I recently went one-on-one with Susie Robinson. Susie is the Chief People Officer of Pagaya and has served in senior HR roles for nine different companies across the fields of finance and healthcare.
Adam: How can we get to a place where we can have difficult conversations in the workplace and have them effectively?
Susie: Such a great question. I think this transcends role, age, time, and career. Businesses are human systems. We are put together in sometimes relatively artificial ways. No wonder there are awkward conversations that need to happen and tensions that arise, or just things we want to achieve that require conversation.
As a Chief Human Resources Officer, or in my training, I’ve had to have many difficult conversations. One thing I’ve realized is really important for me is to invest time in my work relationships before a difficult conversation has to happen. Getting to know people in a context that is not awkward and is less difficult creates a connection that often softens the awkwardness of harder conversations.
So I would say, don’t hide at work. Put yourself out there. Build important relationships and continue investing in them. It’ll pay off in many ways. That applies not only to your boss, but also to your colleagues, mentors, and anyone else important in your workplace.
That brings me to my second point: preparation. When you need to have a conversation, it’s really important to prep. Preparation allows you to focus on the solution and remove emotionality. It helps you avoid internalizing or being distracted by what the other person might say. Think about it, write it down, rehearse if you need to, role-play with a friend, plan what you want to say, how you’d like the conversation to go, and what you expect in return.
The third point is to think about all sides of the issue. Preparation involves putting yourself in the other person’s shoes: What do they care about? How are they perceiving this? What do they need from the interaction?
I often say that everything is a negotiation. You need something, and so does the other person. In a good negotiation, everyone gets what they want and a little bit of what they don’t – that’s compromise. If you understand where they might go with the conversation, you can prepare a better response.
Investing time in preparation, thinking through your message, understanding all sides, and building confidence are all key. That work gives you confidence because you’ve developed logic, talking points, anticipated responses, and created your own replies. All that preparation breeds confidence.
Before I go into a board meeting, I give myself a pep talk. I’m often faced with formidable business minds who may have more experience or knowledge than I do. But I remind myself that I have something they don’t. That could be my point of view, my HR expertise, or insight into the people in the organization, my specialty. That’s what I bring to the table, and I bring it with confidence.
The final piece of having difficult conversations is establishing confidence and a sense of surety in yourself. That helps build your credibility as you ask for or deliver whatever message you need to communicate.
Adam: I love the framework that you shared, starting off with the pre-preparation. You need to prepare before preparing. How do you do that? By investing in relationships. By making the deposit before you need to cash the check.
Susie: Yeah, Adam, I can offer a quick example of how I do that. I’m not constantly in difficult conversations, but a lot of what I do involves guiding people to achieve their goals and helping the company perform. That can include conversations about people’s careers, performance, teams, bosses, direct reports, etc. The people piece is always a bit complex.
When I join a new company, I work hard in the early days to meet as many people as I can. In small or mid-sized companies, that’s often everyone. I won’t know every person by name at that stage, and I won’t understand all their aspirations, knowledge, or skills, but I will have had a one-on-one with them. I’ll shake their hand, understand what they care about, and ask what they expect from me.
Those thirty-minute meetings – sometimes hundreds in the first two months – do several things. They help me learn the business from different perspectives. They clarify what a portion of the workforce expects from me. But more importantly, they ensure that if I ever have to have a difficult or serious conversation with someone, it won’t be the first time we’ve spoken. That connection helps make interactions more successful and more fulfilling.
Adam: You bring up something interesting: different levels of difficult conversations. There are difficult conversations in lower-stakes situations, like approaching someone more senior than you and asking for advice, and then there are higher-stakes situations like asking for a raise or a promotion. The conversations in the second category are generally a lot harder, and the more experience you have with the lower-stakes, difficult conversations, the easier it will be when you have the higher-stakes, difficult conversations.
Susie: I think that’s absolutely right. The same preparation applies: removing emotionality, staying factual. But yes, different conversations carry different stakes.
