The Art of Asking Questions

The Art of Asking Questions

Stop Owning Other People’s Feelings

Better questions for boundaries at work

Andrea Chiarelli's avatar
Andrea Chiarelli
Feb 05, 2026
∙ Paid

Your manager gives a quick end-of-week update. It is mostly positive, but one line lands awkwardly: “This was good, but next time I need you to be more strategic.”

You nod, thank them and head home. Then the weekend begins to shrink. The comment plays on repeat all weekend, while cooking and while walking. Was that a warning? Or a sign of disappointment? Your mind fills the silence with imagined verdicts.

By Sunday evening, you feel exhausted. Not from anything that you have been doing, but from the attempt to read the manager’s mind and pre-empt their judgment.

We often treat this kind of spiral as a personal resilience problem, but I would argue that it is partly a boundary problem. One of the most helpful ways to explore this comes from a book called The Courage to Be Disliked, co-authored by Ichiro Kishimi and Fumitake Koga (special thanks to Colin Gautrey for introducing me to this book!).

The Courage to Be Disliked is written as a dialogue between a sceptical young man and a calm philosopher, unfolding over five “nights.” The conversational format is part of the message: instead of delivering a neat lecture, the book shows how resistance develops over time:

  • The Youth in the book voices the objections many readers carry — that the past has already sealed their fate, that other people’s judgments are unavoidable, that happiness feels like a privilege reserved for the confident.

  • The Philosopher responds through the lens of Alfred Adler’s psychology, repeatedly steering the conversation back to agency and the relational nature of freedom, which is less about controlling future outcomes and more about choosing your stance in the present.

In my view, the idea of task separation emerges as one of the book’s most practical bridges between philosophy and everyday life. This is what I explore below.


A Question To Change The Emotional Flow

The entry point into task separation is a pretty simple question:

Whose task is this?

In this context, a “task” isn’t a piece of work. It’s any responsibility that belongs to someone: what they choose, how they act and how they respond. Your task is what you can own in good faith. Other people’s tasks include their interpretation, their feelings and their next step.

This distinction matters because blurred tasks create two patterns at work: we often avoid clarity to stay liked, or we over-function to keep everyone comfortable. Task separation gives you a way out. It turns boundaries from a personality trait into a repeatable mental algorithm.

Because many workplaces effectively train people to please their boss (though very few organisations would admit it!), task separation can feel almost rebellious at first: it asks you to stop managing your manager’s and colleagues’ feelings and start managing your own responsibilities.

To make these concepts practical, I’ll show you how to apply task separation to four moments where confusion is common: giving feedback, receiving feedback, being misunderstood and watching someone make a choice you wouldn’t make yourself.


Moment 1: Giving Difficult Feedback

Many of us avoid direct feedback because we link clarity to cruelty and boundaries to rejection. The hidden bargain is usually emotional: “If I say this plainly, they might dislike me.” And that fear is understandable; however, this is also a sign that tasks are being mixed.

Your task is to be fair, accurate, timely and respectful when sharing feedback. The other person’s task is how they feel about hearing it and what they decide to do with it. You can influence their receptivity through tone and support, but you cannot own the emotional outcome.

When you lose sight of this divide, feedback dilutes into vague hints and long preambles that try to soften the truth until it becomes ambiguous. In the short term, this preserves harmony; but, in the long term, it erodes trust and limits learning.

A quick internal prompt before you speak

  • What is my responsibility in this conversation?

  • Am I trying to be kind, or am I trying to be liked?

  • What would clarity look like if I were not negotiating with imagined disappointment?


Moment 2: Receiving Feedback Without Collapsing

Receiving feedback is an underrated boundary challenge because it looks passive on the surface. Someone speaks and you listen. But, internally, many of us treat feedback as a referendum on our worth rather than a data point about our work.

This is where the task separation can act as a stabiliser. Your task is to listen well and decide what to do with the information. The other person’s task is to hold their opinion and, if they are your manager, to set expectations that align with the role. You do not need to absorb their emotional tone as if it were a permanent truth about you.

When tasks are blurred, feedback triggers either defensive dismissal (“They’re unfair”) or over-identification (“They’re right, I’m not cut out for this”). Both reactions hand your agency away. A more grounded posture is to treat feedback as a joint attempt to improve outcomes, not as a verdict on identity.

