In college, Maggie Leung had a job that was truly a nightmare.
She worked at a rental car outfit that would routinely overbook their fleet. Her workdays usually involved telling irate customers that they were out of luck. “So I figured I’d use the opportunity to learn — to try to read different types of people and defuse them as fast as possible. What did I have to lose? They were pissed anyway.”
Little did she know she was developing a muscle that would go on to be a key professional asset, first as a news editor and now as VP of Content at Nerdwallet. Today, she manages about 100 writers and editors located across the country. In each of these roles, she’s leveraged her ability to suss out what people around her need to succeed and how every manner of work situation can be constructively resolved.
Today, Leung calls this skill “dynamic empathy” — quickly gaining an understanding of how a colleague feels and figuring out how to act on it in a swiftly changing environment. It’s not innate and can be learned. While learning it herself, Leung crafted lists of questions that would prime her to handle the most difficult scenarios that arise in the workplace. Each set of questions is designed to detangle thorny interactions, get to the core of the matter, and achieve mutual understanding.
We’re sharing Leung's 13 lists here. They’re especially useful for managing people or working to get things done across teams. They’re also relevant when dealing with difficult personalities or situations beyond work. Read on to learn how to deploy dynamic empathy and speed problem-solving with shared purpose and motivation.
As with any other learned skill, you can make considering other people’s motivations an automatic habit if you do it enough. This can help equalize power dynamics and create a competitive advantage throughout a career. Leung devised sets of questions for each thorny work scenario she could think of as a place to start that would ensure compassion, understanding and a constructive approach from the beginning.
“When I understand and can articulate what someone needs from me, that makes it easier to say, ‘Makes sense. This is what I need from you.’ Then it’s a fair exchange rather than ‘I’m just demanding things from you,’” Leung says.
For the most part, asking the sets of questions below is an internal exercise — something you do with yourself to engineer successful conversations before they even happen. They are designed to help you tease apart complex scenarios that might be influenced by high emotions so you can see clearly, identify arguments or suggestions that are more likely to resonate with the other people involved, and establish multiple paths for success. When asked in sequence and truly considered, these questions help you see further down the road so you can avoid obstacles.
The goal is not to make a bunch of assumptions about what people want or what’s going to happen, but rather to think through the many possibilities so that you can remain flexible and nimble while still feeling prepared.
At other times, it might be appropriate to ask these questions directly to others. You can decide what will work best based on the personalities involved. Always, though, your goal should be finding common ground. Regardless, it’s also helpful to jot down or take quick notes on your answers to these questions in advance. That helps you externalize your feelings about the situation, see things more concretely, and remember the points you want to make in an eventual conversation.
There are no right or wrong answers to Leung’s questions. It’s the exercise of thinking through them that provides the value. That way, you’re always able to anticipate and work with another person's response — no matter what it might be.
Don’t be deterred even if you encounter resistance. Keep working the questions and modeling the candor you want to see. “If you keep putting yourself out there, you’ll get results,” says Leung.
Dynamic empathy isn’t just about understanding what’s going on with someone else, but actually doing or saying something about it. It helps you move forward.
Let’s start with the tougher conversations that managers or colleagues have. Whether it’s a performance review or a one-on-one, whatever gets said can make a lasting impact. You want to add value, not create cognitive drag that slows productivity. To do that, ask yourself these type of questions in advance of the meeting:
Does the person you're managing feel invested in your company or team goals? Why should he/she be? Have you clearly explained the vision or goals, and his/her part in achieving them?
Does he/she feel as if you've got his/her back?
Do you know what motivates him/her?
In every relationship, both parties must get something out of it. What are you offering vs. what you're expecting? Is what you're offering good enough, or can your employee do better elsewhere?
Does your direct report understand what he/she is supposed to do? How to do it?
Does he/she have the right training, right scope, right authority, right resources and enough time to do as you need?
Does he/she know how important your ask is?
