Communication – part three: How to approach tough and emotionally challenging conversations to achieve a win-win outcome
Virtual Success Show
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Episode breakdown
In the third and final episode of our three-part special, we take a look at those tough conversations you have to have when things aren’t going as planned and why the approach you take to these is so important in obtaining the most positive outcome for all involved. Let’s face it! No matter who you are, tough conversations are never easy; you’re dealing with humans, and as humans, we all have an emotional side. It doesn’t matter how great your business processes are, inevitably, as a business owner you will have to have these tough conversations. In this episode, Barbara and Matt draw on their own personal experiences and share their tips and insights into how to approach these conversations to ensure that you achieve the most out of them.
- Why shying away from tough conversations is never a good thing.
- Why it’s important to become masterful with your language and communication style.
- The critical steps you need to take when planning for those tough conversations.
- Common conversation hurdles you may encounter and tips on overcoming these.
- Advice on how to respond if the meeting doesn’t go to plan.
- Ways to reduce the number of tough conversations you may be having.
Five hours of you in your genius is worth 50 hours of you in incompetence.
In this episode
00:00 - Introduction
Barbara and Matt open the episode with lighthearted banter before reflecting on how their podcast conversations on communication have helped them grow as business owners and leaders. They stress that they apply the same tips and strategies they share with listeners in their own businesses and see real results. This episode is the third in their communication series, focusing on tough conversations—the challenging discussions that come after trying feedback and other approaches, often when deciding whether to continue with someone on the team.
04:00 – Tough conversations are never easy
Matt and Barbara emphasize that tough conversations are never easy because of the human and emotional element involved. Matt shares that even with experience, he still feels anxious beforehand, but the outcomes are usually positive and not as bad as he imagines. Barbara admits she has struggled in the past due to wanting to be liked, sometimes being less direct or letting emotions affect her tone, but she’s improving with practice. They set the stage to dive into Matt’s strategies and Barbara’s recent experiences with handling these situations.
06:16 – Client case study – shying away from the ‘tough’ conversation
Barbara shares a recent case where HR stepped in after troubleshooting steps failed. On the call, the client was initially upset and frustrated, but when the support assistant joined, the client’s tone shifted to apologetic and avoidant, making it clear she didn’t want the tough conversation. Ultimately, the client canceled the contract, leaving the team feeling it didn’t need to end that way. Matt adds that avoiding tough conversations by being “too nice” can backfire, explaining that “nice” can mean “nothing inside me cares enough,” signaling a lack of real commitment to resolving the issue or improving the relationship.
08:38 – The “tough guy syndrome”
Matt explains “tough guy syndrome,” where people criticize others harshly behind closed doors but avoid saying the same things directly. He stresses that this reflects a deeper issue: if a business can’t foster candid, face-to-face conversations, it signals a fundamental flaw in the organization’s values and culture.
09:19 – Candour
Matt emphasizes the importance of candour, citing Jack Welch’s Winning, where great leaders have direct but respectful conversations that aim for a win-win—even if that means someone leaving the organization. Barbara adds that her approach is to cut through formalities and speak honestly with people, asking straightforward questions like whether they actually like the job. By dropping business talk and connecting on a human level, she finds it breaks down barriers and leads to more open, productive conversations.
11:18 – Becoming masterful with your language and communication style
Matt stresses that while candid conversations are vital, the delivery must match the person’s communication style. Using tools like DISC helps adapt language so the message is received rather than shut down. Barbara agrees, noting that even when approaches differ, the goal remains to go beyond business talk, connect at a deeper level, and find the best outcome—whether that means parting ways, nurturing the person, or even shifting them into a role where they can thrive.
13:56 – Setting up for those tough conversations
Matt emphasizes that tough conversations should never come as a surprise—springing them on people usually leads to panic and poor outcomes. Barbara agrees, noting that people tend to shut down when caught off guard.
14:12 – Set up a meeting with an agenda
Matt explains that springing tough talks on people triggers panic or defensiveness, so it’s best to schedule them in advance with a clear agenda. Barbara adds that it’s important to distinguish between a casual chat and a formal meeting—serious conversations should be structured, with time for the person to prepare. This preparation not only improves the discussion but also reveals whether the person is worth keeping; if they don’t prepare or even quit before the meeting, that’s often the clearest sign they’re not the right fit.
15:52 – Present the facts as they are
Matt stresses that in tough meetings, sticking to facts instead of opinions is key. Barbara admits she sometimes lets emotions cloud discussions but emphasizes preparation and self-awareness to manage that. Both agree that success comes from being prepared, clear, and thoughtful—visualizing the conversation in advance helps keep it on track.
17:28 – Use video communication channels
Matt highlights the importance of using video in tough conversations to read body language and keep focus. He warns against getting stuck on one issue and stresses the need for a clear agenda that drives discussion toward concrete next steps. Framing the meeting with purpose and outcome ensures the conversation stays productive and solution-focused.
18:58 – Conversation hurdles
Barbara shares her struggle with tough conversations where defensiveness stalls progress, as the other person justifies everything and triggers her emotions. Matt responds that he actually welcomes these situations, seeing them as opportunities rather than frustrations.
19:47 – Conquering those hurdles
Matt and Barbara discuss how to handle defensive employees during tough conversations. Matt explains that when someone makes constant excuses, he reframes it by saying, “This is exactly why we’re having this meeting.” He suggests lowering his tone to de-escalate and then asking solution-focused questions like, “What’s the solution here?” or “If you were me, what would the next steps be?”
Often, this approach forces reflection—sometimes leading to silence, accountability, or even resignation. Barbara adds that giving people space and asking them to return with their proposed solution is powerful. It not only pushes responsibility back onto them but also gives both parties time to reflect, often resulting in either a resignation or a genuine plan for improvement.
24:03 – How to respond if the meeting doesn’t go to plan
Barbara reflects that many podcast episodes feel like coaching sessions, as Matt provides practical strategies she actively applies in her business. Matt emphasizes that tough conversations don’t always go smoothly—they can become emotional, defensive, or manipulative. In such cases, it’s better to pause, reset, and revisit later rather than letting emotions take control. He stresses keeping meetings short (around 30 minutes), sticking to a clear agenda, and using respectful, direct language that avoids aggression while still being firm. Both agree that tough conversations are inevitable in growing businesses, and addressing issues early prevents bigger problems and keeps the organization moving forward.
28:29 – Reducing the number of tough conversations
Barbara and Matt conclude by stressing that many tough conversations can be avoided by fixing root causes rather than constantly “putting out fires.” Barbara shares how improving processes and refining recruitment at The Virtual Hub reduced such issues from arising in the first place. Matt agrees, noting that effective upfront communication (as discussed in episodes 1 and 2) prevents recurring problems. They warn that simply firing and rehiring without addressing leadership or process gaps only leads to repeating the same challenges, making it less about the employees and more about leadership responsibility.
30:21 – Wrapping things up
Barbara and Matt wrap up the episode by encouraging listeners to subscribe to the Virtual Success Show on iTunes, share it with others who could benefit, and join the Virtual Success Facebook group to suggest future topics or case studies. They highlight that these conversations are valuable for both business owners and entrepreneurs, covering areas not often discussed. The episode closes with an invitation to visit virtualsuccessshow.com for more insights on outsourcing success.
