1 Big Idea to Think About

  • In negotiation and collaboration, switching from the traditional “win-win” approach to a “can’t lose-can’t lose” approach is a paradigm shift that creates psychological safety and allows you to turn resistance into momentum.

2 Ways You Can Apply This

  • Identify what you and the other party can’t lose by creating the “Can’t Lose-Can’t Lose 2×2” discussed in the episode.
  • Use the 2×2 you created to further a negotiation or collaboration you are working on right now.

3 Questions to Ask

  • What is the win-win situation in this collaboration?
  • What can’t I lose in the process of this collaboration?
  • What can’t they lose in the process of this collaboration?

Key Moments From the Show 

  • An interesting conversation leads to an unexpected dynamic (4:08)
  • Bad is stronger than good (5:26)
  • From “win-win” thinking to “can’t lose-can’t lose” thinking(12:04)
  • The can’t lose-can’t lose 2×2 (12:58)
  • The power of can’t lose-can’t lose thinking (16:19)

Links and Resources You’ll Love from the Episode

Greg McKeown:

Welcome. I’m your host, Greg McKeown. I’m the author of a couple of New York Times bestsellers, Essentialism and Effortless, and I’m here with you on this journey to learn how we can use our precious time to make our highest contribution. 

Have you ever been involved in a conversation where you or the other person’s resistance started to go up? Today, I will share an interesting story, something counterintuitive I’ve learned, and some actionable advice. By the end of this episode, you will be able to turn resistance from other people into open collaboration. Let’s begin.

If you want to learn faster, understand more deeply and increase your influence, all you have to do is teach the ideas in this episode to someone else within the next 24 to 48 hours. 

Some time ago, I had an interesting conversation with a highly capable leader, respected all over the world. We’d been introduced by a mutual friend, and I had just a small idea of something that I thought we could collaborate on together. As we began the conversation, the collaboration moved really quickly, and within just even a few minutes, we had opened up all sorts of possibilities of quite major ways that we could start collaborating together, even starting within the next few days. And this brought with it an unusual, a little bit unexpected dynamic, but I bet it’s one you’ve experienced yourself. Suddenly as this larger higher level of commitment and possible collaboration came into view, so did other concerns.

I could immediately start to see concerns that we would need to address if we collaborated in this, both higher and deep away. And so could the leader I was talking to. The situation I’m describing is yet to be resolved, but here is what it made me think about. People are more concerned with what they might lose in a conversation or a collaboration than with what they might gain. 

So much has been written about the importance of win-win thinking. Nevertheless, what I think matters even more, is not lose, not lose thinking. So let’s dig into that for a minute. It’s well established that negatives are stronger than positives, or as the most cited peer-reviewed article on the subject is called, Bad is Stronger than Good. The article I’m referring to is written by Roy F Baumeister and Ellen Bratslavsky. What they basically did for this article was review all of the other peer-reviewed articles on this basic thread, this basic idea. In their abstract, and I’m just quoting now, they said, “The greater power of bad events over good ones is found in everyday events, major life events like trauma, close relationship outcomes, social network patterns, interpersonal interactions, and learning processes.” 

Continuing from the abstract now, “Bad emotions, bad parents, bad feedback have more impact than good ones, and bad information is processed more thoroughly than good. The self is more motivated to avoid bad self-definitions than to pursue good ones. Bad impressions and bad stereotypes are quicker to form and more resistant to disconfirmation than good ones. Various explanations, such as diagnosticity and salience, help explain some findings, but the greater power of bad events is still found when such variables are controlled.”

Then they add this important line, “Hardly any exceptions can be found.” 

