September 6, 2025
On what really matters in plans
Hi there, and thank you for subscribing to the Coaching Letter. You rock. There are a lot of new subscribers since the last CL (which was quite a while ago, sorry), so can I just say a few things about it? What I’m trying to do here is share what I/we (I work with a team of exceptionally smart, talented and knowledgeable people, so sometimes it difficult to say where my thinking stops and theirs begins—probably a lot more of the latter) are learning about several things in parallel: equity, instructional improvement, coaching, leadership, and organizational development, and how to be a better human, in no particular order. Subscribers to this newsletter are a varied bunch—teachers (especially math, I think, because of our involvement with Building Thinking Classrooms), coaches of all stripes, and leaders, most of whom but not all are in education. I do some advertising for the workshops that we run—“we” in this case being Partners for Educational Leadership—but mostly I write about what I’m thinking about in a way that I hope will be helpful. If you have any questions, or need something, or want to give me feedback, I am very easy to get hold of—just reply to this email—and I do love getting emails. I do actually have some paid subscribers—which is this lovely little hit of dopamine that people love you enough to give you money—but I feel obligated to point out that being a paid subscriber brings no additional benefit, so you can ignore those emails from Substack.
So, speaking of advertising, please join us for (at least) one of these workshops! (We really do run excellent workshops.)
First, we are bringing Peter Liljedahl back to Connecticut for a bunch of workshops in Manchester (late September) and Hamden (early October). Amazingly, there are still some seats left. You can find all of them on the workshop page of our website.
Second,the next Coaching Institute will be held at Mercy-by-the-Sea in Madison, Connecticut, which is one of my favorite events in one of my favorite places; the dates are October 16, 22, and November 6. Here is the flier with registration information. I have lost track of how many times we have run this, Kerry and I—either at Mercy or in school districts that have contracted with us to bring it to them—but it is very fun and interesting and changes slightly each time we run it. Some people come back year after year, which just makes my heart sing. Please join us if you can, and note that this is not only for people with “coach” in their title. I think you are a much better leader if you have some coaching training that teaches you how to listen and ask better questions.
Third, Tom and I are reprising the two-day Next Level Instructional Leadershipworkshop at Mercy on November 13 & 14. We ran it three times last year in different locations, and I’m very happy that we are going to run it again at Mercy, which is one of my favorite places. Day One is all about what we mean by high quality instruction, and why we’re not always paying attention to the right things. Day Two is about creating a strategy for creating and enacting a shared understanding of high quality instruction across a district, which has more to do with teacher teams and little to do with evaluation. Here’s the flier. I know I’m biased, but I think it’s brilliant.
Finally, we are hosting the NATIONAL BTC conference in New Haven on June 29 and 30, 2026! Can you believe it? Registration is not open yet, but if you want to be on the list to get all the latest news, sign up here.
The remainder of this Coaching Letter is copied verbatim from Coaching Letter #203, because if there is one thing I have learned about my readers, it is that they don’t have the time to click through to other publications, so stuff that I think is really important I have to include right here. And I do think this list of reminders is really important, because a lot of plans written in education are utterly worthless. Which is not the fault of anyone involved; there is a whole history of planning in education that I have learned since I first started writing about planning and strategy (an article in The Kappan, which is referenced below and of which I am very proud), but that will have to wait for another time. So all the best for the new school year, if indeed you are starting a new school year, and please let me know if there is anything I can do to help. Best, Isobel
This Coaching Letter is your annual list of reminders about how you should think about planning—school improvement plans, strategic plans, equity plans, any kind of plan. These reminders are drawn from several sources, including but not limited to The Strategy Playbook, which I co-authored with Jennie Weiner; “An Improvement Plan is Not Enough—You Need a Strategy”, an article in the Kappan which is probably my favorite article and functions as a kind of prelude to the book; Instructional Rounds, especially chapters 1 and 2 on the instructional core and theory of action, respectively (the book is grounded in the work of superintendents’ networks, including ours); Coaching Letter #170, which was last year’s set of reminders, focused mostly on goals. Long-term readers of the Coaching Letter and consumers of our workshops will encounter many things that they have heard from me before.
