Colm Doyle A Software Engineering Manager in Dublin, Ireland.

Microsoft introduces a new "Discretionary Time Off" policy

Tom Warren reporting for The Verge:

Microsoft certainly isn’t the first big tech company to adopt unlimited time off. Salesforce, Microsoft-owned LinkedIn, Oracle, and Netflix all offer similar unlimited time off policies for employees.

Let’s be 100% clear on something. Flexible / Discretionary / Unlimited time off, or whatever you call it is a scam. It’s often perceived as a benefit to the employee, but it’s really a benefit to the company and it really needs to be called out as such.

It creates situations where instead of time off being something that you earn and can bank towards a balance, every request is an imposition on your team, versus a clear cut entitlement. It makes your time off almost entirely at the discretion of your manager, and we’ve all had shitty managers. Having the confidence to tell your manager you’re taking your 30th or 35th day off is great, and I applaud you, but you can imagine how a discretionary policy makes those requests a lot harder for most people, especially traditionally underrepresented groups.

But when you have an ever increasing balance of days off, it creates a real signal to you, your manager and your organisation that you should take time off. And that creates a culture where time off is healthy, almost an obligation to be met.

Time off is a monetary benefit, treat it as such

Unlimited Time Off is 100% a balance sheet benefit to the company, as they don’t have to pay out accrued time off when an employee leaves. You’ll find that in most companies with these policies, the contracts of employment, which are really what matters at the end of the day, will be crystal clear on this point. You’ll only accrue the minimum required by law, and not a minute more.

Salesforce in Ireland used to have a policy called “Holiday Buy Back”, where you could sacrifice a day’s salary to buy a day off. When I pointed out it should be more accurately just called “unpaid time off”, I could almost hear the confusion coming from HR. So trust me when I tell you, your company considers time off in financial terms, and you absolutely should too.

If not unlimited, then what?

There’s at least two alternatives in my mind that are better than unlimited time off.

First off, give, you know, actually very generous time off balances. And make them consistent globally. So basically, if as a company, you’d expect a median of 28 days off under an unlimited time policy, then just make that the allowance.

The second, and better way in my mind is Minimum Time Off. All the benefits of unlimited, but without the downsides. Codify a generous minimum, and then let people take more if they want.

When I’ve been a manager at companies with unlimited time off, I have always implemented it as a minimum time off policy. I tell my team that I expect that by the end of the year, everyone has taken at least 25 days off, and that if we get to mid November and people are short of that, I’m going to be sending them home.

So if you’re a manager in a company with “unlimited” policies, I’d encourage you to take a similar approach to me, but always remember to advocate for the policy to fixed org wide, because it’s a better policy for everyone.

Tapbots share a roadmap for their Mastodon client, Ivory

I’ve been using Ivory as my main Mastodon client on iOS for the last week or two, and it’s very polished given that it’s still consider alpha/beta. I suppose I shouldn’t be surprised, given that it’s from the same team that makes Tweetbot, but it’s still nice to see.

I will say that it’s a much more Twitter-esque way of consuming Mastodon, which won’t be for everyone, but for those of us with one foot in each ecosystem, it does make it a bit easier to switch between the two.

Having friends in HR is fine, but HR is not your friend

After the wave of layoffs at Meta (previously known as Facebook) in November of 2022, I recall messages in the Facebook group for former employees discussing how to handle elements of the redundancy process, like if it was possible to max out retirement saving contributions, or spending gym benefits whilst on garden leave, and a common response was to suggest asking Human Resources (HR) or to mention something that HR had told them. And it reminded me how much trust people place in good HR teams. But people tend to mix up the notion that because they have friends who work in the HR team, that the HR team are their friends, and they forget that HR may not always have your best interests at heart.

HR can definitely be helpful

This isn’t to say HR are your enemy or anything. In fact, a good HR partner can be an important resource, especially for a people manager. They can act as a sounding board to ensure you’re treating people fairly and not acting with an unconscious bias. In situations with under-performing team members, they can advise you on what resources are available to help your struggling report, be they career development training, mental health services and more. But it’s also important to remember that HR aren’t paid to be an advocate for employees, be they your reports, or indeed yourself.

Who HR are there to support

HR exist to represent the interests of the company and those interests always have a degree of divergence with employees. Sometimes the divergence is small and this is the ideal, but frequently the divergence is large, and the redundancies we’ve been seeing in the tech industry is a prime example of that.

It’s easy to look at the redundancy packages being offered by the likes of Meta, Stripe or more recently Salesforce and think “oh that’s so generous, they’re really looking after their employees”. That’s the natural thing to do, we all want to expect the best of others and I don’t mean to minimise how helpful these packages are to help people land on their feet, but to suggest they’re selfless on the part of the company is perhaps a bit much.

It’s all risk mitigation

It is almost certain that a calculation has been made as to what is the smallest amount of money they can spend without suffering some kind of consequences, be it brand reputation, or legal action, then present that as a generous offer to employees. We should be grateful, we should jump at it, they would like us to think. But there might be a better deal to be had, particularly if you’re in a jurisdiction where you have a degree of legal protection, like the European Union. It pays to get informed about your rights, because your HR and Legal teams are not going to do that for you.

Just look at the case taken by a senior Twitter executive in Ireland, where not just accepting the company position led to settlement by Twitter on what you can only assume were more favourable terms. So don’t let them railroad you into a decision until you’ve had a chance to get some advice. Your employer definitely got legal advice on anything they put in front of you, why shouldn’t you do the same before signing?

