Doing the right thing poorly

I was halfway through reading the book Flying Without a Net by Thomas J. when I came across the following brilliant insight: in order to improve a particular skill, we have to first start by recognising that however we are performing that skill may not be the best way of doing so, and that to improve some changes may need to be made.

In short, to do the right thing well we may have to start first with doing the right thing poorly.

DeLong used the story of Tiger Woods to illustrate this idea very well:

Tiger Woods won the 1997 Masters Tournament in Augusta, Georgia, by twelve strokes. It was such an overwhelming victory that Augusta National redesigned its course to increase the odds that Woods would not repeat the feat. Yet after woods won the tournament, his coach, Butch Harmon, told him that, while he had played superb golf for four days he had a problem with his swing. He suggested that Woods needed to rebuild his wing from the ground up. Harmon admitted that woods could win sporadically without a change but would never challenge the greats like Jack Nicklaus.

I remember that incident well. Back in the late 90’s, Woods was a rising superstar. Being young and extremely dominant in the sport of golf he single-handedly made golf “cool” — and like many other younger golf fans, I started watching golf because of him.

When Harmon made those comments, many sports journalists were critical. Changing a winning formula? You got to be kidding!

I, too, felt that change was the last thing Woods needed.

In the months that followed it seemed as if the changes that Woods was making did more harm than good, and I wondered when he was going to say, in effect, “screw it!”, and get back to playing great golf again.

But he didn’t.

He soldiered on and went on to win a great many more tournaments, becoming even better than before. (Until his relatively recent marital problems, which has had a detrimental effect on his performance and career.)

Here’s the diagram that DeLong shared in the book:

We start from the top left-hand quadrant. This is our comfort zone; it’s whatever we’ve been doing and things we’re probably already pretty good at doing. In the context of work, it’s going to be whatever we’ve been doing to get to wherever we are at.

Sometimes, the outcomes from doing these “wrong” things aren’t that bad. But in this context, we’re really looking at peak performance. Often, we know that the outcome may not be optimal, and we suffer anxiety because we fear we’re losing our edge.

In order to get to the quadrant of “doing the right thing well”, i.e. the top-right, we have to move down to doing the right thing poorly. This is where it takes “courage and vulnerability”. When we first start changing the things we do, we’re probably not going to be particularly great at it.

We’re going to need to ignore the naysayers and just grind it out, continually practising our new behaviours. Eventually, all that practice will lead us to start performing these right things well.

The problem many of us have is that when we’re doing the wrong thing well, and getting results that may not necessarily be considered “poor”, changing isn’t always easy. The courage and drive to want to get into the next level of performance needs to be stronger than the anxieties we may face to maintain the status quo, especially since short-term results are likely to be poorer.

I did some analysis on my life through my writings from the early 2000’s till present, both personal and public, to see if I had encountered this anxiety-regression-progression movement, and I found that I had.

Whenever I’m trying something radically new like starting my national service in the army,  studying overseas, starting my Master’s degree, changing jobs, getting married, or having a child, I’m always in a state of high anxiety.

During this period I’m constantly asking myself if this is the life I want, wondering what’s going to happen, or second-guessing my job or university choice. What follows though, if I lean into these challenges or life changes, are often periods of my greatest personal and professional growth.

The things I fear the most often turn out to be the very things that shape who I become.

(PS: If you’re interested in Woods, read also this article on swing changes that Tiger Woods had made over the years. The “Harmon” change wasn’t the only one.)

The difficulties of doing “deep work”

These past two weeks I’ve been on leave, staying at home and being a dad to my 2-year-old son.

He’s got quite a standard schedule: the wife and I bring him out in the morning to let him “see the world”, have breakfast, and/or visit the grandparents etc.; he comes back around noon, takes a snack, sometimes a full lunch, then goes to bed for his afternoon nap.

Depending on how tired we manage to get him before his nap, he’ll wake up between 5-6pm. Sometimes though, he surprises us and wakes up at 3pm or earlier. It’s happened enough times for us to unconsciously be in a constant state of high alert throughout his nap, hearing out for his cries.