I mean, that’s really important from a social science point of view where you’re trying to disprove your position. The technical term is falsification. You’re trying to find evidence that doesn’t support what your position is, and they conclude in this abstract, “Taken together, these findings suggest that bad is stronger than good as a general principle across a broad range of psychological phenomena.” (1)

So this is, I mean, this is well established. If we want to go a little step closer to practical application, one could do worse than one of my colleague’s articles, also called Bad is Stronger than Good, but this time written in Harvard Business Review, and this is from my colleague Bob Sutton. In this, he reviews some of the same studies from the larger article I just referenced but also specifies a few additional ones. But he gets to something specific here that we all need to think about. He says, and I’m quoting, “It was confirmed by several studies that among relationships where the proportion of negative interactions exceeds this one to five rule, divorce rates go way up and marital satisfaction goes way down. The implication for all of us in long-term relationships is both instructive and daunting. If you have a bad interaction with your partner, following up with a positive one, or apparently two, three, or four won’t be enough to dig out of that hole. Average five or more, and you might stay in his or her good graces.” (2)

Okay, so now this is the general idea that bad is stronger than good in our interactions with other people, but we have to get a little more specific, a little more clear within that broader body. I found a great description of this at behavioraleconomics.com, in which they define loss aversion. Of course, this is an example of bad is stronger than good, that people would rather not lose something they have than gain something they lack. They write the following, “Loss aversion is an important concept associated with prospect theory.” Don’t worry about that for now. “And is encapsulated in the expression.” Do care about this. “Losses loom larger than gains.” 

So that’s from one of the greatest thinkers in this field. Kahneman in an article that he wrote way back in 1979, but they continue here. They said, “It is thought that the pain of losing is psychologically about twice as powerful as the pleasure of gaining.” (3) (4)

Now that is worth pausing on, especially given how much emphasis has been placed in most of the negotiation literature on the power of forming alignment. What is the win we will achieve? And I’m not knocking that that’s really important. If you don’t have alignment, if there isn’t a mutually desired result that we can agree on, then everything else will become way harder because nobody has a reason to work together. Nevertheless, let me just read it again, their summary. They said, “It is thought that the pain of losing is psychologically about twice as powerful as the pleasure of gaining.” (3) (4) 

That’s a massive effect, and it’s not an effect that’s exactly new to me or new to those that have read Essentialism or Effortless. These are ideas I have explored before. Specifically, you think about the endowment effect. We value things more because we own them, meaning we overvalue them or sunk cost fallacy which again is a different way of saying a similar thing that we continue to invest in something because we’ve invested in it before. We don’t want to admit that the investment before was a waste of our time, money, and effort. So we keep on investing in it. That status quo bias would be another way of thinking about this. 

Okay, so what does all of this mean? What can we do with this? What it means is that in conversations with people, people are going to be more concerned with not losing than they are in what they have to gain. And I think this is just one of the reasons why people in organizations are so risk-averse in communication. 

One of my observations over the last 25 years is that it may be the number one error made in corporate interpersonal communication, and that is not speaking up. We have a risk attached to every time we speak up, and the gain of speaking up is neutralized by the risk of losing our position, looking like we’re not being a good team player, giving the wrong answer.

So what can we do? What is the actionable advice here? And I think it’s the following, and I want you to do this with me. I’m going to draw this out. I drew it out after this recent conversation, collaboration. 

Okay, so it’s a two by two. Write out the two by two, and then you can visualize this. So in the, what is the X-axis. So that’s the top, the horizontal, the first column is you, and the second column is them. And that’s easy enough. So now, as we get to the Y-axis or the vertical, the first row would be desired win. And then the second is can’t lose. So this now leaves us with simple, you’ve seen them many times before, two by two here, and it implies four questions that we can ask. 




         Desired Win     

     Can’t Lose


Here are the questions in order. So in quadrant one, we’d be asking a question. What is my desired win in this conversation? What do I want from this? What is a win for me? 

If you move across horizontally, you get to question two, which is, well, What is the desired win for them? What do I think their win is? 

Then moving down, now the next row down, the question that you’re asking is, What can’t I lose in the process of this collaboration? 

