The Secret of Getting Optimistic and Pessimistic Employees to Collaborate Effectively (Video and Podcast)

7 min read
The Secret of Getting Optimistic and Pessimistic Employees to Collaborate Effectively (Video and Podcast)

Maximize the value that pessimists and optimists bring to your enterprise by helping them work together well. Optimists should generate half-baked ideas and give them to the pessimists, who would select the most viable notions and finish baking them into full-fledged plans. That’s the key take-away message of this episode of the Wise Decision Maker Show, which describes the secret of getting optimistic and pessimistic employees to collaborate effectively.


Video: “The Secret of Getting Optimistic and Pessimistic Employees to Collaborate Effectively”



Podcast: “The Secret of Getting Optimistic and Pessimistic Employees to Collaborate Effectively”



Links Mentioned in Videocast and Podcast

  • Here’s the article on The Secret of Getting Optimistic and Pessimistic Employees to Collaborate Effectively
  • The book Never Go With Your Gut: How Pioneering Leaders Make the Best Decisions and Avoid Business Disasters is available here
  • You are welcome to register for the free Wise Decision Maker Course 


Hello everyone and welcome to another episode of the wise decision makers show where we help you make the wisest and most profitable decisions. Today, I’d like to talk about how you get people who are optimistic and pessimistic to collaborate together effectively in the workplace. And most of us are one type or the other, optimistic or pessimistic now, I am pretty optimistic. That means I see the world as a mostly friendly place, a hopeful place, the future is bright, the glass is half empty, the grass is greener on the other side of the hill. By contrast, my wife is a pessimist. She sees the world is mostly full of threats, mostly full of risks, she is risk averse, whereas I tend to be risk blind. She sees the glass as half empty, and she sees the future as mostly dark and she sees the grasses yellow on the other side of the hill. Those types of personalities again, most people are one or the other. they very rarely are balanced realistic results from too dangerous judgment errors, cognitive biases. Now, if you’ve been watching, check me out listening to the wise decision maker show for a while. You know, that’s what we talk about these dangerous judgment errors that come from how our brain is wired. So neuroscience shows that we have a lot of dangerous judgment and errors. I talk about them extensively in my books like never going with their gut, how pioneering leaders make the best decisions and avoid business disasters, the blind spots between us, how to overcome unconscious cognitive bias and build better relationships, and other books. So those are two books that you can check out. I talk about cognitive biases, and two very common ones, cognitive biases that are diametric opposites of each other. This one is the optimism bias. So the optimism bias has to do with us perceiving the having a positive view of future risks and rewards. So that’s what it’s basically about, we see the future as mostly a positive place, we see the reality with the current reality, the current world is mostly a positive place. And so we tend to be risk blind, we tend to think that the rewards are bigger than they are. And we tend to think that they are smaller than they are. And that’s again, I’m saying we because I am an optimist. Most business leaders are actually optimistic. Most entrepreneurs, I started the disaster avoidance experts, which is a boutique consulting, coaching and training firm in the risk management and decision making strategy. And that’s why I started in part because I’m an optimist, because I saw the future as mostly a friendly place. Even though about half of all startups fail within the first five years and three quarters fail within the first 15 years. I know the statistics on that. So I had to, despite that I decided to start it. And hopeful that the business will not be one of those that fails within the first five years and the other 50% or the 75% fail within the first 15 years so let’s hopefully not, but intrapreneurs. So intrapreneurs tend to be pretty optimistic. and business leaders, those are the top of the business tend to be pretty optimistic. So the startup founder CEO, I’m pretty optimistic. The pessimism bias is the opposite cognitive bias, it’s the opposite of the optimism bias, you tend to see the future as more risky than it actually is less full of rewards, you tend to see the rewards are smaller, and you tend to see the risks as large and of course, in the present to sales find a lot of people who are pessimistic in the number two role in an organization. So my wife was a pessimist and is the chief operating officer of disaster avoidance experts, for example. So that role helps hold the leaders feet to the ground and more of a strategy, big picture. And she’s kind of the more implementer douleur, of helping address some of the two grand designs that I have about the business and lots of great ideas that may unfortunately go nowhere. So optimists and pessimists, that’s commonly the difference between them. optimists tend to generate new ideas. I’m great at generating new ideas. You know, I have 28 years before breakfast, and I think they’re all brilliant. I learned from my better experience. They’re not all brilliant. But most optimists who are not aware of these dangerous cognitive biases that they suffer from the optimism bias. They feel that their ideas are brilliant, and therefore the thing that they’re brilliant, and therefore they claim that these ideas are brilliant, and they push these ideas hard. That’s what happens to optimists most often. pessimists, by contrast, are critical of these new ideas because they perceive these new ideas as risky, sometimes more risky than they actually are. So they pessimists are not great at generating new ideas. But they’re great at finding the risks in these ideas. So they feel threatened. They feel anxious about these ideas coming from optimists. And that is the source of a lot of conflict. Whereas optimists you know, they think that pessimists are just naysayers will never allow good ideas to go forward. They shut down the brilliant ideas brilliant in quotation marks of optimists. And that’s definitely a challenge for optimists like myself to feel that they’re brilliant ideas are being shut down by people like my wife and business partner or of course in any sort of collaborative project. pessimists by contrast, they think that optimists are going off half cocked, always coming up with half baked ideas. And that is a big, big challenge where pessimists simply feel like they have to be critical. They have to be Mrs. No or mister No. So they have to be kind of holding down everyone’s feet to the ground and saying, Okay, are we sure we want to go there, figuring out all the risks, all the problems. That’s the role that pessimists generally take on. Unfortunately, they don’t work together, they just fight each other. That’s not a good recipe for success. You have a lot of team conflict, a lot of struggles, at the leadership level between number one number two and other members in the C suite between team members, some of whom are optimistic, some of whom are pessimistic, that is not a good mode for collaboration. Instead, what you need to do is learn each other’s strengths. What are your strengths? Are you an