaningful. I'm grateful for everything you've contributed.

Ashraf

• With Microsoft offering about 60,000 staff buyouts, many will be deciding whether to take one.
• Business Insider asked HR experts what advice they'd give workers offered buyouts.
• Their advice included budgeting for a longer job search and pricing out replacement health coverage.

About 60,000 Microsoft employees have a choice to make: take a buyout and leave at the end of the year, or stay.

Eligible employees have until early December to decide. Offers reviewed by Business Insider vary by level, location, and length of service.

For US employees at levels 64 and below, the cash offer is one week of base pay for every six months of service; at levels 65 to 67, it is two weeks for every six months. The offers also include continued stock vesting and health insurance.

Buyouts are a reasonably common offering for corporations looking to cut costs, but deciding whether to take one can be difficult. Business Insider spoke to two HR experts to ask which factors employees should weigh and which questions they should ask before signing.

Read their top tips below:

Work out what the offer is really worth

"The number is important," Marjo Miles, founder and principal consultant at The Ember Effect, told Business Insider. "But really, there’s more than that number."

Employees should check what happens to their stock, paid time off, health coverage, and any bonus or commission due after they leave, Miles said. They should calculate how long the payout would cover household expenses after tax and deductions.

Deborah Saneman, CEO of workforce management and HR technology company Würk, told Business Insider that employees should price out replacement health insurance: how long coverage lasts, what they would pay monthly, and whether the company covers any of the premium.

She also recommended checking which shares would vest after their exit. "The headline number is only part of the picture, so get the details in writing," she said.

Plan for a longer job search

"Whatever somebody thinks their job search is going to take, double it in your mind and plan for that," Miles said.

She suggested using the time before the deadline to explore options. "Instead of deciding today, maybe start your job search today, she said.

Contacting people in their network and applying for roles could give employees a clearer sense of their prospects before they commit to leaving.

Saneman said employees should ask about career coaching, outplacement, or training. "A payout covers your bills, but help with the search itself can shorten the runway," she said.

Consider what staying could look like

Turning down a buyout does not guarantee job security, Miles said, though she cautioned against assuming layoffs will follow. Companies could leave vacant roles unfilled or take other steps to meet a savings goal.

"There are a lot of different ways that organizations can strategically get to their goal without just immediately doing a reduction," she said.

Saneman also cautioned against predicting what Microsoft or any other company might do next. "The benefit of a buyout is that it's on your own terms and gives you time to plan your next steps," she said. "A layoff may not."

Miles suggested asking how departing colleagues' work would be redistributed and what support would be available.

Saneman said employees should consider their longer-term plans: "The right choice is the one that fits where you want your career and your life to go, not just the one that looks best on paper."

Questions to ask before taking a buyout

Business Insider asked Saneman and Miles to share what questions they'd advise employees considering buyouts to ask. Read their four key questions below:

Would I be eligible for rehiring?

"Microsoft is a large organization, and professional paths may cross again in the future," Miles said. That may not make or break the decision, but it is worth knowing.

Will the payout be a lump sum or continued salary?

This can affect when the money arrives and how health insurance and other benefits are handled.

What happens to my bonus or commission?

Employees should check whether they will receive any payment due after their exit date and have the answer documented by HR.

What help will I get finding another job?

Saneman suggested asking about career coaching, interview preparation, and training to build new skills.