Difficult conversations rarely improve with age. Whether it’s scope creep, late payment, missed deadlines, or a client relationship turning sour, avoiding the issue can turn a small problem into an expensive dispute.
In this episode of Flying Solo, Cec Busby talks with workplace lawyer Jennifer Bicknell, the “un-lawyery lawyer,” about how to tackle uncomfortable conversations with clarity and empathy. Jennifer Bicknell shares her six W’s for planning a conversation, explains why “help me understand” can change the tone, and offers practical ways to set boundaries without damaging the relationship. Start with the problem while it’s still small, she says, before it becomes a volcano.
1. Why difficult conversations get avoided
Jennifer Bicknell says conflict avoidance is normal, but allowing problems to continue creates bigger consequences. She compares avoidance to trying to will away a toothache at 01:24.
Her analysis of workplace disputes found three recurring reasons: people don’t know what to say, want to be liked, or fear something bad will happen at 02:13.
Avoidance can lead to poor sleep, increased legal costs, and small disputes that grow into “a little bit like a volcano” at 03:42.
Jennifer Bicknell advises dealing with problems while they’re still small, when humour and a lighter approach may still be possible at 31:54.
2. Handling scope creep and late payments
Scope creep often begins with small requests that business owners accept because they want to please the client or protect the relationship at 05:16.
Instead of framing additional work as letting a client down, Jennifer Bicknell recommends presenting it as an opportunity to create more value, then discussing the new price at 06:48.
For unpaid invoices, she suggests finding out whether the issue is financial dissatisfaction or something else before deciding what to do next at 08:06.
If a client hasn’t paid, Jennifer Bicknell recommends pausing further work and saying, “we need to settle our outstanding accounts” before continuing at 08:56.
3. A practical structure for difficult conversations
Jennifer Bicknell teaches the “6 W’s” for planning: define what winning looks like, identify who you’re speaking with, clarify the what and why, choose when to speak, and consider where the conversation should happen at 12:01.
The issue should be explainable in one or two sentences. Otherwise, she warns, people risk delivering “verbal vomit” instead of a clear message at 12:54.
Her execution framework starts with a little small talk, followed by a clear statement of the topic, then space for the other person to respond at 18:43.After listening, move into solution mode, agree on an outcome, and review it later if needed at 20:09
4. Staying clear without escalating conflict
Jennifer Bicknell recommends focusing on behaviour rather than labelling the person. Saying “you are a bully” shuts down the conversation, while describing the behaviour keeps it open at 15:57.
Give the other person the benefit of the doubt and use the phrase “You may not have realised it, but…” to create room for them to acknowledge the impact of their actions at 17:09.
Keep feedback short and explain why the issue matters instead of using a confusing feedback sandwich at 22:06.
When emotions rise, stay calm, speak privately, and return to the relevant contract, terms of service, or position description rather than making it personal at 27:18.
00:00 Reasons for workplace disputes
05:57 Navigating client requests
08:06 Handling client payments and issues
13:20 Discussing timely work delivery
17:09 Discussing communication and conflict resolution
18:43 Starting a conversation with ease
22:06 Effective feedback delivery
27:18 Handling disagreements thoughtfully
30:37 Avoiding Free Work Pitfalls
32:44 Trusting Your Business Instincts
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