May 18, 2025 • 25 mins
It's important to plan ahead when working on large, complex projects. Alas, some people's bias for action keeps them from undertaking what they perceive as wasteful exercise. In this episode, Harry shares an exercise that can help.
Show notes:
- Planning for Everything by Peter Morville
- How Big Things Get Done by Bent Flyvbjerg and Dan Gardner
- On Grand Strategy by John Lewis Gaddis
- Hofstadter's law
- Performing a Project Premortem by Gary Klein
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Harry (00:00):
We don't tend to get celebrated for installing smoke
(00:03):
detectors.
We tend to get celebrated forjumping through the window and
saving the cat.
Narrator (00:12):
You're listening to Traction Heroes
Get Results with Harry Max andJorge Arango.
Harry (00:22):
Jorge, it's great to see you today.
Jorge (00:25):
It's always good to see you, Harry.
How are things going for you?
Harry (00:30):
Things are going well, man.
A little busy.
I don't like to use that wordbecause people think of it as an
excuse, and it sounds terriblecoming from a guy who's supposed
to have written a book onprioritization.
But, yeah, things have beenreally busy.
How about you?
Jorge (00:47):
I am pretty busy as well.
And, when you said that aboutprioritization, what came to
mind is that..
Was it Eisenhower that had thatthing about, planning being
essential, but...
Harry (01:02):
It is the planning, which is important, the plans
themselves don't tend to hold upto reality.
I don't remember what the(quote)is.
Jorge (01:09):
And there's also the Mike Tyson thing about, everyone has
a plan until they get punched inthe face.
So...
Harry (01:15):
Exactly.
Jorge (01:17):
You may have priorities all nicely whiteboarded
somewhere, but then lifehappens, right?
Harry (01:22):
Yeah, exactly.
Jorge (01:24):
Have you brought a reading to share with us today?
Harry (01:29):
I have, and it's totally funny and ironic that it's on
the topic of planning.
Jorge (01:36):
Well, now this won't be the first time that we are
completely in sync unknowingly,right?
Harry (01:41):
Yeah.
I've been listening to this asan audio book and I had to go
back and listen to the wholebook 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 reallylike it.
"Planning is a concept withbaggage.
(02:04):
For many, it calls to mind apassive 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 plannerwrites reports, colors maps and
charts, programs activities, andfills in boxes on flow charts.
(02:26):
"Such plans often look liketrain schedules, but they're
even less interesting.
Much planning does fit thatbill, and that's a problem,
because it's a serious mistaketo treat planning as an exercise
in abstract, bureaucraticthought and calculation.
What sets good planning apartfrom the rest is something
completely different.
It's captured by the Latin verbexperiri.
(02:50):
Experiri means to try, to test,or to prove.
It's the origin of two wonderfulwords in English: experiment and
experience.
"Think of how people typicallylearn.
We tinker.
We try first.
We try that.
(03:10):
We see what works and whatdoesn't.
We iterate.
We learn this is experimentationcreating experience, or to use
the phrase of theorist, it isexperiential learning.
We're good at learning bytinkering, which is fortunate
because we're terrible atgetting things right the first
(03:30):
time.
Tinkering sometimes requirestenacity, and it always requires
a willingness to learn fromfailure.
'I have not failed 10,000times,' Thomas Edison said,'I've
successfully found 10,000 waysthat will not work.' And that
wasn't hyperbole.
Merely to figure out how to makea low-cost, long lasting
(03:51):
filament for a light bulb,Edison had to churn through
hundreds of experiments withdifferent substances before he
found that one carbonized bamboothat worked.
"Experimentation and planningrequires a simulation of the
project to come.
With that, you can make changesin the simulation and see what
(04:13):
happens.
Changes that work, changes thatwill get you to the box on the
right are kept.
Those that don't are chucked.
With many iterations and serioustesting, the simulation evolves
into a plan that is creative,rigorous, and detailed.
Which is to say a reliable plan.
(04:33):
The genius of our species,however, is that we can learn
not only from our ownexperience, but that of others.
Edison himself started hisexperiments on light bulb
filaments by studying theresults of many other scientists
and inventors who had tried tocreate an efficient light bulb
before him.
And once he had cracked theproblem, anyone could skip the
(04:55):
experiments, study what he haddone, and make a working light
bulb.
"Still, even if I know Edison'ssolution to the light bulb
problem, my first attempt tomake a working light bulb will
almost surely be a struggle.
It will be slow, and my lightbulb will not work well.
So I do it again and I get alittle better, and I do it again
(05:17):
and again.
