Unpredictable Patterns #21: On asking questions
On why your helpfulness is dangerous, good politicians, the underestimated RG Collingwood and what we really know about the world
Dear reader,
Next week is the last week of May and it feels as if time is shifting. Not only are we seeing some kind of end of the pandemic in the Western world (although there are many countries now suffering and in need of acute help - I recommend donating to, for example, Vaccine Forward), it is also soon summer here in Sweden, and time always seems more fleeting then. We have this expression - between bird cherry and liliac - that is supposed to express a time span in summer between when the two bushes bloom, and we are right in the middle of that time bubble now - and it is beautiful. A good time to regroup and think through things for the second half of the year. Which questions are you going to try to answer for the rest of the year?
You really don’t know how you think you know
What do you know? What kinds of things do you know? Our tendency is often to answer such a question with a list of things we know and then rank or order that list in some way. We can, for example, list the things we know in decreasing order of certainty or importance. The Cartesian project - Descartes search for a truth that all truths could be built on - can be simplified to such a list, or the search for a possible first statement in that list - if there is one.
The Cartesian project seems profound, and represents a certain kind of mind as well as a certain kind of model of the world. Knowledge of the world consists of knowledge of a set of propositions, and these can, in turn, be ordered in different ways and we can say interesting things about them. This view of the world echoes down the history of philosophy and dominates our thinking still today. But is it true? Is knowledge a series of propositions?
Let’s look at three such propositions in a toy model where I know only three things:
The earth is round.
Joe Biden is the president of the United States.
There is no king of France.
These three propositions seem to be fairly straightforward - right? But let’s look closer. What if someone says that the Earth is not at all a geometrical sphere, or that Joseph Biden has not always been the president of the United States or that there have been many kings in France? They would be sort of right, under certain circumstances - but we usually dismiss that criticism by saying that that was not what was intended, or that this was not what they asked.
Suddenly we have discovered something weird, and just by looking at our reaction to a challenge to our knowledge we have found that there is something circling our propositions, something that anchors our knowledge - and it is this: every proposition is the answer to a question.
If we now try listing our knowledge again, we can get a much more interesting list of questions and answers:
What is a good coarse-grained geometrical shape that describes the Earth? The Earth is round.
Who is currently the president of the United States? Joe Biden is the president of the United States.
Is there a king of France today? There is no king of France.
Our knowledge has an often invisible shadow in the questions that our propositions are an answer to - and when we examine what we know, we should look at the questions and the answers as a complex. The propositions almost remind me of the gravitational deviations in astronomy that reveal the presence of a not-yet-detected planet - the questions.
That was at least what philosopher RG Collingwood thought, and he thought it important enough to devote a large piece of his autobiography to questions. He writes:
”The questioning activity, as I called it, was not an activity of achieving com presence with, or apprehension of, something; it was one half (the other being answering the question) of an act which in its totality was knowing”.
And Collingwood went on to say that this model of knowledge is essential to ever understanding what someone else really means, and again it is worth quoting him:
”I began by observing that you cannot find out what a man means by simply studying his spoken or written statements, even though he has spoken or written with perfect command of language and perfectly truthful intention. In order to find out his meaning you must also know what the question was (a question in his own mind, and presumed by him to be in yours) to which the thing he has said or written was meant as an answer”.
Everything we do can - if we exaggerate just slightly for effect - be understood only as the answer to a question.
Now, let’s dismiss two lines of criticism immediately: the first is that this is not how we think. We do not eat breakfast to answer the question of how should I deal with my hunger, and we do not marry because we want to answer the question of how we should live our lives - not explicitly. But if we assume that what we know is related to how we act, we should understand our action as related to our knowledge, and so, ultimately to the pair of questions and answers that Collingwood points to.
