Q: Why do these VC coffee chats all seem same?

A: Either the VCs you’re meeting with are monotonous or the questions you’re asking are

Ok. That may be a little harsh.

But really, how do you make the most of “informational” interviews?

Avoid asking questions that are already answered online. I’m not talking about funding nuances or even the latest startup news. What I am talking about is knowing the basic structure of the industry, a general sense of the different stages of funding, and the high-level trends in technology and investing.

For example, here some questions you can answer online:

  • What metrics or KPIs do you look at to evaluate companies?
  • Where can I get information (blogs, newsletters)? Hint find out here and here
  • Note: its always ok to ask questions to that dig into these topics, but know what they are ahead of time

And others, worth asking, that may be answered differently by each VC you meet:

  • How do you think about effective sourcing? Inbound or outbound? Generalist or thesis driven?
  • How does your team split up roles and responsibilities?
  • What is your diligence process? How structured is it? How would you improve it?

I ask other VCs these questions, or they ask me (note: these are also fair game, and helpful, for entrepreneurs to ask VCs):

  • How are you thinking about X technology? Y industry?
  • Why did you make Z investment?
  • How do you think about investment pacing, check size, follow on, etc?

To formulate questions appropriately, research the VC beforehand so you can ask about things they know really well and may even have a unique perspective on.

(Also, from the other side, it stinks to get asked about things that you don’t know much about. For example, I know a lot about IoT but very little about healthcare. Ask me about HIT? I’ll be self-conscious the rest of the conversation)

So what can you look at?

First, their firm. What is their focus from a stage or industry perspective? Are there any interesting portfolio companies?

Then, them. Do they have a blog? Read it. Do they tweet? Skim and identify what they care about. LinkedIn? Find out if you have something in common or if there is a part of their background that is relevant to your big questions.

All in all, the key here is to have enough of an understanding so that you can ask more of the “how’s?” and “why’s?” than “what’s?” You’ll get richer information and very likely having to articulate the answers will be a useful exercise for the VC.

P.S. Some other tips:

  • Think about any way you can be helpful. I attempted this before I got a job (albeit I rarely added any actual value). However, it shows that you’re considerate and thankful for your counterpart’s time – this probably means they’re more likely to help you, make intros, etc.
  • If you’re asking for an intro to another VC at the end of the conversation, be able to articulate what type of questions or topics you want to cover and what you hope to get out of the conversation. It’ll help the person you’re meeting with think of who would be best and give you a greater chance of getting another conversation. 
  • Follow up (via email) if there were any action items from the meeting. Its easy to forget and people are effort-adverse 

How can VCs be more helpful?