Empathetic Negotiation

This is going to be a longer post than you’re probably expecting. I composed it from three stories taking place over the past year and the third one pays for all.

I could see the gears turning in the mind of the older man across the table from me. It was just the two of us in a conference room sequestered away from the rest of the loud and lively makerspace, Artisan’s Asylum. Bandsaws and squeeky rollings carts could be heard from all corners of the converted warehouse as makers and engineers worked on everything from joining cabinetry to welding bike frames to soldering robots. Granted, the conference room didn’t have a ceiling in-between us and the 30-foot high ceilings, so it wasn’t much in terms of sequestering.

“You want me to pay you $1000? … That’s crazy!”

Crazy. He used the “C”-word.

His eyes aimed just to the right of my head, not making direct eye contact. His mouth was slightly ajar as I could tell he was repeating the calculations in his head. He was in disbelief, still processing the situation. We were about 10 minutes into a negotiation aimed at restructuring what was a bad contract deal. This gentleman, we’ll call him “T”, had a pair of small motors controlled by a circuit board. A friend made it for him – the problem is that it was no longer working. He had hired me to fix it a couple weeks previous.

This was my first gig as an independent contractor and my first paid gig working with electronics and programming. Given all these “firsts” it may go without surprise that in my initial quote wasn’t water-tight. I suspected it would take only a handful of hours and quoted him thusly. All things considered, I wasn’t too far off with my estimate. I think I actually finished it under my projection. However, feature-creep creeped in as he asked me to do one additional task. It seemed like it would only take me an hour so I started working on it without complaint.

It took 5x longer than all the work up to that point.

Ultimately, I did get it to work but now I’d spent much too much time on a contract with a fixed price tag. That element was the real problem here and is something I was sure to remedy in future contracts. However, I was stuck with the problem in this case. What to do? Roll over and take the hit? I’d done that in the past and it never felt good. 

No, I wanted to take this as an opportunity to practice advocating for myself, to take a different approach. I wanted to practice negotiation.

I was not a natural. Negotiation skills are something I’ve coveted for years but never had a foothold in. I remember listening to an audiobook as I drove into work back in 2015. I remember not getting very far. I didn’t have much context for where to begin. What would I even be learning? It would obviously be a soft-skill but one that must have some hard rules. Was I up to it? Was it not about the approach but about me as a person? Was I too soft? Avoid conflict too much? Was I too empathetic?

You can imagine my excitement that I had a relatively “low-impact” opportunity for project-learning here with “T.” I had only a few days before our meeting to learn whatever it would be that I’d want to apply. The next day, I had a small yellow paperback book in my hands at a new coffee shop down the street in Allston, MA.

“Never Split the Difference: Negotiating as if Your Life Depended on It” by Chris Voss. What caught my interest about this book is that the author was an FBI negotiator. It seemed like this wasn’t going to be a fluffy business book like the others. At the very least, I bet he would have some good stories.

Spoilers: Within the last year since I first started reading this book, I’ve now read through it twice, recommended/bought it for 5 of my close friends, and have made well over a “return” of 1000x from the cost of the book. 2000x? Hard to count, given how some of these contracts are multi-year and/or non-tangible.

I set up a crash course for myself in the book over the next two days. After that, it was game time. No time to fret over it, only time to try.

Scene change: Back to the ceilingless conference room

A customer had just exclaimed that what I was proposing was crazy. He was expecting to pay me $200 and I was now asking for $1000. I can tell you with 100% confidence that this is where I would have broken in the past. This is where the dagger of his accusation would be physically painful in my chest. My ears would start to ring a little and my neck would tense. Honestly, I wouldn’t have even made the ask.

But there I was, sitting in the conference room. Nodding. Unaffected. It’s like the dart of his acquisition had passed over me. I was unscathed. No barbs protruding from me.

I replied with a simple phrase. A phrase that I didn’t need to think about in order to say. Because honestly, he could have said any adjective and my reply would follow the same structure. I simply nodded and replied, “ya, it’s crazy.”

Then I waited. I let the silence sit as he continued to process. 

“I mean, that’s insane.”  He said, finally turning his head slightly in order to make eye contact with me.

Again, I found myself nodding. I felt myself feeling, well, nothing really. Nothing outside of someone saying “good morning!” to me. I replied again, “ya, insane.”

I could write a book about the book Chris Voss wrote – but I’ll leave that to the expert. Without going into all the tactics I used in what would result as an hour-long negotiation, I want to highlight this one. What I was doing was mirroring “T.” I was essentially just repeating the last line in the conversation without adding anything of novelty. It has many uses but in this case I was setting up exit criteria for a mental loop that “T” had created in his head. I was essentially giving him time to process and I was replying in a way that meant I would not take his reactions personally.

