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<title data-rh="true">Questionable Advice: “What’s the critical path?”</title>
<meta data-rh="true" name="theme-color" content="#ffffff"/><meta data-rh="true" property="og:type" content="article"/><meta data-rh="true" property="og:title" content="Questionable Advice: “What’s the critical path?”"/><meta data-rh="true" name="twitter:title" content="Questionable Advice: “What’s the critical path?”"/><meta data-rh="true" name="description" content="Dan Golant asked a great question today: “Any advice/reading on how to establish a team’s critical path?”"/><meta data-rh="true" property="og:description" content="Dan Golant asked a great question today: “Any advice/reading on how to establish a team’s critical path?”"/><meta data-rh="true" name="twitter:description" content="Dan Golant asked a great question today: “Any advice/reading on how to establish a team’s critical path?”"/><meta data-rh="true" property="og:image" content="https://substackcdn.com/image/fetch/$s_!khu1!,f_auto,q_auto:best,fl_progressive:steep/https%3A%2F%2Fcharitydotwtf.substack.com%2Ftwitter%2Fsubscribe-card.jpg%3Fv%3D-281824914%26version%3D9"/><meta data-rh="true" name="twitter:image" content="https://substackcdn.com/image/fetch/$s_!khu1!,f_auto,q_auto:best,fl_progressive:steep/https%3A%2F%2Fcharitydotwtf.substack.com%2Ftwitter%2Fsubscribe-card.jpg%3Fv%3D-281824914%26version%3D9"/><meta data-rh="true" name="twitter:card" content="summary"/><meta data-rh="true" property="article:modified_time" content="2025-12-16T00:59:56.236Z"/>
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class="visibility-check"></div><div><div class="dt-post-body"><div class="available-content"><div dir="auto" class="body markup"><p><a href="http://twitter.com/dangolant">Dan Golant</a><span> asked a great question today: “Any advice/reading on how to establish a team’s critical path?”</span></p><p>I repeated back: “establish a critical path?” and he clarified:</p><blockquote><p>Yea, like, you talk about buttoning up your “critical path”, making sure it’s well-monitored etc. I think that the right first step to really improving Observability is establishing what business processes *must* happen, what our “critical paths” are. I’m trying to figure out whether there are particularly good questions to ask that can help us document what these paths are for my team/group in Eng.</p></blockquote><p>“Critical path” is one of those phrases that I think I probably use a lot. Possibly because the very first real job I ever had was when I took a break from college and worked at criticalpath.net (“we handle the world’s email”) — and by “work” I mean, “lived in SF for a year when I was 18 and went to a lot of raves and did a lot of drugs with people way cooler than me”. Then I went back to college, the dotcom boom crashed, and the CP CFO and CEO actually went to jail for cooking the books, becoming the only tech execs I am aware of who actually went to jail.</p><p>Where was I.</p><p>Right, critical path. What I said to Dan is this: “What makes you money?”</p><p>Like, if you could only deploy three end-to-end checks that would perform entire operations on your site and ensure they work at all times, what would they be? what would they do? “Submit a payment” is a super common one; another is new user signups.</p><a target="_blank" href="https://substackcdn.com/image/fetch/$s_!ABSa!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png" data-component-name="Image2ToDOM" class="image-link image2 can-restack"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!ABSa!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 424w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 848w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 1272w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 1456w" sizes="100vw"/><img src="https://substackcdn.com/image/fetch/$s_!ABSa!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png" width="218" height="185" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/985e741d-1f99-4e15-8927-3cb907310bac_300x255.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:185,&quot;width&quot;:218,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:null,&quot;alt&quot;:&quot;&quot;,&quot;title&quot;:null,&quot;type&quot;:null,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" alt title srcset="https://substackcdn.com/image/fetch/$s_!ABSa!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 424w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 848w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 1272w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 1456w" sizes="100vw" fetchpriority="high" class="sizing-normal"/></picture><div></div></div></a><p><span>The idea here is to draw up a list of the things that are absolutely worth waking someone up to fix immediately, night or day, rain or shine. That list should be as compact and well-defined as possible. This allows you to be explicit about the fact that </span><em>anything else can wait til morning</em><span>, or some other less-demanding service level agreement.