{"id":1314,"date":"2025-06-03T10:07:13","date_gmt":"2025-06-03T14:07:13","guid":{"rendered":"https:\/\/cohort21.com\/garthnichols\/?p=1314"},"modified":"2025-05-19T20:07:47","modified_gmt":"2025-05-20T00:07:47","slug":"book-review-leading-through-strategy-t-olverson","status":"publish","type":"post","link":"https:\/\/cohort21.com\/garthnichols\/uncategorized\/book-review-leading-through-strategy-t-olverson\/","title":{"rendered":"Book Review: Leading Through Strategy (T. Olverson)"},"content":{"rendered":"<p><span style=\"font-weight: 400;\">Leading through Strategy brings to life the role of a Head of School in the Independent School world. <a href=\"https:\/\/rg175.com\/bio\/tom-olverson\">Thomas Olverson<\/a> is the former Head of School of Rivers School, outside of Boston. This is the retelling, by him, of his learning, growth and development as Head of Rivers, alongside it\u2019s growth and development into one the most respected school is this highly competitive market of education. It is full of great anecdotes, lessons and directives for new Heads to consider.<\/span><\/p>\n<blockquote><p><span style=\"font-weight: 400;\">\u201dMy hope is that you can learn what questions to ask, how to frame your strategic challenges, and most importantly, how to think about them logically and creatively.\u201d (Pg. 23)<\/span><\/p><\/blockquote>\n<p><strong>You would be interested in this book is you were:<\/strong><\/p>\n<ol>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">A Head of School that is new to the role (first 5 years)<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">Part of school undergoing a strategic planning process<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">Interested in the business of schools<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">Reengaging with strategic thinking and business approaches in the not-for-profit world<\/span><\/li>\n<\/ol>\n<p><a href=\"https:\/\/cohort21.com\/garthnichols\/files\/2025\/05\/download.jpeg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-1318\" src=\"https:\/\/cohort21.com\/garthnichols\/files\/2025\/05\/download.jpeg\" alt=\"\" width=\"273\" height=\"184\" \/><\/a><\/p>\n<hr \/>\n<p><b>What is Strategic Planning?<\/b><\/p>\n<blockquote><p><span style=\"font-weight: 400;\">\u201c\u2026Strengthening your school\u2019s market position should be the goal of independent school strategic planning. It provides the most powerful lens to ultimately add value to your school.\u201d (Pg. 17)<\/span><\/p><\/blockquote>\n<p><span style=\"font-weight: 400;\">Olverson spends the entire book addressing the problems and challenges that come with strategic planning when led by those that don\u2019t really, truly understand it. He leans heavily into \u201cPlaying to Win\u201d by Martin and Lafely.\u00a0<\/span><\/p>\n<ul>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">A plan is not a strategy: there are common reasons why strategic planning failed for schools:<\/span>\n<ul>\n<li style=\"font-weight: 400;\" aria-level=\"2\"><span style=\"font-weight: 400;\">Lack of vision<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"2\"><span style=\"font-weight: 400;\">Sacrificing the future in the name of solving problems<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"2\"><span style=\"font-weight: 400;\">Overestimating the capacity of the school to deliver any strategic plan<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"2\"><span style=\"font-weight: 400;\">Overly detailed planning becomes checkboxes to tick<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"2\"><span style=\"font-weight: 400;\">Lack of focus on strengthening the position of the school in the market<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"2\"><span style=\"font-weight: 400;\">Lack of training in strategy and business for Heads of Schools<\/span><\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p><span style=\"font-weight: 400;\">\u201dBut most importantly, Rivers\u2019 success came from a way of thinking about change and the future, looking at how the critical components fit together to create a virtuous cycle, understanding the risks and rewards of each strategy, and most importantly, tapping in tot he collective imagining of talented people who want to achieve something big.\u201d (Pg. 15)<\/span><\/p>\n<p><span style=\"font-weight: 400;\">To support strategic planning then, a Head needs to ask 5 key questions:<\/span><\/p>\n<ol>\n<li style=\"list-style-type: none;\">\n<ol>\n<li><span style=\"font-weight: 400;\">What is your winning aspiration?<\/span><\/li>\n<li><span style=\"font-weight: 400;\">\u00a0Where do you want to play? <\/span><\/li>\n<li>\u00a0How will you win?<\/li>\n<li><span style=\"font-weight: 400;\">\u00a0What are the capabilities of the organization?<\/span><\/li>\n<li><span style=\"font-weight: 400;\">What structures are needed to achieve the goals?