Strategic engagement is hard at the best of times. When we have to do it remotely while working through a pandemic, it gets that much more complicated. We often think of online meeting solutions as a poor substitute for communicating in person. Used conventionally, they arguably are. So how can we rethink how we engage in strategic conversations online in a way that makes them work exceptionally well? Some initial thoughts.

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.

It’s the unwritten rules that arguably most influence the culture of organizations. And organizational culture spills over into customer experiences. What is not necessarily clear is where the unwritten rules come from. In many—if not most—instances, they are a reaction to the written rules. Sometimes the influence is constructive. When the written rules are bureaucratic, unthinking or unfeeling, the unwritten rules and resulting behaviours can also be subversive. And sometimes they’re just destructive.

Cultural understanding is critical. Figuring out how we understand culture is a little bit more challenging. Models and frameworks help to understand the broad brush-strokes of culture. But if we want to understand the critical nuances, then we need to know the rules of how things get done. And that’s where things get complicated.

Culture shapes how things get done in organizations. It also defines what gets believed, and what we accept as truths. We create a shorthand for what’s acceptable, and we broadly understand where the lines are that we should not cross. That’s all well and good, until we actually need to challenge the truths, and consider crossing the lines. When we need to stand up and stand out, things get interesting.

It depends. It always depends. Figuring out how to approach situations, address challenges or secure decisions is some of the most difficult work that we do. We might know the outcome we want, but the challenge is successfully navigating the culture of the organization to secure the support that we need. Culture matters. Success in navigating culture means understanding how it works and figuring out how to respond. That’s easy to say, but harder to do.

Simple models can provide powerful insights. So what does a simple model look like, and how do you develop one? And in particular, how do you ensure that it focusses on the things that matter most? Making choices in design—what to include, and what to leave out—are fundamental. A thought exercise in reinventing the project plan.

There are times that I marvel at the value that a simple model provides. And yet we often go out of our way to make things difficult, to be as detailed and comprehensive as we can. Rather than looking for what is essential, we ask for everything. Yet simple models can have surprising depth behind them. And they can be extraordinarily powerful in helping to make sense of complex situations.

Agile approaches are enjoying a very bright place in the sun. And that is to some extent deserved; they represent a very different way of working, especially when we are dealing with ill-defined problems and a need for experimentation and search. At the same time, we often define agile as needing to be different than what came before. The implication being that predecessor capabilities are inadequate, inappropriate and best relegated to the dustbin of history. The reality is very different.

I’ve long argued that organizational practices need to be adapted to an organization if they are going to be effective. They need to fit the culture, and make sense in the way that the organization works. But what happens when you do all the right things, push all the right buttons, and the practices don’t get used? A curious case study.