Olaide

    Two days to thirty minutes

    One change to a live enterprise program could take two days, and only two people knew how to make it. I redesigned how Strategyzer’s program templates and live cohort deliveries stay in sync, and a full round of changes now takes about thirty minutes.

    Role
    Senior product designerThe only designer. I led the work end to end, from discovery to delivery.
    Team
    Me and one engineerWith our Head of Product advising
    Timeline
    About 3 monthsMy first project at Strategyzer
    Status
    Live
    The redesigned program admin: a cohort delivery’s timeline for Growth Symposium I, with Week One’s three events, their actions, and a progress panel showing program completion and learning progress.

    Click any image to see it full size.

    At a glance

    1. The problem
      Strategyzer’s enterprise programs run with up to 20 client teams at once. Changing one after teams had started meant editing code by hand, repeating it for every team and checking every link. A full round of changes could take two to three days.
    2. What I found
      A long list of complaints came down to four causes. One explained most of the pain: once a cohort delivery started, it lost its connection to the template it came from.
    3. The ideaTurning point
      The program template is the single source of truth, and every cohort delivery chooses what to take from it.
    4. What shipped
      Four features built on that idea: template updates you review before applying, copying workspaces to many team projects at once, hiding and showing timeline events, and breadcrumbs inside workspaces.
    5. Results
      2d → 30m
      for a full round of changes to a live cohort delivery
      4h → 20m
      to copy workspaces to every team
      9.5/10
      satisfaction from six of our most frequent users
      6 figures
      enterprise deals supported by faster, more reliable delivery

    One change, twenty copies, two days

    Building a program was manageable. Changing one after teams had started was not.

    Strategyzer runs strategy programs for large companies. A small team of program designers builds each one from playbooks, which mix learning content, exercises and shared workspaces where teams do the work. A single program can have 10 to 20 client teams working through it at once.

    Every program has four layers, and the moment a cohort delivery was created, they stopped talking to each other.

    In the product, a cohort delivery’s timeline is called its playbook instance, so you’ll see that name in the screens below.

    Programs change while they’re live. An exercise doesn’t land, a presentation gets reworked overnight, or a client asks for something new on day two. So a coach’s two-minute decision turned into four jobs:

    1. Update the template, so it stays clean for the next client.
    2. Edit the cohort delivery’s settings by hand, in code, because the admin couldn’t see anything added after the delivery was created.
    3. Repeat that edit for every team, all 10, 15 or 20 of them.
    4. Open every team’s workspaces to hunt for broken links.

    “If there’s a 12-team cohort and there’s changes, it ends up being 2 to 3 days sometimes.”

    Kurt Bostelaar, Program Designer

    What watching the work revealed

    The workarounds nobody mentioned

    I didn’t ask people what they wanted. I asked the program designers who ran deliveries most often, especially Kurt and Latif, to share their screens and walk me through a real program from start to finish. At every step I asked what it was for, and why it happened there. I also spoke with Dora in customer success, who heard clients’ complaints first, and with Alex, our CEO, who runs live deliveries with clients.

    “I literally sometimes spend 2 to 3 days just copying stuff around.”

    Kurt Bostelaar, Program Designer

    Watching the work showed habits so routine that nobody thought to mention them:

    Deleting to hide

    Later timeline events were deleted so teams couldn’t see them yet, then pasted back from the template when it was time.

    Doing everything twice

    Every change was made in the template and in the cohort delivery, because copying it back later could drag client data into the template.

    Building around the system

    A whole separate program was built just so teams could share one workspace.

    Checking every link by hand

    Before each session, every workspace for every team was opened, because at least one link was almost always broken.

    The discovery board in FigJam: a journey map, interview synthesis for four people (Latif, Alex and Kurt from program design and admin, and Dora from customer success), UX audits of the program editor and the admin with notes on every screen, a feature and solution wall, a prioritisation matrix and the opportunity solution tree.
    The discovery board. Interview synthesis, a journey map, screen-by-screen audits of the program editor and admin, and the opportunity solution tree. Click to see it full size.

