Why Founders Don't Ask for Help

Founders are generally really bad at asking for help... but why?

We'd think in a business where we need help with literally everything, we'd be amazing at asking for help. Yet time and time again, we go it alone, or at most make a half-hearted attempt to get the guidance we probably need.

I spend most of my day pleading with Founders, "Please, whatever you do, stop guessing! Let me just tell you exactly what you need to do in order to move forward so you can spend your time getting it done versus figuring out how to do it."

Once we finally break that seal, I get countless questions, which is exactly my goal as someone who helps Founders all day. But the same issue keeps coming up "Why are Founders always hesitant to ask for help?"

We're Used to Giving, Not Getting

As Founders, we tend to spend all of our time helping others, or at the very least fixing everyone else's problems. That has a lot to do with being at the top of the org chart where there's kind of nowhere else to go with our problems. Everyone else can defer to us to make a decision, but the buck kinda stops there.

Like anything in life, it becomes a habit. We're getting used to having to have the answer every time. We get used to being the final word. If we do anything in life long enough, we quickly forget that there's any other way.

That's why it's important for us to create a force function to break that habit. Whether it's an Advisory Board, a Mentor, or even a Founder Group where we can share our challenges, we need a dedicated function that forces us to ask for help, especially when we don't even realize we need it.

We Don't Know Who to Ask

Asking for help implies that we have someone who could provide it. For Founders, that's rarely given. We're often surrounded by people who have no idea what we even do, much less are qualified to give us help. How do we get meaningful feedback on whether we should raise our next round of investment if not a single person we know has ever done it?

The cost of not being able to ask for help is extraordinary, and to make it worse, we don't even realize it because we don't know what getting good help can actually do. I spend countless hours every month helping Founders navigate things like fundraising, so I can speak to this firsthand as both an Advisor and Founder.

90% of the time when I speak to a Founder, their default instinct of how to navigate fundraising is straight-up flawed. Not because they aren't smart (I love all of you!) but because they simply don't have this specific domain experience. What's the difference between guessing (wrong) and getting exactly the right guidance? Just asking the right person.

We're Too Busy to Ask for Help

Asking for help takes work, and it takes time. People often think about asking for help as simply offloading work onto someone else. But that's a total myth. Asking for work requires us to source the right person, spend time with them, and maybe get a better outcome than we would have ourselves. It's a gamble, not a given.

But the problem with that thinking assumes that NOT asking for help is actually more efficient. That's actually true until we've got an efficient source of help. An efficient source of help should be someone we can call on instantly and get an actionable response in a very short period of time.

That's why quarterly Advisory Board meetings or scheduled sessions rarely help - they aren't there when you need them. The key to avoiding the "too busy to ask for help" problem is just making sure the help you do have is right on tap. All of the Founders that I help can message me on Slack, email me, text me, schedule a 1:1 call — anything. I do that as an Advisor because I know if I'm not accessible, they won't ask for help!

Getting help is hard. It really is. But instead of complaining that it isn't available, we should be optimizing for how to find the right sources that are easily accessible.

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