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I have been doing side-contract work with someone for several years now. Our relationship is great. They are receptive, helpful, and absolutely committed to their project.

However, I'm starting to realize that the project will fail. They have only received several hundred signups in the past 2+ years the project has been up. The execution and goal of the website has been interesting to say the least. Without going into details, they are wanting to add more features to the site. As nice as these features are, I don't think it will save the website. They have almost no revenue stream coming in from the project. I suspect these features will cost them up to five-figures to complete.

Here's my question, I've always let them run their business the way they see fit, helping as much as I can to deliver the best product that they can afford. I have stayed away from suggestions on bigger questions like, "What is the primary feature of the website? What direction do we want to go in in the next six months?" With the gut instinct that this project will never get off the ground, should I tell them what I think?

  • What's your business relationship to this person, and what is your risk? If they are just paying you to do what they ask, then keep doing that. – HorusKol Aug 25 '16 at 23:03
  • I have stayed away from suggestions on bigger questions like, "What is the primary feature of the website? What direction do we want to go in in the next six months?" - why? why aren't you asking these questions? – HorusKol Aug 25 '16 at 23:04
  • To be honest, it's been a tight-rope walk for me. It's also hard for me to give an accurate informative response. This is not full-time work for me and they have a better grasp of the industry than I do. At the same time, I see the writing on the wall. – sere donne Aug 25 '16 at 23:12
  • My risk is is that I lose this gig. – sere donne Aug 25 '16 at 23:13
  • Sorry - I meant - what is your risk for continuing rather than pulling the project. – HorusKol Aug 25 '16 at 23:16
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"Give up" is never appreciated and rarely helpful unless it is completely impossible.

If you want to give useful input, document what you see as the remaining challenges to be overcome what you think would be the possible ways to address those challenges, and what you think the costs or each of these will be -- while pointing out that you may be completely incorrect -- and ask if they'd be interested/ willing to discuss with you how whether they agree and how they're going to tackle these. They may be unwilling to be so, or unwilling except under a non-disclisure agreement, but at least this is an effort to help them make a real evaluation rather than to hit them with your own discouragement.

  • I really like this. That said, I believe it to be nearly impossible. I would be willing to bet my entire life savings on it. I think I'm going to approach it your way. – sere donne Aug 26 '16 at 0:29
  • 1
    Difference of opinion is what makes horse races... They may know something you don't, or that you are weighting differently. Remember, if you express this as "I have a question, have you considered..." you are much less likely to either come across as thinking they are idiots or to make them think you are an idiot if you're wrong.For that reason I would also keep this as informal as possible -- do your homework so you can ask the question clearly, but don't present it as a formal statement that you think they are in trouble. – keshlam Aug 26 '16 at 1:22
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The answer depends on how receptive you think they will be. If they are going to get pissed off because you rained on their parade and keep losing money but with someone else in your position, why bother? On the other hand, if they have the same feeling that you have but can not bring themselves up to throwing the towel, maybe they at least be appreciative of your opinion, taking some of the burden off their shoulders.

  • They have always been receptive towards my opinion on things. I don't see them getting angry. I've never seen them get that way before. – sere donne Aug 25 '16 at 23:15
  • If you tell them the project is doomed, there's a strong chance they'll be unappreciative of the news. – Jon Chesterfield Aug 25 '16 at 23:30
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I think that from your viewpoint, you're slowly watching things crumble. Unless you're in a position to execute an entire turnaround, including managing needs that you can't supply yourself, leave things alone.

You'll become less interested over time as a result - this is normal. You'll probably become more frustrated as well. If it's dragging you down in morale, hand the client off. Make a convenient excuse and pick up some work where you can be and feel more effective.

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