    Many symptoms, four causes

    Cause 1
    The template and the cohort delivery lost touch

    Once a cohort delivery was created, it had no link to its template, so every improvement was carried across by hand.

    Cause 2
    Effort grew with every team

    One decision became 20 edits, and each edit was another chance for a mistake.

    Cause 3
    Staying safe meant deleting things

    The only way to release content in stages was to remove it.

    Cause 4
    Everything depended on a name

    Timeline events found their workspaces by exact name, so one stray space or a leftover “Copy” sent a team to a dead end. That one detail explained the broken links, the code edits and the fear of renaming anything.

    Underneath it all

    Program designers had two jobs at once: keep the live delivery moving, and keep a clean template ready for the next client. The platform made them do both by hand.

    Together, this made a process only experts could run, while the business wanted coaches, partners and eventually clients to run programs themselves.

    One idea to hold it together

    The platform didn’t need more controls. It needed one simple rule that people could understand at a glance:

    The program template is the single source of truth, and every cohort delivery chooses what to take from it.

    Four principles followed from that:

    Change it once

    Effort should never grow with the number of teams.

    Stay in control

    Nothing is forced onto a live delivery.

    Nothing is destructive

    Hiding replaces deleting, and every action can be undone.

    Always know where you are

    In a platform this deep, knowing where you are is a feature.

    Choosing what not to build

    With one engineer and three months, I ranked every opportunity by three questions: How often does it happen? Would a failure be visible to clients? Can we build it well in the time we have? Changing live programs came out on top on all three. The opportunity solution tree below shows how it all fits together.

    Built in this release
    Changing live programs
    • Template updates, reviewed and applied
    • Copying workspaces to many team projects at once
    • Hiding and showing timeline events
    • Breadcrumbs inside workspaces
    Agreed for later phases
    Mapped, prioritised and shared
    • The e-learning course system
    • Exercise tracking
    • A library of reusable exercises
    • How playbooks and projects are organised
    Making the trade-offs visible kept the release focused, and nobody felt their problem had been ignored.
    The opportunity solution treeFrom the outcome we wanted, to the opportunities, to possible solutions. It’s in two parts: switch between them with the tabs.
    Opportunity solution tree, part one. Desired outcome: create, administer and manage programs in less time and with little to no friction. Opportunities: release timeline events to participants in stages, with solutions a hide and unhide icon or an on and off toggle for each event; add new workspaces to a program template and copy them to multiple projects at once, with solutions a search field and multi-select in the dropdown; and port template updates into cohorts, with solutions a notification in the cohort and a button to apply updates to the timeline.
    Opportunity solution tree, part two. The same desired outcome. Opportunities: search and filter across the product, with solutions a search and filter option and a card or list view toggle; navigate the platform and understand where to go, with the solution a navigation clean-up and naming; and link workspaces and their assets between cohorts, with solutions still to be decided.
    Changing live programs: all three opportunities shipped in this release. Click to see it full size.

    Four features, one model

    Each feature puts one of the principles into the product. Together they work as one job: send the workspaces, bring the updated timeline into the cohort delivery, then choose when teams see it. Kurt called the result “a MASSIVE game changer”.

    1. Template updates, reviewed and applied

    PrincipleStay in control

    The heart of the redesign. It reconnects the template and the cohort delivery, ends the double work and takes code out of the job.

    Before

    Every template change was carried into each cohort delivery by hand, by editing its settings in code. A new workspace stayed invisible to the timeline until someone typed its exact name.

    Now

    Cohort deliveries are told when their template changes. Program designers review each update and choose to apply or ignore it, and any new workspace they accept appears in the delivery’s timeline, ready to link.

    A strategic call

    Review, not automatic sync. Syncing template changes into every cohort delivery automatically was an option. It would have saved a step, but it would also have changed a live client program without anyone choosing to. So I designed a review step: every update waits until the people running the delivery decide what to apply and what to ignore.

