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When we sat down with Jacob Thomas, Communications Director at Common Defense, for this episode of Reimagining Company Culture, the conversation kept landing in the same place. Most managers know the conversation they need to have. They just do not have a framework that makes the conversation feel possible. Jacob has spent his career advancing civil and human rights work where the stakes of getting hard conversations wrong are high, and his advice for People leaders cut through a lot of the usual platitudes.
His core argument was that hard conversations only feel hard when there is no operating habit around them. The companies that build the habit, the rituals, and the manager support system end up with cultures where feedback flows. The companies that treat each tough conversation as a one-off event keep building up the cultural debt those conversations are supposed to retire.
Why Hard Conversations Are the Single Biggest Manager Skill Gap
Most performance and culture problems trace back to a conversation that should have happened weeks earlier. According to SHRM, the gap between intention and execution is widest in conversations about feedback, behavior, and disagreement. Managers know what they should say. They are not sure how to say it without breaking trust.
That gap costs companies more than they think. A manager who avoids one tough conversation per week is creating two outcomes at once. A small problem grows into a bigger one. The team learns that this manager will let things slide. Multiply that across an organization and you get a culture where issues compound quietly until they show up in attrition data, in exit interview themes, or in a sudden cluster of complaints that look like they came out of nowhere.
Hard conversations are a skill, and skills can be trained. The companies that invest in management training targeted at this specific skill see fewer escalations, faster issue resolution, and stronger trust between employees and their direct managers.
What Hard Conversations Actually Sound Like in Practice
What is a hard conversation at work?
A hard conversation is any workplace exchange where the manager has to say something the other person may not want to hear, and the relationship has to survive it. That includes feedback on performance, calling out behavior that crossed a line, addressing disagreement on direction, and having candid discussions about identity, fairness, or fit. The conversations get harder when they involve power dynamics, identity, or someone's livelihood.
Why do managers avoid them?
Managers avoid hard conversations because they are not sure how to enter them, because they fear damaging the relationship, and because most companies do not give them a script or a structure to lean on. The conversations also feel personal. A manager giving feedback on punctuality is not just commenting on punctuality. They are signaling values. Without training and support, that signal feels too risky to send.
What Actually Works When You Build a Hard Conversations Practice
Principle 1: Make the conversation a habit, not an event
The best managers do not save hard conversations for performance reviews. They are running short, candid check-ins every week so the small adjustments happen in real time. That habit lowers the temperature of every individual conversation. When something tougher needs to be said, the relationship is already wired for honest exchange.
Principle 2: Separate the behavior from the person
Jacob talked about going above and beyond on training because most managers never learn the basic structure of feedback that lands. Describe the behavior. Describe the impact. Ask what the person heard. Agree on what changes. That structure works because it removes the implicit accusation that the person is the problem and replaces it with a specific behavior that can change.
Principle 3: Loop in employee relations early, not late
Hard conversations sometimes uncover bigger issues. A feedback discussion reveals a pattern of bullying. A disagreement about direction reveals a discrimination concern. The mature operating model has managers loop in employee relations the moment a conversation moves outside their lane. Waiting until something escalates almost always makes the situation harder to resolve well.
Where Employee Relations Fits Into Difficult Conversations at Work
Modern human resources teams have moved past the model where ER only shows up after a formal complaint. The high-functioning operating model gives managers a confidential way to flag a concern, get coaching, or escalate a situation early. That same operating model uses anonymous reporting to give employees a way to raise issues that managers cannot or will not surface.
How employee relations supports manager-led hard conversations
The right ER function gives managers three things. A coach who can roleplay the conversation before it happens. A system that captures patterns across teams so leadership knows where the heat is. A clear escalation path when the conversation reveals something bigger than the original topic. With those three in place, hard conversations move from solo acts of courage to a coordinated organizational practice.
Frequently Asked Questions About Hard Conversations at Work
How do you start a hard conversation with an employee?
Start by naming the topic and the goal. Tell the person what you want to discuss, why it matters, and what good looks like at the end. That clarity removes the ambiguity that usually makes the start of these conversations awkward and lowers the defensive response.
What is the difference between feedback and a hard conversation?
Feedback is information about how someone is performing. A hard conversation is feedback that will be uncomfortable to give and to receive. The mechanics are similar but a hard conversation also requires the manager to manage the emotional weight of the exchange and to leave room for the employee to respond.
How do you handle a hard conversation involving identity or DEI?
Approach it with curiosity, not certainty. Ask questions before making conclusions. Loop in DEI partners and ER if the topic touches policy, legal exposure, or organizational patterns. Document what was said and what was agreed using clear, neutral language so the conversation has a usable trail.
What if the employee gets defensive?
Defensiveness is a normal first response. Slow down, restate the behavior in non-judgmental language, and ask what they heard you say. Most defensiveness comes from feeling attacked rather than from disagreeing with the substance. A pause and a restatement usually moves the conversation forward.
When should HR get involved?
HR should be involved any time the conversation touches a protected category, raises a potential policy violation, or signals a pattern across the team. The operating model should make it easy for managers to bring HR in early, including via a open-door policy or a confidential intake channel that doesn't require a formal complaint.
The Bottom Line for HR Leaders
Jacob Thomas's work in advocacy spaces translates directly into the People function. The skill of having a hard conversation is the same skill of building sustainable change inside an organization. Both depend on naming the issue out loud, building a coalition around the change, and creating the operating habits that make the change stick.
HR leaders who want fewer crises and more durable culture should invest in the manager skill that touches every other outcome in the company. Train managers on the structure of hard conversations. Build the rituals that make them routine. Wire in the employee relations support so the manager is never alone in the room. That is how culture stops being a slogan and becomes a system.
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