<\/span><\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<ol>\n<li style=\"list-style-type: none;\"><a href=\"https:\/\/cohort21.com\/garthnichols\/files\/2025\/05\/1742875029273.jpeg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-1317\" src=\"https:\/\/cohort21.com\/garthnichols\/files\/2025\/05\/1742875029273-300x300.jpeg\" alt=\"\" width=\"300\" height=\"300\" srcset=\"https:\/\/cohort21.com\/garthnichols\/files\/2025\/05\/1742875029273-300x300.jpeg 300w, https:\/\/cohort21.com\/garthnichols\/files\/2025\/05\/1742875029273-150x150.jpeg 150w, https:\/\/cohort21.com\/garthnichols\/files\/2025\/05\/1742875029273-768x768.jpeg 768w, https:\/\/cohort21.com\/garthnichols\/files\/2025\/05\/1742875029273-620x620.jpeg 620w, https:\/\/cohort21.com\/garthnichols\/files\/2025\/05\/1742875029273.jpeg 800w\" sizes=\"auto, (max-width: 300px) 100vw, 300px\" \/><\/a><\/li>\n<\/ol>\n<p><span style=\"font-weight: 400;\">These questions need to answered by a few people\/groups: firstly, the community; what insights can your community provide you that may be in your blind spots? For example, perceived cost to quality, lived experience of students as it pertains to your value proposition, and most importantly, what is your value proposition understood by the community?\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Secondly, the administration of the school; what can they tell you about the faculty culture, the internal structures and systems of the school that are working, that are challenging and acting as roadblocks.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Other groups and people to consider are specific slices of your community by grade, by programming, etc\u2026 What might you learn with more nuance about a the experience of the entry grades of your schools? Why they chose your school, and what lived up to their expectations and what didn\u2019t?<\/span><\/p>\n<p><span style=\"font-weight: 400;\">While the consultative process is important, it cannot override the role of the Head in leading the strategy of the school.<\/span><\/p>\n<hr \/>\n<p><b>The Role of the Head<\/b><\/p>\n<p><span style=\"font-weight: 400;\">Olverson\u2019 s message is clear to anyone reading this book: the Head is responsible for the design and delivery of strategic planning and ultimately the success of the school. A political strategy of listening to everyone and trying to answer their concerns and wishes is not going to accomplish a meaningful strategy. (Pg. 27). Likewise, any successful Head of School will have to recognize their formal and informal \u2018power\u2019, and how to use, delegate, give away, and apply it to achieve the outcomes.\u00a0<\/span><\/p>\n<blockquote><p><span style=\"font-weight: 400;\">\u201c \u2026 I wanted to control the narrative and set the strategic priorities. And I was willing to take the heat. What I did not want was a watered-down political document\u201d (pg. 26)<\/span><\/p><\/blockquote>\n<p><span style=\"font-weight: 400;\">To understand the school, a new(ish) Head of School should conduct an in-depth analysis called a SWOT (Strength, Weaknesses, Opportunities and Threats) analysis. This should be done by the Head of School, to develop their own perspective of the school, and form a basis for more inquiry and for formulating impressions. It is also a key process to identify fidelity within the school between the mission and vision and the lived experience of the community. (Pg. 32) Olverson adds: \u201cI have seen the value of being the \u201cexpert\u201d\u201d (Pg. 33) He goes into a great story about how to be an expert, too long to repeat here, but is an example of\u00a0 great analogies that reinforce his perspectives.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Two other key points about being an expert is a Head\u2019s relationship with consultants:\u00a0 \u201cA consultant can help by providing guidance on how to take the journey, but she should not hand the head a distilled set of findings and vision. The Head should never outsource the chance for deep learning.\u201d (Pg. 20)<\/span><\/p>\n<p><span style=\"font-weight: 400;\">And as a Head, it is vital to nurture, develop and seek to understand your own emotional intelligence. This is critical when it comes to leading the school through change.<\/span><\/p>\n<hr \/>\n<p><b>Leading Faculty through Change:<\/b><\/p>\n<p><span style=\"font-weight: 400;\">Without hiring, nurturing and growing a talented faculty, \u201cA school leader can have the greatest ideas imaginable\u2026 but those ideas will only remain dreams.\u201d (Pg. 43)\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">To be an effective leader, you have to be able to connect with the key resource that will make a strategic plan optimized. A talented faculty are the key drivers of putting a vision into reality, and &#8211; most significantly &#8211; understanding how that delivery is going, how effective is it, and what needs to be adjusted once begun. This can only be done through effective relationships between the Head and the faculty. Something that Olverson stresses throughout the book:<\/span><\/p>\n<blockquote><p><span style=\"font-weight: 400;\">\u201cThe Head\u2019s capacity to \u2018read the audience\u2019, seek advice, and choose a strategy that will allow the faculty to see the [vision and challlenges that come with it] without getting defensive &#8211;\u00a0 all of these actions can be crucial to success. Effective Heads of School must have a high EQ\u2026\u201d pg. 21)<\/span><\/p><\/blockquote>\n<p><span