Again, and I get a lot better.
That's called a positivelearning curve.
Things get easier, cheaper, andmore effective with each
iteration.
This, too, is experience and itis invaluable.
There's a Latin saying thattranslates to repetition is the
mother of learning.
(05:39):
A good plan is one thatmeticulously applies.
Experimentation or experience.
A great plan is one thatrigorously applies both."
Jorge (05:51):
You know what came to mind in hearing you talk about
that is a book that our commonfriend Peter Morville wrote a
few years ago called Planningfor Everything, which is about
this subject.
But I don't think that this textis from that book.
Harry (06:08):
No, this is an extraordinary book on how big
things get done, and in fact,that's its title: How Big Things
Get Done (06:19):
the Surprising Factors That Determine the Fate of Every
Project, From Home Renovationsto Space Exploration and
Everything In-Between by BentFlyvbjerg and Dan Gardner, and
it is excellent.
Jorge (06:34):
I heard two things in the text that you read.
One was, what I'm going tocaricature as the distinction
between thinking and doing,which I think is something that,
a lot of us internalized veryearly on.
and a little bit of that cameacross at the beginning of that
(06:56):
passage where I got the sensethat the author was saying
something like we tend tominimize the value of planning
because it feels like thinkingrather than doing, and we tend
to shortchange thinking.
And the other thing that I heardthere was that good planning is
(07:18):
actually putting out what mightbe called like a first draft
that you then iterate on.
And what came to mind there wasthe conversation we had about
the book On Grand Strategy andthis image from the Lincoln
speech about the compass, right?
It might be that your plan is tohead south and you start walking
(07:39):
south, but then eventually yourun into a swamp and you can't
continue walking south, so youhave to turn some other
direction while keeping in mindthat the overall goal is south,
right?
Plan for directionality, butadapt to conditions on the
ground might be one way tosynthesize what I heard there in
the second part.
Harry (08:00):
The thing about this particular reading is it's
really a hook into the book.
Gee, that sounded morealliterative than I expected,
the hook into the book.
So the idea of the book is thatthere are more predictable ways
of achieving success and morepredictable ways of generating
(08:22):
cost overruns and late schedulesand failures.
And there are methods forincreasing the likelihood that
things are gonna go well, andthere are ways to ignore those,
which predictably, based on thedata, generally result in
predictable failures for a lackof a better term.
And part of what the book showsis that the data points to the
(08:44):
absolutely horrific track recordof information technology
projects.
And the author, one of theauthors of the book, has
established a massive databaseof project data and how things
go well and how they don't, andacross three different
(09:04):
dimensions.
One is were they late or werethey on time, or were they
early?
The other is, did they meet theestimates or forecast?
And the other is, did theydeliver what people said?
And information technologyprojects, the things that you
and I are involved in regularly,are the things that do worse.
They do worse than almostanything, which is really
(09:25):
astonishing.
And I think part of what grabbedme about this book was the very
clear direction about how toincrease 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 hiringexperienced people is a really
(09:47):
good idea, right?
There's this trend in theSilicon Valley ethos and the
whole software technology worldthat hire junior people because
they don't know what they don'tknow, and they'll just work
really hard.
But in fact, this book makes anout outstanding case for hiring
(10:08):
experienced people because theyhave embodied knowledge about
what tends to work well and whatdoesn't.
And one of the other things thatthe authors point to is this
notion of using a techniquecalled reference class
forecasting or estimation basedon looking at similar types of
projects in the past, becausethose projects, whatever they
(10:32):
are, tend to include the thingsthat were initially planned for
and the things that wereunexpected.
So if somebody planned a houserenovation, it ultimately ended
up costing$500,000 and took twoyears, which is, in the made up
case of$250,000 too much and ayear late, that if you look at
(10:54):
reference classes, like how dorenovations of a particular type
of house tend to go?
Then your estimates are morelikely 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 twoby four in the back of the head,
(11:18):
we often blame execution whenthings go wrong, but you can
almost always point back to theestimates and forecast because
they're simply too optimistic.
And so, the failures are notbased on the things are taking
too long.
It's that we estimated that theywere gonna happen much faster or
for much less money.
And so much of that is aboutthis bias for action, which I
(11:39):
know we've talked about before,this idea that, we don't tend to
get celebrated for installingsmoke detectors.
We tend to get celebrated forjumping through the window and
saving the cat.
It's what do heroics actuallylook like and that the optics of
heroic looks like the optics ofheroics look like saving the
(12:01):
cat, but the actual heroics areinvolve often stuff that is
totally mundane, like makingsure you've checked your
batteries and your smokedetector.
