How to communicate to friend that his ideas most likely won't work

Question

I have a good friend. He has a few startup ideas and is actively pursuing all of them - he set up companies and got a few people to join him on no salary, pure equity basis.

I think his approach won't work, because to have a go at even just one idea, you need to concentrate on it wholeheartedly. Not only that, I think his business plans are vague, his ideas are quite naive (to be frank) and he simply doesn't have the means to pursue it.

But I don't know how to communicate my concerns to him in a nice way, because

1. Startups are uncertain. As titled the odds are against success, there is a chance (however very small) that he could, in fact, succeed. I don't want to look like a fool afterwards, if he did - against all odds - succeed.
2. I don't know how to phrase my objections to his idea. Simply saying that your idea is terrible because of reasons XYZ sounds to me (this is my actual thoughts) not only lack tact, but also sounds extremely arrogant. I don't want to be seen as an arrogant guy.

I've started and am running a business, which he knows, although my niche and his startup ideas are completely different fields. I am not sure whether he tells me about his ideas hoping I will join him, or he is looking for a feasibility opinion, or just wants to brag.

In the past, I did try to put together a list of possible common problems to him, hoping that it would get him thinking a little bit more, but he quickly switched topics and even got a bit annoyed at me.

So how I can communicate to him that there is a better way of doing the startup without sounding arrogant?

Answer 1

how I can communicate to him that there is a better way of doing the startup without sounding arrogant?

Background: you have experience, he doesn't. You wanted to talk and help, he wanted to do it by himself and wasn't willing to listen. Basically, IMO, we could summarize the story like that. What then? If I start with the following, it's because I think these are reminders that you should see as big red flags and keep them in mind IF you decide to go any further and talk with him again.

You may have already done more harm than good. Hell is paved with good intentions. You wanted to help, but your friend didn't understand it that way. Why? Because, for decades, I've learnt that people, very very often, don't like to be proved wrong. And when you tell/show them something they could/should do differently, they can see it as the "know-it-all-and-of-course-better-than-me-advisor". Even if you don't mean it...

Plus: a very important point is that people who start a business pursue a dream and you can't take it away from them or break it. That'll make them mad or any other negative feeling towards them and/or you.

They want to think that the road ahead is a wonderful highway, easy to drive by, go straight ahead, but, sometimes, blindfolded, so that they can't see that the road is indeed a narrow, dark and full of small/large/tricky and dangerous potholes path. That's what dreams are sometimes made of...

What you have tried: list of possible problems and their outcome = discarded.

What you have as arguments for the pros and cons: your experience + your feelings about what he may be doing wrong + your desire to help him.

He's rejected eveything, as you mention it. What are the options left?

• do nothing more, and let him do his way. If he fails, he'll learn from it, and if he succeeds, great! :)

• try something slighly different. I'll expand on that point, because it seems like the one you want.

As the direct approach failed, you can still try to talk about your problems. The ones you faced when you launched your business. Because, as a (now) business owner, I faced many many problems. Some of them I knew about (but didn't understand or read the signs that others, more experienced, like you, had given), some I discovered. But it has to [ look / be ] like a small talk, and absolutely not like a "trying to help you" or "you should really think this way" type of advice. Offer your own experience, don't challenge him. The latter sounds bad and is often seen a "lowering", while the former is just neutral, and not judgemental.

Before I launch my business, I was filled with hope (51%, or you wouldn't start...) and fears (200%, or you would fail for sure, IMO, if you are too confident, and less careful).

I listened to profesionnals (business owners, bankers, CPA...), but not always understood what they meant. You sometimes have to face it to fully realize the danger. I was craving for any advice. Not everyone is the same. Some believe they can do everything by themselves, and some just fear they'll never be able to make it (like me, at the beginning) and succeed.

If your friends stands in Cat. #1, let it be like that, and everything more than what you already tried may just annoy them more and more. Is it worth a friendship? Be there just in case he's asking for advice, but don't try to step in on your own initiative. That would be my advice N°1. He who pays the piper calls the tune.

If you think he can still hear and listen to some advice (Cat. #2), do it like my second point. Keep in mind that "I used to care about what people thought of me until I tried to pay my bills with their opinions." :)

I often talk with people who run a business or want to start one. They (we) all have the hopes; and some, the fears. If you want to help your friend, talk about yours, and he'll pick what he thinks is important to him. You don't sound arrogant when talking about your problems, and what you tried to solve them, but rather when you talk about how great you've been dealing with them and just focus on that (sounds selfish too), or that won't work because of X/Y/Z (sounds like know-it-all).

Answer 2

TL/DR: You don't. I've been in your position many, many times.

I would first recommend a perspective change on your part. Approach this as trying to help your friend sort his thought.

Let's start with the one exception. If you are close friends, your friend is of sturdy character and the idea is especially bonkers. It's probably fine to just say something along the lines of "Dude, that's the dumbest thing I've ever heard." (This the literal skill of Hyperbole.)

But, for most cases, the Interpersonal Skills involved are Supportivness and (gently) Challenging Assumptions.

You don't want to outright say it's a bad idea, you just come across as a jerk.

As a friend, you should always stay somewhat supportive. For that, you can start the conversation with a mild compliment such as "Oh, that could be cool" or "wow, I never thought of that" then...

Offer related comments, information or questions that cause him actively think about his plans or assumptions.

What are you ideas to differentiate you from the 35 other Widget manufacturers?

or

You know, I heard Elon Musk spent millions on something like this, you should figure out where he went wrong.

Really, anything to get him to think and maybe realize what's ahead. Maybe he will be the one to take down Facebook, you never know.

Answer 3

I don't think there is any interpersonal-skillful way to be a naysayer. What you have to do is give constructive advice, not negative feedback. So you question is how to pass along your negative attitude towards his projects (i.e. you belief that he will likely fail) in a positive manner (i.e. through pointing out better ways for him to approach his projects).

For example, you write that he is working on too many projects. If you tell him directly, "Hey, you've got too much stuff on you plate, and almost no one can succeed with that," you are just putting him down, and not helping. Instead, you can help him see the issue positively, "Hey, you have quite a lot going on. How are you managing with it? How do you balance all the competing demands?" That is a useful question, and does not challenge him, and it can help him see that he is taking on too much.

Also if you see something specific that he is not addressing, you can ask, "How will you deal with X?", instead of saying, "You've got a problem X, and this won't work the way you are doing it". Again, you need to raise issues which contribute to his efforts, not point out roadblocks.

Keep in mind, it is not your responsibility to talk him out of anything he wants to do, or to keep him from making foolish mistakes, and it is definitely not your job to approve or reject his ideas. If you have a gut feeling that its a bad idea, you can offer to share your feelings, but not more than that. When you see a definite problem with what he is doing, then you can bring it up, as suggested, as an issue he can deal with, but not in a way which tells him he cannot succeed.