Harry 0:00

We don't tend to get celebrated for installing smoke detectors. We tend to get celebrated for jumping through the window and saving the cat.

Narrator 0:12

You're listening to Traction Heroes: digging In to Get Results with Harry Max and Jorge Arango.

Harry 0:22

Jorge, it's great to see you today.

Jorge 0:25

It's always good to see you, Harry. How are things going for you?

Harry 0:30

Things are going well, man. A little busy. I don't like to use that word because people think of it as an excuse, and it sounds terrible coming from a guy who's supposed to have written a book on prioritization. But, yeah, things have been really busy. How about you?

Jorge 0:47

I am pretty busy as well. And, when you said that about prioritization, what came to mind is that.. Was it Eisenhower that had that thing about, planning being essential, but...

Harry 1:02

It is the planning, which is important, the plans themselves don't tend to hold up to reality. I don't remember what the (quote) is.

Jorge 1:09

And there's also the Mike Tyson thing about, everyone has a plan until they get punched in the face. So...

Harry 1:15

Exactly.

Jorge 1:17

You may have priorities all nicely whiteboarded somewhere, but then life happens, right?

Harry 1:22

Yeah, exactly.

Jorge 1:24

Have you brought a reading to share with us today?

Harry 1:29

I have, and it's totally funny and ironic that it's on the topic of planning.

Jorge 1:36

Well, now this won't be the first time that we are completely in sync unknowingly, right?

Harry 1:41

Yeah. I've been listening to this as an audio book and I had to go back and listen to the whole book again because it was so good. And the reading's a little long, but let me, just dig into this because I think you'll really like it. "Planning is a concept with baggage. For many, it calls to mind a passive activity: sitting, thinking, staring into space, abstracting what you're gonna do. In its more institutional form, planning is a bureaucratic exercise in which the planner writes reports, colors maps and charts, programs activities, and fills in boxes on flow charts. "Such plans often look like train schedules, but they're even less interesting. Much planning does fit that bill, and that's a problem, because it's a serious mistake to treat planning as an exercise in abstract, bureaucratic thought and calculation. What sets good planning apart from the rest is something completely different. It's captured by the Latin verb experiri. Experiri means to try, to test, or to prove. It's the origin of two wonderful words in English: experiment and experience. "Think of how people typically learn. We tinker. We try first. We try that. We see what works and what doesn't. We iterate. We learn this is experimentation creating experience, or to use the phrase of theorist, it is experiential learning. We're good at learning by tinkering, which is fortunate because we're terrible at getting things right the first time. Tinkering sometimes requires tenacity, and it always requires a willingness to learn from failure. 'I have not failed 10,000 times,' Thomas Edison said, 'I've successfully found 10,000 ways that will not work.' And that wasn't hyperbole. Merely to figure out how to make a low-cost, long lasting filament for a light bulb, Edison had to churn through hundreds of experiments with different substances before he found that one carbonized bamboo that worked. "Experimentation and planning requires a simulation of the project to come. With that, you can make changes in the simulation and see what happens. Changes that work, changes that will get you to the box on the right are kept. Those that don't are chucked. With many iterations and serious testing, the simulation evolves into a plan that is creative, rigorous, and detailed. Which is to say a reliable plan. The genius of our species, however, is that we can learn not only from our own experience, but that of others. Edison himself started his experiments on light bulb filaments by studying the results of many other scientists and inventors who had tried to create an efficient light bulb before him. And once he had cracked the problem, anyone could skip the experiments, study what he had done, and make a working light bulb. "Still, even if I know Edison's solution to the light bulb problem, my first attempt to make a working light bulb will almost surely be a struggle. It will be slow, and my light bulb will not work well. So I do it again and I get a little better, and I do it again and again. Again, and I get a lot better. That's called a positive learning curve. Things get easier, cheaper, and more effective with each iteration. This, too, is experience and it is invaluable. There's a Latin saying that translates to repetition is the mother of learning. A good plan is one that meticulously applies. Experimentation or experience. A great plan is one that rigorously applies both."

Jorge 5:51

You know what came to mind in hearing you talk about that is a book that our common friend Peter Morville wrote a few years ago called Planning for Everything, which is about this subject. But I don't think that this text is from that book.

