How to Win at Mediating Employment Law Claims

  • November 17, 2022
  • Stuart Rudner

I often write and speak about winning at mediation (it’s not an oxymoron), and as a mediator, I remain convinced that most counsel can do a much better job with their advocacy at mediation (also not an oxymoron). One of my mantras has become “help me to help you”; since I will be your advocate in the other room, make it as easy as possible for me to understand and explain your case in a compelling manner when I am speaking with the other side. That is how you win at mediation.

Preparing to win at mediation begins long before the hearing. It starts with choosing the right time to mediate, and the right mediator to help you. It then continues with properly understanding and assessing your case, identifying your strong arguments (and eliminating the rest) and gathering compelling evidence to support them. Deciding to “put all the evidence together if we don’t settle at mediation” means that you go into mediation without your best case; would you ever do that at trial? Of course not. But the reality is that very few employment disputes make it to trial, so in all likelihood, mediation will be your opportunity for advocacy; don’t waste it.

Scheduling Mediation and Pre-Mediation Production

I am a proponent of early mediation in most cases, but it is important to consider the nature of the case before deciding when to mediate. A case with serious factual issues, such as allegations of just cause or discrimination, may well require examinations for discovery before mediation can be productive. Sometimes, when mediation is scheduled before discoveries, we use the time strategically to resolve some issues, such as the notice period or post-termination compensation that would apply if just cause did not exist. We can then agree to adjourn the mediation and resume after discoveries; this is another point to remember: you can be creative with mediation.

At the very least, I would encourage counsel to exchange Affidavits of Documents prior to mediation. Before you can draft a kick-ass brief, you need to thoroughly understand your case. While that does involve some time and cost, it makes sense to assess the evidence you have and know what the other side has; if they have documents that hurt their case, they will have to produce them in their Affidavit of Documents but if that has not been done yet, they may hide them at mediation, which can prevent you from knowing all the strengths of your case and getting the best result you can.

Over the past few years, we have all grown quite accustomed to video meetings and video mediation. I don’t see any reason to go back, in most cases. I have found that if anything, video mediations result in a greater settlement rate. One of the reasons for this is that it’s easier to have the right people at the table; while in-house counsel may not be willing to travel for a wrongful dismissal mediation, they can easily participate in the entire process from their office.

Lastly, when booking, consider booking a full day. I know it is more common to book a half day for an Employment dispute, but the reality is that three hours is rarely enough time to discuss the case, negotiate a settlement, and document the terms. It is very frustrating when people have to leave when we are making progress, which can be avoided if everyone blocks the full day.

The Brief

Your efforts to help me help you start with the brief. That is all I will see before the hearing, and while I never reach any conclusions before meeting with everyone, I can’t help but begin to form opinions about what the key issues are and who has evidence to back up their position. Spoon-feed your case to me so that I can easily understand and, hopefully, be persuaded by it.

To begin with, rather than burying all of the key facts in the body of the brief, consider putting a chart at the very beginning which sets out key things such as

  • Age
  • Length of service
  • Position
  • Compensation
  • Termination date
  • Mitigation information

When explaining compensation, provide clear details and supporting documentation. Providing a figure for “total compensation” along with T4 slips is a start, but we will usually need to understand how any variable compensation was calculated and see the historical payments.

Your mediation brief should not look just like one from 1990. Take advantage of modern technology: embed videos, photos and/or audio clips and hyperlink to key documents. It is much more compelling for me to watch a video of an incident at work than to read a vague description of it, and it is much easier to click on a hyperlink to immediately review a supporting document than to read it later.

If witnesses will be key, I suggest obtaining witness statements and including them. And, as is often the case these days, if messages (text, WhatsApp, etc) will be part of the evidence, don’t just produce screenshots which provide an incomplete and often difficult to follow record; use an app to extract them and produce them in PDF format.

Remember that my job will be to put your case forward in the other room. If I go in there with bald allegations and tell them that you will gather the evidence if the case doesn’t settle, they are unlikely to be persuaded that you have a strong case. If you have the evidence, use it; again, mediation is likely to be your only opportunity for advocacy before a third party.