(I wonder if it’s something akin to gambling addiction, where the release of dopamine is increased when winning is intermittent or unpredictable. Just in this case, it’s more of the opposite in that we’re always in fear that the boy wakes up before schedule!)

What I realised was that during this “high alert” phase, I’ve always found it hard to do anything that requires more than a cursory time commitment, anything that would not be considered “deep work”.

Deep work – the ability to focus without distraction on a cognitively demanding task. It’s a skill that allows you to quickly master complicated information and produce better results in less time.

Deep work requires a commitment of uninterrupted time. Going into a cognitively demanding task and then being interrupted halfway through often means that whatever you’d done up till then is wasted, or at least any progress made set back considerably.

I remember once making good progress on a machine learning project I was doing for work. Suddenly the boy cried and I had no choice but to stop. When I resumed my programming in the night, I found it almost impossible to resume where I left off. What made so much sense just 8 hours earlier made little sense now, and getting back up to speed was a slow and painful process.

What this means is that when I’m in the midst of “expected interruption” I’m gravitating toward activities that are not subject to such a regression. For example:

  • Instead of reading complex works of non-fiction, I’m reading “lighter” books that I can easily dive in and out of, especially great are those where the chapters are short or where stand-alone ideas are wrapped up within a couple of pages.
  • Instead of practicing my technical data science skills or actually writing code, which tends to require a heavy commitment of uninterrupted time, I’m practicing typing on typeracer.com, where within seconds I’m racing against my typing peers and getting an instant hit of dopamine since I win so much but not all the time (see: above link on “gambling addiction”!)
  • Instead of setting my goals for the new year and how I’m planning to achieve them, I’m thinking about what I feel like having for dinner and how to cook it.

Though I always knew this problem also existed at work, I’m now more aware of the impact it might have.

For those of us constantly barraged by “urgent minutiae” or unscheduled projects (i.e. pretty much all of us I bet), the lack of a system or structured approach toward addressing interruptions could lead us to a lifetime of firefighting at the expense of actually doing the impactful, deep work we were brought on board to do.

Personally, these are the things I do to prevent myself from drowning in urgent minutiae:

  • Relagating of e-mails to an hourly or two-hourly affair, which helps you avoid being interrupted mid-thought or while putting the finishing touches on your magnum opus.
  • Scheduling of a “meeting with yourself”, which blocks your calendar and allows you to work, guilt-free, on your most important tasks.
  • Addressing anything that takes 2 minutes or less immediately, which frees the mind of unnecessary clutter, something I picked up while implementing the wonderful Getting Things Done methodology.
  • Focusing on your highest priority tasks while ignoring everything else for the day, which is dangerous but oftentimes necessary.

(PS: To date I haven’t quite found a “hack” for myself at home, though. My kid doesn’t respect my calendar, nor does he bother with e-mails, and he’s just about impossible to ignore.)

(PPS: Above definition of “deep work” found on Cal Newport’s website, whom I *think* coined the term. The term itself came into my consciousness after it was first mentioned to me by S on my team at work.)

Feeling good about one’s work

I was just “thinking about things” when this thought came into my head: To feel good about one’s work, there are two sides of validation: the internal and the external.

  • External validation: somebody tells you, “you’ve done well. This is excellent!”
  • Internal validation: you tell yourself, “you’ve done well; you’d set out to do something well and you did it.”

This past year I’ve had a lot of positive feedback on my work. Still, something was missing.

“This is great work,” they’d say, and I’d smile.

Was it really? I’d think, feeling less than satisfied, tinged with impostor syndrome.

Luckily the opposite was true, too.

The work my team and I do are quite regularly behind-the-scenes “enablement” work. Nobody but us knows; no rah-rah; no fanfare.

They’d say nothing, even after I’d done something I thought was remarkable.

Still, this is awesome! I’d think.

And I’d be satisfied. Almost happy.

Winning first place without ever being first

Or: what I learned from playing too much DiRT Rally (one of my favourite rally racing games.)

