A perspective that I have built into how I teach project management has always been to know what “done” looks like, and to know what “done well” looks like. That’s easy when you are managing something straightforward or familiar. Where there are clearly defined results, and a clear process to follow, we can usually do a pretty good job—with perhaps a little imagination—of figuring out what we are working towards. Not only does this give us a target, it offers guidance on how to proceed and clarity about where the finish line is.
Where it gets complex and messy is where it’s, well, complex and messy. Once we get past the straightforward, and start exploring the outer edges of complicated, getting a clear picture of done and done well becomes a good deal more difficult to establish. It can feel like there are too many options,, and that the path of how to proceed is too uncertain and ill-defined. Knowing what the solution looks like—or even might become—just feels far too vague.
What we are confronting here is the very real tension between knowing what done looks like and what is even possible. Once you have moved past the boundaries of familiar and understood, there are open questions about what you can do, not to mention uncertainties about how you might get there. While this is especially true for genuinely creative endeavours where we are pushing the bounds of tools and craft, it’s also true for work that is simply not familiar to us. Others may have been here before, but for us it is terra incognita. It’s a whole new area of exploration, and we’ve never been here before.
We can find ourselves in these situations because the nature of the work demanded it, or because we deliberately put ourselves there. When I was preparing for the pilot of Strategy Making in the fall, I already had a lot on my plate. I was designing and building a program, putting the technology platform together to support it, and dealing with the marketing and promotion of making it visible. To add to that—because clearly that wasn’t enough to be getting on with—I chose to build all of my presentation materials in Apple Keynote, a software package that I had never used before.
Why I would do this is its own essential question. I had been building presentations in Microsoft PowerPoint for years. I knew it backwards and forwards, I understood how to get the results I wanted, and it didn’t require a great deal of thought on my part in order to use it. At the same time, there were well-worn grooves in how PowerPoint operated for me, ones that the wheels of progress got stuck in most of the time. Those grooves run deep, and tend to lead to a predictable result. Start the program up, and you are already thinking in a default pattern of title and bullet points.
I wanted to break out of that paradigm of predictability. I also liked a lot of the design and creativity I had seen from people that use Keynote. My decision to shift gears—and software—was an intentional choice to shake things up in order to get a different visual result. I wanted the materials for the program to stand out, and this was one way of getting there.
What that journey meant was putting several things in play all at the same time. I was learning how to use the software. To expand on that point, I was learning what the software could do, how the features worked and the essential functions required to get them to produce a result that was in some shape and form close to my desired results. I was also figuring out a new visual way of structuring and presenting the information I was delivering. Underlying all of this was actually building the program, and figuring out how to work through the materials to get to the outcomes that I wanted.
It should go without saying that just because I like the work of designers who happen to use Keynote does not mean that I’m necessarily going to produce work of the same quality, just because I happen to be using the same tool. The instrument isn’t the biggest determining factor here; it’s the skill and imagination of the person behind the tool.
That opens up a different dimension of understanding in exploring what is possible. It’s not just tension between what is done and what can be done. There are several frontiers that define and shape the bounds of possibility. To keep this simple, I’m going to define just three of them, although there are inevitably more. Defining outcomes in these circumstances is shaped by what is possible with the solution, what is attainable with the tools being used, and what potential exists based upon the skills and abilities of the person doing the work.
Defining done and done well then becomes a question of what you are trying to do, how you are trying to get the work done and the skill that you bring to the table in accomplishing it. Changing what is possible now starts to have a number of moving parts. Shifting our ambitions can reframe what a satisfactory result looks like. Employing different tools might open up different technical options, different creative choices or different potential quality of the results. Improving skills can also make a difference, regardless of the tools we are actually using.
What this discussion leads to is a different, altogether more complicated and problematic tension: the desire to get to done, against the willingness to explore and experiment. One of the reasons that defining “done” and “done well” works in managing simple projects is that it helps to highlight the fastest, most direct route to the finish line. Know what you want, be clear about how polished or rough a finished product you need to be successful, and you have a pretty good understanding of the work to be done. The rest is simply execution.
Once you venture into the realm of the more complex and complicated, there are many more variables in play. You aren’t just wrestling with what a good solution looks like. Sometimes you are struggling with clarity of the underlying problem. You are also challenged to figure out the dimensions of the solution that are relevant, the paths that might best lead to producing them, the tools that you might need to employ and the skills that you need to be able to obtain a result. There are a lot of moving parts that are interconnected, but not necessarily in ways that are obvious.