Harry 6:08

No, this is an extraordinary book on how big things get done, and in fact, that's its title: How Big Things Get Done: the Surprising Factors That Determine the Fate of Every Project, From Home Renovations to Space Exploration and Everything In-Between by Bent Flyvbjerg and Dan Gardner, and it is excellent.

Jorge 6:34

I heard two things in the text that you read. One was, what I'm going to caricature as the distinction between thinking and doing, which I think is something that, a lot of us internalized very early on. and a little bit of that came across at the beginning of that passage where I got the sense that the author was saying something like we tend to minimize the value of planning because it feels like thinking rather than doing, and we tend to shortchange thinking. And the other thing that I heard there was that good planning is actually putting out what might be called like a first draft that you then iterate on. And what came to mind there was the conversation we had about the book On Grand Strategy and this image from the Lincoln speech about the compass, right? It might be that your plan is to head south and you start walking south, but then eventually you run into a swamp and you can't continue walking south, so you have to turn some other direction while keeping in mind that the overall goal is south, right? Plan for directionality, but adapt to conditions on the ground might be one way to synthesize what I heard there in the second part.

Harry 8:00

The thing about this particular reading is it's really a hook into the book. Gee, that sounded more alliterative than I expected, the hook into the book. So the idea of the book is that there are more predictable ways of achieving success and more predictable ways of generating cost overruns and late schedules and failures. And there are methods for increasing the likelihood that things are gonna go well, and there are ways to ignore those, which predictably, based on the data, generally result in predictable failures for a lack of a better term. And part of what the book shows is that the data points to the absolutely horrific track record of information technology projects. And the author, one of the authors of the book, has established a massive database of project data and how things go well and how they don't, and across three different dimensions. One is were they late or were they on time, or were they early? The other is, did they meet the estimates or forecast? And the other is, did they deliver what people said? And information technology projects, the things that you and I are involved in regularly, are the things that do worse. They do worse than almost anything, which is really astonishing. And I think part of what grabbed me about this book was the very clear direction about how to increase the likelihood that things are gonna go well. And one of the things that they, the authors, didn't actually say in the book, is that hiring experienced people is a really good idea, right? There's this trend in the Silicon Valley ethos and the whole software technology world that hire junior people because they don't know what they don't know, and they'll just work really hard. But in fact, this book makes an out outstanding case for hiring experienced people because they have embodied knowledge about what tends to work well and what doesn't. And one of the other things that the authors point to is this notion of using a technique called reference class forecasting or estimation based on looking at similar types of projects in the past, because those projects, whatever they are, tend to include the things that were initially planned for and the things that were unexpected. So if somebody planned a house renovation, it ultimately ended up costing $500,000 and took two years, which is, in the made up case of $250,000 too much and a year late, that if you look at reference classes, like how do renovations of a particular type of house tend to go? Then your estimates are more likely to paint a picture of what it's actually gonna take. Because the authors say that, and I totally believe this, that... I mean it just hit me like a two by four in the back of the head, we often blame execution when things go wrong, but you can almost always point back to the estimates and forecast because they're simply too optimistic. And so, the failures are not based on the things are taking too long. It's that we estimated that they were gonna happen much faster or for much less money. And so much of that is about this bias for action, which I know we've talked about before, this idea that, we don't tend to get celebrated for installing smoke detectors. We tend to get celebrated for jumping through the window and saving the cat. It's what do heroics actually look like and that the optics of heroic looks like the optics of heroics look like saving the cat, but the actual heroics are involve often stuff that is totally mundane, like making sure you've checked your batteries and your smoke detector.

Jorge 12:12

I'm hearing a couple of things there. One is about the importance of having... I'm gonna use the word qualified people when planning. And by the way, I recalled now the Eisenhower quote that I had in mind. It's, "Plans are useless, planning is indispensable."

Harry 12:33

Totally.

