Why can't they hear you?

Selling diagnoses before prescriptions

Do you feel frustrated by the foolishness within your company? Do you often feel misunderstood? Perhaps you struggle to get buy-in to work on the things that seem genuinely valuable? If so, this essay is for you.

This essay is especially for you if your insights often unnerve people. If they often call you pessimistic, overly optimistic, arrogant or just ignore you. If whenever you slow down to explain yourself, you lose them because you often need to explain ten other things before you can land a relatively simple insight.

This illegibility eventually infects almost every relationship including the one with your manager. He often can’t understand what you’re saying, so each meeting seems to make him more anxious, which in turn makes you more anxious. His response to not understanding you results in him trying to micromanage you or making promises which he ultimately doesn’t have the bandwidth to deliver. This frustrates you so you either deflect or ignore it causing him to become even more reactive. Everyone’s acting in good faith but the two of you stop being able to trust each other effectively.

Consequently, you start trying to force alignment by “showing rather than telling”, by “letting the results speak for themselves” to deliver value. This ruffles feathers within the org, but you have enough credibility and a long enough leash to pull it off. The results seem magical when you’re right, and lots of people get really excited and ask you to continue. Unfortunately, you find it hard to disentangle yourself from the project when you realize that the results aren’t what you intended, precisely because everyone’s now excited about these magical results. On the other hand, the same foresight that lets you spot broader foolishness gives you early warning when one of your projects is likely to fail. You see this before anyone else does and course-correct accordingly. But then you get labelled as flaky because you see this before anyone else is able to. Moreover, it’s hard for you to get help navigating any of this because no one deeply understands why you’re doing any of this.

This isolation compounds your frustration and loneliness and sets the stage for a vicious feedback loop. It’s hard to bridge the gap to becoming understood. So you lean deeper into “show rather than tell,” but that makes you even more illegible.

You’d love nothing more than to be seen and understood but you just don’t know how. You know that you’ve got the potential to create far more value and beauty within the company you’re already in. But you don’t know how to get your insights and prescriptions to land.

This cycle eventually culminates into the ultimate dilemma - should you stay or leave? Staying at the company is painful because the constant misunderstandings are extremely draining. Leaving is painful because you love the people there. You’ve got a lot of friends there, love your management chain and are otherwise happy. The money doesn’t hurt either. So walking away feels like you’re giving up on something amazing.

Neither choice feels acceptable, but putting it off amplifies the vicious cycle you’re in along with your stress.

Fortunately, this is a false dilemma. Both choices assume that the problem is entirely the situation (i.e. the job, manager, company, etc). The problem isn’t entirely “out there”. Rather, this dilemma and the vicious feedback loop are downstream of your inability to enroll your co-workers into changing their behavior and how they see the world.

You can’t control how others participate in this feedback loop, but you can change your participation. The prerequisite for inviting people to meet you where you are, is to first meet them where they currently are.

Every habit within an individual arises due to some self-protective or self-serving reason. Consider why you look both ways before crossing the street, shake hands with people when you first meet them, or avoid saying things that will piss off your boss. Each habitual pattern arises consciously or unconsciously due to some contextual reasons. Habits can and do fall out of relevance. For example, the same habits you built to navigate your last boss’s behavior may no longer be relevant with some new boss. Similarly, a scarcity mindset can help in an environment with genuine scarcity, but can be less helpful in an environment with more abundance. Inviting someone to change a habit invites them to ask whether the habit is still relevant. This question invites them to face the archetypical dilemma of psychological development - should I change or should I stay the same? Changing is scary for many reasons. This new habit may not “work”, your identity and therefore relationships within your environment have have to shift, or you could get hurt in the process. Staying the same once you’re confronted with the question is also scary because you could be wrong about staying the same, and could therefore get hurt in the process.

Facing and unpacking a developmental dilemma often requires substantial cognitive and metabolic resources. The deepest dilemmas are often repressed into the unconscious precisely because the individual doesn’t yet have the resources to face them. They might even know how to face them. Therefore, forcing someone to face a deep developmental dilemma produces a proportionate amount of fear.

Consider all those “foolish” company processes you point out to coworkers that just don’t “get it”. These processes are ultimately implemented and sustained by individuals engaging in habitual behavior. These habitual behaviors arose due to self-protective or self-serving reasons. Offering a deep insight that points out the inadequacy of such processes without an adequate container of trust and commitment forces people to face their own developmental dilemmas. That’s scary for them. A cascading loop of fear is created as each subsequent explanation for this deep insight triggers yet another transformational dilemma. Eventually, you get labelled as “confusing” or “crazy” because it’s more self-protective to face the dilemmas you trigger.

Your woes of being misunderstood are downstream of accidentally constantly tripping onto people’s developmental dilemmas.

Your relationship with your manager is not immune from this dynamic. He might not understand what you’re pointing at if it’s nested in dilemmas he can’t immediately access. But he’s formally accountable for you so he often experiences these dilemmas with far higher stakes. Inevitably, he copes by reaching for excessive control to create safety, which can start its own feedback loop if he experiences over-care for you. Eventually, you’re both in mutual threat response due to your reactive cycles. Even meta-conversations about topics like career goals might trigger any number of developmental dilemmas within your manager if these conversations challenge his sense of identity. For example, “If I admit that I can’t help him get what he wants, am I a bad manager?”

