{"id":7066163,"date":"2026-09-25T00:23:59","date_gmt":"2026-09-25T00:23:59","guid":{"rendered":"https:\/\/peraltafinancing.com\/advertising\/omar-oakes-strategy-was-never-in-short-supply-courage-was\/"},"modified":"2026-09-25T00:23:59","modified_gmt":"2026-09-25T00:23:59","slug":"omar-oakes-strategy-was-never-in-short-supply-courage-was","status":"publish","type":"post","link":"https:\/\/fivemor.com\/?p=7066163","title":{"rendered":"Omar Oakes: Strategy was never in short supply. Courage was"},"content":{"rendered":" \r\n<br><div data-ast-blocks-layout=\"true\" itemprop=\"text\">\n\n\t\t\n\t\t<h3 class=\"subtitle subtitle-HEEcLo\" dir=\"auto\">A new WFA report says strategic thinking is advertising\u2019s biggest talent gap. That\u2019s always been true, but now AI is making it more expensive to ignore.<\/h3>\n\n<hr\/>\n\n<!-- \/wp:post-content --><!-- wp:paragraph -->\n\nAvoiding hard work, it turns out, isn\u2019t a character flaw. It\u2019s a survival strategy.\n\nIt\u2019s because our brains have evolved over millions of years to conserve energy, which helps keep us alive. Daniel Kahneman called it the \u201claw of least effort\u201d: given two routes to the same goal, we drift towards the one that demands the least mental work \u2013 fast, automatic thinking over the slow, deliberate kind.\n\nResearchers have since measured this directly, establishing <a href=\"https:\/\/journals.plos.org\/plosone\/article?id=10.1371\/journal.pone.0068210\">how much money people were willing to give up<\/a> to avoid a more mentally demanding version of a task.\n\nBusiness leaders do the same thing when it comes to the hard work of strategy. Strategy professor Richard Rumelt, author of <em>Good Strategy, Bad Strategy,<\/em> writes:\n<blockquote><em>\u201cBad strategy flourishes because it floats above analysis, logic, and choice, held aloft by the hot hope that one can avoid dealing with these tricky fundamentals and the difficulties of mastering them. Not miscalculation, bad strategy is the active avoidance of the hard work of crafting a good strategy.\u201d<\/em><\/blockquote>\nRumelt gives three reasons bad strategy persists:\n<ul>\n \t<li><strong>The pain of choosing.<\/strong> Real choices create losers, and leaders would rather not disappoint anyone.<\/li>\n \t<li><strong>Template strategy.<\/strong> Fill in the blanks \u2013 vision, mission, values \u2013 and you get something that looks like strategy without any of the analysis.<\/li>\n \t<li><strong>Positive thinking.<\/strong> Believing that the right attitude is enough, when proper analysis means imagining everything that could go wrong.<\/li>\n<\/ul>\nPut simply: strategy is difficult, it requires courage, and it carries risk.\n\n\nWhich is why I was intrigued by a new report out today from the World Federation of Advertisers and consultancy Mediasense, <em>Humans, Marketing and Machines<\/em>.\n\nIts headline finding: <strong>strategic thinking is the advertising industry\u2019s number-one talent shortage<\/strong>, or so say 72% of the survey\u2019s respondents.\n\nThe explanation? <strong>The pace of change is outstripping the industry\u2019s ability to develop talent.<\/strong>\n\nThe answer? Upskilling, capability-building and redesigning incentives.\n\n<!-- \/wp:paragraph --><!-- wp:paragraph -->\n\nIt\u2019s worth remembering this is a snapshot of what 166 people thought in the second quarter of 2026, not a historical analysis. But it chimes with what I hear from the buy-side these days, particularly in the context of the relentless <em>AI is changing everything<\/em>narrative: as machines get better at delivering information, humans will need to supply the strategic thinking.\n\nAnd yet Rumelt\u2019s warning lands with even greater force, once we start imagining a future of eggheads armed with AI agents producing genius brand strategy and media plans. Because strategy is still difficult. It still means specialising, putting more resource into this and less into that, and making hard choices that carry risk.\n\nNot unlike the 16-year-old turning to Minecraft instead of revising for their GCSEs, the typical agency leader avoids difficult strategic decisions because a mistake feels more dangerous than \u2018business as usual\u2019.\n\n\nI\u2019ve watched this for more than a decade covering advertising and media. I feel this tension myself now I have to sell services as a consultant and writer.\n\nA lack of strategy is the root cause of behaviour that will feel familiar to anyone in agencyland. Familiar symptoms include:\n<ul>\n \t<li>generic positioning (\u201dwe do everything for everyone!\u201d)<\/li>\n \t<li>giving ideas away for free in pitches (\u201dand if you don\u2019t like those ideas, we\u2019ve got plenty more in the back!\u201d)<\/li>\n \t<li>overdelivering on accounts (great customer service papering over strategic cracks)<\/li>\n \t<li>accepting poor payment terms (\u201dwell I suppose 90 days is doable\u2026\u201d)<\/li>\n<\/ul>\nThe result is a concierge model: here\u2019s the menu, pick what you like and \u2013 tragically \u2013 pay what you like.\n\nThis creates the feeling that the sector is oversupplied. I say <em>feeling<\/em> because I\u2019m not convinced there are too many agencies. There may just be too many generic agencies, too broad in what they offer and who they offer it to.