Asking Better Questions

You can’t fix a problem that you don’t see.

Like about ten percent of the world, I am left-handed (Why Are 90% Of Humans Right-Handed? An Evolutionary Biologist Explains). For any situation where hand-dominance matters, odds are the standard design solution will favor right-handers. Scissors, school desks, spiral bound notebooks, soup ladles, screw drivers. The list is surprisingly long. Curiously, you aren’t likely to notice, even as a left-hander. Your dominant hand is your dominant hand; it’s central to the way the world works for you. You don’t notice that the world is harder to navigate for you unless and until someone points it out. The first time I tried a pair of left-handed scissors was a revelation about how a proper tool could work. But someone had to tell me that such a thing as left-handed scissors existed. Until then, I simply felt clumsy. I assumed that the problem was internal, not connected to the tools available.

I’ve been wrestling with a vague sense that I’m not finishing writing at a satisfying pace. The beginnings of noticing a potential problem to solve.

I then made a mistake. A mistake that I spent significant time and effort encouraging my students to avoid when I was in the classroom. If any of them should come across this piece, they should feel free to mock me. I took my vague sense of a problem and framed it in terms of a potential solution. Rather than dig deeper to understand the problem, I jumped ahead to answer a question I had yet to fully formulate. Sometimes the accumulation of scar tissue isn’t sufficient to stay away from that hot stove.

Given that I’ve been concerned about the pace of finishing writing efforts, the question I posed to myself was;

What can or should I be doing to establish a cadence of writing that will more consistently lead to outputs and results that please me?

The lesson you are supposed to learn from all the questions you face in school and on the job is that the best answers flow from the best formulated questions. Your first task is not to answer the question in front of you; it’s to refine the question.

Unfortunately, this is a capstone lesson. It doesn’t surface in formal education until you work your way into doctoral programs. It’s there earlier but obscured by a system that, as a whole, rewards answers. Most people who ask questions get dinged for being annoying. “I’m just asking questions” has become the catchphrase of too many conspiracy cranks and general gadflies. Ask the wrong question of insecure people in positions of power and you risk worse than being deemed annoying.

Years of reinforcement tend to make my default response to questions posed the first answer that comes to mind. It’s a default that is actually pretty effective most of the time. It’s what gets rewarded in most of our educational settings and one I’ve had a lot of experience with. The confounding variable here was that I was answering a question I had formulated, rather than one crafted by a teacher. In my eagerness to supply an answer I made a rookie mistake.

Which is the worst kind to make when you are long past being a rookie.

My mistake was to hide an answer in the question. The question posed assumes that the problem to be solved had to do with “cadence.” It’s prefiguring a solution without any evidence that I understand the problem. I used to teach “Five Whys” to my students and to my junior consultants. One of many techniques to surface the hidden drivers of persistent problems. Techniques I’ve taught and applied for years. To other people’s problems.

Physician heal thyself indeed.

Let’s stick with my initial area of concern; finishing satisfactory writing efforts at a better, more consistent, pace. What are some additional questions that I might seek to answer?

  1. What is it about my writing outputs and results that I find pleasing?
  2. What differentiates those from ones that are not pleasing?
  3. How well do I understand the process I follow to produce those results?
  4. Can I predict how I will judge an output in advance of completing it?
  5. What are the markers that distinguish between outputs that please me and those that don’t?
  6. What can those markers tell me about the path I took to produce these outputs
  7. Can I articulate a process that I follow (whether conscious or instinctive) to get from germ of an idea to finished output?
  8. What can I learn from the practices of other creative sorts whose results I value
  9. How can I apply and adapt my experience evaluating and designing processes to my own process?

What’s the proverb? “Well begun is half done.” Too often, the only word in that proverb I see is “done.” The finish line beckons. And my tendencies to procrastinate make we wary of things that smell of delaying tactics. I have to remind myself to “stay in the question” long enough to unearth the questions that will yield the most return.

I was always a sprinter in my running days. The lesson I need to keep learning and relearning is that sprints are won or lost at the start. It’s a particularly bad start if you run in the wrong direction.

Or answer the wrong question.

Remembering everything you read is a marketing pitch not a useful practice

PKM (Personal Knowledge Management) is in a hot phase these days. A lot of people are busy peddling their solutions to presumed problems of PKM.

There’s a basic truism in sales and marketing that successful products and services solve problems that customers have. In order to sell a new product, therefore, you must identify a problem that they solve. Better to use a breath mint than risk inflicting your (hypothetical) bad breath on your date. My innate skepticism, about this chain of reasoning probably explains why I found marketing such a difficult subject back in my business school days.

One of the go to problems that PKM purports to solve is the need to remember everything you read. Just because “what have you been reading lately” is a routine conversational gambit doesn’t mean that you have to have a clever answer. Stop making it a competition. There have often been cocktail party moments when I struggle to recall what I am currently reading, much less what a recent book was actually talking about.

