
ISSUE 34 · RETAIL REWIRED ROUNDUP
Make the Number. Make the Plan.
11 Moves for the Back Half of the Year
If you are on a retail calendar, Q2 just closed. You are roughly halfway through the year, you owe a number by January, and somebody upstairs has already asked for your 2027 plan.
That is the part nobody says out loud. From here to year-end, every retail leader is running two operating rhythms at the same time. One is a sprint to land the year with the assets you already bought. The other is a slower build where you commit next year's dollars, headcount, and bets. They pull in opposite directions. The sprint rewards fast decisions with existing inventory. The build rewards patience and evidence.
This week showed why the second one is harder than it looks. Walmart raised its full-year sales outlook and still guided Q3 earnings below the street, and the stock had its worst day since 2022. Target raised guidance and got rewarded. The difference had almost nothing to do with the headline number and everything to do with the quality of the growth underneath it. Which is exactly the conversation your 2027 plan needs to survive.
So here are the eleven things I would do if I were sitting in your chair right now.
Track One: Land the Year
Put the two conversations on separate calendars. This is the whole game and almost everybody gets it wrong. When one weekly meeting owns both the number in front of you and the plan behind it, one of two things happens: either next year's strategy gets eaten by this week's fire, or your Q4 execution meeting turns into a 2027 philosophy debate and nothing ships. Different meeting, different day, different pre-read, different attendee list. Say out loud in the invite which clock the room is on.
Rebase the back half on the basket you actually have. Not the one you planned in February. Pull the last eight weeks of transaction data and look at trips per customer against average ticket. Right now across the industry those two lines are moving in opposite directions: more visits, flatter or smaller baskets. If your Q4 forecast assumes the stock-up trip and your customer is buying for the next three days, you are about to over-buy pack sizes and over-spend on threshold mechanics. Rebase the media plan against the same read, because a campaign optimized for basket size is aimed at a behaviour that isn't showing up.
Publish a kill list, and publish it by name. Anything that cannot put revenue on the board by December 15 moves to the 2027 plan or dies this week. The reason to publish it is not tidiness. It's that half-dead initiatives don't stop consuming your best people, they just stop reporting progress. I would rather formally kill four things in September than watch nine things limp into November while my A players split their attention across all of them.
Audit the price cuts you already took. Pull the top 25 items where you invested price this year and check whether the unit lift actually paid for the margin you gave up. Anything that didn't, restore it before holiday sets lock, because after that the price is frozen until spring. This one is worth real money and almost nobody does it, because taking a price down feels like strategy and putting it back feels like an admission.
Recalculate cost-to-serve before peak, not during it. Run the math at today's average order value, not last year's. Find the order size where fulfilment costs more than the order makes, then move your free shipping threshold to sit above it. If digital is growing faster than stores in your business, and for most of you it is, then every point of digital growth at the wrong basket size is quietly buying you margin erosion. Fix the threshold in September or eat it in December.
Track Two: Build the Plan
Strip the one-timers out before you build a baseline. This year has noise in it. Tariff refunds, one-time settlements, price investments funded by money that arrives once. If you build 2027 off this year's reported P&L, you are planning against a number that structurally will not repeat, and you will spend Q1 explaining a gap you created in October. Build off a two-year stack with the one-timers pulled out, and show your CFO both views on the same page.
Pick three bets, not fifteen initiatives. Every plan I've ever seen with fifteen priorities delivered four. Choose three, attach a named owner, a dollar figure, and a kill date to each, and let everything else be run-the-business. The kill date is the part people skip and it's the part that makes the whole thing honest.
Decide your capability gap now, because hiring takes six months. Whatever your 2027 plan requires that your team cannot do today is a Q4 decision, not a January one. Build, buy, or partner. If the answer is build, the requisition goes in this fall. If it's partner, you should be having conversations before the December freeze, not after the plan is approved and the budget is already spoken for.
Where Leaders Actually Lose
Write down your peak decision rights in September. Who can take a markdown without asking. Who can authorize extra labour hours. Who calls the audible on Black Friday weekend when the plan is wrong by 11am. What dollar threshold requires you personally. I have watched more holiday margin disappear to a slow approval chain than to a bad buy. Put it on one page, send it to the team, and then honour it when someone uses it.
Have the retention conversation in October. Your best people get recruited in January, right after bonus lands. The conversation that keeps them is the one about what their role looks like in next year's plan, and it has to happen while you're still writing that plan, because that's when you can actually put them in it. It costs nothing. Waiting until February costs you the person and the six months it takes to replace them.
Bonus Strategy
Start building the content strategy that wins agentic search. This is the one item on the list that lives on both clocks at once, and it's the one I'd fight hardest for in the budget conversation.
Roughly 45% of people in the US and 44% globally now start a search with AI rather than a search engine. That is the AI Moment of Discovery, the point where a customer forms an opinion about your category before they ever touch your site, your store, or your ad. You didn't get a click. You didn't get an impression. You got summarized, and either you were in the answer or you weren't.
Here's the part most teams get wrong. They respond by publishing more of their own content. But the evidence is running the other way: the large majority of citations in AI answers come from earned sources, not brand-owned pages. Which means owned content and earned content are doing two completely different jobs.
Owned content makes you retrievable. Product pages written to answer a question rather than rank for a keyword (materials, dimensions, compatibility, and who it isn't for). FAQs that mirror full customer questions with the direct answer in line one. Structured data and clean product feeds that AI models can parse.
Earned content makes you citable. Active participation in category subreddits, long-form YouTube comparisons, third-party review volume, and creator partnerships that build long-term authority in model indexes.
And measure it before Q4. Segment AI referral traffic in your analytics this month, run your top 20 category questions through the major assistants, and write down who gets named today. Do it again in January. Without that baseline you will have no argument at all when you ask for the 2027 budget.
The honest question for your team: what are you publishing today that a model will cite twelve months from now? If the answer is "campaign pages and promo content," you're building for a discovery moment that's already moving.
(I've put the full framework, the research behind it, and the diagnostic I use with clients into a white paper. You can download it free at aimod.ca. If you're building a 2027 content plan in the next sixty days, start there.)
If You Only Do Three This Week
Split the meetings (1). Rebase the forecast on the real basket (2). Publish the kill list (3). Those three make the other seven possible, because they buy back the two things you're shortest on right now, which are focus and truthful numbers.
The Rewire
Halfway through the year is not a status update. It's the point where the year stops being about the plan you wrote and starts being about the decisions you're willing to make. The teams that finish strong in December are the ones that decided in August what they were going to stop doing.
What is your take?
Which of these two clocks is your team actually worse at: landing the year or building the plan?
Data Snapshot
Primary Search Shift: ~45% of consumers start product discovery via AI assistants
Top Q4 Risk: Misaligned free-shipping thresholds vs. shrinking basket sizes
Core Recommendation: Limit 2027 strategy to 3 high-conviction bets
P.S. If this issue was useful, the long version lives in my book. Retail Rewired: How Modern Retail Leaders Drive Growth and Reinvention covers the four pillars I keep coming back to: invest in your people, stay customer centric, think local, and deliver consistency. It's 25 years of running these plans, including the ones I got wrong. Grab a copy on Amazon.ca or Amazon.com. If you read it and it helped, a review means more than you'd think.
