Diplomacy & Courage: How to Have Difficult Conversations as an HR Professional

As an HR professional, you’ve likely had at least a few difficult conversations at work. But have you ever experienced a situation where you must disagree with your boss or C-suite? If you’ve ever found yourself at that crossroads, you know the anxiety that such a conversation can create.

The corporate world is a complex tapestry of personalities, power dynamics, and protocol. For Human Resources professionals, navigating this environment can be especially challenging when it involves having difficult conversations with, or even standing up to, leadership. Whether it’s about advocating for better employee policies, addressing unfair practices, or pushing back on unreasonable demands, the line between assertiveness and career jeopardy can sometimes seem perilously thin. With the right approach, asserting your views without putting yourself in a difficult position is possible. Here’s how.

I once stood up to my CEO — and I didn’t lose my job. It’s more possible than you might think.


Understand the Power Dynamics

Before you approach leadership, take the time to understand the power dynamics at play. Recognize the experience, authority, and influence of the individuals involved, but also remember the value you bring to the table. As an HR professional, your insights into organizational behavior, employee morale, and legal compliance are invaluable. Framing your concerns within the context of these areas can lend credibility and authority to your stance. In one of my roles, I had a leader who was demanding I focus on something that wasn’t of high value to the organization. In my approach, I said, “Do you want me focused on that, or do you want me to focus on recruiting?” This helped give the feedback that the focus wasn’t on the strategy and helped us reframe the priorities.


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Bring the Data

Anecdotal evidence and emotional appeals have their place, however, in complex dynamics, nothing speaks louder than data. Before a tough conversation with leadership, gather tangible evidence to support your argument. Whether it’s employee satisfaction surveys, turnover rates, or industry benchmarks, presenting your case with clear, objective data can make it harder for leadership to dismiss your concerns outright and, in an ideal scenario, help them reach the same conclusion you did.


Choose Your Battles Wisely

Not every disagreement warrants a showdown. Being selective about the issues you choose to escalate can enhance your credibility and influence when you do decide to take a stand. Focus on issues significantly affecting employee well-being, legal compliance, or the company’s reputation. In doing so, you’ll be perceived not as a contrarian, but as a strategic thinker focused on the organization’s long-term success.


Communicate with Respect and Constructiveness

The manner in which you communicate your concerns can be just as important as the message itself. Approach leadership with respect, and express your viewpoints in a constructive, solution-focused manner. Use “I” statements to own your perspective, and avoid assigning blame or making personal attacks. For instance, saying, “I’ve noticed a trend in employee feedback that suggests we might need to revisit our policy on X,” is more effective than, “You’re not listening to employee concerns about X.”


Build a Support Network

You don’t have to go it alone. Before making your move, identify allies within the organization who share your concerns or could benefit from the proposed changes. Having the support of other departments or influential figures can lend additional weight to your argument and diffuse the perception of a one-on-one confrontation with leadership.


Anticipate and Prepare for Pushback

Anticipate potential objections or resistance from leadership and prepare your responses in advance. By acknowledging the constraints or challenges they may face and proposing viable solutions, you demonstrate a collaborative, rather than confrontational, approach to problem-solving.


Documentation is Key

Document your interactions and key points discussed for your own protection and to ensure clarity of communication. This can also be helpful for follow-up conversations or in case you need to escalate the issue further.


Escalate When Necessary

9 times out of 10, the previous steps should lead you to a brilliant compromise — one where leadership, HR, and employees can all benefit from whatever changes you’ve suggested. But if your efforts to address the issue directly with leadership don’t yield the desired results, consider whether it’s appropriate to escalate the matter. This could involve seeking advice from a mentor within the organization, consulting with a legal or ethics committee, or, in extreme cases, making a formal complaint.


Honor Your Resilience and Well-Being

Standing up to leadership can be emotionally taxing. Ensure that you have a support system in place and engage in self-care practices to maintain your resilience and well-being. Self-care is essential, especially for Human Resources professionals who have so much going on in their roles and must be the team’s pillar of strength and support.

Asserting yourself with leadership as an HR professional requires a blend of courage, diplomacy, and strategic thinking. By approaching challenging conversations with preparation, respect, and a focus on the greater good, you can influence positive changes without compromising your career. Remember, it’s not just about being heard; it’s about fostering a workplace culture where fairness, respect, and integrity are paramount.


Michelle Strasburger has dedicated over two decades to advancing Human Resources (HR) and wellness in the workplace. As the CEO and Chief Consultant of The Wellness Value, LLC, she focuses on transforming companies’ people strategies as a fractional Chief Human Resources Officer and consultant. Her wealth of experience encompasses progressive HR roles in small, medium, Fortune 500, and start-up businesses, and her passion for putting people first shines through in everything she does.