Jorge (12:12):
I'm hearing a couple of things there.
One is about the importance ofhaving...
I'm gonna use the word qualifiedpeople when planning.
And by the way, I recalled nowthe 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 anartifact, it's an outcome, it's
a"deliverable," right?
What he's saying there is onceyou have the plan, you should be
free to discard it.
It's the process of arriving atthe plan that is useful, right?
(12:55):
Because you gain alignment, yougravitate towards shared goals,
right?
When you said, going over by$250,000 or what have you, that
implies that you have some kindof target state that you're
aiming for, right?
You have a goal.
And, it might be that it'sbuying a house, but it might
(13:16):
also be that your goal is tolaunch a new product by
particular date with particularcharacteristics or what have
you.
And, one of the things that isimplicit in all of this is that
planning is an action, like yousay, it's like bias for action,
(13:37):
right?
It's you gotta realize that theprocess of planning actually
entails getting together withother people and doing things.
And what it entails doing issomehow thinking ahead, playing
out in your minds yourcollective minds what it might
(13:59):
take to get to that target statethat you've hopefully aligned
on.
The value is in the process.
It's not in the outcome.
And I think that people conflatethose two.
Harry (14:08):
And it's also value to the optics.
And that's the thing, like theauthors make the exact point
that you're making right here,and they do it brilliantly.
Part of the challenge is theplanning doesn't look like the
kind of action...
it doesn't look like you'reputting the shovel in the
ground, it looks like a bunch ofpeople sitting around a table
with pencils.
And that doesn't look likeaction, even though if they
(14:30):
could see inside the minds ofthe people that are doing that
planning, it's a lot of actionand a lot of thinking and a lot
of preparing for putting theshovel in the right place or
deciding whether or not theshovel's even the right tool.
And I think something that isnot stated in this book, and
it's certainly controversial, isI often tell my clients,"look,
(14:53):
you can lie to other people.
Don't lie to yourself." And I'mnot saying this to give them
permission to lie to otherpeople.
I'm saying that people bend thetruth and they conflate things
and they obfuscate stuff andthey over generalize.
That's okay, fine.
So you're gonna do that.
That's part of the nature ofpsychology and politics.
(15:13):
But don't do it to yourself.
Because then you're foolingyourself, which means you're,
fooling other people and youdon't even know it.
Jorge (15:23):
We've certainly talked about that idea before in our
conversations, right?
This idea of not foolingyourself and trying to get a
clear read on the situation.
I wanna circle back to somethingthat's implicit in what...
you said it explicitly, but Ijust want to shine a spotlight
on it, which is, when goingthrough the planning process if
(15:47):
we buy into this idea thatplanning is acting, right?
It's a very active process.
But the idea that people thinkthat sitting around talking
about things is wasted time,right?
So if we can move past that ideaand assume that we are not
fooling ourselves, one of thethings that's implicit in this
is that the degree to which theprocess of planning is valuable
(16:08):
is going to be determined by thepeople who are part of the
planning process.
And you talked about hiringexperienced people.
What I heard there is, you don'twant people planning things for
whom this is the first rodeothey've been in.
And there's one of these cheekylaws that we have in tech,
Hofstadter's law.
(16:29):
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 accountHofstadter's law.
Harry (16:38):
Oh.
It's that piece of the planningfallacy.
Jorge (16:40):
Yeah.
And the thing is that if youdon't have a lot of experience
doing this, you're going to fallfor the fallacy, right?
You have to have been burned tointernalize that particular
lesson.
At least that's the sense Ihave.
I'm 30 years into my career andI still find myself double
checking my myself when I'mdoing a plan, right?
(17:03):
It's what can go wrong?
I've had so many things go indirections different than the
ones that I expected, that atthis point I feel like I can do
it pretty well.
But I remember a time in mycareer where I was like wildly
optimistic and I think Iwould'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 areference to the box on the
right.
The idea is that the box on theright represents, with enough
definition and enough clarity,the goal.
What are you trying toaccomplish?
And I am a ginormous fan ofassumptive goal setting, which
(17:47):
is a technique in planning andsort of goal setting that says
that for every goal or for everydesired outcome, there are a set
of assumptions that went intoit.
And so, assumptive goal settingcan take three states.
One is often referred to as backcasting, one is referred to as a
(18:12):
pre-mortem, right?
And the third one I'vecompletely forgotten; it'll come
to me in a second.
But let me just talk about thepre-mortem, right?