Jorge 12:35

And I'm bringing it back now because what's implicit in that is that the plan is an artifact, it's an outcome, it's a "deliverable," right? What he's saying there is once you have the plan, you should be free to discard it. It's the process of arriving at the plan that is useful, right? Because you gain alignment, you gravitate towards shared goals, right? When you said, going over by $250,000 or what have you, that implies that you have some kind of target state that you're aiming for, right? You have a goal. And, it might be that it's buying a house, but it might also be that your goal is to launch a new product by particular date with particular characteristics or what have you. And, one of the things that is implicit in all of this is that planning is an action, like you say, it's like bias for action, right? It's you gotta realize that the process of planning actually entails getting together with other people and doing things. And what it entails doing is somehow thinking ahead, playing out in your minds your collective minds what it might take to get to that target state that you've hopefully aligned on. The value is in the process. It's not in the outcome. And I think that people conflate those two.

Harry 14:08

And it's also value to the optics. And that's the thing, like the authors make the exact point that you're making right here, and they do it brilliantly. Part of the challenge is the planning doesn't look like the kind of action... it doesn't look like you're putting the shovel in the ground, it looks like a bunch of people sitting around a table with pencils. And that doesn't look like action, even though if they could see inside the minds of the people that are doing that planning, it's a lot of action and a lot of thinking and a lot of preparing for putting the shovel in the right place or deciding whether or not the shovel's even the right tool. And I think something that is not stated in this book, and it's certainly controversial, is I often tell my clients, "look, you can lie to other people. Don't lie to yourself." And I'm not saying this to give them permission to lie to other people. I'm saying that people bend the truth and they conflate things and they obfuscate stuff and they over generalize. That's okay, fine. So you're gonna do that. That's part of the nature of psychology and politics. But don't do it to yourself. Because then you're fooling yourself, which means you're, fooling other people and you don't even know it.

Jorge 15:23

We've certainly talked about that idea before in our conversations, right? This idea of not fooling yourself and trying to get a clear read on the situation. I wanna circle back to something that's implicit in what... you said it explicitly, but I just want to shine a spotlight on it, which is, when going through the planning process if we buy into this idea that planning is acting, right? It's a very active process. But the idea that people think that sitting around talking about things is wasted time, right? So if we can move past that idea and assume that we are not fooling ourselves, one of the things that's implicit in this is that the degree to which the process of planning is valuable is going to be determined by the people who are part of the planning process. And you talked about hiring experienced people. What I heard there is, you don't want people planning things for whom this is the first rodeo they've been in. And there's one of these cheeky laws that we have in tech, Hofstadter's law. You know this thing?

Harry 16:31

I don't remember it.

Jorge 16:32

It says that it always takes longer than you expect, even when you take into account Hofstadter's law.

Harry 16:38

Oh. It's that piece of the planning fallacy.

Jorge 16:40

Yeah. And the thing is that if you don't have a lot of experience doing this, you're going to fall for the fallacy, right? You have to have been burned to internalize that particular lesson. At least that's the sense I have. I'm 30 years into my career and I still find myself double checking my myself when I'm doing a plan, right? It's what can go wrong? I've had so many things go in directions different than the ones that I expected, that at this point I feel like I can do it pretty well. But I remember a time in my career where I was like wildly optimistic and I think I would've been useless in that room.

