Ask HN: I’m starting a new job and things feel off. Am I overreacting?

Some of these things sound small - IT mailing a computer is standard, and you feeling you had to cancel travels plans to wait for it sounds like an over-reaction. Them using your personal email is a valid point, but something I'd just give feedback on as an improvement to on-boarding. Communicating about tools you'll use is fine. Asking if you want to be on a call is fine.

The one thing that seems out of line is expecting you to be on a call, unpaid, before your start date. That is far enough out of line that it is a problem. I'd just say no to such calls. It is your managers job to keep the place running until your start date, not yours.

But honestly, the bigger red flag to me is $150ARR. First of all, $150 what? K? M? If 'K' this is too small to have 500 people and be looking to IPO - red flag. If 'M', they are too big to not have their act together on having professional managers - yellow flag.

If I were you, I would take this all as evidence that they have grown beyond their current skill level, and it will be a dysfunctional company. But most medium-sized companies are in this boat. The question you need to ask yourself is whether the compensation is sufficient that you can put up with the crap or not?

I think you are exactly right. It smells like a company that has grown beyond the startup stage but key processes, such as employee onboarding, are being led by people that are inexperienced with how to handle all aspects professionally at scale. I would expect some significant dysfunction across most functions and I would really have to believe in the company's mission, and/or have a nice chunk of equity, to push through and hope they successfully can grow to maturity.

Umm... This is a US-based job, right? As someone based in Europe, I find it absolutely shocking you have been requested to work ahead of your start date. This is not even eligible for asking if it's a red flag. It's insane.

edit: I see other commenters are like "well, standard practice, not necessarily that terrible". Am I living in a bubble or is it just Europe?

This would not be accepted in Europe

Agreed. I've had requests ahead of start dates and it was not a problem for those I turned down; accepting/attending has always been optional and appreciated, but nothing more than that.

This is not acceptable in the US either. You’re paid for your time by law.

Not for salaried (exempt) roles your not

> Not for salaried (exempt) roles your not

You are right, instead if you work at all they have to pay you for the whole week.

That’s inaccurate (IMO) and there’s nothing saying the minimum ‘accrual period’ for earnings is weekly as an exempt employee. Potentially differs by state and I’d be interested to learn of any where it is different, please cite?

It’s quite normal to see people start Tuesday on payroll, finish on Thursday, and they don’t get paid those whole weeks. They typically get those days paid, even if for example you “offboard” by lunchtime on your last day of work.

I don't know of any that are different, but salary law is consistent enough to know that the salary starts when the employee begins work, so in this case, moving the start date up is what is happening even if the employer isn't acknowledging it. The same goes if the employer says the start date is 1/1 but you only show up at 1/2. The salary starts when the work starts, and doesn't stop so long as you show up once a week or so.

From California but similar everywhere:

> Pursuant to California law, an exempt employee must receive his or her full salary for any week in which the employee performs any work without regard to the number of days, or hours worked.

https://www.yourlegalcorner.com/articles.asp?id=135&cat=emp

If employers don't like this, they can pay overtime instead.

That’s a good citation (thanks!) but it covers the period of time when you’re legally an employee, thus if you start Tuesday you’re not one Monday, and if you finish Thursday you’re not one on Friday.

In this case with OP, my guess is that left them two choices:

1/ Accelerate start and then as you note, pay the whole period even though it sounded like this occurred before Christmas, was only a few calls then a vacation.

2/ Pay an invoice, which is mucky since it’ll probably involve supplier setup via AP, they’re clearly a W-2 equivalent person so perhaps this complicates other things like tax or benefits, etc.

If the person is “unencumbered” (not currently employed or subject to something contractual like garden leave which prevents them assuming the new employment) and if there was real value to having them participate in the calls then certainly the easiest would be (1.) - and IME, this is how larger employers would do it.