That second point was huge for me. It was a completely unexpected consequence and one that I only fully really realized after the conversation was over. Results of the negotiation aside (he ended up agreeing that I needed to be paid more than we had initially agreed – and did pay me), this one aspect was an incredible confidence boost and made me bullish to finish the book and try all this “negotiation” stuff again. I devoured the book.

It wasn’t long before I got the chance to practice again.

Fast forward to a future gig, this time making a prototype for a startup. I had ordered sheets of acrylic from a local supplier in the Boston area. I ordered them on Tuesday and I needed them by the following Monday. It was an $89 order including $18 in shipping.

By Saturday I didn’t have a shipping notification, which was odd. In the past they had always notified me it had shipped the day after I ordered it. I emailed them asking for clarification. It was Monday morning before I got a response. Again, this was the day I needed it. 

I got a terse response over email that I could either pick it up myself or get it in three days. That means they hadn’t shipped it yet. I focused on questions starting with the word “how” so that she could come up with solutions. I asked “how I could get this today without spending two hours on the subway, since I didn’t have a car.” She replied that I could get a courier. I could call with my credit card information and she could set it up. It would be an additional $15. I had already spent $18 on shipping and I wasn’t keen to spend an additional amount. I jumped straight into another “how” question, asking “how I could get it today without spending more on shipping.” All of these emails were back and forth over a few minutes.

Then silence.

I let 30 minutes pass before I called and asked for the contact by name. 

I got through but things got off to a rocky start. I took an assertive approach but polite – letting it be known that I wasn’t happy but doing so with a smile on my face. I could tell that she wasn’t happy either. I recapped what we talked about over email and then asked the same question I ended with. She immediately replied with:

“We’re not going to eat the cost of the courier. We didn’t promise overnight shipping.”

For me, that was a line drawn in the sand. In the past, I would have left the call defeated at that answer. I would have felt disrespected. I would have felt slighted. Perhaps I would have even asked her to cancel the order. It wouldn’t have been good, regardless. 

I took a gamble. I had thought about “forks in the road” before the call, different approaches I could take depending on information I gleaned during the call. I was prepared. This was one of the greatest lessons I learned in my previous negotiation with “T”. I would hypothesize as to different pieces of gleaned information and have pre-decided how I would change my approach depending on them. One piece of information I predicted I could learn during the call was that “they hadn’t shipped out the order because they were busy.” It’s not an excuse, but a reality. I know what shipping can be like from my time working in the aerospace industry. 

My gut said this was the case. It was a Monday morning and she was already stressed.

“It sounds like you had a really busy week last week. In the past when I’ve made orders they go out the next day, but it sounds like you weren’t able to get this one out when you wanted it to.”

My intuition paid off. She talked for 5 minutes about how busy this month had been. How their cutter was on vacation and everything this week would be late as well. She even told me how she had pushed my order ahead in the queue. While she was talking, I used that as an opportunity to mirror her whenever I could, repeating things like “pushed me ahead in the queue” and “ya, on vacation.”

At the end of it, I repeated my question. But now I was a human and she was a human. I had taken the time to listen to her and she knew I wasn’t angry. She also probably felt like I knew this wasn’t because of her incompetency but because she was in a busy week. That probably made her feel better too. 

This time she offered something different – she would reimburse the shipping fee I had already paid. She also suggested how to get cheaper shipping on future orders (a nice bonus I wasn’t expecting) and that if I ordered the courier it would probably be cheaper than if they did.

This sounded good to me, as long as the courier was in the range of the $18 I was getting back for shipping. But I had never used a courier before, so I took a humbled approach and asked if she had a few minutes to help me set it up.

She said yes. She gave me a couple options for local couriers, I quickly got quotes and found the better one. It was going to be $22 to get it in three hours. Perfect, this was well within my margins of success.

I asked her to refund the shipping cost, and that I would send the courier over to them directly. At the end of the call, it felt like I had made a contact at one of the larger acrylic suppliers in Boston. I was getting my order when I needed it and the $4 extra dollars I spent would be well made up in the future with the tip she gave me for cheaper shipping.

This was all possible by thinking ahead as to the reality she may be experiencing. Not blaming her for it but understanding it and letting her know I saw her as a human being versus just a shipping service. At the end of all this, it feels like I made a friend.

The best thing about both of these stories is that the skills I learned from Voss’ book lead me towards being a more empathetic person. That’s right, one of the greatest negotiators in the world is preaching empathy. All my preconceptions of negotiation being about driving a “hard bargain” and “take what you can, give nothing back” were completely off the mark. In many ways, I was relieved. That’s not really the kind of person I am. Past being relieved, Voss’ approach made me very excited. I already knew that I was naturally empathetic and had focused years on developing those skills. Voss’ approach is a self-proclaimed “tactical empathy.” It’s not underhanded though, it’s just about control. His focus is about ensuring you see the other party as human beings with needs and desires that may not even be readily apparent to them – let alone you. The negotiation is a conversation to bring those needs to light.