    1Before
    2After
    3The designsClick a tab to see each screen and the decisions behind it
    A cohort delivery’s timeline with a banner at the top: a new update is available for this playbook’s original template, with a Review Changes link. The Week One events and the progress panel sit below, unchanged.
    Hover a decision to see it in the designTap a decision to see it in the design
    The Review template updates panel over the cohort delivery’s timeline, listing three updates, each with a checkbox: a new workspace added to Week One, a new activity added to Week Two, and a workspace updated in Week Two. Select all updates sits above, and Cancel and Apply Selected (0) below.
    Hover a decision to see it in the designTap a decision to see it in the design
    The review panel with the first update expanded. It is highlighted, and below it a What’s new section explains that a new workspace called Customer Validation has been added to the template, with a details card showing 4 activities and 2 exercises.
    Hover a decision to see it in the designTap a decision to see it in the design
    The playbook instance after applying the update. A dark message at the top right says your instance has been updated successfully, the update banner is gone, and the Week One events and progress panel are ready to use.
    Hover a decision to see it in the designTap a decision to see it in the design
    Update notice: The notice on the cohort delivery’s timeline that the template has changed

    2. Copy workspaces to many team projects at once

    PrincipleChange it once

    Before

    One workspace could go to one team project at a time. Twenty teams meant doing it twenty times, for every workspace.

    Now

    Pick several workspaces, search for the team projects, and copy them all in one action.

    1Before
    The old Copy workspace dialog in the program editor. A dark, unstyled system dropdown lists every project in one long scrolling list, grouped under headings like Projects managed by Strategyzer and Your personal projects, with one project ticked. There is no search.
    Hover a problem to see it in the designTap a problem to see it in the design
    2After
    3The designsClick a tab to see each screen and the decisions behind it
    The Workspaces tab of the program editor. Customer Discovery and Idea Validation are ticked and shown in blue, Go To Market Strategy is not. A bar at the bottom reads 2 workspaces selected, with Copy, Move and a red Delete.
    Hover a decision to see it in the designTap a decision to see it in the design
    The Copy Workspaces dialog over the workspaces page. Select Workspaces already holds Customer Discovery and Idea Validation as removable chips. Target project(s) is empty and asks to select one or more projects. Cancel and Copy sit at the bottom, and the selection bar is still visible below.
    Hover a decision to see it in the designTap a decision to see it in the design
    The Target project(s) dropdown open in the dialog. It has a Search by project name box and a list where Sprint Team One and Sprint Team Two are ticked and Sprint Team Three is not. The two ticked projects also appear as chips in the field above.
    Hover a decision to see it in the designTap a decision to see it in the design
    The Copy Workspaces dialog with the dropdown closed. Select Workspaces shows Customer Discovery and Idea Validation, and Target project(s) shows Sprint Team One and Sprint Team Two. Cancel and Copy sit below.
    Hover a decision to see it in the designTap a decision to see it in the design
    The workspaces page after copying. A dark message at the top right says workspaces copied successfully, with a close button. The checkboxes on the cards are cleared and the selection bar is gone.
    Hover a decision to see it in the designTap a decision to see it in the design
    Select workspaces: Ticking several workspaces at once

    3. Hide and show timeline events

    PrincipleNothing is destructive

    Before

    Releasing content in stages meant deleting events, with no undo, then pasting them back from the template’s code when it was time.

    Now

    Program designers build the whole program up front, then hide or show one event, several at once or a whole week, and keep editing while they’re hidden.

