The War Room
Question
Post

Questions to ask a CEO

If you were going to dinner with your CEO, what would be some good questions you'd ask?

For context, your Director and another team member would be there as well.

Fire away, Savages!
🧠 Advice
7
GrizzleMcThornBody
Arsonist
+12
EVP - RevOps
- Do you have any vices? - Are you going through a divorce? - What’s your exit strategy? - Did you accidentally screw your self by not understanding the term sheet and cap table when you accepted VC money? - Can I get a raise? - Are you buying tonight?
Incognito
WR Officer
+11
Master of Disaster
@GrizzleMcThornBodyΒ -Β YesΒ 
Stratifyz
Opinionated
+9
Business Development Rep
Do you think it’s appropriate as a BDR to ask about exit strategy?
GrizzleMcThornBody
Arsonist
+12
EVP - RevOps
Sure. It’s your life too.
Show 5 more replies
InQ5WeTrust
Arsonist
+9
Sales Savages, what is our profession? Trauma!
I'd probably ask a question or state an observation about the business from what I know working there.

Any question about wider business direction, where the company idea originated, where he sees market opportunity yada yada
Biggest challenge for the next year etcΒ 
Stratifyz
Opinionated
+9
Business Development Rep
One thing that is shocking is, no one has any equity in the company except him and the CTO. But, I know this definitely wouldn’t be the time to ask about that πŸ˜‚ I like your input though - appreciate it!
LordBusiness
Politicker
+8
Chief Revenue Officer
If your CEO is worth a shit, I doubt you'll be asking most questions as most of them will have a battle plan for the event and driving the direction of conversation flow of the evening, but if you don't.....CEO 101Β  - make everything about THEM.Β  Ask questions about their career path, previous roles they have been at, their hobbies, their family (keep it high level).Β  Ask questions you may already know the answer to about company direction, and upcoming exciting things. Ask about the market, and competitive landscape and what he/she is "hearing from the street". Good luck!Β 
CuriousFox
WR Officer
+13
Senior Account Executive
Exactly this. Don't ask about things you can easily read about on Google or your intranet. Ask about them. Be fascinated. They will remember you.
cw95
Politicker
+6
Sales Development Lead
Definitely ask (after they’ve had a few drinks) who they hate in the office and want to get rid of. Bit of juicy gossip, knowing my luck the answer will probably be me!
Stratifyz
Opinionated
+9
Business Development Rep
It would be real interesting if that was the case. β€œWell, now that you have me thinking…” β€œIt’s definitely you, without a doubt.”
cw95
Politicker
+6
Sales Development Lead
Hahah β€˜damn, I presume I’m paying for this too?’
LegacySales
Politicker
+3
Account Executive
I would ask the CEO about CUSTOMERS. Look, in enterprise tech sales, new logo acquisition is just as important (if not, then less important) than CUSTOMER RETENTION.Β 

Back in the ancient days of the internet, I had a friend of mine working at an Job-Applicant-tracking-software / Resume management company in 2004; there are still moron companies PAYING For it a decade later despite this space being extremely oversaturated with most free versions being pretty good.Β 

Why do they keep buying it? Because #1 they liked it, knew how to use it and it would have pained them to learn how to use something else.Β 

P.S. When Trovix was later acquired in an all cash deal, it made my friend so wealthy that he cried for days. The American dream is still alive and well savages.Β 
softwaresails
Politicker
+4
Sales Manager
I'd ask them what makes them tick. What motivates them.
7
CRO Q&A questions
Advice
5
8
If you had to choose only 3 questions to ask in discovery, what would you choose?
Question
14
10
Interview Questions
Question
16