A Month of Fail – Lessons in Startup Management

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Ever had one of those exceptional months were you have not only caught the fail boat, but threw a fail boat party and no one else showed up? This is the world of failure, deep hard core failure that you have to step back from many of the things you are doing just to get your head screwed on right and come at things with a different approach. As the owner of a startup, failure is a learning lesson, and you either learn from it or you go under. Here is the failure, and while the solutions to this are not all that crystal clear right now, there might be a solution around here somewhere.

Failure is a touch stone, if you are failing there is a reason why you are failing, either through not getting the pulse of what you needed to do, or something went south somewhere in the process. Going back and looking at each one of the failures provides an opportunity to find an alternative solution and see if that works out.

The biggest failure so far has been in management style on my part. I prefer to be open, let people know what is happening, what is going on, what the next steps are, and then trust people enough to go work a creative way of making things happen. I believe very strongly in letting people be their creative best, and what plans I have for the future. So far this management approach has been an abject failure, to the point of melty down personality issues, anger, resentment, and at times the process got bound because there was not enough money to execute properly. This has caused problems that are written with the big “L” on the forehead for me. My management style does not work in this case, meaning I have to change my management style to be more closed rather than open, and more micro managing than not. Personally I resent that, I don’t want to be that way, but this is what looks like is going to have to be the way of doing things.

Politics and political failure, honestly I thought that we could have done away with politics in a small startup, but I am remembering the line that we are all “political animals” at times. The politics caused by the biggest failure of management style has just about destroyed the team cohesiveness I was really working on by being an open and upfront manager. Team, there is no team anymore, which is a startup is devastating, you might as well close the doors because people are more involved in politics than making a great product, or serving customers.

Blame, the blame game should have been stomped the first time it showed up, and I didn’t do that, because I wanted to be a good open manager and I really didn’t care about the politics in a small company. When blame gets to the point where you are starting to feel like a voodoo dolly pin cushion, it is time to grab this tiger by the tail, otherwise the blame will completely destroy everything. People need to be held accountable, including the boss.

The problem with accountability is that when someone who has always won a prize for just showing up to the match resents accountability. They are used to sliding through life, playing the blame game because they don’t know anything about accountability. This is compounded by not paying attention to politics and the managerial style of just letting people go be their creative best.

This all started with leadership, the wrong leadership style for the people who are working for me. What was supposed to be a fun, go be your creative best, solve cool problems, make a great product, and seriously help people has pretty much so come to a complete collapse. Reputation in tatters, branded, labeled, and considered damaged, the whole company is on knife edge. And this is all happening in my little startup. (Has nothing to do with my day job).

So what has to change? Tons of stuff and all going back to leadership style on my part, obviously I cannot be the open manager that I really wanted to be. That is the source and the tragedy of the whole thing, best intentions, and the road to hell is paved with them. While it is too late to undo the raw damage that was done reputationally, I can try to fix the overt problems caused by the management style, and that is the important first lesson of being a boss. The boss has to change if the department is unhappy. People don’t quit jobs, they quit bad managers. And unfortunately in this case, I have been the worst manager of them all for the situation. And that is where the change needs to start, with me, leading the way that the employees want to be lead, sad really, but true. People have an expectation of managers based on what they are compatible with. My leadership style in this case is very wrong for where I am.

(Cross-posted @ TechWag)