    1Before
    The old timeline with a Delete event dialog open. It asks: Are you sure you want to delete the event Welcome to the Discovery Program? No undo! Cancel and Delete sit below. Behind it are the Onboarding Steps events, and a Show JSON Editor switch at the top right.
    Hover a problem to see it in the designTap a problem to see it in the design
    2After
    3The designsClick a tab to see each screen and the decisions behind it
    A cohort delivery’s timeline. Week One is open with three events, each with a checkbox on the left and eye, edit, duplicate and delete icons on the right. The Week One header has its own checkbox and eye icon. Week Two sits collapsed below, and a progress panel is on the right.
    Hover a decision to see it in the designTap a decision to see it in the design
    The same timeline with Testing Preparation and Prepare for the testing prep workshop ticked and tinted blue. A bar above the timeline reads 2 events selected, with Hide, Duplicate, a red Delete and a close button.
    Hover a decision to see it in the designTap a decision to see it in the design
    The timeline after hiding. Testing Preparation and Prepare for the testing prep workshop are faded to grey with a Hidden label and a closed eye icon. The third event is unchanged. A dark message at the top right says events updated successfully.
    Hover a decision to see it in the designTap a decision to see it in the design
    The two hidden events selected again, faded and tinted blue. The bar now reads 2 events selected with Show, Duplicate and Delete. Each hidden event still has its edit, duplicate and delete icons.
    Hover a decision to see it in the designTap a decision to see it in the design
    The timeline with the pointer on the eye icon of Testing Preparation. A dark tooltip reads Hide Event. The icon sits with edit, duplicate and delete on the right of the event.
    Hover a decision to see it in the designTap a decision to see it in the design
    The timeline after hiding one event. Testing Preparation is faded to grey with a Hidden label and a closed eye icon. The other two events are unchanged. A dark message at the top right says event updated successfully.
    Hover a decision to see it in the designTap a decision to see it in the design
    The Week One group header is ticked, and all three of its events are ticked with it. The bar above reads 1 event group selected, with Hide, Duplicate, a red Delete and a close button.
    Hover a decision to see it in the designTap a decision to see it in the design
    Week One after hiding. The group has a Hidden label next to its name, and all three events are faded to grey but keep their icons. A dark message at the top right says event group updated successfully.
    Hover a decision to see it in the designTap a decision to see it in the design
    Timeline: A cohort delivery’s timeline before anything is hidden

    4. Breadcrumbs inside workspaces

    PrincipleAlways know where you are

    Before

    Inside a workspace there was no navigation. To reach another one, you clicked the Strategyzer logo to get back to the project, picked a run, then picked a workspace. Even our CEO got lost inside custom playbooks.

    Now

    Every step of the breadcrumb is a menu. From inside a workspace you can reach any workspace in the run, or any run in the project, without going back. Alex and Carol both called it out.

    1Before
    The old workspace view. The top left shows only the workspace name, Customer Discovery, next to undo and redo. There is no breadcrumb or menu, just the Strategyzer logo in the side bar and an empty canvas with the drawing tools at the bottom.
    Hover a problem to see it in the designTap a problem to see it in the design
    2After
    3The designsClick a tab to see each screen and the decisions behind it
    The top of a workspace. A breadcrumb reads Olaide’s Project, then Strong Value Propositions and…, then Design your A/B test to identify…, with a small circled arrow after each of the last two. Undo and redo sit below, over an empty canvas.
    Hover a decision to see it in the designTap a decision to see it in the design
    The breadcrumb with the run menu open below it. Under the heading Playbook Runs it lists Customer Interviews, Strong Value Propositions and Differentiation with Gen AI with a tick, and Competing on Business Models, each with an arrow.
    Hover a decision to see it in the designTap a decision to see it in the design
    The run menu with Strong Value Propositions and Differentiation with Gen AI highlighted in blue. Beside it, a Workspaces menu lists Learn how customers are using your product, Design your A/B test to identify bottlenecks and gaps with a tick, and Upskill your team with Gen AI.
    Hover a decision to see it in the designTap a decision to see it in the design
    Breadcrumbs: The path at the top of every workspace

    Tested with the people who do the work

    I tested with six of the people who deliver programs most often, a mix of program designers and coaches, using scenarios from real deliveries. The response was strongly positive. It confirmed the core decisions, including reviewing updates before they apply, and helped us decide which parts of the opportunity tree to take on next. I stayed with the work through the build and kept gathering feedback for months after launch.

    9.5/10
    average satisfaction across six program designers and coaches

    Days back on every delivery

    Program designers got days back on every delivery, and the business could promise more.

    How we measured: the times are what program designers reported for their own workflows. Satisfaction comes from a small internal test on a 10-point scale.

    People also reported fewer mistakes and more confidence in what they sent to clients.