So here’s the context: I’m playing “career mode”, in which I buy a car, hire a couple of engineers, and go out to race. In order to win the championship, I have to have the best time across six “stages” or legs. Each stage is located in a different place so they all have their peculiarities: different areas of easy and difficult sections, some more suitable to the car’s set-up than others.

The thing about the game is that unlike real life, you have an unlimited numbers of do-overs – if you crash your car or get a time you don’t fancy, you can simply restart the stage.

When I first started playing this game that’s what I did. A lot.

I was intent on always finishing first for each stage. If I didn’t manage to finish first I would restart the stage. At times I found myself playing each stage close to 30-50 times; some stages I would spend an hour or two on and still not have the fastest time.

Then one day there was a stage in which I just couldn’t be the first for no matter how many times I tried.

I gave up. For that stage I ended up 5th and I accepted it*. The following stages were not much better either, with me ending up no better than third.

* (Side-note: actually my saying I “accepted it” is not really true. It was more of just getting the championship over, closing this chapter of my life, and uninstalling the game.)

Of all six stages of the championship, I ended up winning none.

And yet *drullroll please* I won the championship.

“But how?” I asked myself. “How??”

I couldn’t quite believe it but the overall time I had was faster than all my competitors. I won by virtue of consistency and not completely fouling up. Those who had won a stage had performed poorly for at least one of the others.

To me this was revolutionary and extremely zen: I won by not winning.

Please let me know if you have any questions

“Please let me know if you have any questions,” wrote I in an email I was drafting.

It has long been my signature email sign-off, but this time I was feeling a little reflective and reconsidered writing that line.

What did it really mean? 

But try as I might I couldn’t quite put my finger on it; it made no sense. So I deleted it.

Then I re-read the e-mail.

Ugh. No, it didn’t seem right.

So I put it back in.

The thing is though, I couldn’t reconcile this fact: if the recipients had any questions I’m pretty sure they would have not hesitated hitting “Reply” and asking me those questions. Would having left that line out stopped the questions from coming?

Surely not.

Still, I added the line back in because it “sounded better”, and from then on just accepted that I’d never know and simply kept that line in without too much thought.

Then just today I came across this passage from the book Simply Said by Jay Sullivan:

When you write at the end of an email “Let me know if you have any questions,” you are writing that line for a certain tone. Clearly, the reader will let you know if she has any questions, regardless of whether you make that offer. You add that line because it seems like a pleasant, conversational way to end the message. You include it to set the right tone, just the way you start the message with some basic pleasantry like, “I hope all is well” or “Sorry it’s taken me so long to respond.” Because email can seem so abrupt, it’s important to make sure we soften the tone of our messages.

I now feel extremely validated.

Turns out I’m just naturally inclined to be a pleasant, courteous person.

On Humility and Learning

I’m currently listening to Tim Ferris’ podcast episode with Eric Ripert, chef and co-owner of Le Bernardin, one of New York’s top restaurants.

In one part of the episode Ripert talks about what he looks for in his hires (his cooks). Of the various things he mentioned, what he said about humility stood out most for me.

On humility, Ripert said:

Being humble is very important because it allows you to keep yourself curious and motivated. If your ego is in the way it makes you blind and you’re not inclined to learn, because you “already know” or you don’t want to show your weakness.

When I first started my career, I tended to take advice very willingly. I was young and new to this “work” thing.

Then I started getting pretty good at my job and got a little carried away.

Being technically better than most of the people whom I worked for or with, I thought that technical expertise translated into every other aspect of the job and stopped listening to “suggestions for improvement”.

But then something happened: my progress slowed. I stopped learning.

I went back to soliciting for advice from people I respected, people whom I knew were smart and had tons more experience than I had.

To be honest though, despite my inclination to once again seek “advice” I wasn’t truly convinced I needed it. So, being quite the nerd. I started keeping track of how the times I thought the advice would be poor advice (vs. my own judgement) and recorded the outcome, which could be either positive or negative.

