Find people who compensate for your weakness

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The update on my company is that Ryan Healy and I are not talking to each other. Well, he is talking to me, but I am giving him the silent treatment.

Still, I am confident that things are going well. First, because I am bad at the silent treatment—I have too much to say all the time. Second, there is very good research about what makes a good entrepreneur. And the answer is that there is no single personality, but rather it is the type of person who can see their weaknesses and get a partner to compensate for that.

Ryan and I have done that with each other. And during my short stint of silence, I thought about how in fact, we are doing a lot of things right. Here are six things that entrepreneurs must do in order to have successful partnerships, and I think Ryan and I are doing them:

1. Make time for arguments because they are inevitable. You must consider this part of your job, in order to have constructive conflict.
We fight like we are married. Which says a lot, since I am in the middle of a divorce and he has never had a girlfriend for more than fifteen seconds.

So I call him from my kids’ soccer practice to tell him I am not calling him for a week. And I am the parent at soccer who is on my phone instead of cheering every good kick. This is my way of bringing diversity to Madison: if it were not for me, only men would do this at soccer.

To be annoying, Ryan calls me at 5pm, which is death hour to all parents who have hungry kids who are a half-hour from food, and he says he can’t manage cash flow because any question he has must wait 24 hours if it comes up at 2pm, which is when I stop working.

I want to be like, Duh! If I stopped working at 2pm then I would not have any time to fight with you from the soccer field. But I stay quiet because I am trying to be a more reasonable person to work with.

2. Remind yourself why you picked that person. You probably still need him for that reason.
I remember when Ryan and I were first thinking of going into business together. And we spent two months arguing over equity. There was the day I got so angry that I had to pull the car over to fight with him. And neither of us walked away from negotiations. Someone who really hates fighting would have called off the partnership right there. It was a sign that this is what our partnership would be, and we both signed on the dotted line.

In that fight, Ryan was more mature than I was. I was definitely right on the business issue we were arguing about, but he handled himself better. He was very calm. And that only made me more hysterical. (I hesitate to use the word hysterical, by the way, because I know that it validates Ryan’s propensity to call all women he ever comes into contact with “crazy” but whatever. Now he and his friends can have a four-syllable word they can use for variety.)

So, anyway, that’s how it is now. I envy Ryan’s ability to be even-keeled. I am not an even-keeled person.

3. Give each other feedback on strengths and weaknesses.
I’m also going to tell you the worst thing he said. He has no idea that this even bothered me. So right now is the part in the paragraph where he will jump ahead, amazed that I didn’t tell him something that was offensive. Because believe me, he hears about it every single time he is rude to me.

So, anyway, it was a day when we both got dumped. We had each had about four dates with people from Madison, which is, in itself, a miracle, because we are both fish out of water here, and neither of us really expects to find a long-term relationship.

But miracles happen. And we were both smitten. And then we were both dumped. Ryan is the great analyzer of our social lives because he thinks I am a social mutant and only know how to talk if CNN is interviewing me.

So, he says that he was dumped because she was a college girl and didn’t want the structured dating life that a recent grad wants. Then he tells me that I got dumped because I don’t dress like a girl. “You don’t even try!” he says, with his patented combination of exasperation and incredulity.

I’ve been around Ryan long enough to know what this means. He thinks I look like those moms who throw on designer jeans and a Calvin Klein T-shirt and think they have stepped up their game. And they have, for a going to a preschool play date.

So I wore that and I thought I was dressing up, and Ryan thinks I look like I’m in preschool-play-date mode.

4. Use the other person's expertise to improve yourself.
Really, Ryan gave good information about my wardrobe because there have been many times that I have not dressed quite right for television appearances and people have been largely unimpressed.

Also, I am good at taking criticism (lucky, since Ryan is good at dishing it out). So I implemented his recommendation to be girly in Austin, while everyone was Twittering at SXSW about how Mark Zuckerburg's interview sucked. I was down the street at Nordstrom buying accessories.

(There is no Nordstrom in Madison. I plan all my shopping trips at the intersection of the Nordstrom store finder and my speaking engagement itineraries. And, by the way, the next time I use scientific data to choose where to live I will never move farther than 15 miles from a Nordstrom. Nordstrom customers have good taste and Nordstrom opens stores near their customers. )

5. Be aware of generational differences, and don't assume you're above them.
We know we are a shining example of the generational train wreck in corporate America. And it’s not for nothing that Ryan just wrote a post about how the biggest problem in work life for Gen Y is not the Baby boomers but Gen X.

Sometimes we find ourselves laughing about what a stereotype we are. For example, Ryan always wants to collaborate and I want to be alone and answer emails.

He wants to socialize with everyone at work, and I am all about picking up my kids at school.

I asked him to fax something to a client, and he said, “Fax? Do I look like I’m forty years old? I don’t even know how to use a fax. Can’t they take a PDF?”

Ryan and I have parents who are roughly the same age, yet his parents call all the time because they think the company is so cool, and I don’t even think my parents could tell you the name of my company.

6. Startups are difficult for everyone. So don't get hung up on hierarchy. Or anything else.
I was going to tell Ryan today that his problem is that he doesn’t manage up. I was going to say, “Look at the sidebar on my blog. I write about managing up all the time. How about brown-nosing once in a while?”

