From Raises to Resignation: How to Handle Difficult Conversations at Work

From raises to resignations, team conflicts to troubled processes, one of the most valuable and underrepresented skills in the workplace is the ability to navigate tough conversations. And difficult conversations happen long before the need to involve human resources. Employees need to be able to share their point of view, address concerns about the work…

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    From raises to resignations, team conflicts to troubled processes, one of the most valuable and underrepresented skills in the workplace is the ability to navigate tough conversations.

    And difficult conversations happen long before the need to involve human resources. Employees need to be able to share their point of view, address concerns about the work environment, and elevate issues within their working relationships. 

    It’s not just bad news that precedes a tough conversation. Basic career development conversations such as performance reviews and feedback, organizational development, change management, and personal life updates can be uncomfortable for many people, too. 

    Whether it’s face-to-face conversations or talking with your remote employees, we consulted with a panel of UpCity partners and contributors to get their advice and tips on bringing up, addressing, and conducting difficult conversations in the workplace.

    While this is by no means an exhaustive breakdown of every potential scenario, the advice they offered comes from many years of experience and knowledge gained through productive conversations with coworkers, clients, and supervisors, and should be helpful in a variety of situations.

    General tips for tough conversations

    From career coaches to corporate VPs and consultancy co-founders, there’s a wealth of advice out there about specific types of workplace conversations and discussions. So our panel of experts started out with some general advice that can apply to almost any organization and any difficult conversation.

    In most cases, tough conversations can actually be reduced or softened within companies that have a supportive and open culture of communication.

    “There are far fewer ‘tough conversations’ at companies that listen to each other. Tough conversations are much less difficult when both parties trust each other. Working on trust and hearing each other will have a bigger impact than choosing how and where to have said talk.” – Trace Mannewitz, SEO Manager at Creekmore Marketing

    Given the variety of difficult discussions that can be required in any workplace, one of the key pieces of advice we heard repeated was centered around preparedness. No matter what the topic, successful leaders should focus on being prepared in order to guide and learn from conversations about serious topics.

    “From performance evaluations to disciplinary actions and policies, diversity and inclusion, change management, and conflicts between coworkers, the best thing a leader can do is … (to) take the time to prepare yourself. This includes gathering any necessary information, anticipating potential objections or concerns, and thinking about how you will respond. Being prepared will help you to stay calm and focused during the conversation.” – Michael Murphy, CEO of IT GOAT

    Another key consideration is that everyone involved in a work discussion is a person, and each person is bringing their own backgrounds, emotions, and concerns to any serious conversation.

    “In my experience, it’s best to stay professional but also truly human in difficult conversations. It is also important to accept responsibility and make sincere apologies if and when needed. I enter each conversation with the attitude that we are both meeting to improve something together.” – Diana Bianchini, President + Founder of Di Moda Public Relations

    Cooperation is critical to leading or participating in productive conversations. That includes not only a willingness to listen and learn, but also a willingness to be proactive and engage in conversations instead of pushing them off or ignoring issues.

    “Lack of growth is another difficult conversation in the workplace. If a company is stagnant—or worse, losing business—then it’s very important for everyone to sit together and strategize steps moving forward to get back on track towards growth. Many employees and even business owners shy away from dealing with this problem because it’s an extremely uncomfortable conversation to have. But a responsible company with a healthy company culture would always welcome that opportunity.” – Director ZANE, Video Producer and Director at ZANE Productions

    The tone of a conversation can play a huge role in how things are received, and our panelists pointed out that any discussion can be encouraging. Whether about company changes, raises, or poor performance, coming from a place of support and encouragement is not only possible but incredibly beneficial.

    Two women sitting at a table having a conversation

    “It’s important to use language that is encouraging, even when improvement is needed. This can involve focusing on positive achievements, offering support to facilitate improvement, or asking employees what they need to get to a place where expectations are being met.” – Domenique Comparetto, Head of Content Strategy at Altered State Productions

    Countless examples of potential conversations exist, and it would be impossible for any one person to prepare for every single scenario. But being aware of these common discussions and applying best practices can help you facilitate great conversations, strengthen connections with employees, and maintain a supportive team environment.

    “There are many difficult conversations that managers may need to have in the workplace, including performance issues, disciplinary actions, coworker conflict, ethical issues, layoffs, and restructuring—just to name a few. Handling these…can be challenging, but by being empathetic, clear, and supportive, managers can help create positive outcomes that benefit both employees and the company.” – Calob Hofer-Black, CEO of Allen Art Online Marketing

    Finally, the best approach is the direct approach. Not only should you be proactive about your willingness to have these conversations, but also be direct and use precise language. Everyone involved will appreciate hearing the truth and hearing it directly.

    “You have to engage in difficult conversations directly and promptly, being sure to listen to the position of the employee. Do not be angry, do not be emotional, and be sure to engage the topic head on. Listen and be completely clear in the words you share.” – Eric Silverthorn, President of Semaphore Mobile

    Difficult discussions about raises and compensation

    Some managers may be surprised to see the topic of raises or compensation on the list of potentially difficult discussions. However, conversations about raises can be very challenging because of how compensation and well-being are so closely tied together for most employees.

    Indeed, it’s hard for many people to bring up the topic, and can be difficult for supervisors who know that a raise or a promotion may not be possible. With these factors in mind, we asked our panelists specifically about how to navigate raise, promotion, and compensation conversations.