\n\nBrand-side marketers report the same shortage, but I think for a different reason. Too often, marketing doesn\u2019t have the ear of the CEO or CFO. When your function lacks influence, strategic risk-taking gets you nothing and \u201cdon\u2019t rock the boat\u201d keeps you safe. So business as usual wins again.\n\nThat weakness then feeds the agency problem. Advertisers either don\u2019t see agencies as strategic businesses (\u201dthey make ads and buy media\u201d) or aren\u2019t convinced strategy is worth paying for \u2013 which reinforces the agency habit of not offering it.\n\n\nSo I\u2019m sceptical that AI is why advertisers and agencies now name strategic thinking as their biggest gap. I\u2019d argue the gap has always been there.\n\nBut AI will make it far more urgent. AI gives everyone fast, cheap access to the average. A competent media plan, or a monster targeting spreadsheet, is now a compute cost, not a differentiator. That kills the economic case for the safe, generalist agency.\n\nIt also poses the brand question: if anyone can get off-the-shelf strategy from Claude or ChatGPT, how does anyone stand out?\n\nThe report itself points in this direction. It lists four ways the industry says one thing and rewards another:\n<ul>\n \t<li>We say we value strategic thinking, then reward execution against plan.<\/li>\n \t<li>We prioritise data-driven marketing, then reward activity rather than decisions.<\/li>\n \t<li>We invest in AI, then reward efficiency rather than impact.<\/li>\n \t<li>We talk about integration, then evaluate people in silos.<\/li>\n<\/ul>\nThat\u2019s Rumelt\u2019s avoidance, written into performance reviews.\n\nThere\u2019s another telling detail: agencies are slightly more optimistic than advertisers that their talent models are fit for an AI-enabled future. The report puts this down to agencies experimenting more with AI tools. That may be true.\n\nBut I can\u2019t help thinking this optimism comes down to something worse: this is still a sector selling generalist execution that hasn\u2019t yet priced in what happens when execution gets cheap.\n\n\nIt\u2019s easy for me to opine on this as a highly specialised one-person business with no duty of care to hundreds of employees.\n\nAnd I\u2019ll be the first to admit this stuff is hard. I\u2019ve not got my own positioning, or my own ability to make hard choices, entirely worked out.\n\nBut that doesn\u2019t mean I\u2019m wrong.\n\nAnd, if strategic thinking is our industry\u2019s biggest talent gap, we should be clear about what strategy is for. The answer is surely not to send agency staff on AI training courses so they get better at prompting Claude and ChatGPT into producing yet more mediocre insights.\n\nBetter strategy, at every level, means having the curiosity to ask good questions and the courage to act on where the answers lead. That requires a culture change among us humans.\n\nIn the age of artificial intelligence, you could even call this a survival strategy.\n\n<hr\/>\n\n<em><img loading=\"lazy\" decoding=\"async\" class=\"alignleft size-full wp-image-1844334\" src=\"https:\/\/www.moreaboutadvertising.com\/wp-content\/uploads\/2026\/07\/OmarOakes-2024-750x502-1-200x200-1.jpg\" alt=\"\" width=\"200\" height=\"200\" srcset=\"https:\/\/www.moreaboutadvertising.com\/wp-content\/uploads\/2026\/07\/OmarOakes-2024-750x502-1-200x200-1.jpg 200w, https:\/\/www.moreaboutadvertising.com\/wp-content\/uploads\/2026\/07\/OmarOakes-2024-750x502-1-200x200-1-150x150.jpg 150w\" sizes=\"auto, (max-width: 200px) 100vw, 200px\"\/>This article first appeared in <a href=\"https:\/\/omaroakes.substack.com\/archive\">Ad-verse Reactions<\/a>, a newsletter written by independent journalist and consultant Omar Oakes, covering the economics, power structures and unintended consequences shaping advertising and media. You can subscribe to Ad-verse Reactions for regular analysis at <a href=\"https:\/\/omaroakes.substack.com\/\">omaroakes.substack.com<\/a>.<\/em>\n\t\t\n\t\t\n\t\t\t<\/div>\r\n<br>\r\n","protected":false},"excerpt":{"rendered":"<p>A new WFA report says strategic thinking is advertising\u2019s biggest talent gap. That\u2019s always been true, but now AI is making it more expensive to ignore. Avoiding hard work, it turns out, isn\u2019t a character flaw. It\u2019s a survival strategy. It\u2019s because our brains have evolved over millions of years to conserve energy, which helps [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":7066164,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[12023],"tags":[34242,227507,21654,296,11636,2908],"dealstore":[],"offerexpiration":[],"class_list":["post-7066163","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-advertising","tag-courage","tag-oakes","tag-omar","tag-short","tag-strategy","tag-supply"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v26.4 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Omar Oakes: Strategy was never in short supply. Courage was - Som2ny Network<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/fivemor.com\/?p=7066163\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Omar Oakes: Strategy was never in short supply. Courage was - Som2ny Network\" \/>\n<meta property=\"og:description\" content=\"A new WFA report says strategic thinking is advertising\u2019s biggest talent gap. That\u2019s always been true, but now AI is making it more expensive to ignore. Avoiding hard work, it turns out, isn\u2019t a character flaw. It\u2019s a survival strategy. 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