Most leaders ask “How are you doing?” and accept “Fine” as a complete answer, even when everything is falling apart.
This pattern reveals a fundamental problem with wellbeing conversations at work. The question is too vague to invite meaningful disclosure, and the casual tone signals you’re asking out of obligation rather than genuine interest. When your question sounds like a greeting, you get greeting-level answers in return.
The challenge for leaders is understanding how your team is experiencing work without crossing into territory that feels invasive or performative. You need to identify early warning signs before they become crises, while respecting that people have legitimate reasons to maintain professional boundaries.
Coming up, we’ll explore the specific questions that open honest dialogue about wellbeing, why generic check-ins fail, and how to create conversations that build trust rather than awkwardness. This approach comes from Sara Ross, founder and Chief Vitality Officer at BrainAMPED and author of Dear Work: Something Has to Change, whose research focuses on helping leaders create environments where people can thrive.
Why Generic Questions Get Generic Answers
Before you can ask better wellbeing questions, you need to understand why the questions you’re currently asking fail to get honest answers.
When someone brings a question or concern to you, Ross teaches leaders to respond with curiosity:
How are you doing from an energy perspective, like, mentally, emotionally, physically? What’s really working? What’s getting in the way? What’s distracting for you? Is there anything that we can do as a team I can do as a manager that would help remove some of those obstacles or distractions?
Notice the specificity. Ross asks about energy across multiple dimensions. She invites both positive and negative feedback. She frames her role as removing obstacles rather than evaluating whether they’re working hard enough.
Compare this to “How are you doing?” The generic question gives people no framework for answering honestly. They don’t know if you’re asking about work or life in general. They don’t know how much detail you want. They don’t know if you have time for a real answer. So they default to “fine” because that’s the socially appropriate response to a greeting-level question.
The problem intensifies when you only ask about wellbeing during formal performance reviews or when something seems obviously wrong. These contexts signal that wellbeing conversations are special interventions rather than normal parts of how you work together.
The Power of Demonstrating True Curiosity
Ross emphasizes something most leaders overlook: the quality of your curiosity matters more than finding perfect questions.
I think we get so caught on finding the perfect questions that we completely underestimate how just being present, demonstrating true curiosity and care, and just trying to open up those conversations and be vulnerable matters.
This insight changes everything. You’re not trying to execute a perfect script. You’re trying to create genuine connection where someone feels safe being honest about their experience.
True curiosity shows up in several ways:
You give the conversation your full attention rather than checking your phone or thinking about your next meeting. You ask follow-up questions that dig deeper rather than immediately offering solutions. You listen more than you talk. You make space for silence instead of rushing to fill every pause.
Most importantly, you respond to what someone shares without judgment or defensiveness. When someone tells you they’re struggling with workload, you don’t immediately explain why the workload is necessary. You seek to understand their experience first.
The vulnerability piece matters too. When you share something about your own experience first, you create psychological safety. “I’ve been noticing my energy is lower lately because of back-to-back meetings” makes it safer for them to share their own struggles.
Questions That Address Energy and Capacity
Energy is one of the most important dimensions of wellbeing to understand because it affects everything else. When someone’s energy is depleted, every challenge feels harder. When their energy is good, they can handle more complexity and pressure.
Ross frames wellbeing questions around specific dimensions:
How are you doing from an energy perspective, mentally, emotionally, physically?
This framing gives people concrete categories to assess. They can think about their mental energy (clarity, focus, decision-making capacity), emotional energy (mood, resilience, sense of connection), and physical energy (sleep, health, stamina).
Here are specific questions that help you understand someone’s energy and capacity:
“On a scale of 1 to 10, where would you put your energy level right now?” The numeric scale gives people an easy way to communicate without requiring elaborate explanation. A 3 signals something very different than an 8.
“What’s been draining your energy lately?” This question acknowledges that energy depletion is normal and focuses on identifying sources rather than making someone feel they should have unlimited stamina.
