The Art of Asking Questions

The Art of Asking Questions

The Texture of Working With You

Three sentences I wish someone had told me about the human side of work

Andrea Chiarelli's avatar
Andrea Chiarelli
Jan 08, 2026
∙ Paid

In the first three parts of this series, I wrote about the leadership mindset, about decision-making and about career growth. This final part turns to something less visible but just as decisive: the human side of work. It manifests in how expectations are set (or left vague), in what it feels like to work with you day to day and in how much of themselves people feel able to bring into the room.

These things are much harder to measure than outputs or objectives, but they undoubtedly shape who stays vs. who burns out, as well as which relationships become a source of energy rather than friction. So here are the Three Sentences I Wish Someone Had Told Me much earlier in my career.


1️⃣ Unclear expectations are the fastest route to resentment.

If I look back at the most painful situations I’ve seen at work — from people leaving abruptly to teams that fall apart — they rarely started with a big dramatic conflict. They started with unclear expectations.

I once worked with a team where morale had dropped sharply over a few months. Nothing obvious had changed: deadlines were challenging but not impossible and the people were capable. Yet there were constant complaints about “unfairness” and “moving goalposts”.

When I sat down with different team members separately, a pattern emerged: each person thought they were being measured against a different standard. One believed success meant delivering on time, even if the output was imperfect. Another believed quality mattered more than deadlines. A third assumed that “going the extra mile” was expected every time, while others saw that as optional. None of these expectations had been explicitly discussed. They were inferred from passing comments and previous experiences.

The result was predictable:

  • People who prioritised speed felt let down by colleagues who slowed things down for quality checks.

  • People who aimed for quality felt unappreciated when meeting deadlines was praised.

  • People who regularly over-delivered began to resent those who didn’t, while others else felt defensive about the quality of their work.

There wasn’t a difficult person at the centre of the problem. There was a void where shared expectations should have been. When we finally brought everyone together and surfaced these diverging assumptions, there was a clear sense of relief. It wasn’t comfortable (and a few people were very honest about how let down they’d felt) but it was clarifying. From there, the team could agree what good looked like for this project: how to balance time and quality and what counted as reasonable extra effort.

In cases like the above, resentment grows and festers in the gap between our individual assumptions and reality. Once we close that gap, the temperature drops and collaboration can resume peacefully.

We often worry about saying the “hard thing” explicitly. In practice, not saying it is usually harder for everyone in the long run. And, in fairness, in most cases it’s not really that hard!


2️⃣ People remember how it felt to work with you long after they’ve forgotten what you delivered.

In many lines of work, there is a lot of talk about outputs: reports, slides, strategies. Of course, those things matter during a specific activity or engagement. But, over the years, I noticed that what really stays with people is not what you did for them but how it felt to work with you.

I once finished a complex project with a client who had been under a lot of pressure. The final report was solid: strongly argued and on time. A while later, I bumped into one of their senior leaders at a conference. I expected them to mention the findings or how they’d implemented the recommendations.

Instead, they said this: “What I appreciated most was that you stayed calm when everything around us was frantic. You made it feel manageable.”

They had remembered the emotional tone of the collaboration more vividly than the content of the work. That very tone shapes whether people would to work together again (that client did!).

Of course, this doesn’t mean that feelings replace competence. If your work is poor, no amount of warmth will compensate. But once you’re operating at a reasonable standard, the differentiator is often emotional experience:

  • Do people feel respected when they interact with you?

  • Do they feel heard, or talked over?

  • Do they feel you are with them in the problem, or judging them from a distance?

  • Do they leave meetings more settled, or more agitated?

As you can see, your emotional impact isn’t a “soft skill” or an extra. It directly affects who thinks of you for future opportunities and who recommends you. I have made my share of mistakes here too. There have been times when my own stress leaked into conversations (see sentence 3️⃣ in this post) and left people feeling rushed or dismissed. The work still got done, but the relationship took a hit. Repair was possible, but it took more effort than if I’d been more aware in the moment.

People will forget half (if not more!) of what was on your slides within a week. They will remember, often for years, whether working with you felt safe, constructive and human… or draining and tense!

Your leadership and/or communication style should be welcoming to all humans, regardless of role, background, culture or anything else. In non-management language: Just be nice.