    What the team said

    Straight from Slack, in their own words. Click any message to see it full size.

    Heard at a live client event

    “The UX has improved”

    What participants said during an enterprise client’s workshops, reported by the program designer and coach who ran them. The platform, including the new admin, held up through a full day of live changes. Kurt, who had been nervous about the platform during live events for years, used the new admin all day to change the program on the fly.

    Slack thread. Kurt Bostelaar: Massive credit to @developers and @product-team as the platform performed fantastically at the [enterprise client] workshops. I think I carry anxiety with the platform during live events because years back it always had issues. but thoroughly impressed that it never once got in the way of allowing the teams to work and was great how it helped virtual attendees participate with those in the room. I feel like having the admin feature, the program editor, and the improved UX all came together to allow us to customize on the fly changes that served the teams with where they were at. I found myself constantly throughout the day using the admin feature, the program editor and workspaces and it was truly a light bulb moment for me to see how powerful our platform has become. hats off team for all the work that has gone into getting the platform to this point! Augustin Solioz replied: @developers @product-team This was even mentioned by participants who engaged with the platform during several [enterprise client] events “The UX has improved”. The platform is now a reliable tool that enable us to deliver with confidence during in-person and hybrid events without having to onboard them into how to use it!!
    Program Designer, with a reply from a Strategyzer Coach

    Kurt Bostelaar: Massive credit to @developers and @product-team as the platform performed fantastically at the [enterprise client] workshops. I think I carry anxiety with the platform during live events because years back it always had issues. but thoroughly impressed that it never once got in the way of allowing the teams to work and was great how it helped virtual attendees participate with those in the room. I feel like having the admin feature, the program editor, and the improved UX all came together to allow us to customize on the fly changes that served the teams with where they were at. I found myself constantly throughout the day using the admin feature, the program editor and workspaces and it was truly a light bulb moment for me to see how powerful our platform has become. hats off team for all the work that has gone into getting the platform to this point! Augustin Solioz replied: @developers @product-team This was even mentioned by participants who engaged with the platform during several [enterprise client] events “The UX has improved”. The platform is now a reliable tool that enable us to deliver with confidence during in-person and hybrid events without having to onboard them into how to use it!!

    What changed for them
    Slack message from Kurt Bostelaar: Cheers to @product-team and @developers - I used the copy workspaces feature just now and it literally allowed me to do in 20 minutes with Augustin what would have taken me at least 4 hours in the past. HUGE game changer
    Program Designer

    Cheers to @product-team and @developers - I used the copy workspaces feature just now and it literally allowed me to do in 20 minutes with Augustin what would have taken me at least 4 hours in the past. HUGE game changer

    Slack message from Kurt Bostelaar: Cheers to @developers @product-team. I was on a call with @Latif earlier and we both could NOT believe the features (hide timeline events, transfer sets of workspaces to multiple projects at once, and add workspaces from admin) that we now have at our disposal. This is a MASSIVE game changer!!!
    Program Designer

    Cheers to @developers @product-team. I was on a call with @Latif earlier and we both could NOT believe the features (hide timeline events, transfer sets of workspaces to multiple projects at once, and add workspaces from admin) that we now have at our disposal. This is a MASSIVE game changer!!!

    Slack message from Kurt Bostelaar: Cheers to @developers, @Olaide Arike Kaffo, and @Ashley Underwood. Even while there are still more parts to be shipped, its already AMAZING to work with the new workspace transfer feature. a simple thing that makes such a huuuuuge difference
    Program Designer

    Cheers to @developers, @Olaide Arike Kaffo, and @Ashley Underwood. Even while there are still more parts to be shipped, its already AMAZING to work with the new workspace transfer feature. a simple thing that makes such a huuuuuge difference

    Slack message from Alex: CHEERS to @Olaide Arike Kaffo & @George Montgomery for the breadcrumb navigation. It’s solved my biggest orientation challenge navigating the custom playbooks we’ve design… I ALWAYS got lost in the nav and now it’s seamless… it’s f-ing BRILLIANT!!! 🙌
    CEO