    “We must do away with the notion of needing to wait for our employees to ask us. Noteworthy leaders—the ones you want to emulate—are proactive about offering clarity on career paths early and often. Why? Because doing so communicates a culture of service, compassion, and care to your people.” – Max Zoghbi, Founder + Executive Producer at Loupe Theory

    Just as with any type of conversation, there are some basics that can help anyone have a productive and healthy discussion about raises and salary.

    “It is essential that everyone involved in the conversation feels heard and respected, particularly the employee seeking a raise. When communicating, managers should be aware of their body language, tone, and choice of words so as not to appear confrontational or dismissive. Finally, any decision regarding salary increases should be made in accordance with company policy.” – Glenn W. Richardson II, Chief Executive Officer of Rhodium Talent Advisors

    Positivity is very powerful, and it’s important to look for positives no matter the type of conversation or the subject. Even if you have to deliver bad news (such as “we can’t offer raises right now”), it’s important to acknowledge the contributions and value of the employee you’re speaking to, and focus on the positive impact they’ve had.

    “Be sure to ask your team member about their achievements or what they have done particularly well throughout their employment; this is key when helping them understand why they may be deserving of a raise! Additionally, it helps you better gauge their job satisfaction level as well if employees are willing to discuss further objectives or career goals with you.” – Travis Lindemoen, Managing Director at nexus IT group

    Conversations about raises should never be viewed as “just a talk.” Our experts pointed out that leaders, managers, and supervisors should be prepared and bring information to the discussion that they can share with their employee.

    “Managers should bring two things to these conversations: data and empathy. Without data, you’re just guessing and inviting bias to play a role in any decision that is made. The data should not be used as a weapon to show why someone isn’t getting a raise, but rather as a roadmap to show how an employee can continue to improve. Managers should also show empathy and understand that even a small raise may be the difference in improving someone’s quality of life.” – Adam Statti, Content Marketing Specialist at RevPartners

    Finally and perhaps most importantly, make sure you are really listening to your employee. Even if you know that the organization’s financial or structural situation won’t allow for raises, people deserve to be heard. And you will likely learn something important from the discussion.

    “It’s important to listen actively to the employee’s concerns and reasons for wanting a raise, and to explain the company’s policies and budget constraints in a clear and honest manner. Additionally, managers should be open to discussing alternative forms of compensation, such as bonuses or additional benefits, if a raise is not feasible at the current time.” – Ezra Weeks, Manager of Recruitment and Business Development-North America at Recruitment Canada

    While the “great resignation” may have been exaggerated in recent years, there has certainly been a generational and global shift in people’s attitudes about work, work-life balance, and the definition of success.

    Whether because of relocation for a new job, a competitive job offer, or economic necessity, employers will undoubtedly need to prepare for conversations about resignation. And these conversations can be incredibly valuable learning opportunities for leaders and organizations.

    “Managers should look to learn from a resignation. What caused the resignation? Where might there be areas of improvement for the organization to avoid losing other employees in the future? This is a great opportunity for managers to learn how they or the organization can improve.” – Robb Fahrion, Partner at Flying V Group

    One of the keys to learning from these conversations is to remember that the resignation is most likely not personally directed at a manager or a leader. More often than not, an employee has personal reasons for leaving a job or pursuing a new opportunity, and the feedback can be incredibly helpful for you and the remaining members of your team.

    “It’s important to not take it personal and instead to actually ask if the employee is comfortable with sharing their reasoning in more detail. Was it a specific action, the workload, the coworkers, the environment? Resignations don’t always relate to finding another job; sometimes it has to do with hardships that can’t be spoken.” – Tammy Huynh, Founder/CEO of The Creative Folks

    Two women in professional clothing having a discussion in a window

    If the employee is willing to participate, an exit interview can present an opportunity to greatly strengthen your organization in the future.

    “If the employee is willing to share, ask them as many questions as you can about why they are choosing to leave. Things they liked about the company and role, and things they would change. If they were a good employee, stay in touch and follow their future endeavors. There’s always a chance your paths will (intersect) again.” – Bryce Anderson, Partner at Lightswitch Video

    Awareness is one of the most valuable skills for any leader to have, and it can have a terrific impact on these conversations as well. Specifically, it can help you anticipate difficult situations ahead of time. Having the pulse of your department, your organization, and your employees means you shouldn’t really be surprised when an employee comes to you with their two-weeks notice.

    “A manager who gets caught off guard by this is not a great manager. A good manager works proactively to retain good talent and provides support to help other employees develop and progress…If you are not able to retain (a good employee), then fully support them as they transition so that you maintain the standard you want everyone else in your organization to follow.” – Kunal Desai, CEO of Branding And Promo

    Overall, the best advice for handling resignation discussions and exit interviews is to put yourself in their shoes, and approach the process from a perspective of understanding the employee’s side of the table.

    “Be safe to talk to. Gather information and refrain from defending yourself. Take a moment to pause when you hear something you don’t like. Then, put yourself in that position and think about how you might respond. Work on empathy. Gather feedback. And remember the golden rule: Treat others how you want to be treated.” – Jewel Rodgers, Development Manager at Noddle Companies

    Additional resources for difficult conversations

    Whether you are just getting into a leadership role, you’re an entrepreneur growing your team, or you have been a manager or supervisor for many years, there is still a great deal more to be learned—through experience and education—about workplace discussions.

    In addition to the panelists and experts we spoke to for this article, there are many other HR experts and organizations you can reach out to for training, advice, and assistance. All of them are highly recommended and can help make you communicate with your employees in a more effective and supportive way.