How to make difficult conversations easier
Sooner or later, every business owner needs to have a difficult conversation with an employee, a client or a supplier. Economic uncertainty makes these conversations even more common and important. Still, the prospect of such a conversation keeps many entrepreneurs up at night.
The good news is that there are simple ways to make such conversations easier and more productive, with substantial gains from doing so.
“Difficult conversations can be hard for people for a number of reasons,” says Michael Gatschene, Business Centre Manager at BDC. “Some fear conflict, others have a tendency to people-please, and many of us struggle to control emotions under stress,” he explains.
Recognizing these barriers is the first step to approaching these discussions with confidence.
Best practices for difficult conversations
How can you manage the situation so that everyone involved feels heard, understood and appreciated? Here are some tips.
1. Prepare
“Preparation is crucial,” says Michael Gatschene. “One of the easiest ways to be prepared is to understand the person or group you’ll be speaking with.”
- Know your audience, whether it’s an employee, supplier, or investor.
- Review relevant details about their role, business, or the situation you want to discuss.
- Stick to the facts and clarify the objectives of your conversation.
It can also help to plan your talking points in advance. By preparing thoroughly, you’ll build confidence and set the stage for constructive dialogue.
Preparation is crucial. One of the easiest ways to be prepared is to understand the person or group you’ll be speaking with.
Michael Gatschene
Branch Manager, BDC
2. Act quickly
When issues arise, it can be tempting to ignore the situation and hope it resolves itself.
“Once you’re prepared, don’t procrastinate,” warns Gatschene. “Avoidance is a common mistake. It leaves room for anxiety to grow and will make future conversations even more difficult,” he adds.
Addressing issues quickly helps maintain trust and transparency.
This is especially true in a small company, where every employee visibly affects productivity and team morale. Leaving an issue unaddressed can have a significant impact on the rest of your business.
Failing to solve a problem can even have an adverse effect on the employee involved, as they won’t have the opportunity to learn and improve.
3. Be clear about the purpose of the conversation
When planning for a difficult discussion, clearly communicate the purpose so everyone knows what to expect.
Before the conversation, clarify your objectives and gather any necessary information or materials. Planning your talking points helps ensure the discussion is focused and constructive.
4. Explain why it matters
People respond better when they understand why an issue matters and how it affects the business relationship.
Instead of simply requesting a change, explain the reasoning behind your concerns or suggestions. Preparation is crucial. Know your audience, whether it’s a client, supplier, or colleague. Review key aspects of their business or role to build confidence and trust.
Remember that poor performance is often the consequence of unclear expectations.
5. Listen as much as you talk
Whenever possible, have difficult conversations in person or in a video call, at a time when you can fully devote your attention to the other party.
“Active listening starts by slowing down,” says Gatschene. “Pause before responding to truly process what the other person said.”
Give the individual your full attention, ask clarifying questions, and summarize their points to ensure mutual understanding.
That way, you can have real dialogue, and everyone can voice their concerns and perspectives. You might learn that employees don’t have the resources to do their job properly or that they didn’t understand the impacts of what they said or did.
This solidifies trust and transparency, two pillars of strong business relationships.
Active listening starts by slowing down.
Michael Gatschene
Branch Manager, BDC
6. Manage emotions and expectations
Difficult conversations evoke strong emotions.
Gatschene advises entrepreneurs to stay calm and empathetic: “Step into their shoes. Acknowledge the issue from their viewpoint. This can lead to a more collaborative and constructive conversation.”
Explain why the issue matters and outline next steps. If a solution is available, follow through and manage expectations throughout the process.
7. Make sure corrective conversations aren’t the only ones you have
Maintain regular communication with clients, stakeholders and colleagues—not just when issues arise. Positive comments, check-ins and structured updates are not formalities. They are building blocks to a solid company culture.
Providing effective feedback and keeping open lines of communication helps build rapport and trust. This way, when difficult conversations are necessary, they’re more likely to be received constructively.
8. Establish what happens next
It’s not helpful to simply point out what went wrong. Instead, focus on how the situation can be improved.
Offer constructive suggestions and clarify expectations for moving forward. Discuss possible solutions and manage expectations.
If a solution is available, follow through and keep the other party informed throughout the process. Managing expectations is key to building trust and providing value.
Clarity counts
Misunderstandings and issues often stem from unclear expectations or communication gaps.
Most people want to contribute and succeed, whether they’re employees, clients, or stakeholders. Removing barriers and clarifying expectations can help prevent situations that require difficult conversations. Be empathetic and consider the other person’s perspective. Step into their shoes and acknowledge the issue from their viewpoint. This can lead to more collaborative and constructive conversations.
“You’re equipped to handle tough conversations,” says Gatschene. “Prepare well, stay empathetic and be confident. You’ll build trust every time.”
Next steps
Download our free goal-setting tool to show employees what you expect and how their work supports your business.