Rules define how we approach virtually all aspects of life, not least of which is how we function in our organizations. There are the written rules, and the unwritten ones. Both shape our behaviour, and they interact with one another in fascinating and sometimes unpredictable ways. The larger question is how we interact with the rules around us—and whether or not it is safe, appropriate or advisable to do so. That depends a lot on the organization around us, how it functions and how we perceive our role within it.

We often think we know what we mean when we use the term “strategic.” It’s self evident, right? Except, in my experience, it is very often not. Strategic is often viewed as a vague concept outlining general ideas that don’t really provide much guidance, direction or usefulness. Which is exactly what we don’t need more of. My take on what strategic looks like, and the meaning that you should be seeking.

I more often share how I think, rather than how I work. This week, I shift that around a bit. I’ve been facilitating for decades, and learning and adjusting what that looks like constantly. What I’m finally (mostly) comfortable with is what’s in my kit. These are the essentials that I won’t go into a meeting room without. To some, it may be overkill, but it’s how I go in prepared.

Planning is supposed to be virtuous. Good for us. And yet, plans usually change. To-dos don’t get done. Life gets in the way. And our planning systems don’t keep up. So just what’s the point?

The most common answer to questions that I provide is, “It depends.” Not because I’m being difficult; because it’s the truth. Yet I find I dislike this answer as much as the next person. Nonetheless, it is what opens the doorway to opportunity and possibility.

Actually, the journey continues here. We don’t get a lot of do-overs in life. Life continues. We move forward. We build on what comes before. With luck, we learn from it. It’s part of us. Not only can’t we undo the past, it is pointless to try. What matters is what happens next.

How much guidance do we need for a model to actually be useful? The very value of models is that they are abstractions. They provide ways of taking complex situations and simplifying them through structure, categories and labels. They make the infinite shades of grey a little bit more black and white.