With respect to case law, if you have chosen a subject-matter expert as your mediation, use case law sparingly in your brief. I don’t need references to Bardal, McKinley, or Keays, but if there are nuanced points of law, then include the key case(s) supporting your position.

Lastly, provide me with a view of the negotiation history and your alternative to settlement. In other words, I want to know what offers have been made, and I also want you to turn your mind to what will happen if you do not settle: how much time and money will be spent on the litigation process. I recognize that counsel will inevitably underestimate, but try to be realistic.

Preparing for Mediation

I realize that many counsel don’t put a lot of time into preparing for mediation. In my view, that’s a mistake. As I said earlier, most cases don’t get to trial, so there is no point in saving your energy for trial. Instead, you should put together the strongest case you can for mediation; that will help you get the best deal you can. There is a big difference between settling and getting the best possible settlement.

Hopefully, you have done this when preparing your brief but when you prepare for mediation, ensure that you have all of the evidence you need to prove your case.

Once you receive the other side’s brief, you should then have a thorough discussion with your client in which you assess the strengths and weaknesses of your case. Your role as counsel is not to be a “cheerleader”, simply confirming that your client is right. You should provide your objective opinion and advice, and have a frank discussion with your client about the strength of their case and potential resolution; that should also include a discussion about the alternative to settlement: what continuing with litigation will look like. And if your client won’t listen to that, then you should enlist me to help you (see my discussion below about talking to your mediator).

When preparing, ensure that the right people will participate in mediation. For the employer, it should be someone with authority to settle. Having to call to get instructions renders mediation much less effective; especially with video mediation, there is rarely a good reason for that, as the right people can easily participate. It is also wise for the parties to think about who else should be available, such as a support person, an accountant or financial advisor to discuss potential tax issues, and anyone from the employer who may be able to address factual issues that arise.

Remember that anyone who participates in the hearing should sign the mediation agreement and confirm that they will be bound by the duty of confidentiality. It is quite frustrating when we get halfway through the process and I discover that an unknown person is in the background, listening without disclosing their presence.

At Mediation

Before the hearing starts, consider a brief talk with your mediator. I am more than happy to speak with counsel in order to gain a better understanding of the case and any specific dynamics that I should be aware of. For example, I recognize that for tactical reasons, you may have to include some issues in your brief even though you don’t plan to pursue them seriously. If that is the case, let me know so that I don’t waste a lot of time on them instead of focussing on the real issues, and so that it doesn’t impact your overall credibility. Similarly, if you have a client that will not listen to your advice, let me know so that I can help. Sometimes, I’m not sure if it is the client or counsel that is serious about pursuing a weak argument, and I always try to avoid embarrassing counsel; if I know that you have tried to explain to your client why the point is weak, I can help you.

The approach to opening statements at mediation has evolved over the years, and my current practice is to begin with a very brief joint session in which I introduce myself and review the logistics of the day. It is an opportunity for everyone to “put a face to a name”, but there is no discussion of the substantive issues. After that, the parties will be in their own rooms and I will move between them. If any party indicates that they do not want to have a joint session, then we skip it.

When we mediate in-person, the “hallway discussions” between counsel, or myself and counsel, can be tremendously useful. You should not assume that those don’t exist in video mediations. I have used separate breakout rooms, conference calls, and even text messaging with counsel to effectively achieve the same purpose. If you want to speak with someone outside of the formal mediation arrangements, you can.


There are a million different theories on negotiation strategy. Many still believe that you have to start with an extreme position and then negotiate toward the middle, splitting the difference. While I definitely think you should give yourself room to negotiate, I always ask parties at mediation to skip the “silly round” where the plaintiff asks for millions of dollars and the defendant offers a few thousand. It’s a waste of time and sets the mediation off on a poor note which I then have to get us past. Instead, I encourage the parties to take a realistic look at their case, consider where we can realistically hope to end up, and then work toward that. If the other side sees that you are being reasonable, they usually will be too; if not, we will know that they are  the impediment to a settlement.