At the other extreme, I review books from time to time. One of my very first published pieces was a review of Steven Weinberg’s The First Three Minutes: A Modern View of the Origin of the Universe, which ran in The Hartford Courant. My copy of the review was lost multiple moves ago. As was my review copy of the book. How much better would my life be if I could lay my hands on either of those or on whatever notes I took in the process of writing that review? That seems a precarious hook to hang a marketing campaign on.

If we set marketing puffery aside, how important is it to “remember everything you read”? A Google search suggests there’s a lot of energy behind this goal. If you’re a current student and exams loom, you might be wishing your study habits and note taking practices were more robust. If you’ve finished the reading and your notes are organized and cross-referenced, then we can’t b e friends. If you do any sort of knowledge work, odds are you have more to read and remember than is remotely feasible.

Understand. I love to read. I did it well enough and long enough to finish a doctorate. I can identify over 2800 individual books that I have read at some point. Some, I’ve read and reread to the point of near memorization. Others are a title and a vague memory of what was inside. Your numbers might vary, but I think this is the reality for most of us.

Remembering everything you’ve read is about diligence not value. Diligence for its own sake is a waste of energy. You want to be diligent for activities that make a difference in the world. You’re allowed to do things simply for the pleasure of doing them. Don’t let someone’s marketing agenda distort what makes sense for you.

Reclaiming our platforms: Cory Doctorow on Enshittification

 

Enshittification: Why Everything Suddenly Got Worse and What to Do About It

You’ve figured out something important if you manage to coin a term that becomes the “word of the year.” Cory Doctorow did that when he attached the label “enshittification” to aspects of our technological environment that we’ve grown all too accustomed to. He did so back in late 2022. He’s compiled his thinking and analysis since then into his latest book, Enshittification: Why Everything Suddenly Got Worse and What to Do About It

His initial focus was on social media platforms. He also noted that all technology applications aspire to become platforms, so there’s little opportunity for mere mortals to opt out. Here is his core definition;

Here is how platforms die: first, they are good to their users; then they abuse their users to make things better for their business customers; finally, they abuse those business customers to claw back all the value for themselves. Then, they die. (Pluralistic: Tiktok’s enshittification)

The dying part currently seems to be more wishful thinking than observed phenomenon.

Doctorow does an excellent job of cataloging and describing the phenomenon. As a storyteller by trade, he may do too good a job of storytelling at the expense of understanding.

Stories have villains. Not so much for broken systems. Doctorow’s storytelling skill sometimes gets in the way of understanding. He is often so persuasive that we can fail to notice that his stories aren’t backed by a lot of evidence. The phenomenon is real, but the explanation of evil/malevolent intent is hypothetical at best. Systems are harder to change than evil actors. Change the players without changing the rules of the game and you’ll get the same outcomes.

Doctorow gives us a compelling way to talk about the problem. He’s gotten everyone from Nobel Laureates (The General Theory of Enshittification - Paul Krugman) to the Norwegian Consumer Council talking about the phenomenon. It’s up to the rest of us to do the systems change work to make things better.

Problems, messes, and stories

A good chunk of my early career was spent writing code. In COBOL no less (one more proof that I am indeed an old fart). Someone had developed pretty detailed specifications and my task was to translate those specs into working code. Much like doing math homework, I spent my days solving problems.

One cliched criticism from clients footing the bill for this work ran along the lines of

“what do you really know? You’ve never had to worry about making payroll”

In reality, neither had any of my critics but that was no impediment to the critique.

Unlike those critics, however, there came a time when I did, indeed, have to worry about making payroll. In 1994, I left a secure job with an established company to start a consulting firm with nine other partners and an initial staff of fifteen. We each invested from our savings and took about half our pay as deferred compensation to be paid if and when we were successfully established. We got stock options that might be worth something in a few years if we succeeded.

In our first year of business we did $12 million in revenue. We did close to $26 million in our second year and hired another 30 people. My partners and I were indeed getting a first hand education in “making payroll.” When we weren’t fretting about where the next client or check would come from, we were working to build an organization out of a collection of people who were learning each other’s names.

Two things were going on as we made plans for our third year of business. One, we were making a bet on how much business we could do in the coming year. Two, we were looking to hire the people to do the work we had sold and hoped to sell. We set our revenue goal to double again, this time to $52 million.

Meanwhile, we were on business school and top tier college campuses looking for talent. We were basically complete unknowns competing against established firms ranging from McKinsey and the Boston Consulting Group to Accenture and Deloitte. If you know the industry, these names tell you a lot. If you don’t, think of us as a club ice hockey team thinking it could compete at the Olympics.