What does he/she need from you or other colleagues?
Is he/she encountering bottlenecks? Are those localized or systemic? If they’re systemic, do you need to address this bigger picture?
Dynamic empathy isn’t just for managers. Anyone, at any career stage, should understand their bosses’ motivation as well. Understanding what that is — and how your work can help or hurt — is the secret to mutual success.
What would your boss ideally want from you (and your team, if you’re a manager)? How will you build trust and confidence? How will he/she stayed informed about what's relevant and important?
How will he/she avoid being surprised by what you do, how you do it, etc., in a way that puts him/her in a bad position?
How will he/she know that you're running into problems or anticipate them? How will he/she know how to help you?
What are you asking of your boss? Is he/she committed to delivering it?
Cross-functional work is where startups get a lot of leverage — but it’s also when competing priorities are likeliest to crop up. “If someone from another team makes a request from yours, you need to be clear about what you can reasonably do,” says Leung. “And if you say no, you want them to understand why.” Collegiality matters, of course. But more importantly, it’s vital for team leaders to coach each other on their respective priorities and pressures. That’s so each side can better frame future asks, with the best chance of success.
So when you’re the requester, put yourself in your cross-functional counterpart’s place. “Try to understand the difficulty of your request and where it’s going to fall in their prioritization," says Leung. "That will give you a more realistic sense of whether they can reasonably deliver what you need, and in what time frame. What’s a priority for you or your team might not actually merit being a priority for them. You don’t know, because you lack visibility.”
How well do you know their needs and challenges?
Do you know how they prioritize? Is your prioritization reasonable considering theirs?
If you prioritize something higher, why would they buy-in? Are you able to make a good case?
Which elements of your plan are most likely to turn them off or produce the most friction? How will you address that?
How dependent is a cross-team partner's success on you or your team delivering?
Can your cross-team partner trust you to come through? Why or why not?
Does this relationship need improvement? How do you think your cross-team partner sees you — as a good partner or someone who's not reliable and who puts their team's goals at risk?
Is that partner's priorities something you should be supporting?
Are the asks reasonable from both perspectives?
If you say "no," is the reason clear and does your decision feel reasonable to the requester, even if they disagree? If your logic isn’t explained, why should your partner trust your decision-making?
Quick and smooth adoption is your goal when you’re launching a new process to help teams work better together. “Before you can help people work better, you need to understand what they’re doing now and why. Then you can design processes that create less friction,” says Leung. “And lower friction means people are more likely to stick with the program.”
At NerdWallet, shared processes include onboarding and training, the production and distribution of content and tools, prioritization of work and requests for resources.
The types of questions worth asking when building and introducing new processes, include:
Who are the stakeholders?
How well do you know their needs and challenges?
How are you engaging them in creating the process and getting input? (It’s unlikely that a plan crafted in a silo will work for multiple teams. Even if it’s a great plan, you’re more likely to succeed if you build buy-in earlier, rather than dropping a plan on colleagues.)
Why would they buy in? Are you able to make that clear?
Where is the greatest burden falling? If it’s on their team, are they properly motivated?
How will accountability be handled? Are all parties agreed on that? (If not, you might end up falling short and end up with finger-pointing, which won’t help your company.)
How will you spread word and document your processes? Who’s responsible for doing that and keeping guidance updated?
Who decides when changes are needed?
Effective coaching must be individualized. “Learning and improvement happen in different ways and at different paces,” says Leung. “And you can’t stick with one style, because it won’t work with everyone. Using one approach is like trying to speak to someone in the wrong language — saying it louder or over and over isn’t going to make it sink in any better.”
When you’re training team members on new skills or process — or working to get an underperformer up to speed — start by considering where they are in their professional development.
Make your lessons interactive, adjusting as you see or don’t see progress. “I had to do that when I taught English to new immigrants as a volunteer," she says. "That taught me to keep taking their temperature and understand where we were progressing or getting stuck.”