The second line of criticism is that this is an unnecessary complication and that Occam’s razor suggests that we just deal with the propositions. But the questions are essential, they are needed to really identify what it is that you think you know! And Collingwood is not complicating things to seem interesting or important, he is painstakingly trying to reverse the course of philosophy /back to where it was with Socrates/. Because when we return to Plato we find this beautiful description of how Socrates defines thinking in the dialogue Theaetetus:
”I mean the conversation which the soul holds with herself in considering of anything. I speak of what I scarcely understand; but the soul when thinking appears to me to be just talking—asking questions of herself and answering them, affirming and denying. And when she has arrived at a decision, either gradually or by a sudden impulse, and has at last agreed, and does not doubt, this is called her opinion. I say, then, that to form an opinion is to speak, and opinion is a word spoken,—I mean, to oneself and in silence, not aloud or to another: What think you?”
The soul speaking it to itself, asking questions and answering them, that is how we come to know something. Collingwood’s view is not as revolutionary as it is, in a sense, a return to an older view.
We can speculate about what happened after Plato to end us up with propositions, and there are many possible explanations - one is that writing favors the propositions and the dialogue fell out of use, another is that in medieval ages logic and grammar were taught together so logic was infected by the study of propositions and sentences, and forgot about its questions — but this is speculative.
The more interesting conclusion we can draw here is this: there is a tremendously powerful, cognitive tool available to us in questions if we just decide to use them in the right way.
If we unearth our own questions we can see the world in entirely new ways.
What is the question?
There are many, simple, ways to use questions in our day to day work - and I will draw upon my own craft to give a few examples that I think are helpful to start applying this in other domains as well. In public policy there are a multitude of ways that questions can help us understand the shape and nature of a problem much more clearly.
Let’s start with the simplest observation: companies and politicians often are trying to answer different questions. And this is especially true for tech companies. Many tech companies have heavy engineering cultures (often to their great advantage - engineering culture is a solutions oriented and often cognitively enormously strong tool for an organization to solve hard problems) and the central question for many engineers is if something is true or false, or if it works or not. Let’s simplify and argue that the engineer question is a question of logic (sometimes it is a question of efficiency or simply if something works):
(i) Is this true or false?
Tech companies, the large ones, have often - thankfully - realized that they also need to co-exist with society and so they hire lawyers first, often before they hire policy folks. Now lawyers are drilled in school to answer a very different question, and it is, quite obviously:
(ii) Is this legal or illegal?
Already here we see a clash of questions emerging: engineers who think that what we should care about is if something is true or false - if a certain network topology reduces lag with the greatest efficiency, say, and a lawyer who says that the network has to have local storage in different countries because of data localization laws.
This clash of questions usually ends in the frustration that those of us who work in tech companies have heard so often: engineers realizing that they cannot do something efficient because it is illegal have a tendency to point out in an exasperated way that ”this is stupid”. Lawyers, who believe that stupidity is rather doing illegal things because it is efficient technically, are equally frustrated and find engineers somewhat impossible.
No party is at fault, though - they are just answering different questions.
Cue the policy folks. After a while a tech company also hires policy professionals, and they are dealing with politics as their key domain - and politics, as a field, is not answering questions about legality or logical truth at all.
The basic form of the question underlying all of the political field is this:
(iii) How do we live together?
Now, when you are trying to understand why Commissioner and Vice President Vestager is opening a competition investigation into your company, your tendency will be - if you are engineer - to find it unfair because it is illogical (you believe you are lowering prices and helping users and consumers to a better product). If you are a lawyer you will be astonished at the thin veneer of legal argument that the investigation is sporting and you will find it blatantly political (which is curious criticism, given that it correctly identifies it as a problem in another domain). But both those reactions flow from misunderstanding the question that is underpinning the actions of the European Commission: how Europe can live together with large, fast growing technology companies that seem to be leaving it in the backwaters of innovation and so also causing great concern for its economy for the long term?
