I just posted a piece on Mashable about telling signs that a company is failing, addressed in the perspective of startup employees. This post on the other hand, is addressed in the perspective of startup founders. Here are some indications that it's almost over...and some things to gasp for...
1. You've been thru a funding/M&A process and gotten no bites. If you had a banker involved, you should do a real hard check in at the 90 day point. The market will have at least given you some indication. Get answers fast and put a strategy in place to get to the next funding, be it venture debt, bank loan or additional venture capital.
2. You'd rather walk on coals than go to your board meeting. If you're dragging your board along and fighting every step of the way, you're miserable. Not only does the counterproductive relationship not help, but you're less motivated too. But if they're making you drag them along every step of the way, they aren't satisfied - they need more from you. They need to be able to confidently report your progress back to their partners. Get on the same page with your board on what data is important and how it is best consumed.
3. You can't agree with your other founders, management or other key employees on strategy/product/direction. This is fairly common with certain individuals, but if it goes too far for too long, you'll lose important 'buy-in' from people, which will slow things down and erode the quality. You need to keep people motivated and excited. They want to know why and how you get there. Realize, not everyone has a natural instinct for which moves are the right moves. Nurture them. Have routine staff and/or all-hands meetings.
4. Your office is empty (too late in the morning, too early at night and every Friday or Monday). When your employees aren't motivated, they wear it on their sleeves, as in they won't come to work. Hold an office party, get loose, break the walls down and simply talk to everyone. Tell them what you're going thru; rally them around the cause. Get them back in the boat. Remind them that it's times like these that make a startup what it is or isn't - and that their names are attached to this thing as much as yours is.
5. Key team members are leaving. If you loose one or two key person, you can chalk it up your expected quota of a couple disgruntled employees. If you loose more, there's a pattern. It's clearly saying that people aren't realizing the opportunity they signed up for. This has a negative impact on morale of others and will begin to bleed like an open wound. Quick...stop the hemorrhaging! Be really in touch with people's expectations (and them in yours). It's only when expectations are out of alignment that things go south.
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