Knowing What You Don’t Know: Emily Windsor on the Limits of Courtroom Confidence

Confidence in court is not something a barrister can manufacture from nothing. It has to be earned in advance, through the kind of preparation that leaves no obvious gap unaddressed. Emily Windsor, who has practised at the chancery Bar over a lengthy career, holds a clear view on where genuine confidence comes from — and it is not from experience alone.

The barrister’s working environment makes honest self-assessment particularly important. Most practitioners handle their cases without colleagues who can review their work, challenge their reasoning, or flag what has been missed. In that context, the quality of your preparation depends almost entirely on the quality of your self-scrutiny. Windsor is direct about this: the solitary nature of practice means the responsibility for identifying gaps falls on the individual, and no one else is likely to catch what you fail to catch yourself.

The baseline Windsor sets for herself is exacting. She expects to have absorbed every relevant document, to carry the facts without having to search for them, and to be able to explain the applicable cases and statutory materials to a judge without hesitation — and to field questions about them in the same way. That level of command over the material does not come from a quick read the night before. It comes from sustained engagement that starts well ahead of any hearing date.

One expression of that sustained engagement is her work on practitioner texts. Windsor typically carves out two to three weeks — often during summer holidays, away from the rhythms of active practice — to write contributions to legal reference works. The exercise demands a different kind of thinking from casework: you are not marshalling arguments for a particular outcome but setting out the law with the accuracy and clarity that other practitioners will rely on. That discipline deepens her understanding of the law in ways that daily practice alone does not replicate.

Preparation for what the other side will argue is equally important. Windsor stresses the need to approach your own case as its most demanding critic — to find the weaknesses before opposing counsel does, to think through the questions a judge is likely to raise, and to have considered the precedents that might undercut your position. The advocate who has worked through those scenarios privately is far better placed to react quickly in court than one encountering them for the first time across the room.

Windsor’s capacity for this kind of analysis has roots she traces back to her teenage years, when she was drawn to debating and to the process of constructing and contesting arguments. English and history fed the same instinct — marshalling evidence, building a case, responding to alternative interpretations. Those skills did not need to be rebuilt at the Bar; they needed to be refined and applied in a more formal arena.

The arena has shifted in other ways during her career. Remote hearings have become routine for shorter matters, case management, and proceedings not involving witnesses. Technical preparation has accordingly become part of professional preparation. Windsor’s view is that audio quality matters more than video: a judge who cannot hear submissions cannot follow a case. Fumbling with technology while trying to advance legal arguments is a credibility problem, not just an inconvenience.

Written advocacy, meanwhile, has grown to match oral advocacy in importance. Cases are often shaped — and sometimes decided — by submissions filed before a hearing begins.