A quick internal prompt before you internalise everything

  • Is this feedback about my work, my approach or my identity? (it’s almost never about your identity!)

  • What part of this is useful data?

  • What part is interpretation I can acknowledge without adopting?

Pick the right ‘task,’ and you’ll end up somewhere positive and constructive. Pick the wrong one, and you’ll feel like you’re in a deep dark wood that you can’t seem to escape.

Moment 3: Being Misunderstood Or Criticised

There is a special kind of workplace pain that arrives when your intentions are misread. You send a concise email and get labelled abrupt, or you enforce a process and get called rigid.

This is where task separation can feel almost too blunt: am I supposed to just accept being misunderstood? Not exactly: you can correct the record. You can clarify your reasoning. You can refine how you communicate. Those are your tasks. What is not your task is to guarantee that everyone’s story about you becomes flattering or accurate. That is impossible in any complex organisation.

A useful boundary here is one round of clarity. Offer your rationale once, calmly and specifically. If the narrative you don’t like persists, you are allowed to stop arguing with the version of you that exists in someone else’s head. That’s just how their life experiences and context led them to filtering your actions.

A quick internal prompt before you spiral

  • Am I reacting to facts, or to imagined future judgments?

  • What part of this story is mine to adjust, and what part is theirs to hold?

  • If I stopped trying to control the narrative, what would I do next?


Moment 4: Watching Someone Make a Choice You Don’t Approve Of

This is a boundary test we rarely point to, because it feels very close to mentoring or taking responsibility. A colleague resists advice that seems obviously helpful. A team member chooses a slower path. A direct report wants a role you think they are not ready for.

The temptation is to push harder. We tell ourselves that if we care enough, we should be able to save people from their own decisions. The Adlerian view is restrained and, at times, unsettling. You can offer perspective, information, and support. You cannot live someone else’s life for them. You also cannot make their growth linear or safe.

This is where many leaders accidentally cross from guidance into control. The difference is not the intensity of the feeling, but in whether you respect the other person’s ownership of their path.

A quick internal prompt before you over-function

  • Am I helping them think, or am I trying to decide for them?

  • Have I clearly offered my perspective once?

  • What would different paths look like here?


A Sentence Worth Keeping On Your Desk

If you only retain one portable micro-tool from this article, let it be this sentence:

My job is to be clear and responsible. Their job is to decide how to respond.

To be clear, this is not emotional detachment! It is emotional precision. It helps you show up with integrity while avoiding the corrosion that comes from carrying other people’s reactions as if they were your responsibilities. It also protects your relationships: people trust leaders who are honest and steady more than they trust leaders who constantly try to perform harmony but have lost sight of clarity.


A Small Experiment For This Week

Choose one situation that mildly irritates or worries you. Not the most painful one - start small! Then write down three columns:

  1. What happened (just the facts).

  2. What I’m taking responsibility for.

  3. What might belong to someone else.

Then ask yourself: What would change if I only carried what is truly my task? At that point, reflect on how this compares to the past. What responsibilities could this reflection help you let go of, vs what did it strengthen or elevate?

If the idea is working, you will not feel instantly fearless. But you will likely feel lighter and clearer, and start to notice how often you have been working overtime in someone else’s emotional department.

That is the way boundaries begin: not with a confrontation, but with a reallocation of responsibility.


👉 For subscribers: The “Whose Task?” Script Library

If you want to turn the ideas in this article into a repeatable leadership habit, this is the practical companion piece. In the main article, I’ve tried to keep the scripts light so the core concept stays readable. In this toolkit, I’m providing a full set of copy/paste-ready coaching and boundary scripts, mapped to the four moments above, with a few variations for different contexts (manager–direct report, peer-to-peer, and cross-functional work).

The goal is simple: help you stay within your task without becoming vague or overly invested in trying to manage other people’s emotions that you can’t control.

🔒 What follows is for paid subscribers.

If this post was useful and you want a practical companion for real-world management and leadership conversations, Leader Tools is something I use that might also help you. The referral link below gives you 10% off, or you can use the code ANDREA10 at checkout (I will earn a fee if you purchase through this link, at no cost to you).

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