Negotiation involves extensive reciprocity; good and bad. If one party makes an extreme offer, they will usually be met with an equally extreme one. Conversely, if they behave reasonably and make reasonable concessions, the other side is likely to do the same.

That does not mean that if one party moves by $100,000, the other side has to do the same. Often, one party has to move more than the other because they started with an unreasonable first offer. Splitting the difference or meeting in the middle is not the way to a reasonable settlement; any settlement should be based on a reasonable assessment of the value of settling versus continuing with litigation.

Consider Creative Solutions

One of the benefits of a negotiated settlement is that it can include terms that would not be part of a court judgement. For example, a resolution can include:

  • Tax-effective allocation of settlement funds (so long as they are defensible);
  • A letter of reference;
  • Outplacement counselling;
  • Re-employment; or
  • New policies or training (for example, when there was an alleged breach of human rights or harassment).

If you reach an impasse, consider creative ways to reach a resolution. In many cases, I have found that we can bridge vast differences in positions, only to get stuck a few thousand dollars apart because neither side wants to accept the other’s offer. In that case, I often suggest a Mediator’s Proposal, in which case the “offer” comes from me. If both parties accept, then we have a settlement. If not, then we are finished. It almost always works.

You can also consider med-arb, in which case an unsuccessful mediation is followed by arbitration, guaranteeing that one way or another, the dispute will come to an end. A variation of this is final offer arbitration (also known as “baseball arbitration”), in which case each party has to make a final offer, following which the arbitrator must choose one of them. Since the arbitrator has to choose one of the offers and not substitute their own view, the parties must be reasonable.

Concluding the Mediation

When I was a young lawyer, my mentor explained the importance of making sure all the settlement documents are signed before leaving a mediation. That lesson always stuck with me, and as a mediator, I insist that we ensure that a settlement is fully documented and executed before we call it a day. Every  now and then, counsel will suggest that it’s not necessary, or can wait until another day. I do my best to avoid that, and we have seen recent cases in which doing so has led to protracted litigation. It always pays to document the deal, and to ensure that all terms are clearly delineated. For example, there should be deadlines for any payments, and if a letter of reference is to be provided, an unsigned copy should ideally be attached as an exhibit or, at the very least, it should be clearly stated that a positive letter of reference is to be provided.

It has become customary for Defence counsel to draft Minutes of Settlement, but there is nothing stopping either side from doing so. I encourage counsel to bring a template or outline with them and, if it appears that we are nearing settlement, to complete as much as they can. That can help to avoid lengthy delays after a settlement has been reached in principle.

I also discourage everyone from trying to add new terms that were not discussed. If you want a non-disparagement clause, or for the other side to pay the mediator’s fee, that should be raised and agreed upon during the negotiations. While there may be contentious issues, if counsel have done a proper job of raising and negotiating them, the settlement documents should not cause any surprise.

Lastly, if the matter cannot be completely resolved, consider whether any specific issues can be agreed upon, and document those.

Bottom Line

Mediation is advocacy, and in many cases, it is the only opportunity you will have to advocate before a neutral third party. Our job as lawyers is to zealously advocate on their behalf and get them the best result possible. In order to do that, we should be working hard to prepare for and win at mediation; there is a big difference between getting your client a good settlement and just settling.

About the author

photo of author Stuart RudnerStuart Rudner is a mediator focussing on employment law disputes through Rudner ADR. He is a tenacious problem-solver who takes advantage of more than two decades advising employers and employees, as well as years of mediation experience and training. Stuart is passionate about finding a resolution, and will work tirelessly and strategically to do so. He will adapt his approach to the circumstances, providing evaluative views but also exploring the underlying issues and other matters of importance to the parties when they are necessary to facilitate an agreement. There is no one-size-fits-all in mediation. Contact Janis Buckley,, for available dates and to book a mediation.

Contact Stuart Rudner at

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