Boss In Heels: An Entrepreneur's Guide to Success

One of the most fascinating things I’ve learned in running a business as a woman entrepreneur is how differently I’m treated in my interactions simply because I am a woman.  If I’m aggressive in a negotiation, I’m seen as a raging bitch.  If I don’t make this big show about how guilty I feel about getting my way, I’m a selfish, heartless snow queen.  But if I act any other way, well then I’m a woman.

It’s not shocking that women earn significantly less than men at the same jobs.  That attitude starts long before the workforce, with our deep-seated notions that women are gentle, caring creatures that don’t have what it takes to be ruthless (and if they do have what it takes, then you don’t want to work with them).  Mostly, it comes down to whether or not you have the guts to let people think you’re a bitch (even temporarily).

I’ll use a real-life example to frame my point:  when my boyfriend and I signed a lease on a new house, the agreement said the house would be professionally cleaned before we moved in.  A week before move-in day, I went by the house and noticed spiderwebs, a filthy floor, dirt in the window sills, and windows/mirrors that had not been windexed.  My thought: this place hasn’t been cleaned.  So I sent a very friendly email to the landlord asking nicely if it could be cleaned prior to us moving in.   What I got back was a phone call full of attitude and spite – “it HAS been cleaned,” he said, “what is it that still needs to be done? if I don’t have a list, I can’t have my people do anything about it, I’ve done everything I can, you’re being difficult.”

What’s with the ‘tude?  It was clear from the minute I stepped in the house that had it been cleaned, they had done a half ass job.  How was this my fault?

Frustrated, I asked my boyfriend to send an email that basically said “it’s my understanding the house needs to be cleaned before move-in.”  Hours later, the landlord responded “I’ll have it cleaned again.”

WTF?  I get an irate phone call and basically undertones of “I think you’re a bitch” and he gets back “sure, no prob.”  Sigh.

Personally, I’m not a snow queen by any sense.  I’m actually a very nice person with a big heart and a huge conscience.  I feel bad about hurting other people, emotionally or financially.  It’s one of the things that’s kept me sane in running a business in nutraceuticals and during this recession.  If you’re ruthless, you can rip people off and make a lot of money… but that’s not my style.

No no, instead I worry about other people, to a fault.  I don’t like inconveniencing anyone and I’m largely non-confrontational.  I try to separate business from personal as much as I can, but I’m only human, and the human element drives a large part of the small natural foods industry.  If you piss everyone off, you won’t get anywhere.  It pays to go the extra mile and be nice to people.  It’s an industry of favors and helping each other out – why wouldn’t you be caring and friendly?

I’m a softy to the point where I won’t even tell cold-calling marketing/PE firms that I’m not interested.  Instead, I always use the excuse that I’m in my car and can they call me back next week.  Most of them forget – those who are using a CRM software call in the early morning when my phone is on silent and it goes straight to vmail.  Win win, I suppose.

So when it comes to cutting corners in my business, it’s an emotional, difficult struggle for me.  I run most of the operations myself, so finding ways to do this efficiently hasn’t been a problem.  But when I had to re-negotiate a contract with a third party I was working with, I dreaded it.  I stayed up late nights, stressed out, and spent hours on the phone with friends and family dissecting the situation.  What was my problem?  It was a BUSINESS decision for FINANCIAL reasons.  If I were a man, I thought, and I made the decision that was best for the balance sheet, no one would have blinked an eye.  But when a woman does it, she’s being inconsiderate.

It is amazing how much self-explaining and apologizing we do as women when we make a difficult decision.  We start every difficult conversation with “this has been a tough decision” and “I’m really sorry to end this agreement.”  Sorry?  It’s just so natural, I guess.

I’d like to believe in the natural foods industry, a small and communal group of professionals, everyone feels this way, not just women.  But what I do know is that at the end of the day, I had to suck it up and let go.  I had to leave my emotional baggage at the door and bring only business facts to the negotiating table. I was going to get my way, and it didn’t matter how much I worried about the other person’s emotions.

I think, in the end, it was the right decision.  It wasn’t easy, but I’ll be the first person to tell you that I’m not a stoic businesswoman who can just go through the motions without giving a damn.  I doubt any person is, or at least that’s what I hope.  I hope every man and woman in business cares, deep down, and is appearing perfectly composed and unscathed for show.

Here’s my advice to other young women entrepreneurs: everyone’s an actor and you’re part of the play, so play your part.  It’s OK to leave your emotions at the door.  Everyone’s probably got their own guilt they’re carrying around with them about each decision they make that affects other people.  It’s up to you to appear as if you don’t.  Because as soon as you come out of character, you’ll lose the respect of your colleagues.

Women should feel confident that making decisions on finances alone is perfectly acceptable and does not make you a bitch, no matter what people say or what you think.  It’s also OK to have a conscience.  But you have to do what will keep your business alive, and deep down, everyone in business understands that.  Even the snow queens.

-Written by Lindsay Reinsmith, Founder & CEO of Kaeng Raeng