optimist or a pessimist? Generally speaking, optimism and pessimism are seen as weaknesses. But really, what they are is different strengths. When you use them correctly. You want to use the strengths of each personality to be stronger together. So optimists, for example, as I mentioned, are great at generating ideas, that stress strength, like I said, 20 years before breakfast, I think they’re all brilliant pessimists, by contrast, our greatest optimizing ideas, right now that that’s not the case, in most situations where they’re not optimizing, they’re shooting down babies, and optimists are defending their ideas. And that is not a great dynamic, a much better dynamic is for pessimists, to serve as Devil’s advocates, to improve ideas rather than shoot them down. So once you want to mix up the process of collaboration, you want to create balanced teams, where you hire and promote people who are different from you. Because what you’ll have then, is a balance of optimists and pessimists. Where what how they should work together is you have if you’re an optimist, you have 20, brilliant ideas before breakfast, right? You think they’re all brilliant, then you need to give up ownership of these ideas. You can’t keep ownership of them. It’s something I learned, based on the research on this topic, that you really can’t keep ownership of them, you got to give them to the pessimists and say, Hey, here are 20, half baked ideas, and you got to frame them as half baked ideas. You can’t say these are brilliant ideas, because pessimists will generally see so many holes in your ideas. And you will not see those holes, because you are an optimist. So you got to frame that as half baked ideas, even if you feel that a brilliant frame them is half baked ideas. And what the pessimist will do is that makes it safe for the pessimists that reduces the anxiety and the worry, you know about the ideas being already ready, and that they can take the time to improve them and address all the problems. And of course, giving up ownership addresses the anxiety of the optimists that have brilliant ideas will be shut down because they’re no longer their ideas. They’re just ideas that they’re passing on as notions as half baked potatoes to the pessimist and the pessimists or the pessimist team members, if you’re doing this as part of a team rather than a two person dynamic. The pessimists team members or team member will then look for these 20 ideas and say, Well, you know, these, these 17 just won’t do. But these three may be half baked potatoes that are worth finishing baking. And they’re not koratala generating new ideas because they inherently see the flaws of each idea, bigger flaws than they actually are. But they’re great at judging ideas, evaluating ideas, and then implementing them. So that is a great strength of pessimists judging ideas and implementing them. You don’t want them to do the brainstorming, don’t force them to do brainstorming that will not work well for them. But they’re great at the stage of criticizing ideas. So you want the optimist generating ideas. You want pessimists to be criticizing ideas. And then you want to have those balanced teams. So the problem I’ve seen so often is where teams are hired based on you liking other people who have your personality, whether you’re an optimist or pessimist. As an optimist, it’s very tempting for me to hire other optimists like click with them. Well, you know, we work together and bounce supposedly brilliant ideas off each other. And think about what would happen if I had a team of optimists, let’s say six people. So disaster avoidance experts group currently employs six people. So all six of us were optimists, then we’d have 120, brilliant ideas before breakfast. And we’d be reinforcing each other’s ideas and only be running in 120 different directions. That’s one of the main reasons that actually startups fail. But you’re pursuing too many projects, you’re not focusing enough on the most profitable, least risky, most rewarding projects. By contrast, by making sure that I hire some pessimists, I have a team that is actually able to filter the ideas of optimists like myself, and focus on the projects that are the highest reward for lowest risk. So you’ve got to have those balanced teams. And the same thing for pessimists, you can’t have a team of pessimists, you will not be generating nearly enough new ideas, nearly enough new ideas, you won’t be nearly creative enough. Now in some fields, that may be fine. If you’re, for example, in the field of accounting, you may not want to be generating new ideas, just Just do your accounting pessimists are a good area for that. Or if you are kind of if your role is sales. If you’re a salesperson, that should be mostly an area for optimists, because getting turned down for sales is a hard thing. And you need that optimism to carry you forward. And you can create lots of new ideas and some of the monsters are going to do that. But most teams, you’ve got to have balanced teams and hiring people who are different than you if you want to succeed and make sure that you have optimists and pessimists collaborating together effectively. And that’s the secret to doing so. Hope you’ve enjoyed this episode of the wise decision makers show. Now, as always click like if you liked it, please share it with your friends if you know some optimists or some customers who can benefit from this show. And make sure to follow us on whatever venue you’ve heard us. We have both a video and a podcast version video cast the podcast version of the show. So they’re going to be in the show notes. Check out the video. If you’ve heard the podcast, check out the podcast if you heard the video. Make sure to follow us wherever you prefer to get your media. So do that. Check out the blog that’s linked in the show notes. It has a lot more information on how optimists and pessimists can collaborate together effectively, including some case studies, which will be helpful for explaining what it looks like in a team setting. Also, check out the two books I mentioned. Never go there gut, how pioneering leaders make the wisest decisions and avoid disasters, wise business decisions and avoid disaster? So check out that book that talks about of course, how do you make good decisions? How do you manage risks and plan strategy? The other book that I mentioned is called the blind spots between us on how to overcome unconscious cognitive bias and build better relationships that talks about communication unconscious bias relationship building. Those two books are all very relevant, both very relevant for optimists and pessimists collaborating together effectively. And for a free resource, check out the free free resource course eight video based module course on making the wisest decisions it’s called the wise decision maker course it’s going to be a disaster avoidance forward slash subscribe again, disaster avoidance forward slash Subscribe for a free eight video based module course on making the wisest decisions. And the first module of that course is an assessment on dangerous judgment errors in the workplace, which I think will be really helpful for you to figure out which of the dangerous judgment errors or cognitive biases there’s over 100 of them, you’re most vulnerable to so check that out. And, as always, I hope that this episode has been illuminating, enlightening and profitable for you. And I’m wishing you the wisest and most profitable decisions, my friends 