If the advice given to me was better than what I would have done without the advice, the advice would be marked as having had a positive impact. If the advice was worse, it would be marked as having had a negative impact.

The result? The solicited advice was overwhelming positive.

I found I was wrong in almost all instances. My judgement was poor as hell, and I didn’t know it!

(Well, my judgement has improved considerably since then. But do still take advice though, especially in areas where I’m no expert.)

Be nice

It’s not always easy, being nice.

Especially when we’re feeling anything but nice.

But please, let’s do the right thing and put in a little bit of emotional labour to check ourselves.

Because if we don’t, we may not get a second chance.

(Had read too many badly written, caustic e-mails today. Though I wasn’t on the receiving end of them, I knew the people who were weren’t taking it very well, and I just wished the sender had thought about the consequences on people his words may have.)

What’s Sales Reporting Governance got to do with Bribery?

I lead a Sales Operations team, and one of our objectives for this year is to establish a “sales reporting governance structure”: to ensure that the right reports/tools get developed, with the right specifications, at the right time; and, perhaps most importantly, with the buy-in by the right people.

Essentially this governance structure looks at controlling the reporting life cycle (something like this report life cycle diagram) from when a report is dreamt up in the head of one of our business partners (our “internal customers”), through to when the report reaches its EOL (end-of-life) and can be stopped.

Though you may think this is somewhat dry work, let me assure you that it’s often anything but. Conversations can be excruciating quite colourful, particularly when it comes to prioritisation and negotiating timelines.

Take for example the following conversation between one of our business partners (BP) and us:

BP: “What do you mean you can only deliver it next Friday? I need it by Tuesday.”

Us: “Sure, that can be done, but we’ll need to stop work on the other three developments we’re working on for you that are due next Monday.”

BP: “No, you can’t stop work on those. I need those next Monday, and this one by next Tuesday.”

Us: “Sure, but we’ll have to exclude the new functionalities that you’d asked for.”

BP: “No, you can’t do that.”

Us:“I’m sorry but if you’re not able to budge on re-prioritising the other work, nor reducing the scope, there’s no way we can hit the timelines you’re asking for, especially when you’re asking for this so late in the game.”

BP: “I’m escalating this. You’ll hear from my manager.”

And so on.

In all fairness though, I have to say that in my experience most managers and senior colleagues (and anyone who has worked in, or closely with, IT) tend to understand that we have to satisfy ourselves with but 24 hours a day to do all we need to do.

These sort of escalations tend to end with “the manager” having a cordial chat with us and agreeing on a workable next step forward, none of which involves us engineering more time into the day.

Establishing a Governance Structure

Having a governance structure tends to minimise “unconstructive” conversations like those above, I think largely because of a mutual trust: the business partner trusts our verdict of whether something is possible or not impossible within a specific time frame,  while we trust that they have thought carefully through their requests and won’t be changing or adding to them unnecessarily.

But the problem with establishing a governance structure is that it, well, needs to be established, which can be incredibly tricky to get going. It’s almost like an negotiating a peace deal, where both sides want the conflict to stop, but are worried what might happen the moment they lay down their arms — will the other side take advantage and strike when they are at their most vulnerable?

I will be the first to admit that it takes a leap of faith going from a world of “if I don’t shout loud enough, and often enough, nothing’s going to get done”, to one where we’re all amicably setting and agreeing on priorities, and where promised delivery deadlines are actually being met.

It also doesn’t help that from a developer’s side, without the benefit of having past projects to tune one’s intuition, accurately estimating project scope or determining deadlines is going to be difficult;  often multiple iterations are necessary before this sort of “accuracy” is achieved. What this means is that early on, chances are good deadlines are going to be missed, which doesn’t help in building trust.

After a missed deadline or two, it’s all too easy to fall back into old patterns and proclaim that the process doesn’t work.

There will also be many, especially those more used to the “free-and-easy” days of yore, who will actively fight the change, citing that it creates too much red tape and jumping through hoops to get things done.