How well do I understand what he/she is trying to learn and why?
How motivated is he/she?
How well do I understand the learner's strengths, weaknesses, learning style? (This can increase chances of success.)
Is the learner self-aware about his/her strengths, weaknesses and learning style?
What is the learner willing to do differently, or more or less of, in pursuit of these goals?
How will we know if the learner is making progress?
If we don’t see progress, what can I do differently as a coach?
Do I have a cut-off point for coaching? Does the person I’m coaching know this? What are the consequences?
Workplace negotiations should not be a zero-sum game. “Both sides get what they want in a great negotiation. Second-best is getting as close to that as reasonable,” says Leung. So whether you’re negotiating compensation, divvying up duties on a big project, or angling to fast-track a request in engineering’s queue, your best shot at getting what you want is generating dynamic empathy on your side of the fence.
What does the other party want to get out of these negotiations?
What is he/she likely to be willing to offer?
What are his/her likely deal-breakers?
How does he/she prioritize that's up for negotiation?
Does what I'm negotiating for exist in isolation, or would it potentially create a precedent that he/she would hesitate to produce?
Of course, it’s not always possible to give everyone what they want, and compromise is the grease of most workplaces. To achieve it, though, each side still needs to understand what the other wants. It’s the mediator’s role to surface those desires.
In some scenarios, Leung’s questions are a guide to the information you need to consider in order to be effective, not necessarily an interview script. When mediating, though, it’s important to ask some of these questions out loud. “Then both parties have heard what they're looking for. They don’t have to agree, but at least the important stuff isn't hidden.”
What is each party asking for?
Why is it important to him/her?
What part is negotiable? What are deal-breakers?
Is what's being negotiated actually important, or does it symbolize something else or is it a part of something larger?
Are we trying to solve a one-off issue, or is there history or context that will complicate things? It’s important to know this early, or you can waste a lot of time not addressing what actually matters. That will hurt your odds of success.
There’s mediating and then there’s mediating. When you’re not merely negotiating a compromise, but actually trying to resolve conflict, greater discretion is required. “If the problem is big, I meet with one party at a time to start, to understand what’s going on,” says Leung. But the goal is the same: to surface each party’s needs and get buy-in that, yes, they do need to deal with each other.
“I’ll say directly, ‘I understand that you’re not happy about X, Y, Z. But you and I know that you need to work well with this other person or team to get things done. Are we agreed on that?’” That agreement — and it’s rare that people disagree — is the key to helping each party find the motivation to work toward resolution. “But people can’t always get to that place by themselves.”
Do all parties agree that they need to work well with each other, and that it will benefit the company or their own work?
What’s the cost to the company if they don’t resolve their problem? What does each side have at stake?
What does each party ideally want? What are the key sticking points?
Is this really the issue, or are there bigger issues or more context?
Ask each side to step into the other’s shoes and imagine their perspective, complaints or arguments. Ask them what someone who’s solving for the company would expect from each side.
How is each side going to help contribute to solving the problem? What behaviors will they commit to changing? (The mediator should make clear if there is no option for all change to come from only one side, which usually is the case.)
As a veteran of newsrooms in the 21st century, Leung has particular expertise in this area. After years of individual contributor work, she took her first management role as the chief of copy desks for the San Jose Mercury News. “I figured I’d learn faster if I jumped into the deep end. They had been put up for sale, and had gone through two or three waves of layoffs. Morale was terrible. Clearly everybody was doing more work than normal. Some people had been drafted to do jobs they weren’t hired for.”
Perhaps counterintuitively, Leung found this scenario easy to manage — because it was natural to put herself in her reports’ shoes. “I thought about things like, ‘How would I feel if I had been asked to do way more work than I was normally expected to do at a quality level that was still similar?’ Or to do something I didn’t sign on to do?’ Where would my motivation come from?”
If we prioritize, what must get done vs. what can we give up? Are managers realistic about the tradeoffs?