The pre-mortem I think it's fromGary Klein, from his work.
I don't remember which book.
And he talks about the idea thatif you have an important project
and you're clear enough aboutwhat success looks like, what
(18:33):
you can do is sit around a tableand talk about the imaginary
future where that projectfailed.
And then you can startidentifying and prioritizing
what were the causes of thatimaginary failure, and then plan
for those things, so that youcan mitigate the effects of
those that would lead to thefailure that was ultimately
(18:56):
predictable.
And so this notion of apre-mortem, when you think about
a post-mortem or aretrospective, if you will, so a
project happens and then youlook at it after the fact, a
pre-mortem says, look at itbefore the fact and do it
intentionally and paint thepicture of what would likely
cause it to fail.
Well, an analogous assumptivegoal setting technique some
(19:19):
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, inany sufficiently complex
project, I've been doing thisfor years and years, in fact I
remember the first time Iactually ever went through it
for the design and developmentof Virtual Vineyards, which
became wine.com.
The idea is get really clearabout what success looks like,
(19:42):
not in some kind of pan-galacticstrategic way where you've
written down three documents andyou have a video and a bunch of
pictures and a vision board inthis.
And now I'm not talking aboutthat.
I'm talking about like at leasta paragraph of clarity about
what success looks like, right?
And then you ask yourself thequestion, what would have to
have been true to have achievedthat.
(20:03):
Okay.
That's an interesting question,because you're not saying what
needs to be true.
You're not saying, what do Ineed to do, or what activity do
I need to engage in?
You're asking yourself thequestion, what would have to
have been true to have achievedthis end state that you've said
was so important.
What's really cool about thatquestion is you can ask it again
(20:28):
and again and again.
So if you start at a point inthe imaginary future of this
thing you want to achieve andyou ask yourself the question,
what would've had to have beentrue such that outcome, that
desired outcome, was realized?
You can then ask the questionfor that thing that would've had
(20:49):
to have been true, what wouldhave to have been true?
And so you can work from thisimaginary future back to the
present.
So it's this recursive processof working from the future to
the present, and that tells youwhat would have to have been
true right now today in orderfor you to achieve this future
(21:13):
state that you claim is soimportant.
And so this assumptive goalsetting technique rests on this
very simple question, what wouldhave to have been true?
It's a total unlock for acomplex project and it works
profoundly well with teams.
I've done this for companyfunding events.
(21:35):
I've done this forinfrastructure projects.
I've done this for websites.
And once you have a map from thefuture to the present, you can
now look at, okay, in order forthis to be true, what activities
would we need to engage in?
What decisions would we have tomake and what investments would
(21:59):
we have to commit to in order tostart 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'sadvocate here and bring up the
time objection, right?
What you're doing soundstime-consuming, how much time
should people invest in thiskind 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 havetime to do it right." What did
he say?
He used to say,"If you have timeto do it twice, you have time to
do it right once." So my rule ofthumb there is at least spend an
(22:47):
hour on it.
It's a function of the cost ofthe project and not just dollars
and cents, but the amount oftime and energy.
It's a function of theopportunity cost of getting it
wrong.
Like, how much time would youhave spent planning and can you
allocate a percentage of that tosome assumptive goal setting
(23:08):
technique, which doesn't takethat much time and it is a major
efficiency play.
Because rather than working froma point in the present to a
large number of possiblefutures, what you're really
doing is saying, there's onlyone future and now I need to
(23:29):
work toward that future.
So you're saving time in termsof your forward planning by
investing in backward planning.
And I think in many cases it's anet zero.
And in terms of how much timeyou spend doing it and how often
you do it, how important areyour projects?
How important is it that they'reright?
How important that they land ontime or that they're within
(23:50):
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 Lincolnquote 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 minutessharpening the ax.
Jorge (24:09):
That's right.
Yeah.
So it's the idea that the actingpart of it, like it's going to
go maybe not much faster, butit's going to be much more
effective if you're actuallyworking in the right direction.
And what this process is aboutis directionality.
It's let's get us pointed in theright direction, so that then we
can pour all of this activeenergy more wisely, maybe is one
(24:35):
way to put it.
Harry (24:36):
And it turns out it's just a hidden efficiency play.
Because rather than being lateor being more expensive or
getting it wrong and having todo it again and make excuses and
justifying it, the whole thingjust 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 youand I should set aside some time
to do some planning for thepodcast.
I'm inspired.
Harry (25:01):
Me too.
Let me see if I can make time inmy busy schedule.