</span></p><p><span>And typically the right place to start on this list is by asking yourselves: “what makes us money?” as a proxy for the real questions, which are: “what actions allow us to survive as a business? What do our customers care the absolute most about? What makes us </span><em>us</em><span>?” That’s your critical path.</span></p><p>Someone will usually seize this opportunity to argue that absolutely any deterioration in service is worth paging someone immediately to fix it, day or night. They are wrong, but it’s good to flush these assumptions out and have this argument kindly out in the open.</p><p><span>(Also, this is really a question about service level objectives. So if you’re asking yourself about the critical path, you should probably consider buying </span><a href="https://www.amazon.com/Implementing-Service-Level-Objectives-Practical/dp/1492076813">Alex Hidalgo’s book on SLOs</a><span>, and you may want to look into the </span><a href="https://www.honeycomb.io/blog/challenges-with-implementing-slos/">Honeycomb SLO</a><span> product, the only one in the industry that actually implements SLOs as the Google SRE book defines them (thanks Liz!) and lets you jump straight from “what are our customers experiencing?” to “WHY are they experiencing it”, without bouncing awkwardly from aggregate metrics to logs and back and just … hoping … the spikes line up according to your visual approximations.)</span></p><a target="_blank" href="https://i0.wp.com/charity.wtf/wp-content/uploads/2020/07/bed-13-1.jpg?resize=198%2C264&amp;ssl=1" data-component-name="Image2ToDOM" class="image-link image2 is-viewable-img can-restack"><div 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Advice: \u201CWhat\u2019s the critical path?\u201D\",\"type\":\"newsletter\",\"video_upload_id\":null,\"write_comment_permissions\":\"everyone\",\"meter_type\":\"none\",\"live_stream_id\":null,\"is_published\":true,\"restacks\":0,\"reactions\":{\"\u2764\":0},\"top_exclusions\":[],\"pins\":[],\"section_pins\":[],\"has_shareable_clips\":false,\"previous_post_slug\":\"how-to-make-boba-at-home-without-ruining-any-pans-making-yourself-ill-or-ending-up-with-a-soggy-blobby-mess\",\"next_post_slug\":\"the-official-authorized-list-of-legitimate-reasons-for-deciding-to-become-a-manager\",\"cover_image\":null,\"cover_image_is_square\":false,\"cover_image_is_explicit\":false,\"videoUpload\":null,\"podcastFields\":null,\"podcastUpload\":null,\"podcastPreviewUpload\":null,\"voiceover_upload_id\":null,\"voiceoverUpload\":null,\"has_voiceover\":false,\"description\":\"Dan Golant asked a great question today: \u201CAny advice/reading on how to establish a team\u2019s critical path?\u201D\",\"body_html\":\"<p><a href=\\\"http://twitter.com/dangolant\\\">Dan Golant</a> asked a great question today: \u201CAny advice/reading on how to establish a team\u2019s critical path?\u201D</p><p>I repeated back: \u201Cestablish a critical path?\u201D and he clarified:</p><blockquote><p>Yea, like, you talk about buttoning up your \u201Ccritical path\u201D, making sure it\u2019s well-monitored etc. I think that the right first step to really improving Observability is establishing what business processes *must* happen, what our \u201Ccritical paths\u201D are. I\u2019m trying to figure out whether there are particularly good questions to ask that can help us document what these paths are for my team/group in Eng.</p></blockquote><p>\u201CCritical path\u201D is one of those phrases that I think I probably use a lot. Possibly because the very first real job I ever had was when I took a break from college and worked at criticalpath.net (\u201Cwe handle the world\u2019s email\u201D) \u2014 and by \u201Cwork\u201D I mean, \u201Clived in SF for a year when I was 18 and went to a lot of raves and did a lot of drugs with people way cooler than me\u201D. Then I went back to college, the dotcom boom crashed, and the CP CFO and CEO actually went to jail for cooking the books, becoming the only tech execs I am aware of who actually went to jail.</p><p>Where was I.</p><p>Right, critical path. What I said to Dan is this: \u201CWhat makes you money?\u201D</p><p>Like, if you could only deploy three end-to-end checks that would perform entire operations on your site and ensure they work at all times, what would they be? what would they do? \u201CSubmit a payment\u201D is a super common one; another is new user signups.</p><a class=\\\"image-link image2\\\" target=\\\"_blank\\\" href=\\\"https://substackcdn.com/image/fetch/$s_!ABSa!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png\\\" data-component-name=\\\"Image2ToDOM\\\"><div class=\\\"image2-inset\\\"><picture><source type=\\\"image/webp\\\" srcset=\\\"https://substackcdn.com/image/fetch/$s_!ABSa!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 424w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 848w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 1272w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 1456w\\\" sizes=\\\"100vw\\\"><img src=\\\"https://substackcdn.com/image/fetch/$s_!ABSa!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png\\\" width=\\\"218\\\" height=\\\"185\\\" data-attrs=\\\"{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/985e741d-1f99-4e15-8927-3cb907310bac_300x255.