“Are you getting enough time to recover between intense work periods?” This recognizes that intense periods are normal but recovery matters for sustainability.
“What gives you energy at work?” This flips to the positive and often reveals what’s working well. It also provides insight into what motivates and engages this person.
The goal is understanding the patterns in someone’s energy so you can identify whether their current pace is sustainable.
Questions About What’s Working and What’s Getting in the Way
Beyond energy levels, you need to understand the quality of someone’s work experience. Ross models this with her framing:
What’s really working? What’s getting in the way? What’s distracting for you?
Notice the balance. She asks about what’s working before asking about problems. This prevents the conversation from becoming purely deficit-focused. It also gives you insight into what conditions help this person do their best work.
“What’s been taking up most of your mental space this week?”
This helps you understand what’s dominating their attention:
- Productive focus on important work
- Anxiety about something they feel unprepared for
- Resentment about something unfair
“Are there any obstacles or distractions making your work harder than it needs to be?”
Ross uses this language deliberately because it:
- Positions you as someone interested in removing obstacles
- Avoids evaluating whether they’re working hard enough
- Invites specific feedback you can act on
“What kind of support would be most helpful to you right now?”
This question:
- Avoids assuming you know what they need
- Respects that support looks different for different people
- Invites them to identify what would actually help
“What’s been most satisfying about your work lately?”
This question:
- Prevents conversations from becoming purely deficit-focused
- Surfaces what’s working well
- Often reveals values and motivations
These questions help you understand whether someone’s work experience is sustainable and where you might be able to make adjustments that improve their wellbeing.
The Three Follow-Up Questions That Deepen Understanding
Ross teaches a three-question framework that works powerfully in wellbeing conversations. When someone shares a challenge or concern, these questions help you understand the full picture:
“What have you tried so far?”
This question serves multiple purposes:
- Shows respect by acknowledging they’ve likely thought about the situation
- Gives you information about their problem-solving approach and resources
- Prevents you from suggesting things they’ve already attempted
“What else would be important to consider about this situation?”
This question broadens how someone thinks about their challenge:
- Expands perspective by prompting them to consider other viewpoints
- Identifies stakeholders who are involved or affected
- Surfaces hidden factors they might have overlooked
- Reduces isolation as they realize others are connected to the situation
- Reveals complexity showing the situation has more dimensions
- Opens possibilities since more dimensions means more potential solutions
“What would be most helpful?”
This question:
- Puts them in the position of identifying what they need
- Builds ownership of the solution
- Respects their expertise on their own situation
Ross explains the impact:
When you help people start to recognize and think through solutions, even if they feel overwhelmed, you help build the confidence that they can move things forward. Feeling empowered is genuinely energizing.
These three questions prevent you from immediately jumping to solutions or taking problems onto your shoulders. They create space for the person to process their own experience and identify what would actually help.
How to Ask Without Creating Awkwardness
The questions themselves matter, but how you ask them determines whether someone feels cared for or interrogated. Ross addresses this:
Openness, just I think we get so caught on finding the perfect questions that we completely underestimate how just being present, demonstrating true curiosity and care, and just trying to open up those conversations and be vulnerable matters.
Several factors make the difference between genuine inquiry and uncomfortable interrogation:
Make these conversations regular and predictable. When wellbeing check-ins are routine rather than only happening when something seems wrong, people feel less defensive. Regular one-on-ones create the natural container for these discussions.
Start with your own vulnerability. Share something about your own experience first. This creates reciprocity and signals that honesty is safe.
Give space for silence. Don’t rush to fill pauses. Often people need a moment to decide whether to give a real answer or a safe answer.
Respond with more questions before jumping to solutions. When someone shares something difficult, resist the urge to immediately fix it. Seek to understand first.
Respect boundaries. If someone gives a brief answer and clearly wants to move on, let them. Pushing for disclosure when they’re not ready damages trust rather than building it.