Jorge (25:05):
All right, Harry, thank you.
Once again, I've learnedsomething 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 attractionheroes.com and if you
enjoyed the show, please leaveus a rating in Apple's podcasts
app.
Thanks.
We don't tend to get celebrated for installing smoke
(00:03):
detectors.
We tend to get celebrated forjumping through the window and
saving the cat.
Narrator (00:12):
You're listening to Traction Heroes
Get Results with Harry Max andJorge Arango.
Harry (00:22):
Jorge, it's great to see you today.
Jorge (00:25):
It's always good to see you, Harry.
How are things going for you?
Harry (00:30):
Things are going well, man.
A little busy.
I don't like to use that wordbecause people think of it as an
excuse, and it sounds terriblecoming from a guy who's supposed
to have written a book onprioritization.
But, yeah, things have beenreally busy.
How about you?
Jorge (00:47):
I am pretty busy as well.
And, when you said that aboutprioritization, what came to
mind is that..
Was it Eisenhower that had thatthing about, planning being
essential, but...
Harry (01:02):
It is the planning, which is important, the plans
themselves don't tend to hold upto reality.
I don't remember what the(quote)is.
Jorge (01:09):
And there's also the Mike Tyson thing about, everyone has
a plan until they get punched inthe face.
So...
Harry (01:15):
Exactly.
Jorge (01:17):
You may have priorities all nicely whiteboarded
somewhere, but then lifehappens, right?
Harry (01:22):
Yeah, exactly.
Jorge (01:24):
Have you brought a reading to share with us today?
Harry (01:29):
I have, and it's totally funny and ironic that it's on
the topic of planning.
Jorge (01:36):
Well, now this won't be the first time that we are
completely in sync unknowingly,right?
Harry (01:41):
Yeah.
I've been listening to this asan audio book and I had to go
back and listen to the wholebook 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 reallylike it.
"Planning is a concept withbaggage.
(02:04):
For many, it calls to mind apassive 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 plannerwrites reports, colors maps and
charts, programs activities, andfills in boxes on flow charts.
(02:26):
"Such plans often look liketrain schedules, but they're
even less interesting.
Much planning does fit thatbill, and that's a problem,
because it's a serious mistaketo treat planning as an exercise
in abstract, bureaucraticthought and calculation.
What sets good planning apartfrom the rest is something
completely different.
It's captured by the Latin verbexperiri.
(02:50):
Experiri means to try, to test,or to prove.
It's the origin of two wonderfulwords in English: experiment and
experience.
"Think of how people typicallylearn.
We tinker.
We try first.
We try that.
(03:10):
We see what works and whatdoesn't.
We iterate.
We learn this is experimentationcreating experience, or to use
the phrase of theorist, it isexperiential learning.
We're good at learning bytinkering, which is fortunate
because we're terrible atgetting things right the first
(03:30):
time.
Tinkering sometimes requirestenacity, and it always requires
a willingness to learn fromfailure.
'I have not failed 10,000times,' Thomas Edison said,'I've
successfully found 10,000 waysthat will not work.' And that
wasn't hyperbole.
Merely to figure out how to makea low-cost, long lasting
(03:51):
filament for a light bulb,Edison had to churn through
hundreds of experiments withdifferent substances before he
found that one carbonized bamboothat worked.
"Experimentation and planningrequires a simulation of the
project to come.
With that, you can make changesin the simulation and see what
(04:13):
happens.
Changes that work, changes thatwill get you to the box on the
right are kept.
Those that don't are chucked.
With many iterations and serioustesting, the simulation evolves
into a plan that is creative,rigorous, and detailed.
Which is to say a reliable plan.
(04:33):
The genius of our species,however, is that we can learn
not only from our ownexperience, but that of others.
Edison himself started hisexperiments on light bulb
filaments by studying theresults of many other scientists
and inventors who had tried tocreate an efficient light bulb
before him.
And once he had cracked theproblem, anyone could skip the
(04:55):
experiments, study what he haddone, and make a working light
bulb.
"Still, even if I know Edison'ssolution to the light bulb
problem, my first attempt tomake a working light bulb will
almost surely be a struggle.
It will be slow, and my lightbulb will not work well.
So I do it again and I get alittle better, and I do it again
(05:17):
and again.
Again, and I get a lot better.
That's called a positivelearning curve.
Things get easier, cheaper, andmore effective with each
iteration.
This, too, is experience and itis invaluable.
There's a Latin saying thattranslates to repetition is the
mother of learning.
(05:39):
A good plan is one thatmeticulously applies.