HR aren’t evil, they’re just doing a job

This isn’t to say your HR team are bad people. They’re almost certainly not. They’re just doing their job. But don’t forget what their job is, and it’s not to protect your interests, so make sure you have someone at the table who is.

Shopify clearing their calendars

Tristan Bove, reporting for Fortune:

Shopify will be eliminating all recurring meetings involving more than two people in a bid to give employees more time to work on other tasks, Kaz Nejatian, vice president of product and chief operating officer at Shopify told employees in a Tuesday email viewed by Fortune.

I tend to start every calendar year by declaring email/slack bankruptcy, but this is a pretty extreme version. Clearing the calendars of an entire company is certainly a new one to me, but I can’t say that I disagree with it as an idea. It forces you to be a bit more deliberate about scheduling a meeting rather than relying on the inertia of a meeting just…being there.

Slack was fairly good at async collaboration, and my days didn’t involve too many meetings, but there was always some. Intercom definitely leans on meetings for collaboration more than I’m used to, but I’ve been trying to slowly carve meetings out of my calendar that would be better suited to async collaboration, for example moving from a daily synchronous standup to a mix of meetings and prompts in a slack channel.

In my experience, it’s not so much the number of meetings that’s the problem, it’s the “swiss cheese” effect of having a bunch of small meetings that are spread throughout your week. I definitely agree with a company wide no-meeting day, and compressing larger meetings into a designated time slot as Shopify are doing here. These kinds of seismic changes in the working culture of a company are only possible when they’re an organisation wide mandate as opposed to small experiments by individual teams.

What I’m really curious to see is how this experiment plays out over a longer time frame. If we look at the calendar of a typical employee at Shopify in 6 months time, will it be filled with meetings again? Or will they have found a new way to collaborate? Only time will tell.

Charity Majors on Elon, CEOs and Tech Workers

Charity Majors (aka @mipsytipsy), writing over on Twitter:

I read something that made me really fucking angry. I’m not going to go look it up, but it was something like how most tech CEOs are watching closely, and privately rooting for Elon’s changes to pay off and make Twitter a profitable business.

It had some anecdotes about how excessively generous and solicitous companies have had to be to compete and retain tech workers, including the chestnut about a FB worker asking about toilet paper in the weekly all hands.

It’s gone too far! CEOs are practically powerless now! 🙄

I won’t embed the full thread here, so click above if you want to read the whole thing. But here’s a few highlights:

On Twitter dying off

And while I don’t really want Twitter to die, and neither, I think, do most of them, there would be something INCREDIBLY satisfying and validating if it did.


However, I don’t think that’s a very likely outcome. I’ll say more in a sec, but I think the likeliest outcome by far is one where Twitter survives and Elon claims victory, or at least saves face.


It took the work of thousands of world-class engineers, designers, support, security, lawyers, accountants, etc over 15+ years to build Twitter. They built it to be resilient.

Charity is absolutely correct here, and she clearly has the authority to speak on large scale systems given her background. Twitter has far too many people invested, both in literal terms, but also in a influential sense to let it simply die. It’s the medium of choice for a great many groupings of traditionally powerful people, from journalists to politicians to venture capitalists. It’s not going to just stop working one day, and Elon isn’t just going to actively destroy it, he’s sunk too much money into it.

I’ve mumbled before about the over hiring and bloat that seems endemic at tech companies. But the engineers who are left are likely to be able to keep the lights on.

(How much forward product investment they can muster is the real question mark.)

The way he dismissed people isn’t some kind of 3D chess he’s playing, it’s plain old ignorance of the complexity of a system he doesn’t understand. He has no experience running a large scale social network, but there’s at least enough people left in Twitter HQ (until the get kicked out of the building anyway) who do know enough to keep the service running.

I don’t think anyone would argue that Twitter had exactly the right number of people, but when you cut as many people as he did, in the fashion that he did, you’re going to lose people that have a lot of important institutional knowledge. And that’s going to make it harder to iterate on the product in a coherent way.

If you look at the features that Twitter is shipping lately, there doesn’t seem to be any logic beyond “what Elon wants”, which is going to run out of momentum at some point.

On CEOs and tech workers

When CEOs call their own employees lazy, coddled and opinionated, and openly long for the days when they could just fire their critics (like Elon did!)…what they’re really upset about is the fact that their workers have more relative power than they used to.

They want a say in things, and they’re not trapped here; they have options. So YOU have to compete to keep THEM happy here, instead of them all trying to keep you happy.

To wrap up… If Twitter recovers, there will likely be a push to credit authoritarian leadership, mass layoffs, and treating workers like shit.


CEOs need to learn that “everything would be great if everyone would just do what I say 😩” is neither true, nor an appropriate thing for a grown ass adult to think. Having other stakeholders with power may be personally inconvenient, but usually yields better outcomes.

I think when the current chapter of Twitter comes to an end, assuming the result isn’t a complete and utter failure, fans of Elon Musk and/or his tactics will point to what little regard he had for the people who worked at Twitter and say that he was right to act how he did.

But there’ll be more than a little selection bias in that. They’ll ignore the possibility that Twitter could have been fine if he hadn’t done anything, and maybe given a different style of leadership where the staff were treated with a modicum of respect and dignity, Twitter would have been even better.

And if this is the final chapter of Twitter, they’ll say he had no choice, he did what he could, and that if he couldn’t save it, then clearly no-one could.

Because just like Trump did, Musk manages to create a reality distortion field amongst his followers that Steve Jobs would have been envious of.