We all know that trust is one of the most important aspects in our lives, yet it doesn’t mean everyone can handle it well, and sometimes some people are so bad on it that many problems in their lives are due to that. As far as I know, the maturity of thinking about trust can at least be categorized into following levels - from the most dysfunctional to the most effective and efficient, even though it’s clearly oversimplified and it’s entirely possible that there are even lower and higher levels than those listed below:

Level 1

Some people either always completely trust everything or always completely distrust everything without even assessing what that thing is, and we know that’s it’s so unrealistic and overgeneralized that only very immature people won’t see past that. Fortunately, such naive people are extremely rare, and they won’t remain that uneducated for long.

For instance, some people do deeply believe that they can only trust themselves and everyone else is always completely untrustworthy while they know next to nothing about any of the others. Needless to say, their lives will be in deep struggles when everyone is so connected to each other and the demands of a person becomes so complex in the modern world that it's incredibly hard to be totally self-sufficient forever.

For those who choose to always completely trust everything, they’ll soon fathom the truth that something really can’t be trusted at all, and either they’ll ascend to Level 2, or go to the other extreme - always completely distrust everything, which will cause their lives to be even more miserable. Anyway, they’ll soon see past the false dilemma between trusting everything and distrusting everything, thus it’s very improbable that they won’t ever ascend to Level 2 in their lives.

Level 2

Some people are better in that, they know that not everything can be trusted but there are still something trustworthy. However, they still either completely trust something or completely distrust something, and they’ll quickly judge whether something is trustworthy or not, so it’s still a rather black and white thinking that doesn’t work well in reality, and this inflexibility, albeit not uncommon at all, will soon hit such people so hard that they’ll have to relearn what trust really is sooner or later.

For instance, those deeply suffering from confirmation bias without even knowing will likely just use the first impression from someone to decide whether that person can be completely trusted or is completely untrustworthy, and will never reevaluate the decision until the reality teaches those people a tough lesson. Of course, judging someone using the first impression alone is judgmental to the extreme, and the negative consequences are so obvious that it’s even hard for those people themselves to look the other way.

For the things they completely trust, quite some of them will turn out to be untrustworthy, so those people will turn from completely trusting them to completely distrusting them, and if there are more and more such things, those people will distrust more and more things in their lives, therefore the whole trend will induce them to descend to Level 1 - always completely distrusting everything. On the bright side, because it’s even harder to remain on Level 1 than ascending from Level 2 to Level 3, when those people ascend back to Level 2 after descending to Level 1, they’ll be forced to let go of the false dilemma between complete trust and complete mistrust towards something, and hence ascend to Level 3.

Level 3

Some people realize that trust isn’t either all or nothing, but rather a continuous spectrum, so instead of just thinking whether something is trustworthy or not, they’ll also think about how much it can be trusted, so it’ll take them some time to be familiar with something before evaluating how much it can be trusted. Still, it’s a static thinking that misses the key that how much something can be trusted can change over time under certain conditions(unless such signs are so obvious that it’s impossible for such people to miss them), so they’ll be eventually caught completely off guard, even when there were already so many warning signs that they completely missed(because they never have the habit to actively seek for such signs to begin with), and they’d have long decreased the amount of trust if they noticed those signs.

For instance, let’s say an employee has worked in a company for a year, and the track record of that employee suggests that, while that employee isn’t trustworthy enough to take the most crucial and difficult tasks, that employee is trustworthy enough to take some other important tasks that are still somewhat challenging but nowhere as difficult. However, because that employee mentally suffers deeply from suddenly becoming single without knowing what’s going on, that employee can no longer function as effectively and efficiently as before, so some of the latest important tasks, which is very similar than those done well by that employee, suddenly failed badly, even though that employee didn’t even try to hide the personal suffering in the company.

As the boss decided that that employee is that trustworthy solely based on the performance of that employee over the last year, without even trying to periodically check for any abnormalities from that employee, that boss missed many obvious signs from that personal suffering and assigned those tasks to that employee anyway, hence causing the totally unexpected failure from that employee. While it’s clear that that employee is also at fault and responsible for not actively informing the boss about the personal suffering and its impact of future performance, the point remains that assuming that the trustworthiness of something is a constant to be found can be very dangerous, so unless those people at this level still didn’t grasp the utter horror of even lower levels, they should figure out the problem of not dynamically adjusting the amount of trust of something over time, and thus ascend to Level 4.

Level 4

At this point, some people finally understand that trust is actually dynamic rather than static, so dynamic thinking is needed when thinking about trust, meaning that instead of just using past experience and track record to judge how trustworthy something is right now, they’ll also consistently look for both positive and negative signs at the present moment, therefore they can take these present factors of changes of trustworthiness into account as well. Although it’s already pragmatic enough to think about trust this way and not many has already reached this level, the problem is that it’s just reactive rather than proactive, so while they can quickly adjust the amount of trust towards something after those factors of changes have already manifested, they’re still just passively reacting to these signs instead of actively trying to figure out the essence behind those factors.

Let’s say there’s another employee who was prolific and reliable at the start slowly became less and less effective and efficient, and eventually dysfunctional altogether due to prolonged covert workplace bullying hidden from the boss. So the boss, noticing this trend without knowing the root cause behind this issue, could only try to ask that employee about the lengthened performance drop, while gradually assigning less and less challenging and important tasks to that employee, with the benefits given to that employee being smaller and smaller, and had to unwillingly fire that employee at the end, because the boss failed to know the truth that way.