How can the employee help, given what we face?
What does he/she reasonably need or want to get out of this job?
How can managers help?
You should tout your startup’s strengths, like your innovative product or booming numbers. But don’t focus on your strategic vision at the expense of the prospect’s goals. Learn what you can offer each candidate — given their career stage, long-term plans, or outside commitments — and tailor your pitch.
This mindset will serve you well long after you’ve recruited someone, too. “Assuming you’re hiring good talent, people always have optionality,” says Leung. “So what reason are you giving them to stay besides a paycheck? Asking can work, but sometimes people aren’t direct and you have to dig in and observe.”
Here's what to ask before a conversation with a candidate that you're excited about.
Do you have a good sense of what they want or what motivates them? If not, how are you going to find out?
Do you know why they’re interested in your company or why they joined? How much visibility do you have on your ability to meet those needs? Do you know how their roles might evolve?
What are their deal-breakers or must-haves?
Do they have the temperament that a startup needs, such as high comfort with change and roles that might quickly evolve? If so, what are you basing that on?
Will they take initiative and ownership? What do you base that impression on? Or will they require lots of certainty and guidance (and can you offer those)?
Are existing employees getting what they signed up for? If not, is what the company is offering worth staying for?
What opportunities do you see to leverage their strengths? What would they ideally like to do and does the company need that role?
How will you develop them? How much are you willing to invest in them? If you aren’t willing to do that, are you prepared to deal with attrition?
Are they still at your company out of choice, or is it because they have nowhere better to go? If the latter, what will you do to bring out the best in them? How can you re-engage them? Do they know that they’re slipping and it’s showing?
If they’ve become disengaged, why do you think that’s happened? Can you or they change that?
Think about what has successfully motivated the people who are already on your team and pattern-match accordingly:
Compensation, benefits or perks
Stock options, RSUs or other forms of equity
Work or subjects they enjoy (usually, specialists command more compensation than generalists)
Scope of responsibilities / authority / autonomy / opportunity to build from scratch or build a team / opportunity to help build a business and have influence
Career growth and learning (can include working in a niche, developing valuable expertise with a higher barrier of entry)
A worthwhile mission
A title or company with career pedigree
Self-image or an opportunity to check the box as they advance
Working with high-caliber colleagues
Work-life balance / flexible schedule / parent leave
Telecommuting / location
Given such variability, you need to know what on this list above is important to incoming candidates so you can make an offer with the benefits and opportunities that they want and that you can realistically offer.
Whenever someone significantly underperforms, you want to ask yourself:
Is what you’ve asked of the individual reasonable? (That could include workload, scope of work, level of responsibility, deliverables, goals, etc.)
Did you give him/her the right expectations, context, tools and other resources to set him/her up for success?
What could you have done differently as a manager? What could other coworkers have done differently? How can we avoid this happening in the future?
Could we have spotted this earlier? Did we make false assumptions or read signals incorrectly when we made the hire? Did we put someone in the wrong role?
Did the job outgrow the person or vice versa? (That can happen because startups’ needs change. The bar tends to go up as a company gains traction and roles evolve.)
“Leaders have to hold themselves and their people accountable,” says Leung. “Some things are within a manager's control; some things are within an employee's control. If you must fire someone, you want to at least learn something worthwhile. You don’t want a repeat if you can avoid it.”
In person, you want to ask the individual:
How do you think we ended up here?
What do you think you could’ve done differently? What could we have done differently? (You don’t have to agree with their perspective, but you might learn something useful that you can act on.)
Did we miss signs of trouble? How could we have caught this sooner?
Did our needs as a company grow apart from what you originally signed on for? (Some people are happier as generalists at early-stage startups, for instance. Companies that mature tend to want more specialists.)