They may certainly claim that he wasn't a employee, however he would be working under their explicit direction to accomplish a task they asked him to complete. It doesn't matter one whit how the company classified him, he is a employee from the second he dials into that call. I can't tell you to put a paper hat on and flip burgers then not pay you since "you don't really work here until next week, just thought you might want to get ahead on the burger project."

Consider this, I don't know what this software does but a lot of the conversations around software are confidential. Did they just invite a random stranger into a call with potentially privileged information?

That’s still being paid for your time.

Yes this is crazy. Starting date means what it means, before that one is not in the job.

I think people see it as a manager being kind and trying to involve their future employee in decisions that will impact them directly. (Assuming they are not expected to be actively leading the calls…)

I can envision a scenario where someone could complain for not being included in these conversations. Imagine you start a new job and the manager says “btw, we signed a contract with this vendor two weeks ago, so this is the tool you’ll use for the next three years. We thought about asking your input, but you technically weren’t an employee then.”

I can't imagine anybody complaining about the second scenario being given an iota of sympathy.

Tone matters a lot here. There’s a huge difference between “You’re welcome to join these calls if you like, since it will impact how you work once you start” vs “We need you to be on these calls [with pushback/pressuring if you don't want to]”. This sounds like the latter, which is definitely not “being kind”.

I think you’re confusing “tone” with literal meaning. This is not a matter of “tone.”

This is a prime example of the fabled “soft skills”. Humans and our ways are incredibly squishy and ambiguous, so learning to interpret (and dispense) things like “tone” is incredibly valuable.

> “We need you to be on these calls [with pushback/pressuring if you don't want to]”.

I fully agree, pushback/pressuring would make this unacceptable. But I'm not seeing that in the post, even before correcting for the storyteller's (understandable) bias.

In my mind, the conversation is something like:

"hey can you join this call?"

"not unless you pay me for it"

"that's tricky to set up, but we'll make it up to you when you start"

It's still OK to say no to this, but it kind of feels like you'd start off on the wrong foot. The manager isn't trying to get away with having you do actual work for free -- they are not asking for anything like reports or deliverables. It's just dialing into a few Zoom calls (and "prep", which is extremely ambiguous and could use clarification by OP).

The vacation thing can also be a very real benefit. I don't think a lot of people would take PTO in their first couple of weeks, but your manager can say "thanks for joining the call earlier this month, how about you take this Friday off?"

There is basically zero chance I would do these calls prior to an agreed on start date. I spend enough of my life working already.

Some cultures have problems setting work/life boundaries. Because it is a cultural attitude, often it never occurs to some people they can say "no", or others are scared to. Which if maybe understandable if e.g. your medical insurance depends on your employer, but it's still messed up...

Fun fact though, many US employment contracts also insanely long and come with many restrictions. I don't see why you wouldn't just say "my current contract doesn't allow this, and it's probably in new company's interest to have a clean transition for IP law's sake" or some other vague reason

> … many US employment contracts also insanely long …

Most US employees are employed “at will” and don’t have contracts …

It's not really standard but can definitely happen with smaller companies < 1000. They are less well organized and probably didn't get the role filled in time so are trying to speed ramp-up.

You can always say no or provide strict times where you can help and typically there aren't any hard feelings.

This isn't common in America, that's false information.

It sounds like boss is trying to set you up for success by including you in an important conversation, maybe wasn’t expecting it to be a big deal to you, wasn’t expecting you to push to accelerate your start or to get an invoice for time (both of which will cause them effort outside the normal onboarding flow, and invoicing particularly will probably be “weird” procedurally). They didn’t give you particularly polished answers but I wouldn’t infer from that they’re an unprofessional manager — likely the first time they’re encountering this in their career?

FWIW: I’ve led organizations of 250+ people for years and can’t remember running into something like your situation in that set of experiences. If we had, then we’d likely have just delayed the vendor calls until you were on board, however, <500 companies often have ‘task urgency’ where >25k companies just say “Another 3 weeks won’t hurt much”.