There’s a difference between asking for a raise and filing a complaint about your boss, but they share core elements. In both, don’t assume you know everything. Stick to the facts, present your perspective, and be open about what you don’t understand.
If you’re asking for a raise, for instance, and say, “Sally makes ten times more than I do,” ask yourself: Do you know that for sure? What’s your source? Be open about what you do know.
It’s the same with a complaint about a colleague. Maintain your credibility. Don’t let dilution of facts derail your point.
And once you’ve made your point, let it rest. Many people keep repeating themselves out of fear they haven’t been heard. That only undermines the message. Make your point, pause, and schedule a follow-up.
Before leaving any meeting, agree on next steps and a timeline. Do the same in these conversations. Take the lead when needed, but if you’re speaking to HR or management, trust their process, unless they give you a reason not to. Follow up when agreed. If you don’t get traction, and your concern is valid, have another conversation.
Just remember, you’re probably not the one calling the shots. Present your position clearly, make your ask clear, define expectations, and stay on that path.
Adam: What are the keys to approaching different types of difficult conversations?
Susie: It can be very difficult to have a conversation, for instance, about a complaint against your boss without emotionality affecting how you feel or even how you come across. That’s why you want to take as much emotionality out of it as possible. Focus on the solution and the facts. Don’t present anything as fact unless you are sure of it. But if you are sure, share it openly.
There are a lot of reasons why these situations are hard. Our bosses hire us, spend time with us, and if they’re good, mentor us. We form relationships with them. They represent the company to us. So if you’re having a difficult conversation about your boss, that’s not easy. There’s usually a higher level of emotionality and potentially fear, depending on the circumstances. You might be afraid of the outcome or the consequences of making a complaint.
And just to clarify, not all complaints are created equal. A complaint about your boss could be something very serious, or it could be that they play music too loudly in their office. There are different flavors.
In those emotionally charged cases, you want to double down on your preparation, double down on your facts, and role-play if needed. Ask a trusted friend what they would do. Really think about how you want the conversation to unfold and what you want to get out of it. That will help define your ask, your aim.
When it comes to conversations about compensation, those are almost always a little awkward. Compensation means something to us. It’s not just a number on a paycheck, it’s a representation of the value we provide. We give a lot of ourselves at work, and receiving monetary value in exchange is deeply meaningful.
So again, take the emotionality out of it. If performance is a factor, that should not be a surprise. You should already know about it. If your performance has been discussed multiple times, and you go into a compensation conversation without acknowledging that, it probably won’t go well.
Think through how compensation decisions are made and how your contributions align with that. If it still doesn’t make sense to you, go into the conversation with a solution-oriented mindset.
Someone in compensation once told me, when I asked how he remained so calm under pressure, “Everything related to compensation can be fixed.” And I thought, wow, that’s so true. If we made a mistake, we can fix it. If you’re being paid incorrectly, we can fix it. There’s no need to get overly upset. But there is a need to understand the issue.
Remember, it’s often not your decision to make. Even with the best argument or most compelling case, someone else decides. Maybe the company doesn’t have the budget. Maybe you’re already paid fairly. Maybe your performance has declined, and that’s hard to hear. These conversations can go many ways.
So prepare. Consider their perspective. Think through how you’d respond. See it as a negotiation. Be open about what you want and why. These principles apply to almost every difficult conversation in our careers.
Adam: What body language should you be especially cognizant of?
Susie: That’s a great question. I think in these kinds of conversations, it’s helpful to think of it from a peer-to-peer perspective. As an employee, you’re advocating for yourself and your career. You want your manager – or whoever you’re speaking with – to hear you as an equal, adult to adult.
So sit across from them in a way that feels natural: at a table, in chairs, on a sofa. Avoid sitting across a giant desk if possible. That kind of setup allows for a more open, relaxed conversation. And again, this is why investing in the relationship beforehand is so important. If you’ve already built that connection, the conversation becomes easier or at least more productive.
