What's the *toughest* question you have asked the company you were interviewing with?

I always ask for income of top, median and bottom producers. Is that tough? What tough questions do you ask potential employers while interviewing?

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15
TheRealPezDog
Notable Contributor
5
Account Manager
"Based on our conversation so far is there anything that concerns you about my fit for this position?"  My boss was completely caught off guard, but he hired me anyway. 
TheMatador19
Member
5
Head of Sales
You should ask this question at the end of every interview.  It's an industry standard. 
Phillip_J_Fry
Opinionated
1
Director of Revenue
Correct
CaneWolf
Politicker
2
Call me what you want, just sign the damn contract
I do this all the time. Just letting you know now - people are perfectly willing to lie and say no if they've decided you're not a fit already.
TheNegotiator
Arsonist
0
VP of Sales
Absolutely true, but if you’re good at sales - and many of us are - you’d be able to catch it. They may not give me the truth, but at least I know they’re lying
SaaSam
Politicker
1
Account Executive
Totally going to steal this. I feel dumb that it's never occurred to me before but so much value to asking something like this. Helps lessen the wonder of how you did, gives you a good idea of likelihood that you'll get the job, I'm sure it's an impressive question in the eyes of the interviewer, gives you a chance to explain something in the event there was a misunderstanding, and if there were any legitimate concerns you know where to improve on.
TheRealPezDog
Notable Contributor
1
Account Manager
You hit every single reason why it's a great idea to ask this question.. also for sales jobs ALWAYS ask this:  In the history of your company how many times has the comp plan changed?  (this will tell you a LOT) 
GDO
Politicker
0
BDM
Looking for the objection! Smart!
CaneWolf
Politicker
3
Call me what you want, just sign the damn contract
What would reasons be that I should not come work here? (Phrase this in a way that sounds right for how you speak/communicate).

It forces people to think about what's made others bad fits and where some of the weaknesses might be in the company that you're going to have to confront.
Incognito
WR Officer
1
Master of Disaster
There are some fantastic threads here on this already if you search for them. Definitely helped me when I was interviewing. 

my personal favorite was “what is one thing you wish you could change about this company? What would you never change?”
msp_sales
Opinionated
1
Full Cycle Sales
Mine wasn’t a question, it was a request. I asked to talk with someone on a PIP. I promise that you’ll never learn more about Company‘s culture and support system, or get a better picture of your possible success, than if you talk to someone who is sucking on the fuzzy end of the lollipop at the moment.
UrAssIsSaaS
Arsonist
1
SaaS Eater
I think this is an awesome questions, however what if they set you up with someone who is a bad egg, they are in every sales org and often the ones on PIPs. Do you think you will get a legit understanding of the support system talking with this person? 
msp_sales
Opinionated
1
Full Cycle Sales
When you ask them why they’re failing, what do they say? Do they come across as humble but struggling just hoping that they can trust the company and do the activity? Do they just complain about the company? If they do complain about the company does it sound like their complaints are valid? You will learn so much more from someone who’s about to leave then you will from someone who’s never leaving.
msp_sales
Opinionated
1
Full Cycle Sales
Ask yourself, “if I were them would I be doing any better?“ This will help you get a great perspective on whether or not you should take the job. 
UrAssIsSaaS
Arsonist
1
SaaS Eater
Good stuff, hadnt taken it to that extent yet and appreciate it. 
Sniper
Valued Contributor
1
Enterprise Account Executive
If you could go back in time to the younger you (hiring manager) when you were on my side of the table what is the one most important piece of advice you would give to yourself?
Blackwargreymon
Politicker
1
MDR
What would reasons be that I should not come work here?
Santipodero
Politicker
0
Sanix
If you had to live your life again, what would you change? I loved this
Santipodero
Politicker
0
Sanix
What is your greatest professional achievement? Nothing says "hire me" better than a record or proof of having achieved amazing results in previous jobs, so don't be shy about answering this question! A great way to do this is by using the S-T-A-R method: State the Situation and Task you were asked to complete and give the interviewer some background and context. For example, "In my previous job as a junior analyst, my role was managing the billing process." But spend most of your time describing what you actually did (the Action) and what you achieved (the Result). For example, "In one month, I simplified the process, saving my group 10 man-hours per month and reducing invoice errors by 25%."
dave1
Politicker
0
SDR
Gives us a reason why we shouldn't hire you... 
GDO
Politicker
0
BDM
Good question!

I always ask what traits successful people in the company have. 
Kevinbacon
Opinionated
0
Sales Manager
Not that these are necessarily TOUGH questions, but you'd be surprised by how many managers can't answer these.  This is a red flag if they can't provide me with data. 

- How long was the last person in my role for?  Why did they leave? 
- How long is sales cycle? 
- What is OTE?  What is quota? 
- What % of reps hit quota? 
- What is average deal size?

Panda4489
Politicker
0
Head of Some Shit
How many of your sales reps hit quota? And is that% proportional to how the company did based on annual revenue goals?? 

Or are the quotas so hyper inflated that only 50% of the reps hit while the company does 120+% to goal...
JustTapItIn
Opinionated
0
Territory Manager
I’m not sure if it’s the toughest question I’ve asked but my favorite is “if you could keep something the same at the company, change something at the company, and make a new initiative at the company what would those be?”
MR.StretchISR
Politicker
0
ISR
"Based on our conversation so far is there anything that concerns you about my fit for this position?" My boss was completely caught off guard, but he hired me anyway.
Clashingsoulsspell
Politicker
0
ISR
Honestly, PTO in sales just doesn’t make sense. If you want time off figure out a way to be more effective and hit your goals working less than 40 hours.
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