The answer to the political question is not that what we are doing is efficient and logical, or even that it is legal, but to find a way to structure co-existence to mutual benefit - something negotiated in legislation and regulation, but ultimately solved through habit - time assuages a lot of political fear - and conscious coupling of a corporation with a polis or political community in a way that clearly divides roles through institutional innovation.
This is hard, but answering the wrong question is useless.
Political questions and questions politicians must ask
Well, you may argue, that is a very idealized and rosy picture of what is underpinning the protectionist attack on US tech companies in Europe - but is it also not a little dishonest to completely discount the possibility that European politicians are simply out to get tech, that they are scoring cheap points on attacking companies that have grown to big for their britches? It is all about taking down the successful, when you cannot join them?
The thing about that argument is that it does not change the analysis - you still need to look for the question they are trying to answer, and while it is true that all politicians are ultimately always answering the question about how to get reelected, they do so because they think that there is value in them getting re-elected, and I hold the somewhat controversial belief that no democratically elected politician I have ever met believes in solely individual value for them in their re-election. To the extent it makes me an idealist, I suppose I am — but again: as an operating assumption that is better assumption that the suspicion that everyone are out for themselves.
But the question of re-election is a real one, and one that is interesting to consider for anyone in policy. Part of the job of any good lobbyist is looking at this question as a part of the complex of questions that the stakeholders you work with are trying to answer.
And this gives us a new way to map stakeholders.
Rather than just drawing a network with names in it - try this: draw a network with questions that you believe that the political community is trying to answer and then orient the stakeholders alongside the questions. This network of question is a great model of the challenge you are facing - and it will allow you to also see where the center of gravity in the questioning in the public debate really lies.
The network of questions will also help you understand that there is no simple or single way for you to approach a political community. If we apply this to the tech-lash, for example, and just list the questions we would at least - and this is not exhaustive - have to answer the following questions (in an issues / question tree-model):
Now with this tree or network (the questions are related, and teasing out those relationships is important) you can start to see how different answers address different pieces of the puzzle.
And this also allows us to experiment with meeting formats — some tech companies are already organizing ”ask me anything”-sessions with different stakeholders and this is a great discovery mechanism for designing a question network, and even organizing it per stakeholder group - what do civil servants ask, what do academics ask, what do NGOs ask? Each group has their questions and a map of the questions clarifies the challenges ahead.
Even in the one-on-one meeting far too few companies try to find out which questions are driving their interlocutors. Often - not always - it should be a key objective with a meeting to understand what questions the other party is thinking about and if there is any question that they think is more important than all the others.
There is another aspect to this that is equally important and that is the questions your stakeholder are not asking.
The lack of questions is a guide to map assumptions - and these assumptions are essential to understand what questions the other party thinks they have already answered: how a company makes money or who owns the company or how the company makes decisions (I have found that some of the most thoughtful politicians I have spoken to ask this question and look for practices and habits that they can recognizes as responsible, by the way).
So don’t just map the questions that decision makers ask - spend some time also sketching out the questions they should be asking and why they should be asking them. If you are planning a meeting, one of the objectives should probably be to leave behind different questions than the ones you started out with.
Try it next time! Leave out the lengthy powerpoint and set out to both discover and leave behind questions as a key objective, and - of course - explore your own questions as well. A discussion about questions is also more likely to change perspectives than a solid restatement of talking points - questions prepare the mind for building knowledge.
Planning and leading with questions
Questions are also helpful in strategic planning, and there are a number of ways in which questions can help think through issues and problems. The first point we should make, here, though, is that we spend too little time on understanding and formulating questions - and this is especially true for the kind of people it is lovely to work with: smart, helpful and kind people.
When you ask a question you acting in a social game, where points are awarded not for getting the question right, but answering it. We love answering questions, we even spend our leisure time doing it! Trivia games, Jeopardy (in reverse) and any number of other games are about questions - and answering them fills a cognitive demand and gives us pleasure.
