Ask HN: What are the biggest challenges preventing startups from hiring remote?

  - International payroll: often impacts tax situation
  - Adjusting to remote collaboration. e.g. no more walls of sticky notes; can no longer rely on water cooler conversations or "quick meetings"
  - Timezones

I can recall several times where clearly (or so we thought) laid out plans were given over to have them come back a week later with some measure of misunderstanding. The 2 solutions to this have either been micromanaging the remote team, which is painful or time consuming -- or giving the team enough autonomy to work independently, which is risky.

None of these are big problems. The biggest problem we have is communicating effectively with people in various time zones, and making them feel apart of the team. Video conferencing is still an area that is lacking in this area. I've yet to find a service that meets all our needs. Right now we are using LifeSize because it's the best we've found, and still fairly annoying.

The problem really isn't on the "hiring" end. It's how to work as effectively with remote people as you would with people in the same office. When you introduce friction with remote, it causes problems. That being said, I think it's a worthwhile problem to solve.

Not sure this helps, but this is our biggest struggle right now.

If the person in charge doesn't know what he's doing the rest doesn't matter.

Regarding your options:

1. Hardly any different than on site. 2. Not an issue at all. 3. Huh? 4. For some.

Trying to figure it out on your own is irresponsible at best, so it boils down to hiring a local CPA or tax attorney in each state/city you hire in to go over the implications of bringing someone on in that city.

If the person is right, it's worth the cost, but it's a large, unexpected time-suck.

Communication! Communication! Communication!

If any part of your product requires people to communicate with each other, then the team members lying on vastly different time zones will have low efficiency because information round trip time will be larger than those of the local (or time zone near) ones.

Hiring is hard to begin with, and hiring remotely has additional pitfalls. A company like Triplebyte that would perform additional vetting to prove a candidate's ability to work remotely would be quite welcome.

Re 4. VC systems are still awful and both companies and employees aren't willing to invest to the right level, and commit to workflow changes, in order to make it seamless to work remotely. In particular, latency and packet loss is what just kills VC and makes it very apparent that we're not actually in the same room together. The way to solve that is gigabit home-office Internet connections, but $10k to run lines and an additional $500/month, as well as the hassle of using a wired connection at home to take advantage of it, and then a dedicated VC system, is a total non-starter for many, on both sides, employer, and employee.

Throw in a timezone difference, and the wrong remote employees can take more time to manage than they're worth. (That's not to say there aren't some really really good, really solid remote employees, just that there are also the wrong hires - same as goes for in-person.)

Re. 2. On top of payroll, there are also plain cultural differences between countries that make it more challenging than when there is no difference - holiday schedules, vacation policies, etc, and until you've lived it, it's hard to know what to look for in advance.

For example, bots like http://tatsu.io or http://standuply.com help running standup meetings.

I think remote work will become more and more popular in the future despite its challenges.

Timezone is a tough one. For us, finding a scrum time that works for everyone (in a small team it's doable), and sticking to it daily helped to get the team to communicate more openly with each other, and stay in sync.

Finding the right set of tools to manage remote teams is one the biggest challenge when a team is distributed across the world. Traditional task management tools didn't lets us easily ideate, organize, and share task lists together, hence we were inspired to build Taskade (Disclaimer: I'm the co-founder of https://taskade.com). The idea of having the freedom to work together on task lists in real-time, see each other's progress, and collaborate without any distractions.

Startups and fast growing companies grow quickly and changes happen rapidly. If priorities are constantly changing and communication/the planning process isn't really robust you won't have remote people who are successful.

These are two areas where good solutions may exist at reasonable price-points, but if so that information isn't widely known.

Not sure if it fits with your business model, but it would be extremely helpful for someone to carefully evaluate the effectiveness of various technologies / products / services for those areas, and provide recipes for known-good setups.

I.e., if one of your clients can tell you their current and upcoming team sizes, network connectivities, etc., you can tell them what products and services give them good video / whiteboard quality at various price points.

IME companies with remote workers tend to be "penny wise, pound foolish" regarding these things.

EDIT: To be more specific: For call quality, having good data on what setups result in good call quality in Skype vs. Slack vs. Google Hangouts etc. And for shared whiteboards, having good information on how effective / sufficient teams find various approaches such as (some website + iPads), (some website + a particular Wacom tablet), (everyone on the team having a particular model of interactive whiteboard such as this one [0]), etc.

[0] https://www.cdwg.com/product/SMART-Board-6075-75in-LED-displ...