Harry 17:23

Yeah, it's funny. That's a hundred percent right. And in the reading there was a reference to the box on the right. The idea is that the box on the right represents, with enough definition and enough clarity, the goal. What are you trying to accomplish? And I am a ginormous fan of assumptive goal setting, which is a technique in planning and sort of goal setting that says that for every goal or for every desired outcome, there are a set of assumptions that went into it. And so, assumptive goal setting can take three states. One is often referred to as back casting, one is referred to as a pre-mortem, right? And the third one I've completely forgotten; it'll come to me in a second. But let me just talk about the pre-mortem, right? The pre-mortem I think it's from Gary Klein, from his work. I don't remember which book. And he talks about the idea that if you have an important project and you're clear enough about what success looks like, what you can do is sit around a table and talk about the imaginary future where that project failed. And then you can start identifying and prioritizing what were the causes of that imaginary failure, and then plan for those things, so that you can mitigate the effects of those that would lead to the failure that was ultimately predictable. And so this notion of a pre-mortem, when you think about a post-mortem or a retrospective, if you will, so a project happens and then you look at it after the fact, a pre-mortem says, look at it before the fact and do it intentionally and paint the picture of what would likely cause it to fail. Well, an analogous assumptive goal setting technique some people refer to as back-casting, I refer to it as back-planning for a very specific reason. What I like to do is paint, in any sufficiently complex project, I've been doing this for years and years, in fact I remember the first time I actually ever went through it for the design and development of Virtual Vineyards, which became wine.com. The idea is get really clear about what success looks like, not in some kind of pan-galactic strategic way where you've written down three documents and you have a video and a bunch of pictures and a vision board in this. And now I'm not talking about that. I'm talking about like at least a paragraph of clarity about what success looks like, right? And then you ask yourself the question, what would have to have been true to have achieved that. Okay. That's an interesting question, because you're not saying what needs to be true. You're not saying, what do I need to do, or what activity do I need to engage in? You're asking yourself the question, what would have to have been true to have achieved this end state that you've said was so important. What's really cool about that question is you can ask it again and again and again. So if you start at a point in the imaginary future of this thing you want to achieve and you ask yourself the question, what would've had to have been true such that outcome, that desired outcome, was realized? You can then ask the question for that thing that would've had to have been true, what would have to have been true? And so you can work from this imaginary future back to the present. So it's this recursive process of working from the future to the present, and that tells you what would have to have been true right now today in order for you to achieve this future state that you claim is so important. And so this assumptive goal setting technique rests on this very simple question, what would have to have been true? It's a total unlock for a complex project and it works profoundly well with teams. I've done this for company funding events. I've done this for infrastructure projects. I've done this for websites. And once you have a map from the future to the present, you can now look at, okay, in order for this to be true, what activities would we need to engage in? What decisions would we have to make and what investments would we have to commit to in order to start building from the present back to that future? It's profound.

Jorge 22:07

That sounds really useful and practical. I'm going to play devil's advocate here and bring up the time objection, right? What you're doing sounds time-consuming, how much time should people invest in this kind of work and how often should it happen? I.

Harry 22:26

Uhhuh. Yeah. I always love that. My father, who was brilliant, used to say to me, "If you have time to do it wrong, you have time to do it right." What did he say? He used to say, "If you have time to do it twice, you have time to do it right once." So my rule of thumb there is at least spend an hour on it. It's a function of the cost of the project and not just dollars and cents, but the amount of time and energy. It's a function of the opportunity cost of getting it wrong. Like, how much time would you have spent planning and can you allocate a percentage of that to some assumptive goal setting technique, which doesn't take that much time and it is a major efficiency play. Because rather than working from a point in the present to a large number of possible futures, what you're really doing is saying, there's only one future and now I need to work toward that future. So you're saving time in terms of your forward planning by investing in backward planning. And I think in many cases it's a net zero. And in terms of how much time you spend doing it and how often you do it, how important are your projects? How important is it that they're right? How important that they land on time or that they're within budget?

Jorge 23:52

Yeah, there's all these aphorisms and folk wisdom about this stuff, right? Like measure twice, cut once. And there's the Abe Lincoln quote about, what is it? give

Harry 24:05

If I had five minutes to cut a tree to chop down a tree, I'd spend three minutes sharpening the ax.

Jorge 24:09

That's right. Yeah. So it's the idea that the acting part of it, like it's going to go maybe not much faster, but it's going to be much more effective if you're actually working in the right direction. And what this process is about is directionality. It's let's get us pointed in the right direction, so that then we can pour all of this active energy more wisely, maybe is one way to put it.

Harry 24:36

And it turns out it's just a hidden efficiency play. Because rather than being late or being more expensive or getting it wrong and having to do it again and make excuses and justifying it, the whole thing just ends up being more smooth.

Jorge 24:51

That feels like a really good place to wrap this. I'll just say, I think maybe you and I should set aside some time to do some planning for the podcast. I'm inspired.

Harry 25:01

Me too. Let me see if I can make time in my busy schedule.

Jorge 25:05

All right, Harry, thank you. Once again, I've learned something in our conversations.

Harry 25:11

Fabulous. Thanks Jorge.

Narrator 25:20

Thank you for listening to Traction Heroes with Harry Max and Jorge Arango. Check out the show notes at tractionheroes.com and if you enjoyed the show, please leave us a rating in Apple's podcasts app. Thanks.