And then quadrant four, the final quadrant, bottom right, is What can’t they lose in the process of this collaboration? 

To me, this is simplicity on the other side of complexity. There are so many interactions where people’s immediate risk aversion starts to push resistance to the ideas that you’re exploring with them. And if you can craft this simple analysis before the conversation, now you might get it wrong. That’s fine. We’ve talked about that before in this podcast. You can present it and then say, Look, tell me where I’m wrong. What am I missing? 

But if you are able to articulate clearly, perhaps you just do it together, what you can’t lose, what they can’t lose, as well as what the wins are, I think we would achieve far greater collaboration because we’ll be able to turn resistance into momentum. 

You can go back and listen to the episode in which I talked about the breakthrough negotiations that were had first by Sir John Major and then by Tony Blair, back-to-back prime ministers in England in their negotiation efforts with the 75-year war around Ireland and Northern Ireland. And in that example, it all began when, Sir John Major started to have a discussion, what he called a series of principles, that is, here are the principles that cannot be violated as we continue our conversation. Here are the parameters so that what is happening when he created that?

What happens when you create a two-by-two, as I’ve just described, is that you are increasing the psychological safety of the people in the conversation. Now, one way to achieve psychological safety is to be able to identify what’s the mutual benefit. Of course, that happens, but I think there’s this deeper, stronger, and less addressed area of identifying the can’t lose, can’t lose dynamic. When that gets expressed, then what happens is you’ve got the criteria now, the frame, the space to be able to work together collaboratively. Well, let’s come up with a solution together that addresses not just what we both want but also what we both don’t want so that we can be able to do great work together and not have to fear and worry. 

We’re putting the parameter around the fence. It’s a story about this that perhaps it’s just law, and it isn’t really a true story, but it’s an interesting one nevertheless. And it’s the story of a group of schoolchildren whose school is by a busy road, and at first, they would all play close to the school because it was scary to be so close to the road. And then somebody puts up a decent-sized fence around the school, and then the children can play right to the perimeter. 

And the idea here is that as you create a clear parameter, as people can know, Well, I’m not going to get taken advantage of here, I’m not going to lose in this negotiation, I’m not going to lose in this collaboration, even in this simple conversation with people in our own lives, our own families, our own workplaces, then they’re able to open up more, fully, put more of their creative energy and enthusiasm into the dialogue. So here’s in favor, not only of win-win thinking but of can’t lose, can’t lose thinking to increase that psychological safety so that we can collaborate and therefore make a greater contribution in our lives.

Well, what’s one idea that you can share with someone from today’s conversation? What is one thing that stood out to you? What is one insight you have had that you can share and teach with others? 

If you have found something valuable in this episode, please write a review on Apple Podcasts. The first five people who write a review of this episode will receive free access to the Essentialism Academy. And for the details of that, please go to essentialism.com/podcastpromo. Remember to subscribe to this podcast so that you can be a part of this ongoing conversation every Tuesday and every Thursday. I’ll see you next time.


(1) Baumeister, R.F., Bratslavsky, E., Finkenauer, C. and Vohs, K.D. (2001). Bad is stronger than good. Review of General Psychology, [online] 5(4), pp.323–370. doi:10.1037//1089-2680.5.4.323.

(2‌) Sutton, R. (2010). Bad Is Stronger Than Good: Evidence-Based Advice For Bosses. [online] Harvard Business Review. Available at: https://hbr.org/2010/09/bad-is-stronger-than-good-evid [Accessed 8 Nov. 2022].

(3) BehavioralEconomics.com (n.d.). Loss aversion. [online] BehavioralEconomics.com | The BE Hub. Available at: https://www.behavioraleconomics.com/resources/mini-encyclopedia-of-be/loss-aversion/#:~:text=Loss%20aversion%20is%20an%20important.

(4) Kahneman, D., & Tversky, A. (1979). Prospect theory: An analysis of decision under risk. Econometrica, 47, 263-291.