When I started out I didn't see much value in getting advisors. I think that's partly because I didn't know how to get value from them. Below I've written my thinking around getting advisors for specific problems I encounter. The specific problem could be something like fund-raising, building a sales team or doing lifecycle marketing.
If it’s a new domain for me I’ll typically do a bunch of online research before reaching out to possible advisors to get enough context that I can ask pointed questions.
Once I have some idea of the space I’m trying to learn I look for experts. I'll find these just by browsing LinkedIn, typically searching for employees or founders who work at companies that do the thing I want to learn about really well.
I usually identify 5-10 people who are a good fit and reach out to them on LinkedIn. The response rate will vary wildly based on the quality of your outreach. You should spend at least 10-30min researching the person - reading any blog posts they've written, looking at the companies they worked at and what they do in their spare time. In the reach out I've found you should strike the right balance between being broad and being specific. I typically use a phrase like "I'd love to get your advice on [topic]" and then give them a little context on why.
Before a chat
I write down a set of hypotheses. Essentially these hypotheses are what I’m expecting that particular person to say, based on what I understand about them and the topic. Writing these hypotheses down is a great way of thinking through the subject matter and aids you massively when reflecting on the conversation. Where where you wrong? What assumptions did you make that proved to be false? Do you agree with the reasoning the advisors provided.
Having the conversation
The advisor should be talking 80% of the time. It’s important to give her some context, but don’t overdo it in the initial chat.
Asking Googleable questions is a surefire way to irritate the advisor. When you find yourself asking broad questions like “How do you raise funding for an early stage startup” your alarm bells should go off. There are hundreds of amazing articles, books and videos that answer questions like that. A better question would be much more specific to the advisor you’re talking to, like “How much traction did you have when you raised your first round? What kind of questions did investors ask you about your traction?”.
One very counter-intuitive thing that I've learned is that you should not use these conversations to get advice - you should use them to learn. The difference is subtle but very important. It’s unlikely your advisor has enough context to give you proper advice, and to give them enough context will mean that you spend all the time talking. So you want to limit advice asking as much as possible. Instead, you want to focus on facts and actual experiences she’s had and how she approached situations.
Your goal is to understand their world as much as possible, not to get advice on yours. After the chat you should reflect on what they said and determine what you can apply to your situation or not.
In terms of mindset: I found it best to assume that most of what I think is wrong - and my job in the chat is to find out where I’m wrong as quickly as possible. When you encounter an idea that seems counter-intuitive or wrong, lean into it. Remember, you don’t need to do actually implement any of what she’s talking about. Instead of writing the other person off as being wrong, try figure out why they’re right.
I usually take a few notes during my chats and would recommend you do the same. However, be careful of focusing too much on note-taking and not enough on the conversation. The flow of the conversation is critical and you want it to feel natural - so only write down key points and rather focus on the other person.
A bonus to aim for is examples of pieces of work. For instance, if they’re talking about an operations report that’s critical to their business ask if you could get a copy. There’s often so much knowledge embedded in pieces of work!
The advisor often don’t know what’s interesting or valuable to you. You have to guide them.
Closing the advisor
If the chat goes well and you want another, then you need to close her. Don’t ask her to be your advisor - that’s a big commitment and you'll likely get a no. Here’s how I approach it:
- Tell her that you found her feedback super useful - pointing out specific things that stood out to you.
- Ask if she’s willing to talk again in a month or so.
- Send a follow up email thanking her for her time and confirming the next time you'll chat.
Afterward the conversation
Write detailed notes. I like to separate the facts (things the person said) from the lessons I've taken from the conversation. I use this separation because I like to refer back to the facts every now and then and have found that as I gain more experience I see the facts in an entirely new light.
I find it takes a few attempts to understand the landscape of any particular field well enough to have really great conversations. So if you fumble the first times - just keep going.