The Most Difficult CEO Skill? Managing Your Own Psychology (2011)

A lot of it was just execution problems. But I think it summarizes into a perfect storm of moving the development team to a new product and putting the existing money maker on bug fix only, two rounds of dedicated sales staff that woefully underperformed (sometimes comically so looking back), and the landscape of paying customers going into insecure funding situations of their own.

On those points:

1- Moving the staff to another project was a tough call, but one I think I would have made in the CEO's position, it just was a gamble that didn't work out as well as we were hoping as it took new product iterations off the shelf for too long. But while the old product was keeping the lights on, its growth curve wasn't going to get us to where we needed to be.

2- I'm actually interested in HN's ideas on hiring good sales/marketing staff and how they should best be managed. Across half a dozen companies now I've failed to really find good competent sales people and any effective way of managing them without getting in their way. It's just a very hard position to hire for -- hiring engineering is a piece of cake in comparison. I think if I were CEO of a small startup, sales people would be hired on 90 day probationary periods. But I've heard counter arguments that sales folks in my vertical really require 6-9 months to build out their sales pipeline and start seeing results. However, some of the issues were stupid, like not answering phone calls or failing to handle simple contract negotiations without blowing the deal, or not wanting to manage contract staff to execute on part of the sale and simply moving on to other opportunities.

3- The customer situation was a surmountable obstacle I think by expanding the size of the sales net we were throwing out there. There were several related markets with better funding sources we could have gotten into that we didn't take seriously until it was too late. We also had some immediately good opportunities that got bungled because of #2 above and because the margins weren't as good as other opportunities that we chased instead and failed capitalize on anyways.

How often do you hear of people getting a significant raise and then handing some back because they do not think work enough or hard enough to earn it?

I think you might be misguided in thinking that people should work twice as hard or as long. Isn't the most important factor how much and what they're putting out?

A really excellent insight. It's amazing how people take on entirely new mantles when things get tough, and you just simply can't predict that that will look like.

It reminds me of the Mastermind Rational role variant in the Keirsey Temperament Sorter [1]. A personality type that doesn't want to lead, but when crisis hits and they feel leadership has let them down, will take charge and get shit done. It's a good kind of reserve person to keep in the wings I think.

I don't know of a corollary for the opposite though, who want to lead, but shut down at the first sign of trouble -- even though it seems to be a favorite archetype of writers.

[1] - http://en.wikipedia.org/wiki/Mastermind_(role_variant)

I don't think anything is 100% hardwired. Sure you probably start with a mental preference for one or the other but you can change it.

Now the question is: how?

How do you expose yourself to these kinds of situations gradually so that you have a chance to get used to it?

I'm split on this myself. Devil's advocate, siding with the board he failed to make his goals during that time period and he also had opportunity to simply leave himself.

I think he was hedging that he would have been able to raise more VC to get through the snag, and when that didn't work It didn't appear there was a plan B.

Like I said, I wasn't saying that. I wasn't being dismissive. I was just observing that this is a skill that applies very broadly. I read it, got it, liked it, then thought "hey, that actually applies everywhere". It's not a knock against the author or the article. Just my reaction.

You are getting valuable life advice from an internet venture capitalist? I will say a prayer for you.