

Questions to Ask Before Joining a Startup - pensieri
http://blog.expensify.com/2014/01/24/ceo-friday-5-important-questions-to-ask-before-joining-a-startup/

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aaronbrethorst
A few more (not that they'll necessarily tell you, or offer you the job after
you get done asking):

6\. What percentage of the company are those XX,000 shares you're giving me?

7\. What's the current valuation of the company?

8\. How much runway do you have left? (Although you can probably infer this
pretty easily by when they last raised.)

9\. Since you're giving me a YY% haircut on my market-rate salary, what
reasons other than the almost certainly worthless, say, 0.25% of the company
you're giving me over four years should I be joining you?

10\. I don't believe 60-80 hour weeks are productive, sustainable or healthy.
What do you think about that?

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quinthar
#6 is super important. It's absolutely crazy that many companies won't tell
you this.

#7 is a good question, but don't expect a tangible answer -- unless they just
closed a round yesterday, it's truly impossible to say. That said, it's still
a great question to ask to see how they value themselves, and what they feel
potential acquirers or the public market would value them at.

#9 - I think that's a good question, though might be more diplomatically
phrased. ;) (That said, be aware that "market rate" is extremely hard to pin
down: for the same reasons you should expect an ambiguous answer to #7, your
own "market rate" is similarly ambiguous.)

#10 - Agreed. I target 50, personally.

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aaronbrethorst
Re: 9, totally agree on phrasing a little more diplomatically ;)

But even with the ambiguity, I expect the answers would still be enlightening.

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JonFish85
I disagree with 4 out of the 5.

> "How many people do you hire in a typical month?" Is there such a thing as a
> "typical month" in a startup? Isn't the definition of a startup that it's
> moving fast, things change and you have to roll with the punches?

> "Who was the last person to quit, and why?" Good luck getting a real answer
> out of this question. They're not going to say that "he hated the
> atmosphere", or "the pay was too low". They're going to say something
> positive-sounding and completely bland. It tells you nothing about the
> company at all, unless they completely trash talk the person who just left.

> "When do you intend to raise money, and why?" Again, you'll be lucky to get
> a real answer on this as well. If you get an "X months of runway before we
> need to raise again", there are a million assumptions built into that, and
> things change quickly. "Is the company primarily financed by selling
> product, or selling itself?" is probably a better question to ask.

> "Can I see where I’ll sit?" Seriously? Again: it's a startup, things change.
> In the 2 weeks it might take you to start, the seating plan may have changed
> 3 times. Ask for a tour of the office, sure! Depending on the startup, it's
> unlikely that you'll be spending 2,000+ hours a year sitting at the same
> desk. Offices will move, things will be re-arranged, etc. Look at how the
> workspace is set up, to be sure; but asking something this specific seems
> like an odd request.

> "What do I want to do accomplish in my life, and how does this help me down
> that path?" This one I agree with.

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jtbigwoo
> "Can I see where I’ll sit?" Seriously? Again: it's a startup, things change.

I actually like this question. You can tell a lot about a company by whether
they're thinking about how to integrate new people. If they say, "We put new
people right here next to Michelle for the first few weeks so she can show
them the ropes," that's a pretty good sign. If they say, "We'll find
something," that's a sign that they haven't really thought about what to do
once they have somebody on board.

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codezero
It strikes me that asking "Who was the last person to quit, and why?" is a big
faux pas in this area. Am I wrong, or is it common/OK to ask this kind of
question?

It's been my experience that very few people "quit." Separations from startups
tend to be very neutral, leaving it ambiguous whether someone quit or was let
go. It's not hard to read between the lines, but discussions about this are
not very up-front.

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jiggy2011
That does strike me as kind of rude, plus companies tend to not want to discus
HR issues pertaining to other people since it's a potential legal problem.

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freyrs3
Asking about previous employees is no more rude than asking an employee for
references. If a company has a history of lots of employee churn that's a big
warning sign.

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jiggy2011
When you ask for a reference it's usually because the potential employee has
said it is ok to do so.

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jsun
Good list - Not too sure about this one

> How many people do you hire in a typical month?

1 per month? that seems low. Hiring is like everything else - subject to human
cognitive biases. We all like to think that we can make the right decisions if
we just put our minds to it, but the fact of the matter is a lot of it is just
randomness. If I hired 4 people a month and I really fucked up on 3 of them
I'd at least have 1 good employee left. That's a higher expected value than if
I hired 1 person a month and screwed up just 5% of the time.

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eps
Another question would be how an all around p2p guy ends up running an expense
management company :)

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quinthar
Heh, it was a long road:

1) Have a p2p startup get acquired by Akamai 2) Want to do something financial
3) Financial == PCI compliance == super super expensive 4) Use p2p to build
inexpensive PCI compliance 5) ... 6) Profit!

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kostyk
I like where am i going to sit part.

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morningstar
Yes I like the blog article!

