A question that often comes up in contract work—or really, in any management work—is when to be critical and when not to be. This issue is covered across many of these chapters, but this one will have a slightly different angle.
Of course, many beginners and inexperienced managers take the attitude that you should never throw stones and only be positive. This falls into the class of advice that you can only get away with if you’re the best of the best of the best of the best. And you’re probably not. Statistically speaking, of course. It’s like when someone with a billion dollars tells you, “it’s not too bad to waste money.” Right, it’s not too bad for you, now for the rest of us…
For the rest of us, there is a time and place to be critical. When is that?
Here’s a rule of thumb I try to follow: start out being positive and giving the other party the extreme benefit of the doubt; and as time goes on, get increasingly strong, until you have to be so strong you’re an outright asshole. In other words, use an increasing slope of assholeness along the way.
This is my particular style as well. Some people are assholes from day one and that seems to work very well for them. Others are never assholes and that seems to always fail, so I’d definitely not advocate that, unless you want to fail for a particular objective. So really, then the question is: be an asshole on day 1, or wait until day 100? And this implies a follow-up question: what’s the slope of the curve of increasing assholeness?
Before addressing that directly, you need to decide one thing, do you want to have the asshole reputation or not? One suggestion I gave in an earlier chapter is to try out different styles and personalities. Maybe this is a new personality you’re testing out? Or maybe you’ve decided that you need to be more of an asshole because you’re just too nice? First, decide how much of an asshole you’re willing to turn yourself into and then adjust accordingly.
But don’t forget the point, whether you’re the asshole on day 1 or on day 100, when dealing with clients, you have to be an asshole sometimes. Sometimes, they just don’t get it, or they don’t do what you need them to do.
What happens when they don’t give you the essential materials you need to do your work (that you’ve asked for 100 times)?
What happens when they don’t approve your work so you can get moving to the next task?
What happens when they insist you do 20 hours of work over the next 12 hours, starting one minute from now?
There will be many, many cases in which clients treat you badly, and let’s assume that their treating you badly is unintentional on their part (if it is intentional, you may want to question your choice of clients.) Sometimes your client is under pressure from his client. Sometimes your client just had a bad day. Sometimes your client himself feels overwhelmed. It’s going to happen. And when it does, you need to push back—or else you will be rolled over. And you’ll get rolled over enough and you’ll hate your work. This is what we want to avoid. This is what you want to avoid!
My preferred strategy is to start soft. First, explain their request back to them as you understood it, so you’re clear that you’re all clear, and so that they can hear how they sound. Then gently explain why it’s not doable.
They will insist and maybe you’ll give in. You’re human, that’s okay. At first. Do what they want at first, if you want—maybe it’s an exception. But over time, pay attention to see if it becomes a pattern. If bad behavior becomes a pattern, then it is your obligation to push back. The way to do that is to use fewer euphemisms and more bluntness every time. And you choose the slope of increase. Imagine a client asking you repeatedly to do urgent work ASAP as you’re about to leave for the day.
The first time, “I know you need this design yesterday. I wish you had told me two days ago. I’ll do it now, don’t worry.”
The second time, a week later, “Hey, I understand the urgency. I happen to be busy starting in 30-minutes, but I can do what I can in the next 30-minutes and then continue it tomorrow morning, okay? I’m happy to do it, and a little planning goes a long way.”
The third time, a week later, “Okay, I’m learning how you work and I’m learning that of your many strengths, planning may not be one of them. I actually can’t do it now; I’ll work on it in the morning.”
The fourth time, a week later, “So, you keep on giving me work just when I’m done for the day. We need a new process. Let’s use Asana to assign work to me and I’m going to check Asana up until 2PM each day, so any work you need me to do, you can assign to me by then. Sound good?”
The fifth time, a week later, “I think something isn’t working in our partnership. I may have crazy expectations, but asking me to do urgent work as I finish my day, every day, is too much. Is this something we can change? If not, we may not be a good fit to work together.”
Notice that I used one of my favorite words in the fifth escalation, “fit.” Working together is often not a question of good or bad, but if you guys are a good fit together. And if you’re not, guess what: you can’t change your partner. So, if they’re not a good fit, you need to break up in order to avoid going crazy.