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:185,&quot;width&quot;:218,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:null,&quot;alt&quot;:&quot;&quot;,&quot;title&quot;:null,&quot;type&quot;:null,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}\\\" class=\\\"sizing-normal\\\" alt=\\\"\\\" title=\\\"\\\" srcset=\\\"https://substackcdn.com/image/fetch/$s_!ABSa!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 424w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 848w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 1272w, https://substackcdn.com/image/fetch/$s_!ABSa!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F985e741d-1f99-4e15-8927-3cb907310bac_300x255.png 1456w\\\" sizes=\\\"100vw\\\" fetchpriority=\\\"high\\\"></picture><div></div></div></a><p>The idea here is to draw up a list of the things that are absolutely worth waking someone up to fix immediately, night or day, rain or shine. That list should be as compact and well-defined as possible. This allows you to be explicit about the fact that <em>anything else can wait til morning</em>, or some other less-demanding service level agreement.</p><p>And typically the right place to start on this list is by asking yourselves: \u201Cwhat makes us money?\u201D as a proxy for the real questions, which are: \u201Cwhat actions allow us to survive as a business? What do our customers care the absolute most about? What makes us <em>us</em>?\u201D That\u2019s your critical path.</p><p>Someone will usually seize this opportunity to argue that absolutely any deterioration in service is worth paging someone immediately to fix it, day or night. They are wrong, but it\u2019s good to flush these assumptions out and have this argument kindly out in the open.</p><p>(Also, this is really a question about service level objectives. So if you\u2019re asking yourself about the critical path, you should probably consider buying <a href=\\\"https://www.amazon.com/Implementing-Service-Level-Objectives-Practical/dp/1492076813\\\">Alex Hidalgo\u2019s book on SLOs</a>, and you may want to look into the <a href=\\\"https://www.honeycomb.io/blog/challenges-with-implementing-slos/\\\">Honeycomb SLO</a> product, the only one in the industry that actually implements SLOs as the Google SRE book defines them (thanks Liz!) and lets you jump straight from \u201Cwhat are our customers experiencing?\u201D to \u201CWHY are they experiencing it\u201D, without bouncing awkwardly from aggregate metrics to logs and back and just \u2026 hoping \u2026 the spikes line up according to your visual approximations.)</p><a class=\\\"image-link image2 is-viewable-img\\\" target=\\\"_blank\\\" href=\\\"https://i0.wp.com/charity.wtf/wp-content/uploads/2020/07/bed-13-1.jpg?resize=198%2C264&amp;ssl=1\\\" data-component-name=\\\"Image2ToDOM\\\"><div 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data-attrs=\\\"{&quot;src&quot;:&quot;https://i0.wp.com/charity.wtf/wp-content/uploads/2020/07/bed-13-1.jpg?resize=198%2C264&amp;ssl=1&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:264,&quot;width&quot;:198,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:null,&quot;alt&quot;:&quot;bed - 13 (1)&quot;,&quot;title&quot;:null,&quot;type&quot;:null,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}\\\" class=\\\"sizing-normal\\\" alt=\\\"bed - 13 (1)\\\" title=\\\"bed - 13 (1)\\\" srcset=\\\"https://i0.wp.com/charity.wtf/wp-content/uploads/2020/07/bed-13-1.jpg?resize=198%2C264&amp;ssl=1 424w, https://i0.wp.com/charity.wtf/wp-content/uploads/2020/07/bed-13-1.jpg?resize=198%2C264&amp;ssl=1 848w, https://i0.wp.com/charity.wtf/wp-content/uploads/2020/07/bed-13-1.jpg?resize=198%2C264&amp;ssl=1 1272w, https://i0.wp.com/charity.wtf/wp-content/uploads/2020/07/bed-13-1.jpg?resize=198%2C264&amp;ssl=1 1456w\\\" sizes=\\\"100vw\\\" loading=\\\"lazy\\\"></picture><div class=\\\"image-link-expand\\\"><div class=\\\"pencraft pc-display-flex pc-gap-8 pc-reset\\\"><button tabindex=\\\"0\\\" type=\\\"button\\\" class=\\\"pencraft pc-reset pencraft icon-container restack-image\\\"><svg aria-hidden=\\\"true\\\" width=\\\"20\\\" height=\\\"20\\\" viewBox=\\\"0 0 20 20\\\" fill=\\\"none\\\" stroke-width=\\\"1.5\\\" stroke=\\\"var(--color-fg-primary)\\\" stroke-linecap=\\\"round\\\" stroke-linejoin=\\\"round\\\" xmlns=\\\"http://www.w3.org/2000/svg\\\"><g><path d=\\\"M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882\\\"></path></g></svg></button><button tabindex=\\\"0\\\" type=\\\"button\\\" class=\\\"pencraft pc-reset pencraft icon-container view-image\\\"><svg xmlns=\\\"http://www.w3.org/2000/svg\\\" width=\\\"20\\\" height=\\\"20\\\" viewBox=\\\"0 0 24 24\\\" fill=\\\"none\\\" stroke=\\\"currentColor\\\" stroke-width=\\\"2\\\" stroke-linecap=\\\"round\\\" stroke-linejoin=\\\"round\\\" class=\\\"lucide lucide-maximize2 lucide-maximize-2\\\"><polyline points=\\\"15 3 21 3 21 9\\\"></polyline><polyline points=\\\"9 21 3 21 3 15\\\"></polyline><line x1=\\\"21\\\" x2=\\\"14\\\" y1=\\\"3\\\" y2=\\\"10\\\"></line><line x1=\\\"3\\\" x2=\\\"10\\\" y1=\\\"21\\\" y2=\\\"14\\\"></line></svg></button></div></div></div></a><p>charity.</p>\",\"has_dynamic_content\":false,\"truncated_body_text\":\"Dan Golant asked a great question today: \u201CAny advice/reading on how to establish a 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