style=\"font-weight: 400;\">Another key element to leading through change having an unwavering commitment to talent. Attracting and retaining, growing and sustaining talent within a school should be a top priority. It is this group that a Head will rely upon. (Pg. 53) And it is this group that will be the smartest person in the room. Accessing and attending to the talents of the team is dependent upon a Head\u2019s ability to create the conditions to encourage this talent to shine and be key contributors. (Pg. 53)<\/span><\/p>\n<p><span style=\"font-weight: 400;\">One approach that Olverson advocates is to have clear and transparent expectations for teachers. If we want to tout the special qualities of our faculty as a key value at a our school, we must provide a system and path for meaningful professional growth and accountability. This is what it means to invest in our faculty. What does being a top-teacher mean by way of disposition to relationship building, content-knowledge, and pedagogical skills?<\/span><\/p>\n<p><span style=\"font-weight: 400;\">For Olverson, at Rivers\u2019, it meant looking for candidates that had the desire to learn from mistakes, and a fierce determination to figure out the pathway to success. These were the attributes needed to achieve the strategy he was laying out for Rivers\u2019 at the time. What might be the attributes of your schools\u2019 faculty?<\/span><\/p>\n<hr \/>\n<p><iframe loading=\"lazy\" title=\"Leading through Strategy with Tom Olverson\" width=\"581\" height=\"327\" src=\"https:\/\/www.youtube.com\/embed\/zClS_yVLDek?feature=oembed\" frameborder=\"0\" allow=\"accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share\" referrerpolicy=\"strict-origin-when-cross-origin\" allowfullscreen><\/iframe><\/p>\n<p><b>Challenges to Change That a Head Must Address<\/b><\/p>\n<blockquote><p><span style=\"font-weight: 400;\">\u201dOnly the leadership of the Head can overcome the significant headwinds preventing the school from [abiding by the agendas of others, trends, or manipulative community members whose informal power has gone unchecked]. Pg. 71<\/span><\/p><\/blockquote>\n<p><span style=\"font-weight: 400;\">Therefore, when the agenda of others begin to sway the direction of the school, it is up to the Head to, \u201c\u2026constantly look for ways to solidify the school\u2019s identity while ensuring the mission is being lived.\u201d (Pg. 72) This underscores the role that strategy plays &#8211; it must be tied to the market position of the school, and to the mission, vision and values. These are the anchors.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">This involves hard conversations, such as when a committee has to wrestle with the hard truth that even though some of the market is attracted by a particular quality of the school, it many not be value it enough to pay tuition for it. (Pg. 75) Or, when a board is enchanted by a trend or fad, and wants the school to embrace it, but it would mean taking time and resources away from a key differentiator. The list goes on and on\u2026Therefore the Head must make sure that, as Druckker famously wrote: \u201cThe main this is to make sure the main thing is the main thing.\u201d (Pg. 76) Thus, where will the school compete, and where won\u2019t it compete?<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Another challenge with change, comes with the accountability to the change on the ground. How will qualitative and quantitative data help you tell your story of change and value? For an effective Head and their team, accountability isn\u2019t about looking good, it is about how to work harder and smarter to achieve the strategy. (Pg. 81)<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Here is where Olverson shines. \u201cHead-courage\u201d is a term he uses to describe how many educators tend to be \u2018people-pleasers\u2019 because we care, we nurture and we want our students, and their families, to feel successful. However, \u201cHead-courage\u201d is required because with change comes upset, grief and even people leaving your community.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cWhen a Head want to make bold changes, she must abandon the need to be liked by all\u2026 EQ is critical in navigating the change process; however, Heads beware! The kind of change that I am talking about will inevitably make some stakeholders angry.\u201d (Pg. 82)<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Thus \u201cHead-courage\u201d indicates a Head\u2019s true commitment to building the schools\u2019 value. (Pg. 83)<\/span><\/p>\n<hr \/>\n<p><b>How to Address Challenges Through Effective Systems and Structures<\/b><\/p>\n<blockquote><p><span style=\"font-weight: 400;\">\u201cWell designed structures have the power to promote communication, connect action to purpose, and tap the collective genius of the team. They are a crucial management tool for long-term school improvement but only if their work is connected to achieving the vision.\u201d (Pg. 110)<\/span><\/p><\/blockquote>\n<p><span style=\"font-weight: 400;\">Here Olverson draws upon the popular archetype of the \u201cLeader as Architect\u201d. In this part of the book, he explores the psychology of understanding others, power &#8211; both formal and informal &#8211; and how and where it is expressed, and how systems and structures can harness these to drive value and purpose.