Few workplace discussions create as much unease as conversations about pay. Whether you’re a founder, manager, or team leader, salary and compensation conversations often carry emotional weight, unspoken expectations, and fear of conflict. When handled poorly, they can damage trust, morale, and retention. When handled well, they become powerful tools for alignment, motivation, and long-term growth.
The good news is that discomfort around compensation isn’t inevitable—it’s usually the result of unclear frameworks, inconsistent criteria, or lack of transparency. The 19 strategies below, shared by founders, CEOs, and operators across industries, demonstrate how intentional structure, openness, and shared understanding can transform compensation discussions. These approaches help shift conversations away from tension and toward fairness, collaboration, and mutual respect.
- Share Exact Allocations And Outcomes
- Standardize Criteria Then Present Numbers
- Tie Bonuses To Client Wins
- Lead With Candor And Mission
- Value Drive And Measurable Results
- Go First And Signal Openness
- Offer Noncash Perks To Advance Growth
- Normalize Post-Review Pay Dialogs
- Survey Anonymously To Surface Concerns
- Elevate Expertise And Strategic Contribution
- Map Work To Payouts Clearly
- Let Staff Customize Total Packages
- Link Rewards To Proven Achievement
- Benchmark Roles Against Emotional Demands
- Model Scenarios To Explain Progression
- Invite Peers Into Compensation Decisions
- Align Remuneration With Ethical Exposure
- Respect Autonomy And Sustain Well-Being
- Establish Agenda And Allow Questions
Share Exact Allocations And Outcomes
We noticed that discussing salaries and profits often made people hesitant or uncomfortable. To address this, I began holding transparent monthly finance meetings where I shared clear percentages of revenue allocation and growth. For example, when we introduced a new product line, I explained that 41.3 percent of the profits from that line would be reinvested into the workshop and 23.7 percent would go toward team bonuses. By presenting exact numbers and showing how decisions affected everyone, the conversation became factual rather than personal. Before this approach, only about 12.5 percent of the team felt confident discussing compensation openly. After implementing these transparent sessions, that number rose to 68.9 percent. This method helped remove ambiguity and built trust across the team. Conversations that were once tense became opportunities to align on goals and celebrate shared success. Open and clear communication turned financial discussions into moments of collaboration.
Soumya Kalluri, Founder, Dwij
Standardize Criteria Then Present Numbers
One approach that has worked well for us is to separate emotion from information by using a clear, repeatable framework for every compensation conversation. When people know the rules of the discussion beforehand, their discomfort drops almost immediately.
At Wisemonk, we use a simple structure with three parts: role expectations, market benchmarks, and performance impact. Instead of starting with numbers, we begin by discussing what the role is responsible for today, how it has changed, and how the person’s performance has affected business outcomes. Only after that do we introduce market data, so the conversation feels grounded in reality instead of opinion.
This method helps because it shifts the discussion from personal worth to role value and contribution. It also fosters transparency. Team members understand that the same criteria apply to everyone and that decisions are not based on negotiation skills or seniority bias.
The last part is allowing people time to react. After sharing the data and recommendation, I pause and ask which part they would like to understand better. This makes the conversation feel collaborative rather than confrontational. Over time, it has built trust because employees see that compensation decisions follow a consistent logic, not secret discussions.
Using a shared framework reduces awkwardness and keeps the focus on fairness and clarity.
Aditya Nagpal, Founder & CEO, Wisemonk
Tie Bonuses To Client Wins
The best thing we did at Interactive Counselling was connect bonuses to when clients hit their goals. Suddenly nobody was asking “what’s in it for me” – we were all cheering when someone’s client made progress. The money talk changed completely. Instead of competing, we started helping each other out. If discussing profits makes your team uncomfortable, try hooking it to something everyone actually cares about together.
Amy Mosset, CEO, Interactive Counselling
Lead With Candor And Mission
I learned very early on, both from my diagnosis and from building Aura, that honesty removes most of the anxiety people feel around difficult topics. I deal with death every day, and it has taught me that clarity brings comfort. So when conversations about salary or profit come up, I treat them the same way I treat end-of-life planning. I keep the conversation open, human, and focused on purpose.
My team knows exactly why Aura exists and what we are working toward. We are creating a more compassionate approach to death for families who want something more personal. When that mission stays front and center, money becomes part of the practical side of keeping the work alive rather than something awkward to tiptoe around. I explain where the business is, what we can sustain, and how each person’s contribution supports the service we promise families. I have found that transparency builds trust faster than any formal structure.