“Hiring isn’t scientific, and sometimes jobs aren’t a good fit for various reasons,” says Leung. “Sometimes priorities change — for the company or the person. But even if someone performs poorly at a job, that doesn't give a manager the right to break their spirit or to strip away their dignity. Our jobs don’t define our worth as human beings.”
Content differs widely from company to company — different formats, quality levels, business purpose and so on. Companies typically use it to wield influence, whether the content is internal or external. Telling your story effectively is key, whether you produce blog posts, email, social media, interviews in the media, even the content you create for other employees at All Hands or internally. How do you express what you want, with the greatest impact? You have to have dynamic empathy for your audience — some of whom you may know, and others you may not. These questions are a good start for shaping content that achieves your goals:
Who are we producing this for?
What information or angle is most relevant to them? What key questions will they want answered?
Where will they find it? Will we meet them where they are, or do we expect them to find it on their own with significant effort? (That’s unlikely to happen.)
How will our content best meet their needs? In what format, in what voice and tone, and so on?
If we can leave a brand impression with our content, what would we expect it to be? Is that likely considering the kind of content we produce?
What kind of experience are we producing? Is our content compelling or useful?
Is it easily digestible and robust? It is a drag to get through? Too complicated or dull?
Would someone consume our content and potentially share it? Could they easily describe the takeaways we want?
Is there anything in our piece that will frustrate or annoy them? What gaps or other issues have we left? What can we do about that?
Some of your most active workplace relationships will be with nameless, faceless people: your users. If you can’t engage with them directly (and in many cases, you can and should), there is no doubt endless data to be mined. Dig in, and remember that those numbers represent living, breathing people. If you let it, data can tell a rich and actionable story about your users’ reasons for picking up your product — or putting it down.
Who are your users? How do they live and behave?
How clear is the pain point you’re trying to address? How clear is your value proposition? What differentiates your product from competitors'? What are you basing your answers on? Are those signals clearly coming from users? How can you separate out the noise?
Will they actually value what you're offering in the way you think they will? Why wouldn't they? How can you tell?
If you’re trying to change behavior, does your product signal that in ways that are easy for a user to understand? Or are your asks muddled or scattered? How will you measure success?
Which elements of your plan or your product are most likely to turn them off or produce the most friction?
How will your potential users hear about your product? What are you willing to invest to make that happen? How will you measure success?
It’s nice to have lists to set yourself up for success. But realistically, people don’t always honestly reveal their feelings and motivations easily or right away. Part of the skill of deploying these questions, then, is understanding how to read signals in the moment and keep pushing your conversations to a place of candor.
It won’t happen overnight; building trust rarely does. “It’s consistency over time,” says Leung. “If people see consistently that things aren’t punitive or judgey, that you don’t hold things against them or look for the ‘right’ answer, that it’s OK to trust, your interactions will become increasingly open and productive.”
Leung shared some of the tactics she’s found most effective to build that trust and consistency:
When you start rolling out these questions in a one-on-one, for example, be open about it. “I say to people, ‘Hey, there's this thing I want to try and these are the reasons why I want to try it. I want to see if you think there’s value in doing this.’” And if you sense that someone is hesitant to open up about concerns or challenges, address the elephant in the room. “Say explicitly, ‘Hey, you can talk to me about this and it's not going to impact your performance.’” As people see that you’re employing this tactic to build better relationships, that can engender trust.
Ask Specific, Open-Ended Questions
“I do one-on-ones with everybody on my team on a rotation. Often the conversation starts out with superficial responses. ‘How are things going?’ is followed by ‘I'm fine,’ or ‘Things are going well,’” says Leung. “You let them direct the conversation for a bit and see whether they get to the heart of things. If not, then you nudge them.”
I ask this question a lot: ‘What’s harder than it should be?’ It helps you surface things in a blameless way.
"It helps you identify patterns when you talk to various people. It helps you smell smoke early. That question could apply to many situations, jobs and companies. And it isn’t judgmental.”