Experimentation or experience.
A great plan is one thatrigorously applies both."
Jorge (05:51):
You know what came to mind in hearing you talk about
that is a book that our commonfriend Peter Morville wrote a
few years ago called Planningfor Everything, which is about
this subject.
But I don't think that this textis from that book.
Harry (06:08):
No, this is an extraordinary book on how big
things get done, and in fact,that's its title: How Big Things
Get Done (06:19):
the Surprising Factors That Determine the Fate of Every
Project, From Home Renovationsto Space Exploration and
Everything In-Between by BentFlyvbjerg and Dan Gardner, and
it is excellent.
Jorge (06:34):
I heard two things in the text that you read.
One was, what I'm going tocaricature as the distinction
between thinking and doing,which I think is something that,
a lot of us internalized veryearly on.
and a little bit of that cameacross at the beginning of that
(06:56):
passage where I got the sensethat the author was saying
something like we tend tominimize the value of planning
because it feels like thinkingrather than doing, and we tend
to shortchange thinking.
And the other thing that I heardthere was that good planning is
(07:18):
actually putting out what mightbe called like a first draft
that you then iterate on.
And what came to mind there wasthe conversation we had about
the book On Grand Strategy andthis image from the Lincoln
speech about the compass, right?
It might be that your plan is tohead south and you start walking
(07:39):
south, but then eventually yourun into a swamp and you can't
continue walking south, so youhave to turn some other
direction while keeping in mindthat the overall goal is south,
right?
Plan for directionality, butadapt to conditions on the
ground might be one way tosynthesize what I heard there in
the second part.
Harry (08:00):
The thing about this particular reading is it's
really a hook into the book.
Gee, that sounded morealliterative than I expected,
the hook into the book.
So the idea of the book is thatthere are more predictable ways
of achieving success and morepredictable ways of generating
(08:22):
cost overruns and late schedulesand failures.
And there are methods forincreasing the likelihood that
things are gonna go well, andthere are ways to ignore those,
which predictably, based on thedata, generally result in
predictable failures for a lackof a better term.
And part of what the book showsis that the data points to the
(08:44):
absolutely horrific track recordof information technology
projects.
And the author, one of theauthors of the book, has
established a massive databaseof project data and how things
go well and how they don't, andacross three different
(09:04):
dimensions.
One is were they late or werethey on time, or were they
early?
The other is, did they meet theestimates or forecast?
And the other is, did theydeliver what people said?
And information technologyprojects, the things that you
and I are involved in regularly,are the things that do worse.
They do worse than almostanything, which is really
(09:25):
astonishing.
And I think part of what grabbedme about this book was the very
clear direction about how toincrease 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 hiringexperienced people is a really
(09:47):
good idea, right?
There's this trend in theSilicon Valley ethos and the
whole software technology worldthat hire junior people because
they don't know what they don'tknow, and they'll just work
really hard.
But in fact, this book makes anout outstanding case for hiring
(10:08):
experienced people because theyhave embodied knowledge about
what tends to work well and whatdoesn't.
And one of the other things thatthe authors point to is this
notion of using a techniquecalled reference class
forecasting or estimation basedon looking at similar types of
projects in the past, becausethose projects, whatever they
(10:32):
are, tend to include the thingsthat were initially planned for
and the things that wereunexpected.
So if somebody planned a houserenovation, it ultimately ended
up costing$500,000 and took twoyears, which is, in the made up
case of$250,000 too much and ayear late, that if you look at
(10:54):
reference classes, like how dorenovations of a particular type
of house tend to go?
Then your estimates are morelikely 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 twoby four in the back of the head,
(11:18):
we often blame execution whenthings go wrong, but you can
almost always point back to theestimates and forecast because
they're simply too optimistic.
And so, the failures are notbased on the things are taking
too long.
It's that we estimated that theywere gonna happen much faster or
for much less money.
And so much of that is aboutthis bias for action, which I
(11:39):
know we've talked about before,this idea that, we don't tend to
get celebrated for installingsmoke detectors.
We tend to get celebrated forjumping through the window and
saving the cat.
It's what do heroics actuallylook like and that the optics of
heroic looks like the optics ofheroics look like saving the
(12:01):
cat, but the actual heroics areinvolve often stuff that is
totally mundane, like makingsure you've checked your
batteries and your smokedetector.
Jorge (12:12):
I'm hearing a couple of things there.
One is about the importance ofhaving...
I'm gonna use the word qualifiedpeople when planning.
And by the way, I recalled nowthe 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 anartifact, it's an outcome, it's
a"deliverable," right?