Your work is to practice the skill of enrolling people to change their habitual behavior to overcome their developmental dilemmas.

Developing this skill requires both internal and external work. External work changes your actions and internal work changes your being. Your internal work is to integrate various shadows in your unconscious that may stymie your ability to effectively enroll someone. For example, your need to demonstrate intelligence might override your desire to help. Or you might habitually dismiss pushback without genuine consideration. Or get really frustrated and impatient when others can’t “keep up” with you. In each case, your shadows stymie your attempts at enrollment by making it more about proving your worth rather than providing value.

Most people directly jump into selling a prescription to enroll a change in behavior. This only works if the recipient already knows what the problem is, and trusts you enough to accept your prescription. But they’re unlikely to recognize that they have a problem if you’re advocating for a change to a habitual, possibly unconscious self-protective behavior. Or perhaps they’re too scared to act on the prescription with you, if they already know they have a problem.

Effective enrollment involves successfully selling the diagnosis before selling the prescription.

Selling the diagnosis first builds trust. It shows you know what you’re talking about and it helps them feel seen.

The persuasiveness of a prescription depends on the persuasiveness of the diagnosis.

For example, I’ll likely just ignore you if you start insisting I eat broccoli to get healthier. However, if you convince me that I have diabetes and I’ll die within the year unless I eat better, I’ll likely start shoving those greens down my mouth.

The deepest developmental diagnoses generate more fear than shallower ones. The greater the fear, the more trust is necessary for them to even hear the diagnosis. They then need even more commitment to act on its prescription. On the flip side, each successful diagnosis generates more trust in the relationship. That trust, in turn, affords opportunities to create more commitment to enroll them in the corresponding change. Getting to the other side of a prescription then creates the ground to sell them on a scarier diagnosis. A skillful and measured interplay of diagnosis and prescription allows you to gracefully walk up a stair-step of trust and commitment. It feels “slower” in the short term but is often “faster” for landing durable change.

Enrolling others to undergo change is a deep topic. One essay can’t possibly hope do it justice. However, my coach has taught me an overarching sequence that’s been effective for me. Each step in the sequence sets up the subsequent one.

1. Name their unmet need.

   • This helps them feel seen. It lowers their defenses enough to hear what comes next.

   • Warning: Jumping straight to your diagnosis of why their need is unmet signals you care more about your insight than their experience. You’ll trigger a bunch of fear with nowhere for it to go, so they’ll write you off.

2. Describe visible symptoms of the unmet need.

   • Each symptom should err on the side of being “observable objective reality” that any reasonable person within the context would find hard to argue with. Your goal is to describe reality, not interpret it.

   • Warning: Rushing to explain the cause of each symptom signals you care more about demonstrating what you’ve figured out than helping them feel understood.

3. Paint their dream.

   • This shows you know what they want beyond merely pointing at what’s broken. This earns their permission to name the dilemma that’s keeping them stuck.

   • Warning: Skipping this might suggest you’re more interested in the problem than in them.

4. Name the dilemma keeping them stuck.

   • Naming and describing the competing purposes keeping them stuck should create both fear and excitement in their body. Excitement because they’ll start hoping that this is their opportunity to get unstuck. Fear because they’ll know that this is an invitation for change.

   • Warning: You can’t really proceed until you’ve landed this step well. Articulating a dilemma they don’t recognize signals you’re more interested in solving your puzzle than demonstrating that you deeply see the pain of their stuckness.

5. Deliver the diagnosis.

   • Skillfully laying out the deeper pattern underneath the dilemma should produce an “aha!” moment that simultaneously addresses fear and builds trust.

   • Warning: This step is load-bearing for everything that follows because it consolidates the trust that allows them to hear your prescription.

6. Land the key distinction

   • “Confusion” comes from the Latin verb “confundere”, which means “to pour together”. The boundaries of things “poured together” get dissolved, leading to foolishness and disorder.

   • Every developmental dilemma is downstream of some deeper confusion where multiple ways of being have become unhelpfully mixed up. The key distinction separates this confused mixing to make the prescription obvious.

   • Warning: A distinction that doesn’t click means you’re teaching your framework rather than resolving their confusion.

7. Sell the prescription.

   • The prescription should feel inevitable and unsurprising if you’ve done your job up to this point correctly.

   • Each successful delivery builds enough trust that they’re now willing to commit to the change you’re pointing at.

   • Warning: A prescription that surprises them often means you’ve skipped some important steps.

Steps 1-4 meet them where they are. Step 5 sells the diagnosis. Steps 6-7 sell the prescription.

The point of this essay isn’t to convince you to stay at your job or leave it. It’s to show you that your woes stem from your inability to enroll people within your current environment. Staying at this company may be a bad idea if the environment isn’t conducive to practicing enrollment. Similarly, leaving may not fix the problem if you leave and then don’t improve at enrollment.

Getting better at enrollment is the highest-impact path for you to feel seen, understood and to have your insights land for other people. Enrollment is a skill and therefore requires practice. Success won’t be overnight, but you’ll know you’re on the right track when you’re increasingly able to influence people over whom you have no formal authority.

Acknowledgements

Thank you to Brian Whetten for teaching me everything I’ve articulated in this essay.