Finding A Way In

There comes a time in any project where you have to get started. The challenge, very often, is exactly that. Where do you get started? How do you find a way in? How do you get traction and move forward?

It is something that you would think—with experience—gets easier to do, to know and to tackle. It doesn’t. We’ve all experienced the taunting flash of the cursor at the top of a very blank, very white, very empty screen. Waiting for us to write something. Daring us to start. Mocking us for our inability to do so. Or that might just be me.

What all too often is the source of this conflict is not that there isn’t a way in, it’s that there are too many ways. Especially when what we are starting has a level of ambition or complexity or uncertainty about it. Our minds wrestle with the fact that progress needs to happen on a number of fronts. All of those different areas have questions that need answering, work that needs doing and details that need following through on.  There are interconnections and implications between them. The result is a rats nest of string, with no clear end to grab on to and pull.

I’ve had some familiarity with this state over the last few months. In particular, I’ve been grappling with the launch of Strategy Making, my personal strategy development workshop. This should theoretically be an easy job, in that I delivered an incredibly successful pilot of the workshop at the end of last year. Take what you did, do it over again, and keep going. How hard can it be?

If only it were that easy. The pilot experience went far beyond what I had hoped. It connected with participants at a level that I’ve seen (occasionally) with in-person experiences, but would not have expected to be possible online, mediated through the internet. Some magical combination of participation, content, engagement and circumstances played together in a way that created an amazing and transformative experience for many. It was wonderful to experience, and I can’t wait to do it again.

For me, the pilot was about proving out the content and making sure it hung together and made sense. I wanted to know how well the material came across, and if I was presenting it in a way that worked. I already had an idea of how the program would come together and be delivered afterwards, but the pilot was a way of testing what worked and what needed changing before the work of building out the program.

All of this should mean that I finished the year with all of the ingredients for success baked in. Successful pilot, relatively solid content, plan for development and now just the work of getting it launched. This was wishful thinking.

What became clearly evident during the pilot is that what I had hoped was going to be a delivery approach was going to need some adjusting. Part of what made the experience successful was the interaction, between me as facilitator and with the other participants. There was depth of discussion, exploration of ideas, lightbulbs aplenty and also accountability to keep committed to the program and each other. Self-paced access to the same content online—while possibly appealing to some—was not going to replicate the same experience.

The result has been two months of pondering the optimal program structure, delivery approach, length, cost, facilitation approach, level of interaction and pace. For all that the pilot workshop was successful, there were content gaps that I would like to fill. While the duration of the program was appealing in getting people to sign up, it felt too short and participants felt overwhelmed in doing all the work in the time available. The exploratory discussions as part of the workshop were really valuable, but people also wanted some more clarity around structure. What should have been an iterative update was starting to feel like wholesale reinvention.

It’s this kind of complexity that makes finding a way in challenging. There isn’t a clear order of actions or hierarchy of decisions that gets you to an easy point of resolution. Everything is disordered. It is—to put not too fine a point on it—an utter mess to figure out. Because everything is intertwined and interconnected, pulling on one thing just points out that you are also tugging on two or three or four other loose ends.

The good news is that there are strategies to work through in terms of managing this. There are ways to sort through the complicated and get to some clarity. . It’s important in advance to declare that patience is required. Sorting out messy isn’t the same as solving for simple. There is no single answer that has been eluding us up until now that we just need to leap upon unawares and wrestle to the ground. This is going to still feel difficult at times, it will certainly be frustrating and there will be some backpedaling and retracing of steps inevitably involved before you get out of the maze on the other side. But there is a way through.

The first and most constructive piece of advice—even if it might not seem like it on its face—is to just start. Move forward. Write something. Make a choice. Pick up one piece of the thread, and see how far you get. This might not be very far at all. Your first tangled knot might emerge in minutes. Seconds, even. That’s fine. You’ve learned something. You’ve made an attempt that has revealed part of the problem and if nothing else, you know one thing that doesn’t work. 