What he's saying there is onceyou have the plan, you should be
free to discard it.
It's the process of arriving atthe plan that is useful, right?
(12:55):
Because you gain alignment, yougravitate towards shared goals,
right?
When you said, going over by$250,000 or what have you, that
implies that you have some kindof target state that you're
aiming for, right?
You have a goal.
And, it might be that it'sbuying a house, but it might
(13:16):
also be that your goal is tolaunch a new product by
particular date with particularcharacteristics or what have
you.
And, one of the things that isimplicit in all of this is that
planning is an action, like yousay, it's like bias for action,
(13:37):
right?
It's you gotta realize that theprocess of planning actually
entails getting together withother people and doing things.
And what it entails doing issomehow thinking ahead, playing
out in your minds yourcollective minds what it might
(13:59):
take to get to that target statethat you've hopefully aligned
on.
The value is in the process.
It's not in the outcome.
And I think that people conflatethose two.
Harry (14:08):
And it's also value to the optics.
And that's the thing, like theauthors make the exact point
that you're making right here,and they do it brilliantly.
Part of the challenge is theplanning doesn't look like the
kind of action...
it doesn't look like you'reputting the shovel in the
ground, it looks like a bunch ofpeople sitting around a table
with pencils.
And that doesn't look likeaction, even though if they
(14:30):
could see inside the minds ofthe people that are doing that
planning, it's a lot of actionand a lot of thinking and a lot
of preparing for putting theshovel in the right place or
deciding whether or not theshovel's even the right tool.
And I think something that isnot stated in this book, and
it's certainly controversial, isI often tell my clients,"look,
(14:53):
you can lie to other people.
Don't lie to yourself." And I'mnot saying this to give them
permission to lie to otherpeople.
I'm saying that people bend thetruth and they conflate things
and they obfuscate stuff andthey over generalize.
That's okay, fine.
So you're gonna do that.
That's part of the nature ofpsychology and politics.
(15:13):
But don't do it to yourself.
Because then you're foolingyourself, which means you're,
fooling other people and youdon't even know it.
Jorge (15:23):
We've certainly talked about that idea before in our
conversations, right?
This idea of not foolingyourself and trying to get a
clear read on the situation.
I wanna circle back to somethingthat's implicit in what...
you said it explicitly, but Ijust want to shine a spotlight
on it, which is, when goingthrough the planning process if
(15:47):
we buy into this idea thatplanning is acting, right?
It's a very active process.
But the idea that people thinkthat sitting around talking
about things is wasted time,right?
So if we can move past that ideaand assume that we are not
fooling ourselves, one of thethings that's implicit in this
is that the degree to which theprocess of planning is valuable
(16:08):
is going to be determined by thepeople who are part of the
planning process.
And you talked about hiringexperienced people.
What I heard there is, you don'twant people planning things for
whom this is the first rodeothey've been in.
And there's one of these cheekylaws that we have in tech,
Hofstadter's law.
(16:29):
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 accountHofstadter's law.
Harry (16:38):
Oh.
It's that piece of the planningfallacy.
Jorge (16:40):
Yeah.
And the thing is that if youdon't have a lot of experience
doing this, you're going to fallfor the fallacy, right?
You have to have been burned tointernalize that particular
lesson.
At least that's the sense Ihave.
I'm 30 years into my career andI still find myself double
checking my myself when I'mdoing a plan, right?
(17:03):
It's what can go wrong?
I've had so many things go indirections different than the
ones that I expected, that atthis point I feel like I can do
it pretty well.
But I remember a time in mycareer where I was like wildly
optimistic and I think Iwould'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 areference to the box on the
right.
The idea is that the box on theright represents, with enough
definition and enough clarity,the goal.
What are you trying toaccomplish?
And I am a ginormous fan ofassumptive goal setting, which
(17:47):
is a technique in planning andsort of goal setting that says
that for every goal or for everydesired outcome, there are a set
of assumptions that went intoit.
And so, assumptive goal settingcan take three states.
One is often referred to as backcasting, one is referred to as a
(18:12):
pre-mortem, right?
And the third one I'vecompletely forgotten; it'll come
to me in a second.
But let me just talk about thepre-mortem, right?
The pre-mortem I think it's fromGary Klein, from his work.
I don't remember which book.
And he talks about the idea thatif you have an important project
and you're clear enough aboutwhat success looks like, what
(18:33):
you can do is sit around a tableand talk about the imaginary
future where that projectfailed.