The goal is creating conversations that feel natural rather than forced, where people can be honest without fear of judgment or unwanted consequences.
Questions That Reveal Whether Someone Feels Supported
Part of wellbeing involves whether people feel they have the support they need. Ross frames this as asking what you can do as a manager to help:
Is there anything that we can do as a team I can do as a manager that would help remove some of those obstacles or distractions?
This question positions you as someone who wants to support rather than evaluate. It invites specific feedback about what would actually help rather than making assumptions.
“Do you feel you have what you need to do your work well?” This broad question surfaces resource gaps, unclear expectations, missing information, or inadequate tools.
“When you’re dealing with something challenging, do you feel comfortable asking for help?” This assesses psychological safety. If someone says no, you’ve identified a serious problem that affects everything else.
“What would need to change for this work to feel more sustainable?” This question acknowledges that sustainability matters and invites concrete suggestions.
The responses to these questions tell you whether your support is landing effectively or missing the mark entirely.
The Leadership Behavior That Makes Honesty Safe
Your team watches what you do more than they listen to what you say. Ross emphasizes this point about setting the tone:
If you’re a leader, I mean, you set a tone, whether you realize it or not you lead by example, whether you choose to or not. And so I think for leaders to also express some of the things that they’re experiencing what’s working for them, and what has been really challenging.
When you’re open about your own challenges, you give permission for others to do the same. When you share that you’re adjusting your schedule to manage energy better, they feel safer doing the same. When you acknowledge that a particular week was difficult, they feel less need to pretend everything is always fine.
The opposite is also true. When you never admit struggle or always project that everything is under control, your team learns that vulnerability is not acceptable. They hide their challenges until they become crises.
This doesn’t mean oversharing or making your struggles your team’s problem. It means being human and honest about the reality that work sometimes involves challenges, and that managing those challenges skillfully is part of the job.
When to Check In Beyond Regular Conversations
While regular check-ins create the foundation, sometimes you need to initiate conversations based on what you observe. Ross’s framework helps here:
If you notice changes in someone’s energy, behavior, or engagement, that’s a signal to check in more directly. But how you frame the check-in matters.
Don’t say: “You seem stressed. Are you okay?” This puts someone on the defensive and makes them explain themselves.
Instead try: “I’ve noticed your energy seems different lately. What’s going on?” This is observational rather than judgmental. It opens space for honest conversation without accusation.
Don’t say: “Why are you so tired?” The word “why” sounds accusatory and demanding.
Instead try: “I’ve noticed you seem tired. What’s been going on?” This shows concern without judgment.
The principle underlying both examples is simple: wellbeing questions should open space for honest conversation, not make someone feel judged or defensive.
What to Do With the Information You Gather
Asking wellbeing questions creates an obligation. Ross is clear about this:
Is there anything that we can do as a team I can do as a manager that would help remove some of those obstacles or distractions?
You cannot ask someone to be vulnerable about struggles and then do nothing with that information. When someone shares concerns about their wellbeing, you need to respond with action.
This doesn’t mean you can fix everything. But it means you need to:
Acknowledge what you heard:
- Summarize back to them to confirm understanding
- Example: “It sounds like the back-to-back meetings are leaving you no time for focused work, and that’s affecting your energy and effectiveness”
Identify what you can influence:
- Be honest about what’s in your control and what’s not
- Example: “I can’t change our Q4 deadline, but I can protect your mornings from meetings for the next three weeks”
Create a specific next step:
- Avoid vague promises to “work on it”
- Example: “Let’s block out 8 to 11 AM on your calendar starting Monday for deep work. I’ll decline any meeting requests during that time”
Follow up:
- Check back in after implementing changes to see if they’re helping
- Example: “We’ve had those morning blocks in place for two weeks. Is that making a difference?”
When you consistently follow through on what you learn from wellbeing conversations, people trust that it’s safe to be honest with you. When you ask but don’t act, people learn that honesty has no benefit.