Think of it as a peer-to-peer conversation where you’re laying out facts in an open way. We’re all animals at the end of the day. We’re constantly reading each other. Our brains pick up on subtle visual and auditory cues. Tiny facial expressions matter. So aim to come across as authentic, solution-oriented, open-minded, and ready to listen. Your body language will naturally reflect that mindset.
Now, from a manager’s perspective, it’s also important to understand what motivates your team, what drives your people at different stages of their careers. Generally, there are six core motivators: family, compensation, impact, schedule, and so on. Compensation is usually on the list, though not always at the top. But those priorities shift over time.
Early in a career, people are building. They’re ambitious and focused on growth. Mid-career, priorities may shift to family. Later, maybe it’s about paying for college. It’s not that other things stop mattering; they just become more or less important at different times.
As a manager, you should listen carefully, not just to what people say, but to what you observe over time. Know your team. You may not change your decisions based on this knowledge, but it will inform how you communicate those decisions. That can make a big difference.
Adam: Are there other tips on this topic that you would like to share?
Susie: Going back to what I said at the beginning, investing in relationships is key. No matter your role, no matter how introverted or extroverted you think you are, we are all placed remotely or in person, globally or domestically, to build something together.
That relationship is crucial. Even if we don’t love our jobs every day, most of us get something meaningful from our work. Humans want to make an impact. Work gives us that opportunity, if we choose to see it that way.
And the relationships we build, locking arms with others, matter deeply. They will serve you well, no matter how many difficult conversations you have. But they also set you up to succeed in the important and serious conversations that ultimately lead to collective success.
Adam: Pay transparency has become an increasingly important topic in the workplace. What is it, and why is it so important?
Susie: It has become a pretty hot topic over the last several years. My peers and I have been watching closely as developments unfold. Pay transparency is essentially a set of legislation at the state level that has emerged over the last ten years. It outlines companies’ obligations to share compensation information with employees or candidates, and also restricts what can and cannot be asked during the hiring process.
A few years ago, the first change in New York, and in several other states, was the law that prohibits employers from asking candidates what they currently make. You can ask what their salary expectations are, but not what they are earning. This law helps prevent the continuation of existing pay gaps, such as those between men and women in similar roles.
More recently, another example of pay transparency legislation is the requirement for private sector employers of a certain size to post salary ranges for their job openings. There are many new laws and many gaps in the guidance, which employers have had to interpret. Some companies have found workarounds.
From a business perspective, there are challenges. Sometimes the range is extremely broad. Smaller companies may not have the compensation data readily available or may not know yet what they are willing to pay. For example, a company may post a salary range and then meet a more senior candidate and decide to increase the compensation target. There are also concerns about missing out on candidates who may see a posted salary range that appears too low, without ever having a conversation with the company.
All of these considerations have likely affected companies over the past two years since this part of the law took effect. But overall, it seems to be going fine. I have not seen or experienced any major disruptions.
That said, it depends on a few things. Let me take a step back. For me, pay transparency is not new. In fact, during the first 14 years of my career, I worked in human resources at a publicly held pharmaceutical company in Irvine, California. We had about 5,000 employees across the US, both hourly and salaried. Our compensation structures were very transparent. Everyone knew the pay range for their level.
When we posted a job, internally or externally, the range was included in the posting. For example, if someone was making 17 dollars an hour and got promoted to a role with a range starting at 20, they would begin earning 20. Each year they would receive a percentage increase. The process was very transparent, and people were well educated on the structure.
That’s an important point. Transparency must be accompanied by understanding. After that role, I worked at Wyeth, another pharmaceutical company, later acquired by Pfizer. I led human resources and labor relations there, and again, we were very open and transparent. People knew what they should be making, and often what others were making in similar roles.
In large industrial companies like those, and in many others today, a few things matter. First, people must be educated on your compensation structure so they can understand how it affects them. Second, there needs to be clarity and a sense of fairness. If your structure is chaotic because of past decisions, you can clean it up. Create something more rational and then start sharing it. It may not happen all at once, but you can get there. And it usually does not require a huge investment.
