July 4, 2024
Good books about, in some way, psychological safety and failure
On failing & psychological safety. Again.
Happy 4th of July! Or, if you’re in the UK, I hope you voted! Also a shout out to my friend Tinkhani—this is the anniversary of her arrival to the US. I, by the way, don’t remember the exact date I came here. It was late August 1990, I do know that, having just got married three weeks before… Anyway, wherever you are, I hope you are well and happy. Thank you for reading the Coaching Letter—you rock.
This Coaching Letter has little that’s new. It’s a recap of my favorite posts about failure and psychological safety over the past few years. I figure maybe at this time of year you’ll have time to read them…
Summer definitely feels different for me, work-wise. I’m still busy, but there’s less of a rhythm to the week. During the school year, I tend to work from home a day or two a week, and then the rest of the time I’m away doing workshops, and then I have standing meetings with individuals or groups. During the summer, I realize, I’m either home all week or gone all week, and there are far fewer meetings. One of the best parts, however, is getting to do leadership retreats. I was with Cheshire last week with one of my colleagues, and that was a blast. We had a great conversation about psychological safety, and I was going to write about that, but then I realized that I already did—Coaching Letter #158, so please check that out.
One of the things that I pointed out in Cheshire was that most of the wee stories I tell when I’m facilitating are about mistakes I’ve made, or failures I was somehow implicated in. I do that for multiple reasons. First, I’m particularly good at self-deprecating humor, and I like to make people laugh. Second, people are intrigued by stories about failure, and they are not so interested in hearing you talk about success—at least, that’s how it feels to me, but it may just be that… Third, I find it awkward to talk about success, it always feels self-aggrandizing. I do realize that people who know me well would not call me modest, but it feels different when I’m in front of a group. Fourth, stories of failure are also stories of resilience—shout out to Rydell, who talks about testimony service and how that accomplishes the same goal; and to Anthony, who is legit humble about failure and eloquent about resilience; and to Tosh, who has taught me a lot about overcoming. Fourth, we should be normalizing failure as essential to learning, and leaders need to model that. It is simply not credible for a leader to tell teachers that they should be taking risks in their practice without being able to talk about falling on your face. Fifth, and this may actually be the same thing, the message should always be: the only way to fail is not to try. Please read Coaching Letter #86, which is an argument for not thinking of not getting the result you were hoping for as failure, but as learning—shout out to Andrew for modeling that ALL THE TIME.
Please read Coaching Letter #36, which was the first time I wrote about my own failure, and interestingly, I agonized over that post. It was very stressful to publish, and now I can talk about myself with regard to failure without blinking. Which I consider an achievement.
Please read Coaching Letter #187, which is about culture and intelligent failure, and features Amy Edmondson’s book about failure, called Right Kind of Wrong. I ended that CL with this:
I realize as I’m writing this that it’s really hard to talk about failure or organizational learning more generally without talking about culture, and vice versa. It is worth knowing, as a coach or a leader, what people in your organization think the culture is, specifically around learning and failure. A good way to find out is to ask them. And a good question to start with is: What happens in this organization when you tell your supervisor bad news?
But now I would expand that to ask, what happens when you disagree with people in your organization? What meaning do others make of that? Are you seen as difficult? Do people complain about you behind your back? Then you probably don’t feel psychologically safe, and you’re less likely to contribute your thinking, and the organization is worse off as a result.
I write about failure so much because we fail so much, and yet also fail to exploit that failure, when actually it is an invaluable source of learning. At the same time, I’m also aware that failure is not equity neutral. Rydell’s and my book has a small section about psychological safety, but it includes an important caveat:
It is worth naming that making mistakes is often represents high risk, because women and people of color are under stereotype threat of various types: appearing less intelligent, lazy, weak, indecisive or incompetent. Additionally, many strategic choices to change direction or abandon a project may appear to be mistakes because they are filtered through negative stereotypes, when those same actions may be laudable when carried out by a White man. There are many books, articles, and podcasts featuring the benefits of “failing fast” and “failing forward”, but this space tends to be dominated by White men.
So the job of leaders is to minimize that risk, to make it safe to fail in the service of a worthy goal, to express good faith disagreement (even if inelegantly put), to tell the bad news. Above all, take care of your people.
Thanks, as always, for reading, thanks in advance for your feedback, and please let me know if there is anything I can do for you. Best, Isobel
Isobel Stevenson, PhD PCC
860-576-9410
@IsobelTX
Author of The Coaching Letter
Author with Jennie Weiner of The Strategy Playbook for Educational Leaders: Principles and Processes Routledge, 2021
Author with Sarah Woulfin & Kerry Lord of Making Coaching Matter: Leading Continuous Improvement in Schools Teachers College Press, 2023