So, when someone asks you a question at work, and you are smart, helpful and kind - what do you do? Do you challenge the question? No - nine times out of ten you answer it! And you do so fast - especially if it is over email or slack or some other form of communication - and you do it even faster if it is someone higher up in your organization that asks you the question.
This helpfulness is detrimental to good questioning, and very hard to counteract - but if you are careful you can catch yourself doing it and if you are the one asking the question you can preface it by saying that you want to understand if it is the right question and have an answer tomorrow rather than a fast answer today.
There is a special case of this where a manager wants to be responsive to the team’s questions and immediately answers every single one as soon as a team member comes up to them. I had a number of such managers - smart, helpful and kind - in a course several years back at Google. They had all been identified as micromanagers, and I had been asked to discuss with them why they though that was - and they were all mystified: they said they thought they were just helping, and that they were really responsive all the time and that they tried to give guidance and….
But the reality is this: when someone who works in your team comes to you with a question they often have an idea of an answer and would like to share that with you. They have worked on this and approach you in a humble way, with a question, and are hoping to walk you through the way they have thought about the answer - and then, bam!, you answer it! What you see as helpfulness thus breeds helplessness, and a sense of lesser worth.
I am exaggerating, of course, but only a little. Good management sometimes means not answering the question. And good work often means not answering the question as it is initially asked, but rather exploring the question to understand what it really means and what we should perhaps be asking instead.
Out of a 100 hours working on an issue, how much do you think you spend on finding out if you are answering the right question? Would you benefit from using more time for that?
Moving on to strategic planning: there are several ways in which planning is helped by focusing on questions, but the perhaps most interesting is that questions can shift your perspectives in interesting ways. The planning questions I like most - but there are many others - are questions like this:
Assume we have solved all of our current challenges in policy, what would we then be focused on? (This is an invention I first learned of from a company memo written by Larry Page in which he encouraged Googlers to think about what he called ”the next problem” - assuming you solve the problem you have now, what new problem will you face?).
When will this issue be solved? If we look at some challenges - like privacy - it is interesting to think about if we think that it is an eternal issue or if we believe that we in ten years will be treating it much more as routine compliance. There are few issues that persist over time (death and taxes, I suppose).
Where will this issue be solved? Figuring out where the debate is coming to a head is always helpful - is this a local issue, a market issue, a legal issue or is it one that will be solved nationally? Internationally?
Which questions are we not asking ourselves? A hard one - but again, meant to tease out assumptions for our own planning.
What is going on here? Richard Rumelt’s key question for diagnosing any strategic situation before setting out searching for solutions. I cannot state clearly enough how crucial and important this question is - not least because when we agree to the answer we have arrived at a shared model of reality, and this helps immensely.
Who is playing? This is a question from poker - understanding the table is key in understanding the game!
Who benefits? Marx, the first of the great suspectors, noted that this is a question that helps us understand many social phenomena (albeit not some of the more complex, I would argue - then the question should rather be ”Who thinks they benefit?”).
Strategy can be summarized in questions a team is trying to answer - and while it seems clunky it is sometimes a helpful way to describe a team to other teams - it is also a way to show why some teams, like policy teams, may not be organized in the same way as product teams - since they are answering the political question of how we live together, rather than building products.
We can end with a question to work on: what would happen if you spent 10 to 20 percent more time on the questions you are asking? Would you be willing to engage in that experiment?
So what?
Questions are tools, and I would argue they are tremendously undervalued. Developing questions and working on how we use them in our daily work is a key opportunity that with a minimum of effort can yield interesting results. More than anything, understanding the questions others are asking is crucial to figure out where you can meet in conversation and debate.
And examining your own questions is a great way to change your mind - indeed, probably the only thing that helps you do so, as Socrates noted. I have tried to make the case that working with questions will improve the work you do - especially in policy - across the board, and also will encourage you to change your own mind accordingly, something we all benefit from learning to do.
All questions welcome!
Nicklas