“We need to establish our reporting as soon as possible or we’ll just be flying blind — we can’t afford to go through this process!”

But the thing is, we often can’t afford not to.

When the number of development projects are small, I have to agree that the process, this “bureaucracy”, adds little value. We could simply get on a phone call, or write an e-mail, and agree among ourselves what needs to be done and when. If the requirement changes, no biggie, we simply tweak until its perfect – there’s sufficient slack in the system that will enable us to do just that.

But problems will occur when the number of projects starts to creep up, and more stakeholders are introduced.

The Need for a Tighter Process

The first problem is that due to the higher workload, the slack in the system that allowed for changes in between a development cycle will be gone. This means that changes or additions to the original requirement will likely have to be parked until development time opens up, which could be weeks down the road.

Business partners are not going to like that. “It’s a simple change for God’s sake!”

The thing is, no matter how small a change is, it’s going to be work. Somebody’s got to do it, and that means time out from other projects, which also have agreed timelines. If we focus on that change now, it risks jeopardising the timelines for every other project down the line.

If the change is important enough, then maybe we can take time out from another project and put it into executing the change. But it needs to be agreed by the team owning the other project. Which leads nicely to the second problem.

The second problem is that everyone will have their own agendas, and everyone’s pet project will be “of the highest priority”.

What happens when Team A, B, and C all have “high priority projects” that need to be done by next Monday, and development team only has the capacity to complete one or two? Without a proper process or governance structure, can we guarantee that the project of the highest priority for the business will be one that’s completed?

In the end, more time will be spent explaining to each of the stakeholders why their project was not completed; people will be upset, and the next time they’ll just be sure to shout all the louder, and all the more frequently. More time will be spent on meetings and e-mails, people “ensuring” this and that and never really ensuring anything at all. Estimated delivery dates will be given, but nobody would trust them because they know someone else coming in with an “urgent” request would likely take priority. If it’s “last in, first out”, why should I raise a request early only to be relegated down to the bottom of the delivery pile?

This just struck me as very analogous to the concept of bribery, which I was reminded of on my reading of the book Treasure Islands by Nicholas Shaxson:

Some argue that bribery is ‘efficient’ because it helps people get around bureaucratic obstacles, and get things done. Bribery is efficient in that very narrow sense. But consider whether a system plagued by bribery is efficient and the answer is the exact opposite. [Bribery undermines] the rules, systems, and institutions that promote the public good, and they undermine our faith in those rules.

Despite any short-term drawbacks, there are plenty of longer-term benefits, not least that of supporting stronger surrounding report development structures and a generally healthier culture.

Though setting up the governance structure thus far has been tough, with plenty of push-back and many of our business partners trying to circumvent the process we have established, I think it’s one of the most important things we can, and have ever attempted, to do.

On meritocracy, luck, and giving back

Kottke’s post on meritocracy, a concept that I had in my younger days considered infallible, reminded me that even those of us who have worked hard and achieved so-called “success” have much to owe to “luck”.

Even the smartest, hardest working, most beautiful of us all, would likely have not fared well, had we been born in the midst of a famine to parents who couldn’t even afford to feed themselves.

And even the dumbest, most slothful, and ugly of us all, would not have fared too badly, had we been born to highly influential and powerful parents whom held us in even the slightest regard.

So let us all remain humble if are ever lucky and become “more successful” than others.

We probably owe more to chance and luck than we think.

Lucky

I met up with a friend last week over lunch, and one of the things that was brought up in the conversation was on our work, our careers. He was genuinely happy and excited for me that I was (finally) going to graduate from my Master’s degree in Analytics.

To him, my having these analytical skills, backed with a Master’s degree, would easily propel me to the top. I would, he said, be in high demand.

Being quite the realist, though, I didn’t exactly share his optimism.  I knew that even if I was the best in the world at what I did, if nobody knew what I did, it didn’t matter. There would be far too many people like me with similar qualifications and experiences.

But I knew where he was coming from.