And then you can startidentifying and prioritizing
what were the causes of thatimaginary failure, and then plan
for those things, so that youcan mitigate the effects of
those that would lead to thefailure that was ultimately
(18:56):
predictable.
And so this notion of apre-mortem, when you think about
a post-mortem or aretrospective, if you will, so a
project happens and then youlook at it after the fact, a
pre-mortem says, look at itbefore the fact and do it
intentionally and paint thepicture of what would likely
cause it to fail.
Well, an analogous assumptivegoal setting technique some
(19:19):
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, inany sufficiently complex
project, I've been doing thisfor years and years, in fact I
remember the first time Iactually ever went through it
for the design and developmentof Virtual Vineyards, which
became wine.com.
The idea is get really clearabout what success looks like,
(19:42):
not in some kind of pan-galacticstrategic way where you've
written down three documents andyou have a video and a bunch of
pictures and a vision board inthis.
And now I'm not talking aboutthat.
I'm talking about like at leasta paragraph of clarity about
what success looks like, right?
And then you ask yourself thequestion, what would have to
have been true to have achievedthat.
(20:03):
Okay.
That's an interesting question,because you're not saying what
needs to be true.
You're not saying, what do Ineed to do, or what activity do
I need to engage in?
You're asking yourself thequestion, what would have to
have been true to have achievedthis end state that you've said
was so important.
What's really cool about thatquestion is you can ask it again
(20:28):
and again and again.
So if you start at a point inthe imaginary future of this
thing you want to achieve andyou ask yourself the question,
what would've had to have beentrue such that outcome, that
desired outcome, was realized?
You can then ask the questionfor that thing that would've had
(20:49):
to have been true, what wouldhave to have been true?
And so you can work from thisimaginary future back to the
present.
So it's this recursive processof working from the future to
the present, and that tells youwhat would have to have been
true right now today in orderfor you to achieve this future
(21:13):
state that you claim is soimportant.
And so this assumptive goalsetting technique rests on this
very simple question, what wouldhave to have been true?
It's a total unlock for acomplex project and it works
profoundly well with teams.
I've done this for companyfunding events.
(21:35):
I've done this forinfrastructure projects.
I've done this for websites.
And once you have a map from thefuture to the present, you can
now look at, okay, in order forthis to be true, what activities
would we need to engage in?
What decisions would we have tomake and what investments would
(21:59):
we have to commit to in order tostart 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'sadvocate here and bring up the
time objection, right?
What you're doing soundstime-consuming, how much time
should people invest in thiskind 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 havetime to do it right." What did
he say?
He used to say,"If you have timeto do it twice, you have time to
do it right once." So my rule ofthumb there is at least spend an
(22:47):
hour on it.
It's a function of the cost ofthe project and not just dollars
and cents, but the amount oftime and energy.
It's a function of theopportunity cost of getting it
wrong.
Like, how much time would youhave spent planning and can you
allocate a percentage of that tosome assumptive goal setting
(23:08):
technique, which doesn't takethat much time and it is a major
efficiency play.
Because rather than working froma point in the present to a
large number of possiblefutures, what you're really
doing is saying, there's onlyone future and now I need to
(23:29):
work toward that future.
So you're saving time in termsof your forward planning by
investing in backward planning.
And I think in many cases it's anet zero.
And in terms of how much timeyou spend doing it and how often
you do it, how important areyour projects?
How important is it that they'reright?
How important that they land ontime or that they're within
(23:50):
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 Lincolnquote 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 minutessharpening the ax.
Jorge (24:09):
That's right.
Yeah.
So it's the idea that the actingpart of it, like it's going to
go maybe not much faster, butit's going to be much more
effective if you're actuallyworking in the right direction.
And what this process is aboutis directionality.
It's let's get us pointed in theright direction, so that then we
can pour all of this activeenergy more wisely, maybe is one
(24:35):
way to put it.
Harry (24:36):
And it turns out it's just a hidden efficiency play.
Because rather than being lateor being more expensive or
getting it wrong and having todo it again and make excuses and
justifying it, the whole thingjust 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 youand I should set aside some time
to do some planning for thepodcast.
I'm inspired.
Harry (25:01):
Me too.
Let me see if I can make time inmy busy schedule.
Jorge (25:05):
All right, Harry, thank you.
Once again, I've learnedsomething 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 attractionheroes.com and if you
enjoyed the show, please leaveus a rating in Apple's podcasts
app.
Thanks.
Popular Podcasts
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.
24/7 News: The Latest
The latest news in 4 minutes updated every hour, every day.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.