My Last Day at PivotDesk

"The constant pitching, the t-shirt wardrobe peppered with company logos and talking about the business at every holiday, lunch with friends or phone call with Mom really adds up. It’s what you live and breathe as a startup founder and I wouldn’t have had it any other way."

These should be huge red flags. The author describes thinking about nothing but work for three years, then reproaches himself for... not having spent more time thinking about work.

Do not be this guy, you will burn out and you will destroy relationships on the way down that you cannot repair.

I don't understand this blog post at all. It seems to only show the very tip of the situation because, based on the text alone, the story/situation doesn't add up. Especially the part where he says he was doing everything perfectly for the week, yet everyone still wanted him gone. It seems like there was a much deeper personality conflict or something we aren't seeing. Maybe this is my fault, but unfortunately, it also makes the lesson/point a lot weaker and more muddy.

Seriously one of the more confusing blog posts I've ever read.

> Letting my week fill up with sales, finance, pr and exec team meetings and not leaving myself enough time for deep product focus.

i would posit that no single person in a company with more than one person should be working on all these things in a primary capacity. they're all over the spectrum in terms of complementary skills. even in a two-person team, you need to split those roles up so that one person "owns" each of those things. there are exceptions to this rule but you don't see it often.

moving further down the timeline, one of the things i learned quickly as a founder is that if you hire someone to do a job, you have to let them do it. you can't do it for them, and you sure as hell can't micromanage them. mistakes will be made, there will be misunderstandings, but that's just part of working on a team. you just have to accept it.

if you are operating with a decent staff (~10+ people), and are a co-founder and find yourself doing all these tasks, the problem is you.

it sounds like this guy just would insist on working on other peoples' workloads, while skipping out on a lot of company meetings, and they eventually started resenting him for it. you can't wipe that away in a week.

Interesting read and seemingly a very professional response to what must be a heart-wrenching situation on a personal level, but I don't really understand the rationale behind "giving it a week".

If your team has lost confidence to the point where it "doesn't really know what you do anymore" this will not change in a week, no matter how well things go that week.

I think that this post, with it's main point "No one really knows what you do anymore" completely removes value from previous post "3 Tips Product Managers Can Use To Do Great Work", and others too. Quite funny to see so much posts about productivity in that blog, while knowing final.

Harsh reality.

Without having the PivotDesk side of the story, I can't help but feel that there's a second, undocumented failure here: the lack of a strong feedback culture.

Did the cofounder really not receive any performance feedback until "It might be time for you to go"? Did his team members not feel comfortable talking to him about it, or perhaps even the other cofounders, until the situation reached a boiling point? Did other team members know they had an open communication channel to provide feedback about a cofounder?

Unless the issues he describes are intrinsic personality quirks -- in which case he probably needs to understand his tendencies and find an environment where he can thrive -- this whole situation seems avoidable. All employees, but especially managers, should create time and space to have candid, mostly unstructured one-on-one conversations with a handful of direct reports / superiors / peers. Leaders should invite criticism from the very beginning and make sure everyone knows it's safe to challenge ideas and decisions. And ideally, this starts during the hiring process. Let potential employees know that you value productive dissent and do your best to evaluate them on that axis.

If you don't have people within the company that can effectively evaluate you, find someone outside of the company that can provide advice. This seems more common at the (co)founder level, although could apply e.g. to a technical person at a highly non-technical company as well.

EDIT: As a cofounder, he had the power to engineer some of these support structures himself. This isn't "mean company ruins struggling cofounder," but rather a reminder to spend time on soft skills and the human element of running a business.

This captures the fact that what is inside your head is not always in everyone else's head. I struggle with this, when things seem "obvious" to me but are completely missed by others. Sometimes checking in and asking how folks see things is a good way to figure out what the team is seeing versus what you are seeing.

The "No one really knows what you do anymore" is a murmur that follows senior leadership role all the time. And while it CAN mean that you're not doing anything, in this situation I think it was a case of some people struggling to assess the value of all the activities you do through their own lens. More likely than not, you were making valuable contributions to the company; much more so than your employees realized.

So when they weighed their perception of your contribution against their negative feelings towards you, the fulcrum was positioned against your favor.

Departure like this can be a turning point for the company for worse, especially at a small company like this. I hope this isn't the case.

Take a vacation and enjoy your family, buddy. Everything will work out in the end.

You're probably feeling terrible right now. And that sucks. But remember, shit happens. And while ultimately you are responsible for your own success, it's your CEO's job to build the organization and make sure that people––including you––are setup to succeed. And my guess is that the organization itself is losing a lot by losing you. Bummer.

But as you will quickly discover, the past is the past in startup world and the only thing that matters now is what you're doing next. Enjoy the endless possibilities that are future. Be proud of what you've built. And be proud of yourself.

I have no insight on this situation in particular but Kelly has always been kind and helpful to me in my experience. He's a sharp dude and I wish him the best with whatever comes next.

Seems like some post-facto rationalization. What exactly is the lesson here? Don't be a jerk to your teammates and make sure they know what you're doing? Why not just say that instead of publicly apologizing like this?