The Pattern That Prevents Helplessness
One of the most important insights from Ross’s work addresses how we talk about challenges. She observes:
We now talk about stress to represent every single thing we don’t like, whether we are bored, we’re stressed, we’re busy, we’re stressed, we’re overwhelmed or stressed, we have a difficult person we’re dealing with, we’re stressed.
This generalization creates helplessness. When everything becomes “stress” and stress feels universally negative, people lose their sense of agency.
Part of asking good wellbeing questions involves helping people distinguish between different types of challenges. Some pressure is productive. Some stress signals growth. Some discomfort indicates learning.
Problems arise when pressure is too intense or sustained without recovery. When you help someone name the specific nature of their challenge rather than generalizing it as “stress,” you help them identify what would actually help.
This is where Ross’s follow-up questions become powerful:
- What have you tried so far?
- What else would be important to consider?
- What would be most helpful?
These questions move someone from “I’m stressed and helpless” to “Here’s the specific challenge I’m facing and here are potential ways to address it.”
The Importance of Agency in Wellbeing Conversations
Ross emphasizes a critical point about agency:
I cannot think of a situation outside the immediacy of something occurring where there was not an opportunity for someone to do something for themselves to change that situation.
This perspective matters for how you approach wellbeing conversations. You’re not trying to fix everything for people. You’re trying to help them identify what they can influence and what actions they can take.
When you immediately jump to solving every problem someone raises, you accidentally reinforce helplessness. You send the message that they need you to fix things for them.
When you use the three-question framework to help them think through their situation, you build their confidence in their own problem-solving ability. This is especially important for wellbeing because so much of wellbeing involves the choices people make about how they manage their energy, set boundaries, and respond to challenges.
Your role as a leader is to remove obstacles you control, provide resources and support, and help people develop the skills to manage their own wellbeing effectively. It’s not to carry responsibility for everyone’s wellbeing on your shoulders.
Making Wellbeing Conversations Part of How You Lead
The most effective wellbeing questions are the ones you ask consistently over time, not just during annual reviews or when someone seems obviously struggling.
Ross emphasizes the importance of regular check-ins and creating openness:
I think we get so caught on finding the perfect questions that we completely underestimate how just being present, demonstrating true curiosity and care, and just trying to open up those conversations and be vulnerable matters.
Build wellbeing questions into your regular rhythm:
In weekly team meetings, start with a quick energy check where everyone shares on a scale of 1 to 10. This takes two minutes and surfaces early warning signs.
In monthly one-on-ones, dedicate the first 10 minutes to wellbeing conversation using the questions we’ve covered. This signals that the person matters as much as the work.
In quarterly reviews, include specific discussion about sustainability alongside performance topics.
The goal is making wellbeing conversation as normal as discussing project status. When these conversations become routine, people stop seeing them as special interventions and start viewing them as how you work together.
Moving From Questions to Culture Change
Asking better wellbeing questions is a starting point, not the complete solution. These questions reveal what needs to change in how your team works together.
Ross’s research emphasizes that you need to address not just individual wellbeing but the systems and culture that affect it:
We have created an environment where I think work is supposed to fix people, and people are waiting to be fixed versus saying have I done everything in my power to change the situation.
The pattern you’re building is one where people feel safe being honest about their experience, where you respond to that honesty with genuine support, and where the culture evolves based on what you learn.
This requires courage. You’ll hear things that are uncomfortable. You’ll discover problems you don’t immediately know how to solve. You’ll need to make difficult decisions about workload, resources, or how you operate.
But the alternative is worse. Without these conversations, you lead blind. You miss warning signs until people burn out or quit. You lose talented people who would have stayed with better support.
Start with one question in your next one-on-one. Notice what happens. Build from there.
If you’re ready to examine how your leadership approach affects team wellbeing and build more sustainable practices, book a complimentary strategy session with one of our business coaches. Sometimes the most important question is whether you’re creating an environment where your team can thrive.
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