My health journey made me value time more than anything. I do not waste it by dancing around subjects that matter to people’s lives. When you speak plainly and keep the mission in view, even sensitive conversations feel grounded and respectful.
Paul Jameson, Founder, Aura Funerals
Value Drive And Measurable Results
I strip out the drama by framing every number around one thing: energy. Meaning, I talk in terms of what someone brings to the table day in, day out. If someone brings high energy, solves problems, and keeps jobs moving… that is what we are paying for. It has nothing to do with seniority or tenure. I use phrases like “your impact per hour” or “your result-per-day ratio.” Sounds weird, but it makes the entire conversation feel like a scoreboard, not a guessing game. Nobody gets blindsided because the math is simple—energy in, outcome out.
To be honest, when people know what they are being measured on, the tension goes away. Now it is just a game of doing better, faster, smarter. And guess what? That gets people fired up instead of feeling shortchanged. The numbers tell the story… and the story is earned.
Tyler Hull, Professional Roofing Contractor, Owner and General Manager, Modern Exterior
Go First And Signal Openness
I tried bringing up compensation in a team meeting once. Dead silence. So I just put my own numbers out there first. Suddenly people started talking. It was like a switch flipped. Once I shared, others were willing to share, and we actually figured out something that worked for everyone. You just have to go first, even when it’s awkward.
Falah Putras, Owner, Japantastic
Offer Noncash Perks To Advance Growth
When raises aren’t happening, I offer other things instead, like covering conference costs or certification fees. It really takes the edge off those compensation talks. Instead of my digital marketing team hitting a wall, they get to suggest what matters to them. The conversation shifts from “I need more money” to “Here’s what I want to do next.” It feels more personal and focused on their actual growth.
Josiah Lipsmeyer, Founder, Plasthetix Plastic Surgery Marketing
Normalize Post-Review Pay Dialogs
One approach I do is to regularly hold conversations about compensation a few weeks after performance evaluations to create a sense of normality surrounding compensation talks within the company. I find this to be the best way to naturally integrate it into Cafely’s culture and eliminate any kind of discomfort it may cause between my employees.
We’ve made it a habit to send out any important changes or updates via a group chat in our preferred communication channel while also sending individual emails to each employee to serve as formal documentation they can use, if needed, as future reference.
What makes this even more effective, though, is encouraging them to freely schedule one-on-one meetings if they want to discuss their compensations or have any comments on some changes we’re making. Not only will this keep them informed, but it will also show how much we value and consider their feedback when making these kinds of decisions.
Mimi Nguyen, Founder, Cafely
Survey Anonymously To Surface Concerns
Here’s how I handle pay conversations. I send out a quick anonymous survey to my team before we talk. This helps me spot any brewing issues and get a read on the room. It’s not a perfect fix, but I go into those meetings way more prepared. People are more willing to open up because they know I’m actually using their feedback to guide the talk. It takes a bit of practice to read the results right, but these talks have become way more transparent and less of a headache.
Branden Shortt, Founder & Product Advisor, The Informr
Elevate Expertise And Strategic Contribution
I usually initiate the conversation about compensation around the concept of Strategic Value Added and Intellectual Property (IP). I understand there is a tendency to think about hours worked; however, I have shifted the conversation from hours to the individual’s specific knowledge base and the unique defensibility of their expertise. I am more concerned with how that knowledge base and/or educational qualifications complement my core value proposition. Therefore, the discussion about salary becomes a discussion about strategic career planning that provides a motivation for the employee to continue to raise their expertise and level of intellectual contribution so that they command a premium for their services.
Joel Butterly, CEO & Founder, InGenius Prep
Map Work To Payouts Clearly
At Fotoria, we stopped having those vague salary negotiations. We made a simple chart showing everyone how work like building a new AI model translates into pay. The conversation went from weird to practical. Instead of haggling over numbers, we focus on what’s next, which just feels better for everyone.
Edward Cirstea, Founder, Fotoria
Let Staff Customize Total Packages
When it comes to pay, I take a cue from software, but in a simple way. I let team members adjust their own packages within set boundaries. At Tutorbase, this turned a tense talk into a practical discussion. I remember someone traded cash for more remote work days, and it worked out great for everyone. Just be clear on the limits, and people will tell you what they need.