Figuring all of this out can be fun and enjoyable work. It can also be frustrating and maddening. Your experience is going to be determined in part by the mindset with which you approach the task. It will also be shaped by how urgent getting to a solution is, how many roadblocks you encounter along the way and your general tolerance for ambiguity, experimentation and switching gears. You will have good days and bad days. You will experience elation and despair. You will be teased with possible results and then humbled by the realization that what you thought might work doesn’t.. Recognizing that all of this as normal is an important first step in accepting the rest of the journey.
The example of what presentation software I used in building Strategy Making was a relatively simple instance. It is a useful one to illustrate the point, and while there is complexity inherent with the journey, that’s not to say that the experience was pushing the boundaries of what is known and possible in any meaningful way. It pushed what I knew and could accomplish, certainly, but many more before me had wrestled with the same challenges. Their experiences informed my learning. I embarked on the learning with a reasonable certainty that I’d come out the other end reasonably successful in delivering the results I was hoping to attain.
Embarking on the design of Strategy Making as a program was an altogether different problem. Within the broad framing of what I wanted to accomplish, there was a question—and many possible answers—about how to best produce the desired results. There were choices in program structure, delivery, module design, creating experiential opportunities and helping participants to get to meaningful results by the time the program was complete. Defining what topics to address, in what sequence and in how much detail was a considerable struggle. The design process went very quickly from feeling that I had plenty of space to do what I wanted to fundamental questions about how to incorporate everything that I wanted to cover.
It is in wrestling with these kind of challenges that complexity can get exponential quickly, and messiness—of ideas, of notes, of thoughts—can rapidly become overwhelming. It’s not so much about making one choice and moving forward from there. The implications of one decision can cascade into others. Do it one way, and that can have implications here, here and here. Disagree with one of those implications, and you are not only tracing back your steps, but also unwinding other work that might have been quite promising.
The awesome news is that there are options. The challenge is also that there are options. Once you stray out of the relatively safe zone of simple problems with clear solutions, you get into choice and variation pretty quickly. The more complex the situation you are wrestling with, the more that is at play. The landscape becomes filled with possible features, considerations and potential answers. What you now need to do is assess which options are viable and have potential, and also to recognize and set aside those that might seem tempting or interesting or fun, but ultimately don’t serve what you are trying to do.
There is no objective, external guidepost to what is right in these circumstances. There are only internal and subjective ones. Designing the updated version of Strategy Making, for example, I went through a variety of options in terms of how to structure the modules, the time it should take to deliver and what participation and discussion should look like. Several of those options started with considerations and examples from other programs. There were also times when I was trying to be far too clever, force-fitting options to conform to arbitrary structures. There were also choices I was trying to impose for reasons of simplicity or convenience or simply ego.
The right answer needed to be what best served the program, and what helped deliver optimal value for participants. Imposing someone else’s structure or forcing an arbitrary timeline didn’t get to a good or useful answer. Recognizing this, though, required reconnecting back to the principles of what the program was trying to do, and the audience it was intended to serve. It meant figuring out what was true in this instance, and for this particular program, and not simply repeating what had been done elsewhere. It wasn’t about what I wanted, what someone else did, or what other programs looked like. It was about what the program needed.
Remembering this is hard. When you are out on the edge of the problem, looking for answers and not finding them easily, it can be very easy to retreat to familiar territory. Repeating previous successes and recycling previous solutions can feel like a tempting way out. If you genuinely care about the final result, though, you realize the compromise as soon as you make it. The trick is latching on to the underlying truths that inform why this is a lesser solution. The quiet inner voices that call out when you are trading-off and settling for sub-optimal have something important to say. Teasing out those truths, and giving them visibility, is where you start to build a defined picture of what a good solution actually looks like.
It can be easy to go with what is safe, what is familiar, or what has been done before. That’s how we create those well-worn grooves in the first place. Once there, they can be hard to navigate clear of. Stepping out of the objective comfort of simple answers means holding firm on the principles that matter. That means defining them, keeping them close, holding them front-and-centre to the greatest degree possible, and continuing to course-correct back towards them when things start to get out of control.
Know what is true for you and the work you are doing, and keep focusing on that. Be patient in finding solutions that align with your goals, and graceful when you discover roadblocks and dead ends. Persist in caring enough to find the right answer, and you will eventually surface a path. The process might not be perfect, easy or happen on the timeline that you intended, but most problems are solvable with enough persistence, effort, creativity and patience. The test is getting focused on the truths that matter; that is what will ultimately define what “done well” actually looks like.