Asking for help is a skill. Some are very skillful at it and some are pretty poor. From having observed skillful people, I’ve seen it come down to one operating principle at each stage.
Before: Thoughtful – This is demonstrated by asking for the right thing the right way. Asking for the right thing requires you to have knowledge of how this person can help you without it being too much of a burden to them. This often requires a degree of homework – for example, most famous venture capitalists have blogs where they explain what they look for and how they normally operate. All of these offer clues on what to ask. Asking the right way just means acknowledging that they probably get many such requests, being concise and asking nicely.
During: Authentic – It sucks to be in conversation with someone and feel like they’re putting on an insincere show. As people become more senior, this happens a lot and it is fairly easy to detect. Be yourself. This will mean accepting that there is a good (>50%) chance that you might not “click” with the person you’re speaking to. This can be hard to accept if there are high stakes around what you are asking for. But, it is the only way to do it right.
After: Follow up – If ever there was a sign of character, it would be how the person follows up, if at all. This means sending a genuine thank you (it is amazing how so many thank you’s can feel cursory) after your conversation. And, most importantly, it also means staying in touch with updates if they’ve made a connection. For example, if they helped you get a job interview, it means staying in touch with them and sharing quick updates through the process.
Most people remember to be thoughtful when asking. A much smaller subset remember to be authentic. And, very very few remember to follow up. In my opinion, that is one of the reasons psychologists who study influence recommend that you ask people you want to connect with for help or advice. One part of the rationale is that we flatter people when we ask for help from them. But, the other part is that, the way you ask for help speaks volumes about your character.
Good character indicates high personal net worth. And, the size of your network is directly proportional to your net worth.