Having Useful Conversations

We all find our identities in various communities, whether friends, family, colleagues, or allies. In those communities we speak to people who largely echo our views, both about the world and about our own decisions and conclusions. Experiencing agreement and reciprocal emotional support makes us feel good about ourselves and our decisions, and it answers the persistent question in our unconscious “Am I good at [fill in the blank] and did I do the right thing?” with a resounding “YES!”. But doing this is costly if you are out to accomplish improvement and better decision-making or performance. To succeed in those goals, it’s critical to refine our thinking and improve the mental models we employ. That’s a different kind of engagement.

Imagine yourself chatting with a buddy over a beer and recounting an experience at work. You tell your story the outcome of which is instead of your getting the assignment you wanted, your colleague gets it. The tale has a subtext, that you have been wronged, misunderstood or unlucky. There is a formula to the apt response from your friend. He will commiserate, and perhaps share a tale of his own. And you will reciprocate his sympathy. We do this about our jobs, relationships, employees, sports, etc.  And we feel better afterward. But we have learned nothing about how to do things differently next time.

When a sales person complains about not getting a sale, she’ll say it was a bad prospect who wasn’t really looking, or didn’t “get” the technology, wasn’t really the right decision maker, or almost anything other than admitting she failed and perhaps could have done something differently along the way. A good manager will not allow that to pass without correction, because it’s only by exploring the process through which the sale might have been closed that the sales person can improve. But the sales person here is, like all of us, likely to respond defensively or shut down emotionally. The unconscious impulse to protect her personal identity as “good at her job” takes over. Her ego wants the absolution of sympathy and agreement about her explanation. Will that help her close the next deal, or at least increase the chances of doing so? No.

There’s no shortage of similar examples. The startup leader blames a lack of funding on biased investors, or a middling employee blames his poor performance review on a peer’s grudge, or the development team blames its failure to meet a deadline on interruptions or infrastructure – all can be met with agreement and commiseration – and the justifications may even be true. But approached with a different mental model they can provide opportunities for fine-tuning performance and decision-making.

Professional poker player, Annie Duke, in her book, Thinking in Bets, talks about her first meeting with Poker Hall-of-Famer Eric Seidel, and her attempt to bond with him as a fellow poker pro by telling him a “bad beat” story (poker lingo for a sob story) about her poor luck in the last game. He flatly shut her down, telling her that if, in fact, it was bad luck, there was no point to the story. However, he said that if she was interested in discussing strategy and the quality of her play– in other words, if she was interested in critically assessing her decisions during the match –he would be interested in the conversation. She was momentarily stunned but wanted to earn a place in his peer group. So, she regrouped and adopted the mental model and agreements shared by Seidel and his poker peer group. The groups goal was to explore the nature of their decisions along the way, the assumptions, biases, beliefs and errors in judgment that could be seen by each other but were invisible to the individual. Their mission? Improve, learn and become better as fast as possible. That meant, no stroking or feel-good sympathizing. It meant each person being honest with disagreements and pointing out bias when they saw it in a peer. It wasn’t about arguing or attacking, but about an open dialogue with a specific goal. In fact, not only was disagreement welcome, but to withhold a perspective that might cast light on a member’s bias or misstep or suggest that an assessment along the way might have been based on flawed reasoning would be a violation of the group’s “charter”.

Peers often use their time together to whine. In those exchanges, humble-bragging and sympathy-provoking hard-luck tales tend to convey social status. But it was different in that group of poker pros. Honest and critical self-assessment was what gained cache. With the explicit “I will call you on your bull**** and you call me on mine” agreement, the currency became discovery of one’s own faulty decision or unwitting bias.  Moreover, the explicitness of the agreement and the frequency of the conversations inoculated group members against the natural tendency to be defensive. It pays off though. In my article about Learning to Love Criticism, I talk about Ray Dalio and the culture at Bridgewater where they have a practice of radical transparency. The same phenomenon has occurred. That doesn’t mean it feels good, but neither does an Olympian’s toughest training session.

How can you get this kind of no BS brain trust?  My clients depend on me for that. But your executive coach shouldn’t be your only resource.  There are lots of ways to this kind of relationship. Join a Vistage group or collaborate with some peers, for this purpose – or even a single colleague you trust. But remember, the social conventions are deep and largely undistinguished. To have it be different you will need to explicitly create it. It will NOT happen without a discussion about rules, expectations and agreements.  Once you are all synced about your intentions and promises to each other, and the mental model at play, get ready for serious strides.

An earlier version of this article was first publsihed in August, 2018 on

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