Sandro Kratz, Founder, Tutorbase
Link Rewards To Proven Achievement
I handle salary and compensation conversations by linking them to an employee’s and team’s accomplishments. Rather than focusing solely on salary numbers, I recognize achievement milestones for employees, whether that’s completing project work, achieving performance targets, or improving customer satisfaction. The way I frame salary conversations based on performance and employees’ contributions creates a much more pleasant experience than if the conversation were centered on salary numbers alone.
I also present educational opportunities that help demystify the financial aspects of our company. Those educational sessions include training related to budgeting, profit margins, and how the compensation structure relates to company performance. In doing so, I create a sense of comfort around employees discussing pay while helping them to participate meaningfully in those discussions. Awareness around compensation for all employees will help demonstrate the connection between their efforts and the organization’s overall financial well-being.
Josh Qian, COO and Co-Founder, LINQ Kitchen
Benchmark Roles Against Emotional Demands
I seek to create an environment where compensation is seen in terms of Mission Contribution and the Value of Work through Emotional Labor. We have created a framework for discussing how the compensation for each position aligns with the demands of client service. To diminish unease with this, we implemented an Internal Benchmarking Model, based on the complexity of each role and how much exposure to Emotional Burnout it causes. This Internal Benchmarking Model will allow people to believe they are receiving just compensation for the time and commitment necessary to meet ongoing client care needs while maintaining their dignity and respect throughout the process.
James Mikhail, Founder, Ikon Recovery
Model Scenarios To Explain Progression
We use scenario examples to explain how compensation structures adapt to growth. Concrete illustrations help clarify abstract decisions. People understand how different outcomes influence salary progression. This creates understanding based on real operational context.
This approach reduces fear around hidden information. Teams see how decisions connect to company health. Clarity builds confidence in leadership integrity. Transparency protects morale across compensation cycles.
Ivan Rodimushkin, Founder, CEO, XS Supply
Invite Peers Into Compensation Decisions
Talking about pay is always a bit tense. What I’ve seen work is pulling in a few people from different teams to help make the decisions. People get nervous when it feels like some secret directive from on high. But when others are part of the process, they understand the trade-offs. They might not love the final number, but at least they see how we got there.
Bennett Maxwell, CEO, Franchise KI
Align Remuneration With Ethical Exposure
Having conversations about ethical stewardship and governance responsibility, I facilitate ethical stewardship as a topic of discussion. Within that discussion, compensation would directly correlate through the amount of moral and regulatory risk that role presents. Instead of focusing the discussion solely on an individual leader’s perception of the overall ethical standard and level of accountability demonstrated, I am lifting the discussion above an individual leader’s personal need, therefore reducing discomfort because the compensation is strictly tied to the highest level of moral and ethical standards associated with dual diagnosis care.
Saralyn Cohen, CEO & Founder, Able To Change Recovery
Respect Autonomy And Sustain Well-Being
When I conduct compensation discussions with staff, I will make sure that they have an emphasis on Individual Dignity and Autonomy. The process will create a respectful and personalized environment while acknowledging the emotional and mental work needed to reach an agreement. I will aim to increase comfort with the negotiation process by framing compensation not only as a monetary value, but as an instrument for supporting Well-Being and Life Choices. The content of these discussions will include the fact that the compensation structure must also be sustainable so that the staff member can provide the highest level of Compassionate Care, while still being able to operate autonomously.
Tzvi Heber, CEO & Counselor, Ascendant New York
Establish Agenda And Allow Questions
Here’s how I handle salary talks. I treat it like any other business process, the same way we tackle a tough client objection. I always start with a clear agenda and make sure there’s plenty of time for questions. It takes the awkwardness out of it. When people know what to expect, they relax and the conversation gets more productive. It’s that simple.
Yarden Morgan, Director of Growth, Lusha
Conclusion
Discomfort in salary and compensation conversations rarely comes from the numbers themselves—it comes from uncertainty, secrecy, and misalignment. As these expert insights reveal, clarity is the great equalizer. When compensation is tied to outcomes, mission, benchmarks, and transparent systems, the emotional charge dissipates and trust takes its place.
Whether it’s sharing exact allocations, standardizing criteria, inviting peer input, or framing pay around growth and well-being, each strategy reinforces the same principle: people are more comfortable when they understand how decisions are made. Leaders who approach compensation with structure, empathy, and openness don’t just reduce awkwardness—they build credibility, loyalty, and healthier organizational cultures. In the long run, mastering these conversations isn’t just good management—it’s good leadership.