It was true that my skill set was in demand. And it was true that I probably had an easier time than most in finding career opportunities. Unlike many others I knew, I was in the rather envious position of not worrying whether or not I’d find another job if I left my current one, by choice or otherwise, because I knew I would. I only stayed because I wanted to.

It then occurred to me how lucky I was.

Living the Dream

“I am living the dream,” I said to the group, “doing what I love.”

I was in a management development workshop organised by the company, and that was my response to the question, “tell us something nobody else in the workshop knows.”

It had come spontaneously and was as much a surprise to me as it was to everyone else.

It wasn’t that my career was perfect — I still had much I wanted to do; much I wanted to achieve.

But given all the million-and-one constraints, my career’s turned out pretty good: leveraging my business-IT background, I work within Sales but deal with technology (even doing some scripting and programming) every single day; I develop data products that are used by hundreds, from the frontline through to senior management; I regularly get to present my ideas and train Sales on technology and data literacy; and I lead a team of wonderful colleagues who do excellent work (and at the same time have a great boss); it’s almost precisely how I would have envisioned a “good” career outcome (shame about the pay!)

But it could have been so different.

I knew was lucky.

Right Place, Right Time

I was lucky in that my parents weren’t poor, and had purchased a computer for the home even when that wasn’t a very common thing to do. And I was lucky that I was allowed to use this very expensive toy, which exposed me to technology at a very young age.

I was lucky that I grew up in a time when the Singapore government wasn’t too interested on clamping down on software piracy — I suspect the government did this on purpose because many of us, though not poor, were not rich enough to actually purchase professional-grade software to play around with. 99% of what I know I learned on bootleg software.  This move alone probably bumped up Singapore’s technological literacy a fair bit.

I was lucky that I was never stopped in pursuing my love for technology — when I opted for a technology-focused polytechnic education (i.e. the Diploma route) instead of going the more traditional “junior college” (i.e. the A-Levels route), I never met any parental resistance (which in a way, was because I was lucky enough that my grades were good but never exceptional, and so my parents didn’t really care — had they been exceptional, my guess would be that the would have been far more opinionated).

I was lucky that I was hired for an analytics position at the very last interview that I decided to go for before heading into the world of Financial Advising, thereby leading me to my current world of technology and analytics… what were the chances?

Right place. Right time. And if not enabled by the luck, at least not hindered.

But not everyone will be so fortunate, and it is up to us, the lucky and empowered ones, to give back and to try to provide opportunities to others who may not be as lucky.

Yet.

On Giving Back

My one simple philosophy on giving back: that anyone whom I work  or in any way interact with should find that if I had never appeared in their lives they would have been a little poorer for it.

I seek to be the luck in people’s lives.

Because so often they are in mine.

What you do determines what you see

Author’s note: This post was originally titled “Déformation Professionnelle”, but I had trouble understanding it myself and have renamed it for easier future reference!

This post in three words: Profession -> Perception -> Truth

The following text is taken from the excellent book The Art of Thinking Clearly, by Rolf Dobelli.

A man takes out a loan, starts a company, and goes bankrupt shortly afterward. He falls into a depression and commits suicide.

What do you make of the story?

As a business analyst, you want to understand why the business idea did not work: was he a bad leader? Was the strategy wrong, the market too small or the competition too large?

As a marketer, you imagine the campaigns were poorly organised, or that he failed to reach his target audience… As a banker, you believe an error took place in the loan department.

As socialist, you blame the failure of capitalism.

As a religious conservative, you see in this a punishment from God.

As a psychiatrist, you recognise low serotonin levels.

Which is the “correct” viewpoint?

The above is also what is known as Déformation Professionnelle (what a term!) — a tendency to look at things from the point of view of one’s own profession rather than from a broader perspective.

I’m only too wary of falling into this trap, which is especially easy for me to do because my expertise lies in data and its derivatives and the scientific method , things I hold dear and believe are as close you can get to a panacea for all the world’s ills.

Which is why I often preface the ideas I share with, “if I put on my analytics hat…”, because I know not everybody will share the same view. And I respect that.