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cNew Heads should remember that not all operations need their attention early on. I paid very little attention to the work of the various parent volunteer organizations at the school, not because I was unappreciative, but because I needed to concentrate on those capabilities vital to reaching [our goals].\u201d (Pg. 113)<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Olverson\u2019s second major point is about the composition of the board. Open and honest communication with the Head and Chair are vital from the outset. They have to be working not only to an aligned purpose, but they must be working alongside one another. This begins with effective onboarding of the head that allows for critical questions, deep understandings of the history of its members, as well as understanding the structure and purpose of the board committees. (Pg. 117)<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Early on, the Head is the best person to connect the dots between the vision and mission with the strategy and tactics. Successful Heads are obsessed with results, understand the risks, and it is the work of the Head and the Chair to drive the implementation of these goals. Thus, annual goals for the Head of school must reflect a partnership, not an evaluation. Annual goals and the assessment of a Head must be in service to achieving something great &#8211; the vision and improved position in the market. (Pg. 145)\u00a0<\/span><\/p>\n<blockquote><p><span style=\"font-weight: 400;\">\u201cOnce Trustees assume that the school is playing the long-game, they will much more readily jettison the unrealistic short-term goals that all too often sacrifice the future of the school.\u201d (Pg. 151)<\/span><\/p><\/blockquote>\n<p><span style=\"font-weight: 400;\">I highly recommend this book, as it brings to life the lessons provided by leaders in industry, like Martin and Lafely, as well as Drucker. It also puts them into an educational context and through storytelling and anecdotes, really brings to life the role of the Head in this complex, demanding job.<\/span><\/p>\n<p><span style=\"font-weight: 400;\"><strong>For classroom teachers,<\/strong> how might strategic thinking support understanding school decisions or their role in achieving strategic goals. Reading this book can provide bottom-up understanding of the business of independent schools. This will allow you not only to seek to understand the why and what of decisions, but also to get more involved and engaged with the decisions &#8211; either supporting them, or effectively questioning how they are helping the overall purpose and mission of the school.<\/span><\/p>\n<p><span style=\"font-weight: 400;\"><strong>For CIS Ontario educational leaders,<\/strong> there is a clear provocation in this book: The current landscape and educational trends (e.g., financial sustainability, enrollment shifts, market positioning amidst demographic changes) are fraught with uncertainty, and no \u2018standard\u2019 playbook. The only thing that can be viewed as standard are the approaches and mindsets that we know will provide an effective direction, agility and self-assessment for schools as they chart their own path through strategy.<\/span><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Leading through Strategy brings to life the role of a Head of School in the Independent School world. Thomas Olverson is the former Head of School of Rivers School, outside of Boston. This is the retelling, by him, of his learning, growth and development as Head of Rivers, alongside it\u2019s growth and development into one&#8230;<br \/><a href=\"https:\/\/cohort21.com\/garthnichols\/uncategorized\/book-review-leading-through-strategy-t-olverson\/\">Read more <span class=\"meta-nav\">&rarr;<\/span><\/a><\/p>\n","protected":false},"author":8,"featured_media":1316,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"wds_primary_category":0,"footnotes":""},"categories":[18,23,1],"tags":[49],"class_list":["post-1314","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-21st-century-skills","category-leadership","category-uncategorized","tag-book-review"],"_links":{"self":[{"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/posts\/1314","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/users\/8"}],"replies":[{"embeddable":true,"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/comments?post=1314"}],"version-history":[{"count":2,"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/posts\/1314\/revisions"}],"predecessor-version":[{"id":1319,"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/posts\/1314\/revisions\/1319"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/media\/1316"}],"wp:attachment":[{"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/media?parent=1314"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/categories?post=1314"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/cohort21.com\/garthnichols\/wp-json\/wp\/v2\/tags?post=1314"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}