Leadership and Line-Drawing


They usually sit in little groups — little clumps of humans playing in the sand at the beach. They squat together, armed with mossy, soggy sticks that are doubling as instruments of art. What looks to you like a mangled mess of lines carved into the sand is undoubtedly a masterpiece in their minds, it being the result of at least 37 seconds of effort with the aforementioned sticks. Sometimes, if you look at it from the right angle, you can make out something. Maybe it’s a heart. Or their name. Or what appears to be random scribbles inscribed in the sand. Whatever it is, they’re proud of it. And so they should be.

Drawing a line in the sand may seem like a simplistic art form used mostly by young children at the beach, but in an organizational setting, it’s a fine art.

Drawing that line in the sand happens in different ways, at different times, and definitely with different results every time. Sometimes we draw the line on a small scale, right? We approach a teammate about their negative attitude. Or maybe we decide that what used to be good enough in a report we’re compiling isn’t good enough anymore, so we make it better.

There are other times, however, when drawing that line is a bigger deal. Within the broader scope of an organization, drawing that line can be ridiculously tricky. I think part of what complicates it is that no two organizations are the same. No two react identically to internal and/or external stimuli. Organizations are like squishy, amorphous organisms sometimes, moving and jiggling in ways you don’t expect them to. Kind of like David Hasselhoff’s chest on Baywatch.

Another thing that complicates drawing that line — and please don’t misunderstand what I’m saying — is that humans are involved. We’re all wired a little funny, right? (Please tell me it’s not just me.) We’re all unique. Something may irritate the heck out of me but not bother you at all. Some people are more sensitive than others. Some folks like detailed and structured environments, while others prefer the opposite. It’s a difficult and wonderful dynamic at the same time.

In my line of work, the line is most often being drawn as part of some sort of organizational shift or change, usually in the area of culture or leadership. It can be super challenging trying to figure out when and how to draw that line, or if you should even draw it at all. Sometimes events will unfold that force your hand in some respects; other times you might have the advantage of getting to choose exactly when and how it goes down.

By its very nature, drawing that line is going to tick some people off. I mean, if no one’s getting at least a little perturbed by your line-drawing, perhaps you’re not drawing the line you think you’re drawing. In and of itself, drawing that line is often implying that something that was once the norm, cannot be any more. Well, some of those humans you’re working with may like that thing that was the norm. They may hate that you’re trying to change the norm. In some ways they may even take it personally, since they might have been part of creating the norm you’re changing.

Humans are fascinating and awesome, and they’re especially those things when they get together in groups. They can do amazing things together. They can also do crappy things together. In both scenarios, they often feed off of each other, further propagating the amazing or the crappy.

Either way, they’re humans with emotions and feelings just like you. They’re not emotionless drones (and thank goodness for that), and consequently when you or someone else has to draw a line, you have to know it’s going to affect folks in one way or another.

So the trick becomes navigating that tension. You have to ask yourself tough questions and give honest answers. Is this thing a big enough deal that you need to draw the line? Are you drawing the line out of arrogance, ego, or anger? Or is it out of genuine concern for the well-being of the organization, whether they realize it or not? Does it come from a place of humility and service? Is it tough love? Is it just mean? Is it a power play? Or is it for the betterment of the team? Does it align with your core values, both personally and organizationally? Is the timing right? Is the line really necessary? Does it matter? Does it not matter? Is it the right thing to do? Should you get more advice first? Did you get advice at all? (If your answer to that last question is no, please stop immediately and do that.)

As leaders, we’ve got to be willing to challenge our own assumptions and thinking. We’ve got to press ourselves and our teams to answer those tough questions. If after that, to the best of your knowledge and understanding, you think that line needs to be drawn, then do it.

But know this: When you draw it, you might be wrong. Then again, you might be right. Some people are going to love you for drawing the line. Others are going to hate you. Sometimes folks might talk about you behind your back. Other times it’s going to be really awkward because they’ll do it to your face.

But that’s why it’s so important to know why you’re drawing the line, because if it’s meaningful and important, and it’s ultimately for the good of the organization and team, you have to have the guts to draw the line even though you know it may or may not be well-received.

It may be really difficult, but many of the important things are.

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