Subject matter expertise is always nice to have in leadership for sure but isn’t guaranteed. I’ve no idea your skill set or that of your new manager but particularly with larger teams you’ll invariably have multiple disciplines, of which they’ll be more comfortable with some and less with others.

I think you’re reading too much into IT mailing your productivity equipment - all the usual suspects like FedEx and UPS support “Vacation Holds” as well, so you could likely have taken off and everything would have just been there when you returned.

“Unlimited Vacation” at most companies is a bit of a trap. Primarily, in my experience at least, it exists to avoid both process overhead (tracking time) and financial liability (since accrued vacation counts as such). Many US companies still train their managers to expect the amount of time someone takes off to be roughly equivalent to what they had in vacation days before the switch to “unlimited” occurred, so 10-15 days PTO, and 7-10 observed holidays. Maybe a handful of sick or personal days.

Being consulted on tools you’ll use is reasonable- perhaps being expected to be on the call is a bit much.

I think the company is a little disorganized- perhaps no professional managers for the size of the company.

That said, I think you’re overthinking it and to me you come off a little as a high maintenance employee.

you come off a little as a high maintenance employee.

They are obviously excited to have you and are onboarding you quickly. For every story like this, there’s another where someone doesn’t even get a laptop the first week, or they don’t even have time to invite the person to meetings (sometimes they don’t have a desk, a keycard, etc).

The vendor calls might need to happen sooner to meet budget deadlines, who knows? You could easily say you are on vacation but would be happy to listen in via phone, which seems like a fine compromise for both sides.

> budget deadlines

Aren't the people who were slow on the hire also the people who set the budget deadlines?

High maintenance? More like self respecting.

It's obvious OP is getting onboarded by a company with no or a borked onboarding process - I get that it's red flag but the entire writeup came off whiny to me.

I realize "high maintenance" has a negative connotation... but it has nothing to do with self respect. Admittedly it's not a popular view but that was my honest feedback.

I think unless you've been very fortunate about work experiences, there is a huge portion of the population that has very good reason to be sus about a company they've just been hired at. I can see how it might sound whiny or entitled, but I think you should never trust a company.

I have managed people for decades and I would never disrespect a new hire by asking them to work before their start date. I say huge red flag.

I absolutely agree.

On the flip side, I’ve been upset to find out a major software suite that I was going to manage was chosen right before I started. I’d be happy to have some say in the decision. I expect you had to do this at the end of the year when the sales rep needed to close and the biggest discounts were available.

Same for me.

And same applies to hiring. In my last 2 roles i wad hired as a team leader or engineering manager, while the company was actively interviewing for juniors to be placed in my future team. I asked to be involved in the hiring process before my start date in order to avoid surprises.

I would say a bit off but within the realm of sanity.

The laptop & e-mail things is not unusual and a not a big deal in the grand scheme of things. Communication could be better and BCC should have been used. But e-mail addresses are not exactly secret.

The joining calls is a pretty big red flag. But seems to have reasonable logic behind it. It sounds like you're going to be the expert & primary user of these vendor's software. Probably best for both sides if you're involved ASAP. In the end, 4-5 hours worth of unpaid calls isn't that big of a deal. Not a bad thing either to start working with a favor in the bank.

It sounds like a startup company with inexperienced people across the board. The red flag is the expectation of unpaid work and a 'free' vacation day, which amounts to nothing because of the 'unlimited' vacation policy. The other things are garden-variety mistakes. However, if there are 30 people starting in a cohort, then it sounds like a larger company, in which case everything is beginning to look like poor management across the board.

If you have a bad gut feeling about your boss, trust your gut and look elsewhere if you have a choice.

While I wouldn't necessarily say any of that is a red flag it does all fall into what I think you called the "maturity level" of the whole org.

