You finally did it. You decided to hire an assistant, or a virtual assistant, or even a full-on employee, with payroll and everything. Yahooey! You’ve hit the big time now. You’re business is sure to take off.
And then your new assistant sends you an email, or leaves a voicemail, or comes to your office. “Uh… I made a bit of a mistake. I hope it’s not too bad.”
But it is. It’s a big mistake. And it’s actually going to cost you some money, and time, and it needs to be cleaned up.
After you’ve taken your ten deep breaths, or thrown your tea mug across the room, or had a private tantrum with your significant other (not mention scaring the heck out of the cats and the children, who either ran under the couch, or are now crying inconsolably)…. what do you do?
Do you make them pay for the mistake? Do you give them a verbal tongue lashing, so they really get how bad it is? Do you dock their pay? What happens?
This is a break-through moment… only if nothing happens.
Nothing happens? No punishment? Your assistant can just wreak havoc with no consequences? How can that possibly be right?
Well, there are consequences, but not imposed by you. Let me explain. You see, employees of small companies really care about the well-being of the company, and their bosses. They do.
We’ve been inundated by stories of employee sabotage and apathy, but those are in global corporations, where the employee doesn’t feel any sense of connection to the whole. If you hire someone to work with you as a small business, they are going to care.
They won’t care as much as you do, but that’s okay. A parent always cares more about their children than the children’s playmates, or even than siblings, because of that deep bond of giving birth.
But, they do care, and they care deeply. If they make a mistake, chances are they already feel horrible about it. And here’s the critical point:
If you act harshly, or punitively, you’ll destroy 90+% of the value of having an employee. The 90% of having someone you trust, who can act independently, make decisions with confidence, and trouble-shoot without needing your input at every turn.
Where does success come from?
Mistakes. Lots and lots of mistakes. The best leaders I’ve always heard from have said things like “Fail early and often.” “Never trust an entrepreneur who doesn’t have a failure in their past.”
Mistakes are sign of creativity. A willingness to be bold, to try something out, to test the waters and see what happens.
The biggest complaint I’ve heard from business owners who have employees is that “it’s like running a kindergarten! I have to babysit them.” But, do those business owners give their employees leeway to make creative mistakes?
But isn’t that shielding them?
People who care aren’t shielded from anything. The worst punishment is already happening- in their heart. They are awake at night worrying about how they messed up. They feel bad, and they want to do better. This natural tendency in people who care will keep them from being careless with your business.
Your job is twofold: to hire people who care, and then to make sure that their caring doesn’t paralyze their creativity.
Veiling mistakes is a path to success.
The spiritual teaching that my Sufi guide gave to me is to not point out the faults of others. The wisdom that I’ve seen in this is that when someone is sincere, pointing out the fault can leave them paralyzed with shame. And when someone isn’t sincere, pointing out the fault usually results in defensiveness, and blame coming back at you.
And besides, who says I’m right anyway? What if there’s a larger wisdom, or some aspect that I haven’t seen? Maybe it’s not a mistake at all…
So do you do nothing then?
This is not to say that mistakes are never discussed. If someone, like your assistant, comes asking to learn about a mistake, then it is important to share experience and insight with them. But not by pointing out the fault and hammering it in. Instead, by finding the strengths, and demonstrating what is wanted.
Not always an easy or straightforward task, but let me share some of the gems I’ve learned.
Keys to Avoiding Crime and Punishment.
• Be slow to hire, and long to train.
Just because you need the help, like, NOW, don’t grab just anyone and throw them into the position. It’s a big step and needs time, care and attention. For starters, have a drawn-out interview process, that involves one or two days of working along with you, and not just Q&A, so you can see the chemistry.
Then, when you do hire them, hire on a probationary basis, so that you have one, two, or even three months so you can get to know each other before considering it a lock-down commitment.
Finally, give them that time to get up to speed. Realize that you’re going to be giving a fair amount of time to training and communication, and it will at first seem as if you are less efficient and productive after hiring someone. You will be. It’s an important step in building the relationship.
• It’s not “if,” it’s “when.”
As my motorcycle driving instructor told me, “It’s not if you go down, it’s when you go down.” Your assistant is going to make a mistake, and it’ll be a doozy, or at least seem like one. Prepare yourself for it now, so it won’t surprise you.
And, start out by asking this question when they first start with you: “When the big mistake happens, how should we handle it? How do you react when you make a mistake?” By having a conversation about it before the event, it lays the ground for an easier discussion when it does happen, and gives guidelines to fall back on, instead of your emotional reactions.
• Don’t hide your emotions.
You don’t have to appear to be superhuman, “Ha ha ha, I don’t care if the world falls down around me. Just keep being creative! Good work! Carry on!” That’s crazy- it’s natural for you to be upset, as it’s natural for your assistant to be upset as well.
Share your upset with them, but be honest about your emotions, keeping it personal to you. This is harder to do than you think, and if you plan on having employees, I highly recommend learning how to communicate without blame or guilt. Personally I’ve found the book Nonviolent Communication, by Marshall Rosenberg, to be amazing. Reading it, and working with an effective NVC facilitator will pay itself back a thousand-fold as your business grows.
And, if your upset is a big one, get outside help. The first time I ever had an assistant, a few years back, was a perfect time for emotional and spiritual healing. I was able to find relief and compassion for those parts of myself that want to blame, punish and attack myself and others when mistakes happen, and to break the reactive patterns.
Hiring an assistant is a necessary act for any business that wishes to attain success, because you can’t do everything yourself. But, the only way to get the most out of this frightening step is to hire someone who cares, and then allow them to make creative mistakes even if they cost you. You may have to endure some bumps, but I promise you won’t end up running a kindergarten.