- Goals are not as powerful as they are generally thought to be. Goals are not as important as the strategy required to achieve them. And yet, when I ask coaching clients if they have received feedback on their plans, I almost always find that the only feedback they get is on their goals—they must be appropriately ambitious, and they must be SMART. But these features are meaningless by themselves—like judging the potential of toothpaste to keep your teeth healthy by whether you like the taste. Goals matter when they direct attention, communicate purpose, marshal resources, and enable measurement. But very few plans that I look at lay out a strategy for improving achievement that has a hope of making a difference for equity and achievement. Because…
- The plan is only as good as the strategy. Frequently, a ton of energy goes into creating plans. Too often, the energy is expended on the wrong things. Those wrong things include: making the plan look pretty, long lists of action items, wordsmithing, generating strategic objectives, and benchmark data. But none of that matters unless you implement a strategy that will improve student achievement, and almost always the only way to do that is to improve instruction, and almost always the only way to improve instruction is to increase the capacity of teachers. (The most useful resource I have found on this lately is the book Systems for Instructional Improvement, and, usefully, the next session of our book study series is about the Teacher Learning Subsystem, i.e. what the researchers learned about improving the capacity of teachers to deliver equitable and ambitious instruction. More details below.) Here is my coaching technique for having a conversation that gets beyond goals to strategy. I ask clients for their plans, then I copy and paste just the goals and the action items onto a single sheet of paper—usually they only take up one side of the paper, because most of the length of plans is typically taken up by the formatting. Then I hand the paper back to the client and say, if you do everything that’s in this plan, will you reach the goal? The answer, so far, has always been no. So then we can have a real conversation about what would actually get them to the goal—this usually involves creating a version of a flowchart on a big piece of paper. My experience is that people’s thinking is very much constrained by the format of the typical improvement plan, and we should ditch it, at least as a tool for creating strategy. It works OK as a communication tool.
- At the time of writing the plan, you are very unlikely to know everything you need to know to meet the goal. Multi-year plans are almost always very weak. If you look at the action items, there is almost nothing that would take more than 12-18 months to execute. But even year-long plans are probably too far in the future, for several reasons, only one of which I’m going to talk about here. We talk about cause and effect in education as though it is deterministic: one thing leads to another, predictably, and not to anything else. Like a clock. But a clock is an almost closed system—the only input is the energy created through winding it—and classrooms are not at all like that. Classrooms are more like weather patterns—you can make some predictions about which conditions will create what outcomes, but you are always dealing with probabilities, not certainties. Very small changes in initial conditions can lead to large changes in outcomes. They are also full of feedback loops—as Octavia Butler says, whatever you touch you change, and whatever you change changes you. As a general rule, the more the system is about people and not things, the less predictable it becomes. So your best bet, when it comes to improving instruction, is to collect data about improvement in student learning, formulate a hypothesis about what you predict will cause improvement, try something small, immediate, and low stakes, collect data about what happened, revise your hypothesis and/or what you tried, and try again. Under these conditions, you can’t plan more than a week ahead. The Matrix: No one can see beyond a choice they don’t understand. Robert Burns: The best laid schemes o’ Mice an’ Men | Gang aft agley. Both Eisenhower and Churchill: plans are worthless, but planning is everything. We need to stop claiming that we know everything that needs to be done to achieve our goals, because if we did we’d be doing it already. We need to get serious about the process of improvement.
For this last point in particular, big shout-out to my colleagues Tom, Andrew, and David, who have been doing a ton of reading and thinking about complexity—in David’s case, for quite a long time—and I am very grateful for the help in thinking through these ideas. More next Coaching Letter. In the meantime, if you are looking for things to read, you might try Mitchell Waldrop’s Complexity, Judea Pearl’s The Book of Why, Nate Silver’s On the Edge, adrienne maree brown’s Emergent Strategy, or Meg Wheatley’s Leadership and the New Science—actually, any of her books.
I have two fridge magnets on the side of my computer tower that sits on the corner of my desk. (It’s actually my son’s computer and my son’s desk—I know that doesn’t matter but I have this overwhelming compunction to be accurate even when it’s completely irrelevant.) One has an unmentionable word in it. The other says “Every dead body on Mt. Everest was once a highly motivated person, so maybe calm down.” I project onto it the meaning that educational leaders who judge others according to some moral urgency scale benchmarked to their perception of their own hard work and commitment should take a beat. Think about it this way: people are doing the best they know how to do, and if you want them to do something different, they need to know what that is and they need to know how to do it, and if they don’t know either of those things, that’s your fault and not theirs.
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



