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15+ Years of Working in Family Businesses: Lessons Learned

Business and pleasure don't mix, or at least that's the conventional wisdom. But for 100s of years, the family business was the only business. I was brought up in a family that's run a series of businesses. Here's some of what I learned.

Sam Kite, Blogger

March 9, 2017

12 Min Read

Preamble: Denial

Ok, that's not really what this first section is about. All right, kind of. Yeah, I mean. Yeah.

Business and the household were synonymous in my family. There were day jobs, but that was unusual compared to working on the latest business.

I grew up in a family-run art studio. When the art studio flagged, my parents restored stained glass windows, renovated the house to create rentable subunits, applied to create sprite art for video games, traveled to Japan to teach english, created interactive cooking CDs, started their own Microsoft Vendor, and now, lately, a boardgame company. I remember helping my father floor an attic, handed him tools while he framed new walls and ran plumbing, and, later, helped measure the cuts and rip boards for construction of workshops or rental units. I've written code as part of intranet projects for MS, and spitballed endlessly about the current family project late into the evening.

Somehow in the midst of all this, I grew up thinking "these are my parents' projects, and I'm just helping out in the periphery". In point of fact they were always trying to gently nudge me in the direction of starting from scratch and finding something useful to do. In particular, with them.

In some sense, this sunk in, and I was happy to help, or at least excited at the prospect of helping. In another, larger sense, I managed to convince myself that I was a meaningless part of the process, and therefore had no duties, responsibilities, accolades, or ownership.

To be clear, I had my own things going on, and needed to leave the nest, but after recently coming back together to work on our first boardgame project under the new company, Pelta Games, I decided to take an inventory on what this was like, with a view to thinking through production relationships in the Game Industry, a place famous for personal feuds, singular figures, and dramatic studio stories.

So here's some lessons earned.

Ideas Aren't the Same As The People Who Have Them. 

But Nobody Actually Feels That Way When They're Criticized

My father grew up in a house where every night over dinner, some arbitrary debate would occur. You couldn't leave--you had to have an opinion, stand your ground, and keep arguing. This made dinners pretty obnoxious, but despite how little my father liked the process, it affected how he acts and how I was raised. 

We debate every goddamned thing in my family. If someone has a great idea, then, enthusiastically, we ask about it. Enthusiastically we declare it great. Then enthusiastically we begin tearing at the edges of it. Anything poorly thought out gets inflated in importance--because that's how you win arguments. Anything well thought out gets reshaped, undercut, and put in different contexts to see how survivable it is--because that's interrogating ideas. 

Ideally, this is supposed to be powerful. You can be sure any idea is tested and is better thereby. If someone is genuinely unsure about something, a carefully considered debate and the ability to field criticism is paramount. In practice, what usually happens is that someone has an idea they're enthusiastic about, and whatever lip service is paid to debate as a technique, they still invest in that idea.

That investment is more important than the idea itself.

If you want to have the ability to call someone on a bad idea, you need to be supportive. That builds a trust that gives you the opportunity to jump in later. People are not able to process criticism every single time they offer an idea. If everything they do is met with resistence, then they'll stop bothering to talk to you. It's also easy to forget the cost of debating every idea, and when people get slammed, they don't have room, anymore, to seriously consider criticism or adjust their ideas. People only have so much bandwidth, and how open minded they think they are isn't how open minded they really are when they've just finished something exhausting or are stressed.

People Have Tools, and If They Don't Have The Right One, They Use What They Have.

You can drive a screw with a hammer, and if you do it enough, you forget that somebody else might have a screwdriver.

There's an old Snoopy cartoon where some kid says 'you're stubborn' and the other kid says 'I'm tenacious. Stubborness is a fault, tenacity is a virtue.' Every skill has a dark and light side.

Let's say you're the marketing guy. You love convincing people to do something. You're good at it! The only problem is, you can convince them to do the wrong thing, and, to an extent, you don't know or care about quality when you're in the throws of a good 'convince'. Man, when you're on a good convince, things like facts, or qualities, or reality are just so much irrelevant crap. Who has time for it? Not you, that's for sure.

If the body politic needs you to convince, then great! But if you're, like, really into the Seahawks, and you want everybody to make the application in their team colors because you're a superfan, then you're a vampire. How do you make sure you're not using your skill to do wrong? 

Here's the subtle thing. If you're a functional person, particularly a professional, you build a thick skin. You learn to believe in your tools because you're always under attack. People look to undermine your sense of skill for all kinds of reasons. They're worried about the product. They're worried about the consequences if you don't come through. They don't know the difference, and perceive a competent criticism as an attack. 

That ability can make a completely insufficient skill become a liability when they come together. Especially when the person happens to also be the gatekeeper on something vital--say you're a coder/artist pair, and the coder thinks they need to manage social media. They need to be coding--it's indispensible, but now they're blowing time trying to figure out how to edit video, or god forbid, engaging with people on the internet (or chasing trolls in the blue ocean).

When you feel responsible for other people, it brings out the animal need to figure things out no matter what. That can mean you gut it out, step into something complicated and confusing--learning as you go--and come up with success. It can also mean you have a tendency to 'grab the controls' and get in the middle of things you don't do well, because you feel like if you don't, no one will. 

