How startup founders should actually ask for help

Old phone

I get a lot of emails asking me for help. They’re entrepreneurs and creatives who are struggling with their careers, and they want guidance and advice.

I love offering that to them, and when they come to me and say they need someone to show them a path, I don’t whip out Xero and start billing them.

I remember what it was like when I was at the start of my career, had no idea what I was doing and felt lost roughly 24/7. So I do whatever I can to help them out.

The problem is, a lot of people don’t make that easy for me. When I’m asked for help, and the request is really vague, I have no idea what to do. I’ll receive an email that says, “hey, I want to run my own business, what should I do?”

And there’s just so much scope, and so many possibilities, and so little information that I don’t know how to respond.

I’ve been thinking about the way people ask for help, and how clear it is that when they don’t know what they’re asking for, they won’t know if they’ve heard the right answer.

I think it’s incredibly important to think about how you ask for help, the way you phrase it and the questions you’re seeking a response to long before you reach out to someone.

This is going to apply in almost any situation, it’s definitely not limited just to when you’re talking to me. Any time you want to ask for help, I think you should do it – but do it right.

Have up to 3 questions locked and loaded

When I ask someone for help, I like to have my top one to three questions already good to go. The top things that I want to learn from whoever I’m reaching out to. I find any more than three is going to blindside someone and make them think twice about responding.

Additionally, nobody wants to get an email that says, “hey, can I ask you something” – then they have to respond and say, “sure”, and wait for the question, then answer it and get a bunch more.

I have up to three questions, I make sure the questions are detailed enough that I won’t need to clarify them when I get answers back, and I send through those questions in my first outreach.

Be detailed and brief

Nobody wants to answer a vague, open ended question, or one with so many facets that they have to analyse it over and over again. When I reach out I provide enough information in each question that anyone reading the email in a hurry can blast through their responses as quickly as possible.

I also keep the information in each question to just three bullet points. Let people scan and answer, don’t make them sort through a jumble of confusing sentences to get to a badly worded question at the end.

For example, I recently wanted some feedback on using Squarespace, so I got in touch with a blogger who I know swears by the platform. What I was really curious about, was whether it’s worth using. But that’s too vague, and it’s not going to get me much more than a response of yeah, obviously it is, because the blogger keeps using it.

So here’s what I asked?

  • I’m a writer and blogger on Medium
  • I’m building a personal brand
  • I’m building a lifestyle business.
  • Does Squarespace have enough flexibility to service those three needs?

Never reach out blindly

I never reach out blindly and I never think about who to talk to before I think about what I want to know. That means that I’m not sitting here right now thinking, “gee, I want to ask Richard Branson something…what should I ask?”

I’m thinking “fuck, I want to know how to turn a single company into an empire. I’ll bet Richard Branson would know some of the answers around that”.

You’ll find that if you think about who you want to ask, instead of what you want to ask, you might end up having some cool conversations with some awesome people, but you’ll never learn what you need to know.

Do some research first

One question I get asked a lot, is how do I build an audience? Well, I’ve written pretty extensively about that in a bunch of posts. Before you email a writer with a question, it’s going to save you a lot of time if you look into their work first and see if the answer is already there.

Also, you might not be emailing the right person. I’ve written before about how I don’t accept payments to endorse products, and I don’t write about any platform or tool that I don’t love and use myself on a regular basis. So I’m the wrong person to email asking me to do that stuff.

That being said, I’ll always respond politely when I get emails from people who haven’t done their research – and I’ll never just send a link to a blog post instead of replying with some advice – but it’d just save everyone time if you looked into it a little before reaching out.

Follow up politely

I can’t get to my emails all the time. I tend to respond to everyone, even if it takes me a few weeks, but it’s not always going to be immediate.

So sending me a question, waiting a few days and sending another email that says “I always suspected you’d be a douchebag who doesn’t even care about their readers” is pretty annoying.

Nobody wants to be a tool. You’ll find in general, bloggers and writers and people like me love having anyone read our posts. We’re just busy people, and it can take time for us to respond. Being a dick isn’t going to make us respond any sooner.

You have to give us space, wait a while, and if you don’t hear back, send a polite reminder and say you sent us an email and you’d love a response. I don’t have any problem with people chasing me up, as long as they’re polite about it.

The last thing I want to say is that if you feel like you need help, if you feel like you need to ask someone for help, do not hesitate. I wish I’d done that more when I was starting out, instead of thinking I was such hot shit that I didn’t need feedback or guidance from anyone.

I was so arrogant, and so prideful, and I made so many mistakes that could have been avoided if I’d asked, if I’d just put my hand up.

But when you do ask for help, whether it’s from me or a blogger you admire, or an entrepreneur who’s changed the world, or a school teacher who’s seen a fair bit of it, try to do it in a way that makes it easy for them to answer you.

You’re not alone in the world and you’re not an island. People out there do give a shit — I’m one of them — but you’ve got to make it possible for us to help. We’re all struggling, and we all feel lost. You have no idea how many times a day I ask myself, “Jon, what the fuck are you doing?”

I seek help and advice from people constantly, because there’s so much I don’t know and so much I need guidance with. I know a few trails through a few rough patches, but there are pathfinders out there who’ve spent years learning better ways, and I love asking to see them.

This article was first published on Medium.

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Jon Westenberg is an entrepreneur, startup advisor and writer.
  • Ron

    Was a wonderful – and truthful – article.