Difficult conversations without the dread

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.