The goal is to normalize these human moments — not veer into accusation. “If you say, ‘Hey, are you stressed?’ that attempts to force a confession in an awkward way. Instead, you could say, for example: ‘I know that you're juggling a lot of work right now. I know you're doing X and Y. If I were in your position, I might be a little stressed.’ Or, ‘Your team is under a lot of pressure right now, how is everyone dealing with it? Everyone responds to stress differently.’ Or ‘I’m not sure how you’re feeling about this, but if I had to guess, I’d say. …’ It’s OK to be wrong or off, as long as you give the person a chance to set you straight, to be direct with you.”
You want to get to the heart of things as quickly as reasonable. Leung’s one-on-ones usually take 30 minutes. If you ask the right kind of questions, you can get past small talk more quickly. To that end, your questions should be specific but open-ended.
Other questions she asks during one-on-ones include: “What can I do to help?” or “Is there anything you'd like to ask or highlight?” It’s their time to surface things, says Leung. “Sometimes they need to hear that explicitly from us as managers.”
People will trust if they believe their managers genuinely care and want to help. “It’s our job to care. That’s how we help people do their best work and grow. That makes them more valuable to our company and in the job market. That’s a fair trade.”
Lead with a Weakness
As in any interpersonal interaction, though, true candor rarely comes down a one-way street. So don’t just interview your reports — make a point to share something vulnerable with them. “Show that you have weaknesses too in some ways,” says Leung. “You realize that everybody's human and that you're human, too. For instance, I'm very open about the things I'm working on, or that I’ve had to learn to handle.”
Don’t speak in high level terms — use examples they can relate to and have probably recognized in you already. Leung’s particular challenge at the moment is pausing in her fast-paced days to ensure that she’s fully hearing people. It’s not like her team doesn’t know that — they’re the ones having conversations with her. So she brings it up. “I’ll say, ‘Hey, sometimes I jump ahead and anticipate your answer. That's not a good thing. Clearly you want me to hear you out.’ I acknowledge it.” That’s human, yes, but it’s also empowering. Acknowledge something you're working on and take ownership.
“It's helpful for managers, or any leaders, to be open about the things that they're struggling with and need help with," she says.
As managers, our team grades us all the time, whether we realize it or not. Ideally, we want to know how we’re doing and what we can get better at.
Repeat, Repeat, Repeat
Understanding where the person sitting across from you is coming from is only part of this process — they also need to know that you understand. Accomplishing that can be as simple as confirming what you’ve heard.
“Throughout these conversations, I repeat back or I reinterpret or I consolidate what I’ve heard,” says Leung. ‘I’ll say, ‘I’m hearing this,’ or ‘I want to make sure I understand correctly.’”
The benefits of this simple technique are manifold: You clarify anything you’re misunderstanding, of course, or move the conversation forward. But this very act also builds empathy. “You care enough to double-check. You’re actually trying to understand that person. If you don’t, you’re like that person who asks ‘How are you,’ then doesn’t wait for an answer.”
Look for Patterns
It’s okay to ask the same questions again and again. Advisable, really. Beyond opening meaningful conversation in the moment, one of your goals with this exercise is pattern identification. “If I hear two or three people talking about the same thing that's hard, that makes me wonder why,” says Leung. “It could be that the process is broken or that we're asking them is too much. I might make myself a note and follow up later. Then I circle back or have someone do that. No one wants to be asked for valuable input and have it ignored.”
Finally, remember that this is not “one and done” — it’s a mindset, a new way to manage and to co-work. Even when you’ve reached an understanding with someone, keep applying these questions. After all, lives change — people change — and with them, the very motivations you’re trying to understand.
“Somebody who might've joined you for amazing career growth might be looking for more work-life balance now because they have children,” says Leung. “In a Venn diagram, a company’s needs fall into one circle and the individual’s needs fall into another. What’s in the circles might change. That’s fine, as long as the size of the overlap stays strong. You won’t know unless you keep asking questions.”