Although it’s hard to blame the boss for not knowing what’s really going on with that employee when that employee didn’t even try to report anything, it still shows the issues of just passively reacting to the changes of the amount of trustworthiness, as it could’ve been become more rather than less trustworthy if the underlying conditions of changes were revealed. If the boss tried to proactively investigate what makes the employee appear to be less and less trustworthy besides just asking that employee personally, the boss might have discovered the workplace bullying in secret and kept an originally competent and loyal employee, rather than having to reluctantly fire that employee and possibly repeating the history in the future unknowingly.

Level 5

This is where proactive thinking comes in, but people of this level are hard to find as it's hard to keep being on this level, and the paradox is that they don’t consciously emphasize trust anymore, because to them hypothetical thinking is much more flexible and responsive when it comes to constantly reassess the essence of the ever changing conditions behind the factors that increases and decreases the amount of trustworthiness towards something. So instead of thinking about how much something can be trusted at any moment, they think about on what probability that how something will behave under what conditions, and the essence behind the when and why of such correlations and causation hold, so once those underlying conditions change, those people can immediately adjust and correct their hypotheses while reconsidering whether and which previously established contingencies need to be executed(or swiftly come up with a backup plan that didn’t exist beforehand), and when they’ll be executed to what extents.

For example, an employee formerly working for a rival company has demonstrated extraordinary competence and willingness to take the most challenging and important tasks in the current company without asking anything extra in return, and that employee can get them done all exceptionally well, so the current boss happily give that employee more and more privilege and recognition within the company, and thus that employee can ascend incredibly quickly there, regardless of the fact that that employee was frequently badmouthing the previous employer, which is the rival company.

But as what that employee has shown is far too good to be true and the badmouthing of the rival company from that employee doesn’t match what the boss knows about that company, the boss can’t stop to suspect that that employee, which worked for a rival company, is just acting and up to something even bigger, so on one hand the boss appeared to have complete trust over that employee by giving that employee sole discretion over a new and large project that demands access to valuable company secrets to lower the guard of that employee, but on the other hand privately asked a trustworthy security expert in the current company to silently monitor the activities in that project from that employee behind the scenes. It turns out that that employee being suspected is actually an industrial espionage still working for that rival company, and is assigned to elusively install an undetectable backdoor deep inside the new project using internal software systems that can access the most confidential and sensitive algorithms and data of the current company, so the rival company can later invisibly hack into that backdoor to steal those crucial information while keeping a low profile, and the frequent badmouthing from that employee about that rival company is just a cover-up.

Hypothetical Thinking

While it’s clear that it’d be overkill and exhausting to use hypothetical thinking over trivial matters as well, when it comes to the key moments of determining the trustworthiness of something vital, hypothetical thinking can still come into handy. Also, do note that thinking about trust and hypothetical thinking don’t have to be mutually exclusive, and in fact they can work well together, even though such unison will never be easy nor cheap.

Although there are many factors affecting the trustworthiness of someone, usually the most subjective and unclear one is motivation, which can be broken into at least these following 5 basic building blocks:

1. What does that someone need to get right now?
2. What does that someone need to avoid right now?
3. What does that someone want to get right now?
4. What does that someone want to avoid right now?
5. What is the emotional statuses of that someone right now?

Other factors, like whether that someone has the experience, knowledge, information, resources and technique to get something done, while still absolutely necessary to determine the trustworthiness of that someone over that something, are usually much more tangible and visible to the others, so if one can reliably comprehend the basic building blocks constituting the motivation of someone, the other factors should also be of little challenge. As long as one can keep in touch with the factors constituting the trustworthiness of someone, that someone will unlikely to suddenly change from very trustworthy to very untrustworthy without being noticed beforehand, so it’s generally hard to back-stab those with hypothetical thinking as their second nature, at least not with them unprepared.

When using hypothetical thinking, one doesn’t just come up with a single hypothesis and call it a day, but should instead explore at least several ones that are reasonably likely to warrant further verification, and act on the currently most probable one, with contingencies designated to handle cases when that hypothesis is proven to be wrong, until it’s proven to be wrong and act on another hypothesis. Do note that besides having to actively and consistently look for signs both supporting and negating the hypotheses, while a hypothesis can be the most probable one right now, after some time with some changes, another hypothesis can become the most probable one later, and sometimes one even needs to generate new hypotheses on the fly, so the whole hypothetical thinking is a constantly dynamic process, and there should be as few unsupported assumptions as possible at any moment.

Of course, it’s impossible to be even near perfect, so no matter how experienced, knowledgeable and skillful in practicing hypothetical thinking in real lives, there will always be times where one will be caught completely off guard, so hypothetical thinking isn’t about trying to eliminate uncertainty and the concept of trust altogether, but rather minimize the amount of uncertainty and reliance of trust while accepting that uncertainty is a nature of lives and trust that one can deal with most of the remaining uncertainty most of the time. Because of that, those practicing hypothetical thinking should also be ready to be completely caught off guard, and that means they’ll have to be able to be very flexible, spontaneous and versatile at any time, even though one will have to take very complicated and convoluted paths to get there.

Combining everything, those with hypothetical thinking in mind first observe and test someone for a while, then act on a hypothesis based on the initial track record of that someone collected during that period, and those people will continue to look for signs that indicate both the increase and decrease the trustworthiness of that someone. If the hypothesis suggests that some such positive or negative signs will manifest and they mostly do, then the hypothesis is somehow verified and should be kept, otherwise it’s shown to be less and less accurate and should be tweaked somehow, and when there are enough such significant mismatches, the hypothesis will be proven to be dead wrong so those people will have to act on a new hypothesis, and the whole cycle will repeat again and again.