I have a US company and trying to build a remote team as "employees". Going crazy trying to figure out how to set this up other than the usual option of "pay them as freelancers and let them do their own taxes". Not everyone is cut out for that and not able to attract good talent.

I'm going to use this comment as a way to talk about remote hiring generally, rather than respond directly to your comments. I want to help others understand some of the challenges it has been being one of the larger (relatively) fully distributed companies.

I think there is a common misconception that the world is mostly flat and that our company can hire from anywhere. I am commonly criticized when tweeting job postings (almost always remote) when the countries we can hire from is limited to a select few. "Not real remote" "first world remote only" "remote != 8 countries" etc. are common criticisms.

Disclaimer for the remainder: I am not a lawyer and my exact details because of that may be wrong. Please consult your own legal team.

When hiring remote, there are a few things to keep in mind:

1.) You have to adhere to employment laws within the country you're hiring from. Employment laws vary widely between countries and getting them wrong can be very expensive. For example: vacation time will vary, holidays will vary, the ability to let someone go will vary, what you can/cannot expect from an employee varies. In one country, emailing an employee outside of work hours is legally considered harassment; when working with multiple timezones that's a challenge because "in work hours" for one country may be "out of work hours" for another country.

2.) To employ someone full time, many countries require you to have a legally entity within that country. Establishing a legal entity takes a lot of time and a lot of money.

In the past 12 months, we've had at least one member (more now) on our HR/finance teams establishing legal entities _full time_. I've had my signature on at least 8 incorporation documents in the past 6 months. By the way, most incorporation documents require a "wet" signature so if you're remote like we are, be prepared to be FedExing a lot of sensitive legal documents around.

Beyond just paperwork, there are often requirements to establish a legal entity: a real, physical, local address is one. In one country, we had to pay out of a local bank account in local currency (which has its own red tape), and this country also required we maintain a minimum balance to pay 3 months salary in the local account in local currency at all times. For a startup, that much cash "not working" can be problematic depending what stage you're at.

In one country we're establishing an entity in, the process just takes a LONG time. We've been responding to any inquiries and sending paperwork immediately and we're 8 months in and still probably 2 months away from completing the process. Meanwhile, we still can't legally hire there.

A lot of legal paperwork is understandable in the local language of where you're creating the entity. This means that you also have to pay lawyers fluent in that language to vet the paperwork. We employ full time lawyers, but primarily in English, so this requires us to go to expensive outside counsel.

Finally, this is all expensive. There are fees to creating entities but also recall that we have multiple full time employees that spend their entire day establishing legal entities. So we have our own full time salary costs plus filing costs plus legal costs.

3.) Hiring contractors DOES work around some issues, but has its own downsides. First, we can't offer options/stock to contractors and we'd like all our employees to benefit from this. Second, we often can extend the same full time benefits we want all our employees to share such as healthcare, 401K, etc. Put another way: we want all HashiCorp employee...

Think about it: the benefits of remote work go mainly to the employee, but the drawbacks (harder to communicate, harder to evaluate productivity) fall disproportionately on the manager. Since the manager is the one making the hiring decision, they don't hire remotes.

So to give a really broad answer, my suggestion would be "change the incentives so managers will hire more remote workers". That could mean internalizing costs of on-site workers, better communication tools, etc.

- Which payroll companies, if any, will be the best solution for handling international (or even just inter-state within the U.S.) payroll / tax issues?

- What communications technologies and practices work best for various team geographies / network-connection-quality / local-hardware setups?

- What's the optimal frequency, duration, structure, etc. of whole-team face-to-face meetings for teams that are typically distributed?

- What management training is most helpful for managers of all-remote teams, or of teams where only some members are remote?

PS. We are hiring

Personally, I find the toughest part to be actually managing the people. You really need to trust your team to be self-motivating which can be tough for a manager to do, especially new ones, because you need to give up some control.

But even though you trust them you need to have a way to measure results. That means being more disciplined and mature in your project planning than you might be if everyone is co-located.

For a startup that is key. Startups often skimp on disciplined project management.

I also find it tougher to do things like say, identify when someone is having a rough time (personal or professional) and take steps to correct or accommodate for that. If a co-located employee starts underperforming but I can see they are clearly checked out (like their head is somewhere else) I might suspect there is something going on at home and adjust my management style with that person. If they are remote it is harder to tell those things. Communication becomes extremely important when body language / behavioral clues are lacking.

So to pile on a lot of the other answers here... communication, communication, communication.