Transcribed by 


Bio: Dr. Gleb Tsipursky is an internationally-renowned thought leader in future-proofing and addressing cognitive biases. He serves as the CEO of the boutique future-proofing consultancy Disaster Avoidance Experts, which specializes in helping forward-looking leaders avoid dangerous threats and missed opportunities. A best-selling author, he wrote Never Go With Your Gut: How Pioneering Leaders Make the Best Decisions and Avoid Business Disasters (Career Press, 2019), The Blindspots Between Us: How to Overcome Unconscious Cognitive Bias and Build Better Relationships (New Harbinger, 2020), and Resilience: Adapt and Plan for the New Abnormal of the COVID-19 Coronavirus Pandemic (Changemakers Books, 2020). He has over 550 articles and 450 interviews in USA Today, Inc. Magazine, CBS News, Time, Business Insider, Government Executive, Fortune, The Chronicle of Philanthropy, Fast Company, and elsewhere. His expertise comes from over 20 years of consulting, coaching, and speaking and training on change management, decision making, and risk management strategy. It also comes from over 15 years in academia as a behavioral scientist, including 7 as a professor at Ohio State University. Contact him at Gleb[at]DisasterAvoidanceExperts[dot]com, LinkedIn, Twitter @gleb_tsipursky, Instagram @dr_gleb_tsipursky, Medium @dr_gleb_tsipursky, and register for his free Wise Decision Maker Course.