Complexity
One question that you could ask is how complex might the dispute be. Complexity introduces multiple variables into a dispute – in particular, it increases the chance that the actual costs will exceed the estimate. It also brings greater uncertainty into any assessment of the outcome. Will the large amount of evidence support your position, or is there something in there which will tip the balance in the other side’s favour? Will the decision-maker agree with your interpretation of a difficult area of law or think you are being unreasonable? Complexity is difficult to judge, and can change over time, but an experienced lawyer should be able to provide some guidance to you.
Modes of communication
You might also ask your lawyer what types of communication with the other side would be appropriate. The transition of a dispute into formal proceedings is a shift of communication. No longer do the parties speak to each other; it is now left to their lawyers to correspond. But will a single mode of communication bring about a resolution, or merely prolong the dispute?
What about a multi-modal communication – with both correspondence between the lawyers and conversation between the parties? What about communication protected by “without prejudice” labels; between different individuals on each side instead of those originally involved in the dispute; or moderated by a mediator? And what about other ways of approaching the communication – looking at other options rather than contractual rights and legal proceedings, and placing an emphasis on listening rather than arguing? This is something you and your lawyer can think through together, bearing in mind the personalities involved on each side and what your ultimate goals are.
Emotional impact
Something else that is worth considering is the impact that the dispute is likely to have on your emotional wellbeing. Time and cost can be accounted for, but damage to your mental health (and, sometimes, your physical health) might not be recovered. What criticisms will be made during the dispute of you and your behaviour? How will you bear the antagonism from the other side – made all the worse, perhaps, if you had a good relationship with them in the past? How will you feel as the dispute drags on, knowing that a losing outcome is a possibility, and what might you suffer if you do ultimately lose the dispute? These are all things you will have to endure.
Time is a factor here, too. Legal proceedings may start on a rush of emotion but spirits can be dragged down as the months pass, and each time a filing is made by the other side. What may have appeared a sure thing at the outset can seem less certain later. Also, your attention may be distracted by other things; the dispute may become less urgent; and anxieties may rise as costs mount. But at the end a final burst of energy is needed because hearings require concentrated effort. Moreover, it is at the hearing that the dispute finally becomes real. Submissions and evidence swapped by impersonal email over many months look very different when you are sitting in a room facing your opponent.
Your lawyer should have been on this journey many times before, with a range of clients. They can tell you what to expect from the rollercoaster.