So are you there to help build the maturity level of the whole org or is it something you can contribute to and assist others in developing? It sounds like you have a sense for such things. Working on the company's pre-IPO maturity could be a huge win for stakeholders like yourself ( or could land yourself solidly on the side of the stakeholders ).

On the other hand, if the assumptions you operate on depend on the maturity of other systems - no sense in building up their K8s helm if all they have now is Windows Server pets - then you might find it very hard to pull the direction you thought you were brought onboard to work toward.

Regard the place the same as they'll regard you. Make a list ( not on their computer ) of things you see, file under Good | Meh | Bad, and track for BIG RED FLAGS until your 90-day point. If you make it to 90 with no BIG RED FLAGS, and the data leans positive, then you have a list of things to work on. Otherwise, line up some interviews.

Your boss sounds like a narcissist. Abusing your time before you even begin, saying he’ll “take care of you”, confident but uneducated. The comment about vacation is especially telling; by company standards it shouldn’t be a big deal to take a day (within reason) but in your boss’s world, vacation is a valuable commodity that he controls for his employees. If this is the case it will only get worse when you are in close contact. If he actually scoffed (an intentionally demeaning gesture) at your reasonable boundary (i.e. getting paid to work) imagine all the emotional crap he’ll pull once you’re actually in his domain of influence as an employee!

Also I don’t buy the “we just want your input” line. You’re a new employee, why would their decision on vendor tech rely on someone who hasn’t even started? Sounds fishy.

As a final thought, a boss (or company!) who creates feelings of “just wait, it will be better when ___” is probably abusive. If you feel that way before starting, tread very carefully and be very observant.

Great comment. I’d love to learn your thought process behind this part:

> As a final thought, a boss (or company!) who creates feelings of “just wait, it will be better when ___” is probably abusive. If you feel that way before starting, tread very carefully and be very observant.

Assuaging peoples concerns about the present by promising a better future is ok in the short term, but I tend to see it as a long-term pattern of some managers. Stringing people along for a nonexistent promotion, letting on-call remain bad because next quarter we will have enough time to fix it (we won’t), that sort of thing. I say “abusive” but maybe “manipulative” is better.

"On-call will get better when we get more people on-boarded" (but the secret is turnover is so high that they'll never fully staff)

The higher the role in the hierarchy, the more common is for me to see involving the new person as soon as possible, specially if there is a rare opportunity, like participating in an offsite or event that could provide a lot of context and happens close (some weeks before) the starting date. Many the times the new hire himself request it.

Said that, if you are not comfortable doing it, you shouldn't. It would be a warning signal if they make a situation about it. I wouldn't make it a thing of whether you should be compensated or not but in the future I would expect the same consideration when you ask for an hour here and there as well. It is about trust.

The HR and IT things are more common than you believe, shit happens. That might or might not mean that some processes are not working well, just send the feedback. I do not see why you feel obligated to wait for the FedEx package if they did not ask you if you could wait for it. It makes me feel you are not comfortable being candid.

Probably overreacting, or at least expecting a different culture than you're going to get.

Not all companies has their stuff together, and depending on perspective, they may feel like they're doing you a favor by letting you join these calls, since you'll be the one using it.

Unlimited vacation is a bit of a red flag, it can mean culture of no vacation.

You're under no obligation to stay home to wait for a package, you could have gone about your biz, and if the package is gone when you get home, that's not your problem.

Still, try and stay both observant and open-minded the first months of your new position, and evaluate with the people there, maybe you're not a good fit (maybe it's because they're a terrible place to work for, but maybe they're not and would be willing to accommodate you if they're informed in a polite and constructive way).

I suspect this is your first rodeo with a scaling stage startup, or smaller, company. In that respect, don't expect any of the operational details like IT, legal, onboarding, etc. to be worked out. That's the price you pay for the lottery ticket that is startup equity. That's not to say all equivalent stage companies won't have a few things worked out... but, generally, it's a shit show.