Come April 1st, we had a budget and offers out to about twenty five students set to join us come the summer. If we were an unknown to prospective clients, we were a complete unknown on campuses. We had a good story for students looking for something a bit less safe than signing on with a name firm. Recruiting offices on campus were skeptical but tolerant. We were making investments for the longer term.

Two weeks later our largest client, representing half of our revenue, was acquired by another company who immediately shut down all active consulting projects. We were faced with the question of do we withdraw our outstanding job offers? How would we ever recruit at any top tier school if we did? Meeting payroll now seemed such a simple problem.

Some immediate decisions were straightforward. The budgeted bonus pool for the partners was zeroed out. So was our future deferred compensation. The risks that come with being an entrepreneur.

What happened next was the interesting story. We elected to lay out the entire situation to our staff. Their very first question was why did we still have a line item for staff bonuses. There was also universal support for maintaining the outstanding job offers and signing bonuses for incoming recruits.

We weathered the storm, although we didn’t hit our revenue target. We did do $36 million by year’s end. We continued to recruit on those campuses and others. Those graduates who stayed with us became partners. Others moved on to C-level roles elsewhere.

The late Russell Ackoff was a student of organization and complex systems. One of his core lessons was that organizations rarely get simple problems to solve. They are routinely challenged with amorphous, ill-defined messes that must be managed.

Mess is the default state of human organizations. Keeping the level of mess to a manageable level is the lot of anyone who aspires to rise within them.

Familiarity breeds comfort

In high school I got pushed into public speaking opportunities by my teachers. I was as uncomfortable as anyone I suspect, although I never quite understood the level of anxiety and fear that others report.

One of my early experiences came from a high school science fair. A classmate and I took first and second place in St.Louis in the spring of 1971. One of our rewards was a trip to the Marshall Space Flight Center in Huntsville, Alabama to compete at the regional level. For a science fiction fan (a proto-nerd before the term became popular), this was akin to an invitation to the Vatican. I didn’t advance any farther, although I did wangle a private backstage tour because my advisor had professional connections to the staff there.

We got feedback from the judges after our presentations. The bit that sticks in my mind fifty years later was an observation that I handled the Q&A session much like an experienced engineer.

As a consultant, and later a professor, I’ve spoken in front of audiences in Beijing, Prague, and Stratford-on-Avon. I know my way around a stage and with an audience.

All of which is built on practice and repetition. Scarcely a new observation.

Familiarity breeds comfort not contempt.

Desires for that secret class

As I get older I often wish I had done a better job of keeping track of things (people and events). My brother-in-law seems to be especially good at this. He has the advantage of spending his youth and his career within the same community but I think it also ties into his perspective on the world. He remembers people and events with clarity. We often joke about his ability to connect with complete strangers in a matter of moments. He’s always got a story about an old friend he’s still connected with or a new one he made at the market this morning.

Perhaps this is simply the difference between extroverts and introverts. I’m partial to the distinction that introversion/extroversion is largely about whether social interaction consumes or generates energy. I can be perfectly sociable at a party but it wears me down.

But the odd thing on my mind this morning is what I do and don’t remember. Particularly about my interactions with other people. Bookish things stick (although I seem to have forgotten the mathematics I once knew), human connections feel fuzzier. I often feel as though I’m faking it on some level. Not “imposter syndrome”; this is something different. The stories and sense memories that come so naturally to my brother-in-law take work for me. I’ve often wished for a class to teach me how to navigate the world of other humans as readily as I manage to navigate words and ideas.

I know that no such class exists other than living life itself. Doesn’t mean I still don’t wish that it did.

Trusting the team

Our 8:30 class was about to begin. I was settling in to my assigned seat in the top row trying to project an air of invisibility. I was a bit worse the wear from a class party the night before. This was a class I normally had under control, but not today. I hadn’t even opened the day’s case study and a very low profile was in order.

Our professor finished organizing his notes and looked up;

Today, we’re going to use a little role play to make the discussion more interesting. Jim, I’d like you to take the role of John Weldon. Jay, I’d like you to play the role of Peter Smith, John’s general counsel.

He then selected two other pairs of students and dispatched all of us into the corridor while he briefed the rest of the class on what was about to transpire.

In the corridor, I revealed my non-existent preparation to Jay with a simple question, “Who’s John Weldon?”

Jay was an attorney by training and, clearly, I was not the first befuddled client he had counseled:

Relax Jim.

Weldon is the CEO of Acme Industries and we’re in the middle of a negotiation with two other companies.

Keep your mouth shut, nod your head from time to time, and follow my lead

We were called back in to class. Jay and I sat in two chairs in the center of the pit across from our classmates in their roles, and I played my part as per Jay’s instructions. The negotiations were soon over and I was back in my regular seat as we debriefed the experience.