    CHEERS to @Olaide Arike Kaffo & @George Montgomery for the breadcrumb navigation. It’s solved my biggest orientation challenge navigating the custom playbooks we’ve design… I ALWAYS got lost in the nav and now it’s seamless… it’s f-ing BRILLIANT!!! 🙌

    Slack message from Latif: Cheers to @developers @Olaide Arike Kaffo @Ashley Underwood, this new workspace feature is really making my life easier! Really grateful for all the work you’ve put in 🙌
    Program Designer

    Cheers to @developers @Olaide Arike Kaffo @Ashley Underwood, this new workspace feature is really making my life easier! Really grateful for all the work you’ve put in 🙌

    Slack message from Carol Hill: Cheers to the product team especially @Olaide Arike Kaffo and @Vlad Gerasimov cc @Ashley Underwood - loving the new navigation by organisation. SOOO much easier to find things this way. WOW!! 🎉
    Program Director

    Cheers to the product team especially @Olaide Arike Kaffo and @Vlad Gerasimov cc @Ashley Underwood - loving the new navigation by organisation. SOOO much easier to find things this way. WOW!! 🎉

    On working with me
    Slack message from Ashley Underwood: Wow @Olaide Arike Kaffo! I’m super impressed with the diligence and structure you have applied to synthesising and analysing the product discovery work you have been doing on our editor and admin features this week. Really fantastic work 👏 🚀
    Head of Product

    Wow @Olaide Arike Kaffo! I’m super impressed with the diligence and structure you have applied to synthesising and analysing the product discovery work you have been doing on our editor and admin features this week. Really fantastic work 👏 🚀

    Slack message from Kurt Bostelaar: Cheers to @Olaide Arike Kaffo for jumping straight in and iterating on designs in your FIRST week!! Keep rocking 🔥
    Program Designer

    Cheers to @Olaide Arike Kaffo for jumping straight in and iterating on designs in your FIRST week!! Keep rocking 🔥

    Slack message from Kurt Bostelaar: @Olaide Arike Kaffo +1 super cool to see you truly sinking your teeth into this project. I’ve been really impressed by how you keep asking the simple questions in order to make sure you deeply understand the problem. Love it!
    Program Designer

    @Olaide Arike Kaffo +1 super cool to see you truly sinking your teeth into this project. I’ve been really impressed by how you keep asking the simple questions in order to make sure you deeply understand the problem. Love it!

    Beyond the numbers

    Program designers are Strategyzer’s scarcest resource, so giving them back days changed what the business could take on. These were shared results. My part was removing what slowed the team down in the product, so they could build and deliver more.

    Enterprise
    More programs, with confidence

    Faster program building and more reliable delivery gave the team confidence to commit to and close more enterprise programs, each worth six figures.

    Individual subscribers
    A richer library

    Faster turnaround put more playbooks into the library, which made the subscription more valuable for individual users.

    Scale
    Coaches can change programs themselves

    Coaches can now change a program mid-delivery without waiting for a program designer. It’s the first real step toward clients running their own programs.

    What this project shows about how I work

    I look for causes, not symptoms.

    A long list of complaints came down to four causes, and those pointed to one idea. That’s how one designer and one engineer made a change this big.

    Four causes
    I simplify the model before the screens.

    Better screens alone wouldn’t have fixed this. A clear relationship between a template and its cohort deliveries did, and then the screens could stay simple.

    The one idea
    I treat scope as a design decision.

    With a small team, what we left out mattered as much as what we built. Clear criteria made the trade-offs easy to explain and agree on.

    What we didn’t build
    I stay close to the people doing the work.

    From the first screen share to feedback months after launch.

    What they said

    Where the work goes next

    The rest of the opportunity tree points to the next phases:

    • Search across the product.
    • Linking workspaces by a fixed ID instead of by name, so renaming a workspace never breaks a link.
    • Reliable links between workspaces.
    • A simpler structure for playbooks and projects.

    The aim for these next steps: someone who first heard the word “playbook” last week should be able to run one with confidence.