Asking for extra stuff in exchange for is fine, but given your level, you sorta get what you get / take it or leave it. I've seen startup executive hires ask for and get all kinds of stuff...but, asking for anything non standard is always a cost benefit for the company and you're probably in the rank and file ranks. So, you get what you get.

If you like things to be more established, by the book and, generally, a more mature tenure... this stage probably isn't the right place for you.

Most of what you have shared can be easily explained. IT trying to be responsive to you by making sure you have a laptop seems reasonable -- they may be concerned if they wait after Christmas, it would lost in the shuffle. They just made not have had the EQ to think delivery affected you, especially if you gave them address to ship it to them.

Since you're working with a tool (and want education), your manager just may want to expose you to the vendor to help you succeed. It may be that talking with the vendor in this way may not be easy to set up.

And I say this because it sounds completely normal to me for this size of a company.

That said, if "best intent" is still not enough to justify their requests and actions to you, then that's on you to decide the work style and company you like. And if you feel you have the opportunity to pursue opportunities elsewhere that best fits your comfort zone, then you should.

These are some bad signals... but you are also being very serious. And if you are like this, it may be the wrong company for you.

On the other hand, I always assume people are trying to do good... Sometimes it may not look like it, but maybe that's because of some other factors.

just maybe:

- there are some new topics with vendors, that you will need to steer when you join, and actually it would benefit you later to join these calls.

- they couldn't set another date, but maybe the vendors are not that flexible and company will have to wait another month or so

- 4-5 meeting, it's like 4-5 hours, if you are going to work there for 6 months it's gonna dilute to nothing

- maybe he asked you to join the calls, but you can just not accept the invite, refuse, and nothing bad happens

- principal-agent problem, sometimes bosses do not know the details

- they mailed you the computer, why do you care, they can re-mail it

Anything you’re going to do for work is going to be a significant part of your life. It’s a serious situation. Unless it’s selling lemonade on a corner as a kid.

> I accepted an offer and I was asked to join four to five calls with vendors ahead of my start date. This felt like “work” to me since each call takes prep and led to follow-up calls. Having not yet worked in the role, I’m also lacking context on the business problems leading us to chat with these vendors in the first place. To be frank, it feels very unnecessarily rushed which is ringing some alarm bells.

Bizarre.

> My new boss says it’s not really a big deal to ask me to join these calls before my start date. I suggested we either move my start date up ahead of the calls I was asked to join or I invoice for my time ahead of starting. He scoffed at both but mentioned “they’d take care of me” with “maybe an extra vacation day”. Vacation time at this company is “unlimited” so I don’t really see that as a perk.

Bizarre, and it might suck to work under this boss.

Everything seems to point to a picture of a mess of a company. I'd say your course of action depends on what you have available right now. Did you have other offers lined up you wish you had taken? You could reach out to one of them. If not, it doesn't hurt to just give it a shot for now and see how things feel in 6-12 months.

It really depends on what you think you can handle and where you are in your life right now. If disorganization and bumbling drives you mad, obviously stay away. If you can't handle looking for another job right now (for financial reasons or otherwise), you may just have to stomach it.

But you are absolutely right: things are off here.

a boss that scoffs at your concern sounds like a boss without empathy. that can hurt for even more important issues like when you really need time off. i’d talk to him about how you’re interpreting these events and see how he reacts as a final signal before bailing

Talking is good. This seems very aggressive and probably illegal. Also, the next person may be tasked with whatever OP decides without any input themselves.

Charitably, the new boss just has some tight constraints making them need someone to start immediately. Less charitably, new boss is seeing how far this person can be pushed regardless of laws or normalcy.

Sounds like serious disorganization, pushing boundaries, and trying to get stuff from you for free right from the start.

This might be expected in a 40-person company that was 5 ppl six months ago and heading to 100 this quarter.

But a 500+ person company, hiring cohorts of 20-30+ people, supposedly preparing for an IPO?

Nope.