Eventually, you will have a structure that fits your company and is fair to employees. At that point, there is nothing to hide. There is no reason not to share it once people understand how it works.
The real upside of pay transparency, beyond legislation, is that when employees understand expectations, both individually and collectively, when they know how performance ties to compensation decisions, and when the entire system is rational and aligned, it becomes the most powerful driver of motivation. That is when people begin to trust management.
If I do this, in this way, at this time, I will likely see a certain outcome. Maybe even a better one. And if I do not, there are consequences. That sense of predictability and fairness builds trust, and trust fuels motivation and effort.
Adam: What rules and regulations pertaining to pay transparency should employers and employees be aware of?
Susie: There are two key things employers and employees should be aware of.
First, it is now illegal in many places for employers to ask a candidate what they are currently earning in a present or past role. What you can ask is what their salary expectations are. How you respond as a candidate is up to your judgment. My advice would be to answer transparently. Transparency works best when it flows in both directions.
Second, certain employers, based on size and other criteria, are now required to include a salary range or target compensation in job postings. Review these postings carefully. Many of them are quite broad, so they may not tell you everything, but they give you a ballpark figure.
If the salary you are being offered, or are currently making, does not match what you see posted, you can ask about it. Approach your HR department and have a professional, open discussion. In companies with strong cultures, where performance and achievement are valued and the HR team is skilled, such a conversation can benefit both sides.
Compensation is a very important part of motivation. Employers who want their people to succeed must understand that monetary rewards matter.
In the US, we have not taken it further yet. For example, outside the US, some countries such as the UK have stricter pay transparency laws. These include publishing detailed compensation data across workforces. There are many rules and details, but so far, we have not seen that kind of movement in the US.
Adam: What are some of the potential pitfalls of pay transparency and how can they be averted?
Susie: I think one of the biggest pitfalls is having a messy compensation structure. This happens when a company has not used structured or data-based decision-making for a period of time and ends up with multiple people in the same role earning completely different compensation packages. That becomes very difficult to manage, especially when you are required to post salary ranges or when employees start asking about the ranges for their roles.
The solution is to make sure your employees are educated about your compensation philosophy. Even if you have not had one until now, you can develop a clear point of view. Do some analysis to understand where you are, address any major issues such as large pay gaps, and develop a plan to resolve the rest over time. This helps prevent the continuation of inequities.
Start making compensation decisions based on reliable data. Today, even small companies can access good data, and it is generally affordable and dependable.
As we continue to talk about this topic, and if future legislation expands on what exists now, employees will become more aware and informed. That is not always easy for employers to manage because compensation is complex. Many factors influence what someone earns, what the appropriate range is for a role, and what the compensation targets should be. There are also different elements, such as base salary, bonuses, and sometimes equity, depending on the company. The way these elements work together can be confusing for people who are not compensation professionals.
That is why it is important to have a clear philosophy, a structured program, and an education process for employees. Help them understand what they can expect and what is expected of them. Keep your approach updated over time.
Twenty years ago, this kind of structured and transparent approach may have only been feasible for large companies. But now, it is possible for many more organizations. If you are thoughtful and strategic, you can create a system that balances company needs and costs while ensuring fairness for employees. That helps motivate people and supports better performance.
Adam: Is there anything else that you think listeners should know about pay transparency?
Susie: I don’t foresee us going much further than where we are today. There may be more enforcement around the existing laws, but I do not expect a significant expansion in the near term.
In my experience, employers have generally followed the rules about not asking candidates what they are currently earning. Instead, they ask about salary expectations. Often, candidates voluntarily share what they currently make, which is fine as long as it is their choice.
The requirement to post compensation ranges has been more challenging. For some employers, it is uncomfortable to comply, especially when they are unsure how to set the range. Right now, I do not see a lot of active enforcement, but in the spirit of transparency, I believe it is still the right thing to do.