I actually quite enjoy it now.

I’ll close with a third story, as the third pays for all. Recently a very good friend of mine has been on the job hunt in the software world. He’s been through a number of interviews that ended in rejections and, as one may expect, his confidence was beginning to take a hit. One in particular was painful to him because he knows he failed the last two questions in a six-question interview not because of his lack of technical knowledge but just because the interview was hours long and he was exhausted. It hit him hard.

I suggested to him to be bold. If he knew how to solve the interview problems, he should complete them and send them to his contact. He liked this idea because it felt like he could take action in an otherwise hopeless scenario. I had one condition though, that I would need to read over his email before he sent it. All specific names removed, here is what he initially wrote:


Hi L,

Thank you for your quick response. I appreciate the time you have spent on this process. 

I wasn’t able to exemplify my full ability at the end of the six-part interview. I performed well at the beginning but was overwhelmed by the end. I went ahead and finished the two programming challenges and have attached them to this email. If the day to day environment at your company isn’t as tiring or as stressful as the six interview process, I’d like to request the team reconsiders my application with the new code samples I have included.

Thank you again for your time and help in this process.

Best Regards,



This is a fine email. It’s honest but firm in its ask. I could very well see myself having written this exact same type of email a year ago. But by now I had a different approach. I rewrote everything but a line of his original. My letter:


Hi L,

This is going to be hard to read. I’m going to sound like every other candidate who was rejected – asking for reconsideration in the face of knowing “nothing can be done.” But given how successful the interview process was up until the last two sessions, I want to bring this to you before going to another company. 

I’m as aware as you that I failed the last two challenges of the six-part interview. I performed well at the beginning but was mentally overwhelmed by the end. Of my own volition, I have finished the two programming challenges and have attached them to this email.

I intend this to show that it was not the technical aspect of the challenge that I failed, but the rigorous structure of the six-part interview.

It seems like your company is using the six-part interview format because it filters out all but the best of the best. I understand that hiring is one of the most critical aspects of a startup and is not taken lightly or with exception. My question is, though, does the rigor of the six-part exam represent the day-to-day at your company? Is that a fair way to gauge an employee’s ability to succeed?

Best Regards,



Before I even showed it to him, I told my friend that the letter was going to be longer than he would like and would come off stronger as well. Turns out both of those were true. Turns out I did this on purpose. By accusing myself of these negative aspects in the beginning of the conversation, it anchors a laser-focused expectation of what is to come. In short, it’s being courteous. It’s highly tactical but it turns out to be quite kind. If these accusations are true, you immediately give the other party a platform in which to air their grievances. If it’s not that big a deal, you’ve cleared the air. I have found this approach to be wildly successful and increasingly empathetic. I took this same approach in the beginning of the letter I wrote for him, saying “this is going to be hard to read.” Bonus points if you are now noticing or already noticed that I indeed started this very blog post in the same manner, saying “This is going to be a longer post than you’re probably expecting.” It’s true, really. This is the longest blog post I’ve written. And you knew that on line one versus getting in a few paragraphs and scrolling to the bottom to see how much was left.

Back to my friend: I wanted to give him the best chance at actually getting a response from this company versus just being ignored. I don’t normally like to merely “give a man a fish” versus teach them to fish, but in this case he was in a dark place and I wanted to help him quickly. I’d been there.

In my letter, I specifically use five different tactics I learned from Voss’s book. A few of them I’ve talked about so far already in this blog post and you may be able to pick them out. A couple others… well, I’ll just leave this here.

I’m happy to report that it did indeed get my friend a reply – and an earnest one at that. This was no canned response but one he feels they actually took a moment to write. He feels closure from that. Their reply:


Hi D,

Thank you for the email. As someone who just recently went through the job search process, it is definitely challenging and discouraging at times. I wish you the best as you continue your job search! Your persistence and dedication to growth will definitely help you to be successful at your next position.

At our company, given our current size and flat management structure, we have a very high bar for the skills we expect engineers to bring on day one. It has taken time to craft an interview structure that helps us assess the skills that we are looking for, and we are certainly always looking to improve. However, we do feel that the current structure has helped us to identify employees that will succeed at our company.

That being said, we do encourage you to apply down the road as you continue to develop your skills and experience.



Being a better negotiator has made me a better human being. It makes me more confident in my abilities and the knowledge that I can stick up for myself. It has made me a more empathetic person, which I would have had a very difficult time imagining being the case before starting to read. I could not imagine my life now without the perspective I’ve learned this past year. If you find yourself wanting to take more control of your life, be more confident in your stance, be more persuasive, charming, or influential – I highly recommend giving Voss’ book a read. Or two.

.gif – Hercules [2014]
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