3️⃣ The human side of work is an asset to steward; treating it like a risk usually backfires.

Many organisations still treat “being human” at work as something to be tightly controlled: emotions should be minimised and vulnerability is seen as dangerous. The intention is often to keep things professional. The effect, paradoxically, is to make work more a lot more brittle.

I’ve seen this most starkly in teams where any sign of strain is immediately reframed as a performance problem. People will (obviously!) stop admitting when they’re overwhelmed and will also stop asking for help. They will start hiding mistakes until they become crises. In that environment, leaders spend more time managing fallout than doing the work they’re supposed to be doing.

By contrast, some of the healthiest interactions I’ve had were in cases where people had clear stopped pretending that others are robots. One example stands out: in a recent project, the pace had become relentless. I called a meeting and said, “We’re going to hit points where this feels like too much. When that happens, I want us to say it early so we can adjust together, rather than letting the stress leak into everything else. We can’t change the pressure on the client side, but we can decide how we handle it as a team.” From then on, it became a norm to just say when someone was stretched thin, when a deadline was unrealistic or even when personal life was affecting capacity.

Importantly, that acknowledgement didn’t mean that accountability disappeared. It meant that there was room to adjust plans and redistribute work, as well as to simply pause and process the pressure. The result of this is trust. People didn’t have to spend energy pretending and could instead spend it solving the actual problems.

Stewarding the human side of work looks like:

  • making room for honest check-ins (not just status updates)

  • allowing for different working styles where possible

  • treating mental and emotional load as factors to design with, not ignore

  • responding to vulnerability with clarity and care

When leaders treat humanity as a risk to be managed, people hide it. When they treat it as an asset to steward, people bring more of their intelligence and creativity to the table.


For more on the impact of empathy on high-performing teams, see this article I worked on with Colette Molteni!

Empathy Elevated
Empathy In Flow
It’s my absolute pleasure to welcome Andrea Chiarelli on this guest post for Empathy Elevated. His piece unpacks a challenge so many of us face: how to find flow in a world of constant context-switching and ever-shifting teams…
Read more
a year ago · 16 likes · 5 comments · Colette Molteni and Andrea Chiarelli

Closing reflections

The human side of work is easy to overlook because it doesn’t easily show up in dashboards (unless you’re monitoring turnover - but that’s too late…). Yet it does shape how work actually feels day to day, as well as affecting who grows and who stays long-term in an organisation.

The three principles I wish I’d learned earlier are that:

  • You need to set clear expectations or be ready for resentment.

  • You have to watch how you show up every day, because people remember how it felt to work with you long after they’ve forgotten what you delivered.

  • The human side of work is an asset to steward and should not be treated as something that needs risk-managing.

These principles ask you to be clear, emotionally aware and deliberate about the conditions you create for yourself and others.

With this piece, we’ve reached the end of the series:

  • Part 1: how you think as a leader

  • Part 2: how you make decisions

  • Part 3: how you grow over time

  • Part 4: how you relate to the humans around you (this article)

Taken together, this set of small, sentence-sized anchors will help you navigate work when things are complex and the path isn’t obvious.


👉 For subscribers: Two Tools To Strengthen The Human Side of Work

If the ideas in this piece resonated, you’re probably already thinking of a specific situation where expectations are drifting or the emotional tone of collaboration is starting to feel heavier than it needs to. The human side of work tends to fray in small, almost invisible ways. It rarely looks dramatic at first, which is precisely why it catches good and well-intentioned people off guard!

To make this part of the series more actionable, I’ve added two tools for subscribers. They’re designed to help you prevent resentment before it forms and to understand the experience you create for others with more clarity and less guesswork. Both are lightweight enough to be used in real life without turning into yet another process.

What’s in This Guide

1. Mini-toolkit: Aligning Expectations

A fast way to surface hidden assumptions about quality, pace, roles and boundaries. This includes a 10-minute audit, a concise “what good looks like” template, and a simple reset script you can use when things have already started to drift.

2. Reflection: “What Is It Like to Work With Me?”

A practical way to assess your emotional footprint and improve it in small, concrete ways. This includes a short self-scan, four micro-feedback questions you can send to trusted colleagues and a two-week improvement menu.

Try one of these this month. The returns are often disproportionate to the effort!

🔒 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).

Check out the Leader Tools decks


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