Many smaller companies have a far better process that actually gets people up to speed better. This looks -at best- like consistently haphazard scrambling, with low ethics.

Also, if they want you to do work before your "start date", they can move up your start date and start paying you. If they even said, "hey, we'd like you to participate in a handful of calls the weeks before, we'll pay 1/3 of your pay as a signing bonus, is that OK with you, or do you really need a break /moving time / etc. before you start?" that'd be cool. But just expecting you to drop everything for their disorganization up front is bad.

Unless there are some contrary huge positive indicators, I'd keep looking.

(also note that you are concerned enough to write this, which also tells me that you kind of already know the answer and are just looking for confirmation)

In any case, I wish you good fortune with your decision.

> "they’d take care of me” with “maybe an extra vacation day”

This boss does not sound good to work for. This is a bad response. It is patronizing and dismissive. Expect to hear this sort of thing constantly, and expect to work a lot of unpaid overtime.

How I would respond if I was the boss:

" Yeah, I know it sucks to be in these meetings.

I really apologize. I hear your concern.

Moving your start-date up and doing external billing is really not on the table, unfortunately, due to overhead with HR.

My reasoning here is that you will be the one handling these vendors and decisions around these vendors, and I wanted you to be able to weigh in during these important conversations, even if your start-date isn't for a few weeks.

This project is very time critical, and I need you to be able to hit the ground running when you start on X date. Because of this, I request that you continue to attend if possible.

Again, I apologize for the inconvenience. We will find some way to make this up to you, and make sure you get this time back as vacation. "

Sounds like basically any company - asking for extra hours, giving BS excuses (vacation day thing), late requisitions, etc.

I have experience in recruiting and onboarding at a big company you’ve heard of, and you would be surprised (or maybe not) that their practices come down to lack of internal tools, and sometimes competency of the staff. I would email onboarding to hide attendees/recipients in the Zoom call or to transition to work emails moving forward. I would also suggest that they establish compliance practices with your personal data.

The story of receiving your equipment early is probably made to be a favor to you more than anything. The team that likely initiated the send out did it at their earliest discretion, not because they wanted to hold up your holiday plans. They get a request and fulfill it. The timing was just inconvenient, call it unlucky.

I would share this feedback with the relevant people. If those teams were managed competently, they would use your experience to improve practices.

I think there can be reasonable asks for you prior to getting paid. For example, I was invited to a company-wide call prior to my start date, but it was optional for me and was only suggested on the basis that I would learn a little about the company prior to my start date. It was not a problem that I elected not to attend.

I am not aware if it is illegal but it is certainly unprofessional to ask someone to contribute to the business while not being a representative of the business yet, leaving pay issues aside. It's unclear why they are comfortable having you make decisions when, for all they know, you may do something that makes the company legally liable. Further, many vendors require NDAs, depending on the sort of vendor call. Seems like silly risk to me.

Certainly it is a red flag but I don't think I would sound the alarm quite yet.

How senior is your role ? It's not uncommon when you part of leadership (however that maybe defined) to be consulted on decisions that will impact them down the line, almost immediately.

Big companies will NEVER do this -> too much risk for them from a HR / bad reputation standpoint.

I've had a startup have me do this, it was sold well to me as "hey, join in and make decisions for your Product that you'll be running" It turned into a burn out situation for me trying to manage current job and hop in on future company calls. And I just refused after a certain point.

However, it's not uncommon. Not a red flag is probably where I would leave it. Keep an eye out though on how they manage you and your time after you join them.

This is very poor onboarding experience by the employer.

Not necessarily a signal that your future with the business is going to be bad, but also not a signal to ignore either; there are elements here - lack of care (IT sending laptop), cavalier attitude to legality (being on customer calls before being employed likely does contravene some privacy laws) and poor inter-department coordination - which are likely to be endemic in the business.