It's a weird paradox which leads to the next point.

Asking For Help Is Harder The More You Care About The People Around You

It's easy to waste the time of people you don't like.

This is probably why a lot of managers who aren't well liked can still do their job well. If you hate that guy, then you'll come to him with problems. This is good for a manager, they need to be the go-to when something's wrong so they can manage the eFF out of it.

Here's the problem. Asking for help is necessary. It's part of ceding control when you're not able to do everything you think you need to (or have been told to). If you're in a small team, or really, any walled off group, whether it's a family, homestead in rural Siberia, or an Indie studio, your assets are finite. When you go to someone else, you feel the pressure of sucking the life out of the group--of costing more than you put out.

People can also get addicted to being the hero. Always letting other people beg off problems on them, because it puts the weight of everything on their shoulders. Except, when you do that, you've just made yourself the liability. The liability doesn't go away, it just moved around. If you manage to grab too much, you end up being worthless to everybody, and at a certain point, the partnership breaks down or gets suspended. In a real tight group, this can be devastating, since there's only a couple people, and when one of them feels pushed out and doesn't know how to get back in, you've lost a third or half of your capacity.

It's Easy to Be A Naysayer

So keep a lid on it for when everyone isn't already at their max stress capacity.

Sometimes you've got to be a shark and just keep going. A real partnership is a committment to not jump ship. If someone becomes impossible to deal with, you have to figure out how to wait it out and be there when they come out of it.

Obviously, there's some partnerships where this can't happen. People get divorced, families don't always speak to each other, and it's usually because there's no reciprocation, but assuming there is, then you've got to say your piece and then let it go and get on with the program. Sometimes it's important to be a soldier, or at any rate, a booster. This is another side effect of an intense environment and relationships. Especially in small groups, you've got to remember that what you really need is for the person to be there beyond the project, either because it's over, or because after the work day is done, these are the people who're are going to be able to understand what you went through and help you blow off steam.

Especially in environments where free-form debate is considered important, you get people who evolve to have a demeanor that's conservative and ready to shut things down, rather than look for ways to make things happen. The only check on this in most environments is that there's a management structure that separates people into different silos, where they're individually responsible for getting things done. So if you gainsay something, it won't matter if they don't answer to you. In a small group, things tend to be flat, and it can be a fine line between being useful and being a roadblock. 

Sometimes all it takes it to get on someone's side emotionally first. Hey, man, yeah. I love it. I especially like how you did This Here. But man, wouldn't it also be great if you Didn't Do It? Did you try that? How'd it look? Was it better in every way? I bet it would be! Man. Awesome stuff.

Don't Go To Bed/Hang Up The Phone Mad.

If possible get some partners who aren't completely in the middle of the shit all the time to be go-betweens.

Here's the bottom line. It's a rare group of people who get along all the time. Most arguments in a family happen because of external pressure, not something between the people who are having the argument. There needs to be a voice in the back of your head to deescalate. Someone's not listening? They're raising their voice? You're raising your voice? Try to stop it. It's never too late! Until it is to late, because you or they left in a huff.

Apologizing doesn't really work necessarily, either, because everyone knows that apologies are fundamentally uncomfortable, and, more or less, pointless. They're an admission of fault but in some sense, if I'm apologizing, then you made me do it. Which isn't fun for anybody. It's also hard to be sincere when you apologize unless you have fear, and it's nearly impossible to fear someone in a small partnership. That kind of thing really only works in a larger corporate environment where someone can threaten you with being fired or disciplined. Or humiliated, or whatever.

Basic set of strategies:

  • Ask questions when you'd rather tell people how it is.

  • Say what you want. Not what you think you want or what you think they think you want, but what's important to you without editorial comments.

  • Be clear if you can and try to distill down what you care about. Are you saying no to something because a) it's a bad idea b) you disagree with the feature or c) you're worried about being embarrassed in public because you think it's your job to announce it or answer questions about it or whatever. If it's c, then maybe explaining that you're nervous lets everybody else get to why they're nervous. Maybe they're nervous for the same reason, but the only way they see to get past it is to barrel through.

  • Let other people who aren't directly in the argument or frustrated ask questions for you and hear what you have to say. They can be filters and shock absorbers to prevent something from festering and getting worse.

  • Always remember the good times and assert what the partnership really is. Do you love the person? Mention it occasionally. Especially when it's hard to remember that it's true. If they're an old friend say that. If you respect their work, say that. If all you've got is the thing they did last week that you thought was cool, say that. Don't be passive-aggressive. Mean it.

Give Up, It's Not Worth It.

Just not on the partnership.

One thing I respect my father for, and try to emulate, is that when we're out of sight and mind, he takes the time to reset. That means giving up on whatever was making you angry and rezeroing the scale at 'trying to get along'. As long as you can trust the people you're working with to come back tomorrow ready to forgive, forget, and move on, then you will never be afraid that something that's wrong right now, has to be wrong forever.


Try To Remember It's About The People And Not The Business.

And that's it.

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