It's one of the most lampooned phrases in the VC and startup community and for good reason. It’s truly one of the least effective and worst questions to ask at any meeting. Why is that?
Whether you're a VC trying to curry favor with founders who MAY give you the opportunity to invest at some unknown future point… or a founder trying to build a relationship who might be able to help connect you with investors. “How can I help” is one of the least effective ways to actually help! Why is that?
1) It's not a question that most people are contemplating regularly. They're not consistently thinking, “If someone asked me how they can help, how should I answer?” Because of that, when someone is put on the spot, “How can I help?” mainly results in a flustered set of thoughts and either a polite turndown or an ill thought out request.
BTW - you should realize that the “polite turndown” can feel like a win for VCs where they believe they scored some reputation points by making the offer, but didn’t actually have to pay up (see my article on VC gift cards). But you’re not a VC. And even if you were a VC, I wouldn’t want you to behave like that. As a founder trying to build your network, not having the opportunity to meaningfully help someone is a lost opportunity!
2) It puts the other party in uncomfortable situations and nobody likes those. That’s because the question begs a response in the form of “You could ______ for me” which for some can feel selfish (I would put myself in that camp). Even for those whose cultural upbringing did not shackle them with such baggage (dang you Confucian ideals!), it can feel like you’re voluntarily entering favor debt as opposed to being given a gift. It’s a subtle difference, but significant. Either situation likely leads to them not answering truthfully because they feel embarrassed or because they don’t want to feel beholden.
3) It’s an ineffective question! If it’s someone you’re just building a relationship with, the person likely doesn't know all the ways you’re best positioned to help! So even if they overcome #2, they’re not even going to ask for help in the ways you're most capable. So even if they do say something, it might not be something you can actually deliver.
Person 1: “How can I help?”
Person 2: “Well you could do X”
Person 1: “Oof… I can’t really help with that”
Wompwomp. No one wins. Awkward.
Instead of that epic fail of a question, try asking a question that takes the onus and responsibility off of the recipient. Your goal is to ask them something easy to answer that allows you to creatively come up with ways that you can help. If you can accomplish that, you’ll get to the best way to engage with another party and build a relationship around valuable support.
Asking someone a question they are constantly thinking about will deliver a much quicker, more accurate response. It will also uncover a topic that will allow you to brainstorm ways that you are uniquely able to help. Depending on how important the relationship is, you can either think of easy wins you are uniquely positioned to give them OR think of a more substantive way to help.
It is also easy to continue the conversation if you can’t think of ways that you want to help. You can just react positively about the things that they're focused on, “Wow, that sounds amazing!” and call it a day.
So avoid becoming a Twitter meme and get rid of “How can I help?” from your meeting lexicon. Try out this approach and see how your networking and conversations flow.