That said, it might be typical of a 'rocketship' business trajectory - it is and will be a bumpy, messy ride. The bottom line is does this type of messiness suit your working style / personality type? The answer tells whether to stay or go

What others have said about the onboarding process so far sounds pretty spot on for a startup that is growing faster than its processes. Tbh, the onboarding process sounds exactly like my current workplace's process when I was onboarded.

However, your manager sounds dismissive of your concerns which potentially is a red flag. I'd try not to focus on the messy onboarding process but rather pay attention to whether your manager is someone you would like to be working under. Maybe these vendor calls might be a blessing in disguise.

I had a job offer from a U.S based company in Oct, after something like 5 or 6 interviews, numerous calls to discuss the start date and so on and how I was to be paid. I thought everything was fine, start date was a few weeks out, and so I booked a trip home to see my family, counting on money to come in and help me afford it. As soon as I land, I get an email that vaguely indicates "we might need to reconsider the start date". I get them on a call the next day, and it's all off, they won't have me, and I'm broke. Never trust a company, especially one that's not totally forthcoming.

I don't think you're overreacting, each one of these is a red flag. It's not obvious what you can do right now though. Do you have any other offers still open from your job search? Keep applying if you don't.

The real question is can you do without this job?

You are dipping your toes. Once it all starts be sure to seriously think about how things happen on the ground. Don't let yourself be overworked just because finding something else feels unappealing.

Honestly it sounds like red flags to me. If they need you to determine what tool to use, then they need to be paying you for those choices since it sounds involved. If they cannot move the start date up, they should wait until you start. I think your boss is probably going to hit you with as much overtime as they can out of incompetence (best case scenario).

What is the risk to you when you start? Sure these things are red flags, but what is the cost of finding out? You can just start, get an even better feel and quit if you still don't like it right?

Its a red flag. Happens to one if my friend, where they ask to go through the product document and get on call to discuss. But eventually found that(after joining) the company was in complete mess, more of co-founder were clearly lacking vision to run the company. Friend left that company after a year.

My advice would be if you do not any other offer, join. See how things are on the ground and take decision whether to continue after 6-12 months.

You are not overreacting, I think you should listen to the signals. BUT I communicate to your boss and your team on boundaries and anything else you feel.

I was in a similar situation where I was pulled into calls right away, but I was dealing with fires and clients. I communicated to my boss and it helped. I had the most growth at that company, but a lot of the major red flags that showed up during my first week were the same problems I was dealing with when I left.

Get your resume out there. You appear to be signing up with an inept fuckup who will casually mess you around. He's testing boundaries with you before you've even started, to see what he can get away with.

Even if you stick with it, these are the traits of a guy who will accept you spending 80 hours a week wiping his backside, then screw you over on the startup payoff.

A manager offering an extra vacation day as an incentive when you have flexible time off is everything that is wrong with FTO.

The flags sound real and its lucky for you they are showing up early. I would suggest to talk to someone in the inside through your network (may be from another team). If that chat doesn't seem to go well, then definitely back off this offer and start interviewing again.

>My new boss says it’s not really a big deal to ask me to join these calls before my start date.

Then it's not a big deal if you tell him you are not joining the calls as you will have a medical appointment at the time.

We can't decide for you. But it sounds just like a normal disorganized company.

asking you for time before your start is iffy, but everything else seems an overreaction.

it sounds like a growing startup.

it's probably really hard to move start dates or cut 1099 pay to soon to be employees and if they were picking the tool i'd be using for the next 1-5 years, i'd probably want to sit in on that as well.

you will probably have to be clear to establish boundaries all around, but that's likely the case with any growing company.

I think you need to set firm boundaries and stick to them.

Can you just reject the call? Are you still working with your current company before the start date?

I'd keep talking to recuriters and interviewing in your situation.

If you feel the need to make a post about it, you already know the answer. Get out.

Trust your gut.

Nope sounds like a trash company. Just ghost ‘em and move on. No mercy for these boomers.