What you’ve learned may not feel like learning. It may feel like just another obstacle. In reality, both of those statements are possibly true. Sorting out what the obstacles are, and how they are connected, is part of the exercise of problem solving. Starting means that we’re at least engaging with the problem, rather than leaving it as a festering, tangled mess in the corner. The fact that you’ve discovered another obstacle is meaningful, because it’s another point of connection, and another variable that will need to get taken into consideration as we figure out a solution. Not discovering the obstacle would just mean risking that it trips us up that much later in time. It’s much better to discover it now, and have to factor it in, even if it does just make things feel more complicated.

In starting, pick one thing and try to define it as best you can. Give it some sort of structure that makes sense for the moment, and then take the time to map out what is possible. As an example, working through the results of the Strategy Making pilot, I had feedback from a variety of sources. There were comments that came in along the way about the content, the delivery and the exercises. Participants were also asked to provide more feedback at the end of the program, and many did. I had my own notes that extended from original development through delivery and then to reflections after the pilot was done.

Processing this was its own challenge. It came in at different times, and was offered from different perspectives. We should also not pretend that all of the comments that were received were in agreement. While the program overall was great, some aspects that resonated strongly with some participants didn’t land in quite the same way with others. While some people responded well to unstructured exploration and realization, others would have liked the pathway to be a little clearer and more well defined at times. That’s all fair and reasonable. It just needs to get managed.

To make sense of it, I started with three columns on a page. The columns were labelled “successes,” “improvement opportunities,” and “things to consider.” I went through every note, email, evaluation and comment I had access to, and built up lists, separated by whether the source of the feedback was me or one of the participants. What had been an amorphous cloud of ideas and observations accumulated over three months became, in the space of an hour or so, a useful summary of the various perspectives on the experience.

That isn’t to say that everything was solved. But I had information on one perspective about the pilots, and that had its own value. Going through that exercise provided clarity in one context, although it raised questions in others. This leads to the next part of working through the problem: Take the time to ask yourself what the open questions are. As you get started with obstacles, figure out the questions that need to get answered to get past the obstacle. Write them down, preferably in one place. Maintaining a list of the questions that need answering is a helpful way of making the complexity somewhat easier and your eventual progress to answer questions visible.

At this point, it’s probably helpful to acknowledge what should be obvious, but is nonetheless an uncomfortable truth: We aren’t going to get this perfect at the outset. For anyone harbouring more than a hint of perfectionist tendencies, that’s going to be a difficult task. Whether because of pride of accomplishment or not wanting to waste unnecessary effort, you might bristle at this. I certainly know I can. I like getting things done, and I want them to be the best they can be. I also want to know what done well looks like at the outset, and build to that. This is where feedback or requests for changes after the fact get frustrating: if the expectations were clear at the beginning, the belief is that they could have been addressed at the outset.

For work that extends past simple and straightforward, getting to this level of precision is unlikely. The reality is that rework, revision and repeating of steps are inevitable. This isn’t a failing, though. It’s a mark of progress. It means we’ve learned something—even if what we’ve learned is that one pathway isn’t viable—and we’re able to course correct. Accepting this as learning rather than failure is an important realization. Solutions to complex situations won’t be perfect at the outset, they will have rough edges, and there are times where everything will feel on the verge of falling apart. That experience is normal. The challenge is being okay with it, and continuing to work through to the other side.

Most importantly, experimentation is a significant part of getting to solution. Take the time to play “what if.” Recognizing that there you have many dependencies and interconnected options of how you might proceed, take the time to paint out a few different scenarios. Make one choice, and explore the options and consequences of how that choice unfolds for the other variables in play. Consider the pros and cons, how promising an option it seems, and what the compromises still are. Then do the same again for another option. And another.

Playing out different scenarios is a good way of making the connection points and the interconnections visible, and gaining some knowledge of how they interact. That doesn’t mean that what will emerge is one good, exact solution. There may be better solutions. There will be worse options. There are going to be trade-offs and compromises. What you are trying to navigate towards is the best option available given the circumstances, with the greatest possibility for success.

What comes out of this exercise might not be perfect. It certainly won’t be perfect for everyone. Not only is that okay, it is expected. Finding a way in is about finding a solution that works for you, as best as you can, in working towards the outcomes that you value.

The good news is that you’ve found a solution that works. You’ve discovered a way in, and made it out the other side. Others might follow a different path. That’s their choice, for their circumstances. There will be no one right way that works for everyone. But if you can find the way that works for you, then you are that much further ahead.