But he would not take that criticism well. And anyway, he’d tell me he managed up the only night maybe in my whole life that I was drunk: at TechCocktail in Chicago, which I promised I would blog about, so thank goodness I’m getting it in now.

Ryan took off my nametag in an attempt to gain some anonymity while I was totally drunk and probably inappropriate. For us, that qualifies as managing up, probably. But then again, that was the night he told me I am the most socially eccentric person he has ever met, and I’ll never get a date.

I told him that men like socially eccentric because in bed it’s not about being social, so there’s just eccentric left, and men think that means a likely possibility of anal sex.

Ryan was silent. He was driving. But I don’t think he was silent because he was driving.

I said, “See. I told you I’ll get dates.”

70 replies
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  1. Boomerbust
    Boomerbust says:

    Hugh has a lot of material for you but based on your last comment this may be an appropriate banner –

    http://www.gapingvoid.com/0804dirty.jpg

    You went WAY over Ryan’ head with your comments; one day just give him some quick casual sex (bj?) to make his eyes roll.

    Maybe then you can get back to work and make your company rock.

  2. Chris Young
    Chris Young says:

    Penelope – Nice post, I think you bring up some important issues on skill sets and personalities in the workplace.

    I’m reminded of the quote by General George Patton – “If everyone is thinking alike, then someone isn’t thinking”

    This is paramount in business. If an organization is made of up people who all think alike and behave the same, it can be in for some real trouble.

    Different personality styles and skill sets are critical for organizational balance. We are all good at different things and nobody is good at everything.

    Thanks for bringing this thought to the masses!

    Chris Young

  3. Steve Kettering
    Steve Kettering says:

    Penelope just doesn’t get it. It’s one thing to deal w/crazy for the possibility of emotionally vacant but out-there sexcapades. It’s another to go to work every day, and tie your economic well-being, to it.

    Ryan wasn’t quiet because he was nonplussed at the power of her argument.

    Ryan was quiet for the same reason all guys go quiet, when they just realize they’ve stepped in a large pile of feces. That is, his brain is simultaneously processing: ‘oh hell’; ‘how’d I let *this* happen’; & ‘where’s the exit’.

  4. KT
    KT says:

    Penelope – I get such a chuckle out of your posts…the mix of business, real life (dating) is fabulous. You rock.

  5. karen
    karen says:

    Seriously…I’m laughing. You and RH sound like me and some dork, if you know what I mean. ;) In fact…he’s getting a link to this post so he can laugh at the fact that we’re not the only ones in this situation…compensating for each other’s weaknesses. We’re definitely experiencing 1, 2, 3, 4, and 6.

    Love this post as it gives me hope for my future and reminds about why I’m doing this. *Cheers!

  6. J Bird
    J Bird says:

    #4 “Also, I am good at taking criticism”

    What B.S. THAT IS!

    A while back I emailed you about how there are plenty of tech people in this country, but companies don’t want to pay for them. You blew me off with a comment like “too bad” and “good luck”. I disagreed with you and turned it into a none event.

    You are NOT good at taking criticism!

  7. Dan Owen
    Dan Owen says:

    You really are very funny. I don’t buy it that you’re a boring date.

    As for you and Ryan dating: Don’t be stupid. Don’t. Be. Stupid.

  8. Kristin White
    Kristin White says:

    Wow, Penelope, this is really enlightening…one could found a startup with their best friend, which could be fabulous, but one definitely needs to think through the impact on the relationship, and that subsequent impact on the company! It makes me think twice about starting a company with my husband! ;) But you and Ryan seem like a great team, with a good rhythm and way of working with each other!

  9. Pokupka Ssylok
    Pokupka Ssylok says:

    Could you help me. Choose the life that is most useful, and habit will make it the most agreeable.
    I am from Azerbaijan and know bad English, please tell me right I wrote the following sentence: “Seo is very time consuming but unfortunately if you want to drive traffic from.Leading search engine marketing company providing natural search engine optimization and seo, link building, ppc management, press release distribution and.”

    Thank you very much :p. Zada.

  10. Noel
    Noel says:

    Penelope, no offense, but after reading a number of your posts, you come across as an extremely neurotic woman. I can’t imagine working for someone like you.

  11. sophiz
    sophiz says:

    Funny conclusion.. however, I think a post like this is very unprofessional, and that’s something you need to learn the definition of.. for one, I’m not sure that this colleague consented to his name being published online and this blog post showing up in search engines potentially. If he stops working at your company, you should know that other companies can do searches online and some people would rather remain anonymous for that reason & their own privacy. I’d caution and say to use nicknames or initials instead. Saying his real name doesn’t really add much anyway, to your audience. He’s just some other unknown character. 

  12. sophiz
    sophiz says:

    Funny conclusion.. however, I think a post like this is very unprofessional, and that’s something you need to learn the definition of.. for one, I’m not sure that this colleague consented to his name being published online and this blog post showing up in search engines potentially. If he stops working at your company, you should know that other companies can do searches online and some people would rather remain anonymous for that reason & their own privacy. I’d caution and say to use nicknames or initials instead. Saying his real name doesn’t really add much anyway, to your audience. He’s just some other unknown character. 

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