How to Have Honest Conversations with Your Friends About Their Businesses

Business is all about relationships, right? So what happens when a friend comes to you wanting to know if you have any feedback on their incredible business idea? I get hit up by fifty entrepreneurs a day who are seeking my two cents about what they should do to make their ideas a reality. And, honestly, I wish I could help every single one. But if I took everyone up on getting that cup of coffee, my head would never touch a pillow again.

Still, I do help friends who are excited about starting a new project. Recently, a friend pitched me a voting app. He wanted to develop an easy and effective way for people to vote in political elections. Great idea, right? On the surface it seemed like a simple and elegant solution to driving voter turnout and marrying digital solutions with the needs of our democratic process. But I had to drop some truth bombs on his grand ideas. Did he have any experience working with the federal government? Nope. Did he have a sense of the timeline required for getting the app through legislative and budgetary processes. Another, no. Who would he want to meet with to make this business happen? He wasn’t sure.

I’ve learned a few things about having honest conversations with friends about their businesses. For a long time, I felt it was my duty to swoop in and tell friends exactly what the potential pitfalls could be in order to save them years of heartache for businesses that had serious deficiencies. But here’s the thing. Talking to enthusiastic entrepreneurs is a lot like talking to my teenage sons. As soon as you say, “Um, no I don’t think so,” they say, “Yeah, right. Watch me.”

Look, I’m not in the business of crushing people’s dreams. But I am an advocate for helping people ask the right questions before investing incredible amounts of time, energy, and money into ventures that don’t make sense. More often than not, people get excited about the solution, and not so much of the problem. And that can be disastrous.

So I started implementing something I call “self-evident decisioning” — because nobody wants to be told, “You can’t do that.” In an entrepreneur’s mind (and a teenager’s) that’s basically an invitation to prove you wrong. But when people can find their own answers, they can make decisions that stick.

So if a friend asks you, “What do you think of my business?” have him explore these questions on his own before trying to find investors:

  • Am I spending 80% of my time considering the problem and 20% with the solution? Good. You should.
  • • Be honest. Is the market big enough?
  • • Do you have any professional experience or a credible source for the solution?
  • • If you could get three ideal customers this afternoon, who would they be?
  • • If you could get three meetings, who would you schedule?
  • • If you got your investment money today, could you start your business right away?

If your friend doesn’t know the answers to these questions, they’re not ready to find seed money. It’s important that entrepreneurs understand how to execute a business plan in their weight class, and that they are 100% convinced that their business is scalable with teams ready to go.

Working with friends on their business plans is obviously a great way to build relationships and provide support in competitive spaces. We all need each other to help us imagine what’s possible. But a friend can truly be helpful by offering up honest, straightforward questions that can lead to sound decisions.

Venture Capitalist-Entrepreneur- Best Selling Author “What you know about startups is wrong.” “BIM for Owners and Developers”

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