One of my section mates, who had been with me when I was busy not preparing the night before, oh so politely asked the professor how he had selected people for the various roles. Choosing three attorneys from the class was an obvious choice and no one objected. The rest of his explanation, however, was derailed when he said “I picked Jim because I knew he would have the case cracked.” The laughter this provoked required a confession on my part. Sadly, I’ve lost the certificate for “Best Bluff When Called on Unprepared” that my classmates awarded me at the end of the semester.

Lessons learned? I no longer drink, so staying sober before big meetings wasn’t one. Being prepared for the unexpected is a cliche and largely meaningless advice in the real world. Surrounding yourself with good people that you trust, on the other hand, is something you can control and puts you in a position where you do have a good chance to cope with the surprises that are inevitable.

Innovation in the small

I got two pieces of practical advice about writing many, many years ago. One from my mother. The other from one of two writers (Jerry Weinberg or Jerry Pournelle). Which one is lost in leaky memory.

Along about 1969-1970, Mom encouraged me to learn to touch type. This was when keyboards were connected to typewriters rather than computers. Her reasoning was that this would come in handy when I got to college and had to turn in papers on a regular basis. After a summer’s practice I was moderately skilled. Sixty years later, we’re somewhere deeper than muscle memory.

The second piece of advice was to learn to think at the keyboard. Handwritten drafts were too slow to keep up with my brain. Keyboards got closer. This is such routine practice today that it isn’t noticeable. I know that there are those who find the feel of pen on paper helpful to their thinking and writing practices. I am not one of them.

Doing this in the days before word processing was an option made me an oddity. Secretaries typed things. Professionals wrote longhand. Who was I to sit down at a secretary’s desk and write a rough draft? What other heresies might I commit in full view of the hierarchy? These may have been the seeds that led to my study of organizations, innovation, and technology.

There is always a layer of received wisdom that you either submit to or fight. Progress does not come from those who submit.

What could possibly go wrong

My MacBook is now five years old and in need of a new battery. Which meant a trip to the local Apple store for diagnostics. I’ll need to let them have the machine for several days so they can ship it off to a repair center. That will require a bit of juggling to figure out when I can be without one of my primary tools.

I do keep regular backups for this machine which reminded me of a story from my consulting days. Appropriately enough I suppose, it was the same project I wrote about when I kicked off this effort; giving the state of New York a new accounting system (Addressing the Mess - McGee’s Musings).

We were at the point of cutting over from the old system to the new after two years of development work and extensive training for all the users of the system across the state. One of the critical steps in the conversion was to map all the appropriations and budgets from the old system to the new system. My team had worked out a clever way to do the cutover given that we were talking about several hundred agencies and state departments identified in the 1,500 page state budget.

The results existed on six computer tapes. Each tape was on a reel about a foot in diameter containing several thousand feet of magnetic tape. Today all of this would likely fit on a thumb drive. The tapes were stored and managed in the State Comptroller’s Office computer room on the ground floor. The computer center manager assured us that the data was safe but I was skeptical. I asked Mitch, one of my analysts, to make absolutely certain that no one could touch our tapes. I had requested that we take possession of the tapes for the duration and deliver then to the data center when needed. I was overruled by their manager. He assured me that his systems were reliable until the night that one of the operators tried to use the tapes to run their nightly backups.

The only thing that prevented the data center operators from grabbing our tapes was Mitch. He had secured our tapes in the data center with a chain and a bicycle lock. The data center director was torn between being mad at me for bypassing his system and embarrassed that his staff had nearly wiped out months of work.

Mitch got a nice write up in his performance review and a story about just how trustworthy systems can be when you’ve got people in the loop. I got one about putting faith in your people.

Older and wiser heads

My time as a stage manager contained my first lessons in managing something bigger than myself. This was during my university years, where I was usually at a rehearsal or work session when I should have been in class. Everyone in the group was a student with three exceptions. We paid for a costume designer, a choreographer, and a director. In my role, I worked with all three, but our director, Milt Lyons, was the sources of the lasting lessons.

It was past midnight and we had just finished a full run-through of the show. The cast and crew were slumped in the theater seats as Milt was about to go through his notes of what worked and what needed fixing. I was on stage with Milt, standing just a little behind him and to his left. I was ready to jot down the notes that I needed to worry about and was thinking about what I needed to do as soon as he finished.

I was surprised by his first note of the evening. Or morning to be more accurate.

Milt deputized two cast members to escort me to my dorm and put me to bed. I handed my clipboard to my assistant and followed them. It was the first time I had left the theater in the preceding 120 hours. Twelve hours of sleep later, I was back.

You do some foolish things when you’re twenty. If you’re lucky, there are older and wiser heads to keep things from getting too foolish. I want the world to be orderly and under control. For all my grumbling about chaos and mess, I prefer to be around creation and creators. But that creative energy can be a distraction from responsibilities.