Conceivian ← The Briefings Every judgment a leader makes invents or destroys a future. Most are made unexamined.
“Enlightenment comes from being able to tell the difference between assessments and assertions.”
Human beings are assessment-making machines. Every time you open your mouth as a leader, you invent one future and destroy another. The only question is whether you are doing it awake or asleep.
Notice what has been happening since you began reading. Your own assessment machine has been running in parallel the whole time. This is interesting. This is obvious. I already know this. The weather is nice. You cannot turn it off, and you cannot not have an opinion. These constant, mostly invisible judgments silently inform every action and decision you take, and in doing so they quietly build the reality you live in. Our aim is not to stop making assessments, which is impossible, but to wake up to the opinion-making machine that you are, so that in the moments that matter most, hiring and firing, raising money, expanding or contracting, changing direction, you are choosing rather than being swept along.
Where do these assessments come from? From your sensory biology and your background narratives working together. Something happens, a sharp message, a missed deadline, a tone of voice, and it perturbs your nervous system, and that perturbation becomes an invitation to make an assessment. But the assessment that arrives is rarely as personal as it feels. It comes pre-loaded from your history, your culture, your biases, what the tradition calls your historicity, the long-running story of norms and beliefs that shapes how you understand things before you have consciously thought about anything at all. A naive person accepts every invitation of the nervous system and trusts whatever opinion arises from this background programming. A wise leader learns to choose which assessments are worth caring about and which are not.
The first thing that comes to mind is usually not your insight. It is your bias, speaking before you do.
If you trace organizational error back far enough, you arrive again and again at a single confusion. We mistake our opinions for facts. So before anything else, the distinction has to be clean. An assertion is a declarative statement that can be verified true or false against mutually accepted evidence. It is nine in the morning in Seattle. The release shipped on Tuesday. We can check these, because we have built shared infrastructure, clocks, calendars, records, for establishing them. An assessment is different in kind. It is a judgment, an interpretation, an opinion about what something means. Assessments are never simply true or false. They can only be grounded or ungrounded, effective or ineffective, opening or closing.
This is the distinction Flores called enlightenment itself, and the reason it matters so much is that when we treat an assessment as if it were a fact, we doom ourselves and others to it. "Anjali is lazy and unreliable" gets spoken as though it were a measurement, and Anjali is now pinned in a box with no recourse. The leader who can hold the line between the two keeps the future open where the careless one quietly seals it shut.
A grounded assessment is not an accurate analysis of the past. It is a responsible investment in the future. Grounding one does not mean hunting for facts that flatter an opinion you have already committed to, we are all expert at that. It means subjecting the opinion to three questions before you let it drive a decision.
For the sake of what am I making this assessment?
This is the question of care. Is the future of a person, a team, or the business genuinely at stake here, or are you assessing to protect yourself, to look good, to be right, to win a small private victory? Consider the difference. "Jose is a controlling jerk" is a categorical verdict that declares a person into a permanent type and leaves nowhere to go. "Jose has checked three times on a task that is not due until Friday. He may not yet trust me, and I should talk to him" is grounded in care for a shared future. You cannot build anything with a controlling jerk. You can build a great deal with someone you can speak to, confront, and negotiate trust with. What matters was never the fact that Jose checked three times. It was the assessment you made about it.
What assertions and facts support this assessment?
This is the question of evidence, and of scope. Is your judgment a sweeping characterization of a person or situation, or is it bounded to a specific domain and a specific timeframe? "Anjali is lazy" pins her character forever. "Anjali was ten minutes late twice last week, and this began when she was promoted six months ago" is bounded, checkable, and points somewhere useful. Those same facts may lead the head of sales to a completely different and more accurate assessment, that Anjali is not lazy at all but overloaded in a new role and in need of support. The facts did not change. The grounded assessment did, and so did the future it opened.
What possibilities does this assessment open or close?
This is the question of responsibility, and it is the most consequential. Making assessments is serious business, because every one of them invents or destroys a possible future. This is a great company. He is a nasty manager. We are a star team. This market is dead. Each opens certain futures and forecloses others, and the leader is responsible for which. Resignation itself, the mood that nothing new can happen here, is simply an ungrounded assessment that has hardened, and as always, it says far more about the assessor than the situation.
Here is where leadership is truly tested. An effective leader must be able to make and to receive negative assessments, and most cannot do either well. Many are so uncomfortable with a negative judgment that they swallow it, and a company where people are afraid to voice negative assessments is a company where no innovation happens and waste accumulates in silence. Others can only deliver a negative assessment by losing their temper. Neither serves.
The skill is to make negative assessments with care and with permission, grounded in the three questions, so that they land as wake-up calls rather than attacks. And to receive them the same way. When someone offers you a hard judgment, you do not have to accept it as truth. Accept it as what that person thinks, and then ask what concern sits behind it. If you trust their competence and their care, the perturbation of their negative assessment is a gift that can open real insight. If you do not, you can decline it without trying to fix their opinion, because you cannot fix another person's opinion, you can only explore the concern beneath it. Assessments, after all, almost always reveal more about the assessor than the assessed.
And do not forget the other side of the ledger, which modern workplaces have nearly lost: the positive assessment, the act of acknowledgment. Acknowledgment is not flattery or inflating something beyond its worth. It is naming a real possibility you see in a person or a piece of work, and in naming it, making it more real. A leader who has lost the practice of grounded acknowledgment has lost one of the cheapest and most powerful instruments available to them.
Negative assessments are like nuclear energy. Handled with care, they power everything. Handled carelessly, they level the room.
Everything new in the world, every enterprise, every mess, every opportunity, begins and ends with an assessment. The conviction that something must change, that you are the one to change it, that a different future is possible, these are assessments before they are anything else, declarations that do not merely predict the future but bring it into being. Look back at your own life and you will find that the assessments you once made, however unfounded they seemed at the time, are the reason you are where you are now.
So the practice is simple to state and demanding to live. Wherever you are stuck, look for the ungrounded assessment you have quietly accepted as fact and built a wall from. Wherever you are avoiding a hard truth, find the negative assessment you are too uncomfortable to ground and voice. Wherever something deserves to grow, find the possibility worth acknowledging into reality. Your capacity to make grounded assessments is what builds your networks of trust, breaks your cycles of resignation, steadies your hardest decisions, and opens futures you could not previously see. It is, in the end, one of the most serious responsibilities a leader carries, because every time you open your mouth, you are building a world.
“Every time we make an assessment, we invent a possible future, or we destroy one.”Saqib Rasool
If your company is stuck somewhere, there is often an ungrounded assessment quietly holding it there. Finding it together is the kind of work we do. Let us talk.
Request a Conversation →These distinctions come alive when you put them to work. COROS AI holds this Briefing and the rest of our work, ready to think through your situation with you, in private. Begin exploring at app.coros.ai.
This Briefing draws on the tradition of Fernando Flores, our teacher Chauncey Bell, and the speech-act philosophy of J. L. Austin and John Searle. We offer it in their debt.
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