One Fortune 500 company Whynde Kuehn worked with had a customer experience problem that no single plan would have shown. Each product area had its own plan, and each plan looked good. Each had funding and a clear case for what it would deliver. Taken together, those plans produced an inconsistent experience, duplicated effort across the business, and product teams that didn't know the customer already owned something from another part of the company.
Whynde, founder and managing director of S2E Transformation, traces problems like this to a gap between strategy, which is abstract and high level, and all the plans people build to respond to it. The gap opens early in the cycle. It often only becomes visible at the end, when the year's results are in and next year's plan is already taking shape.
She joined Alex Lee, Cascade's Chief Customer Officer, to talk about using that moment well: what to look for in the year that's ending, what to carry forward, and how to set up 2027 so the pieces add up. Whynde is the author of Strategy to Reality, co-author of The Execution Challenge, and co-founder of the Business Architecture Guild.
Check Whether the Pieces Add Up
Alex summed up the Fortune 500 story this way: everyone had their own plan, each one seemed to be on track, and from the leadership seat the parts still didn't make a whole. It's possible, he said, to succeed locally and still fail globally.
That's the first thing Whynde looks for when a cycle closes, and she checks for it from both ends.
"Did what we delivered, or were about to deliver, move the needle for real on strategy? And I would also look from the other way to say, what were our strategic objectives, and did we miss anything? Sometimes we have big ideas and we respond to them, and I've seen organizations not have enough initiative to move the needle on certain parts of the strategy. So it's gaps as well as delivery." - Whynde Kuehn
A year-end review that only grades delivery won't catch the second kind of failure.
Some of what broke shows up earlier, as symptoms during delivery. Teams discover two efforts doing similar work, or a dependency nobody mapped until it got in the way. Other failures never get a clear cause. Whynde was candid that with something like customer experience, it can be hard to trace a complaint back to a specific decision.
The early signal she watches for is siloed ownership: one part of the business pursuing its own focus in a way that doesn't fit what the enterprise needs. Often it's the squeaky wheel that always gets priority. With finite resources, the question is whether you're funding things that look good on their own and don't fit together.
Use Capabilities as the Bridge
Whynde closes that gap with business capabilities. Capabilities are the things an organization does, often many times over in different places: customer information management, payment management, product design. Because they cut across departments, they give leaders a shared view of how the organization works and delivers value.
They also turn strategy into concrete change. Ask which capabilities the strategy needs you to be good at, then what has to change in each one, and the initiatives that respond start to line up. Some will stay local while others need several teams working together.
Tracking capability maturity changes the governance conversation too. Whynde defines maturity as a set of planned changes across people, process, and technology, delivered in increments. For a customer insights capability, that could mean naming what you can do today, what you want to do next, and where you want to end up. Measuring this way lifts the review above whether a system or a project got done, and gives leaders a capability roadmap pitched at the level executives care about.
"What does the business get? What does the customer get at these points in time? That will translate to many different projects, but it gives us the direction, and it bridges that gap we talked about between the big idea and how we respond to it." - Whynde
Defining change across all three dimensions also guards against a habit she sees often, where an organization implements the system first and plans to train people later. Alex added a pitfall of his own: if the outcome of an objective is vague, a team can usually convince itself it succeeded, because it can make the outcome mean whatever it wants.
The relationship runs both ways. Knowing where your capabilities stand can show that a strategy needs something you don't have, can't build fast enough, or will need a partner for. Whynde was also clear that capabilities won't cover everything. Every organization has work that keeps it running and sits outside the strategy, and that work has to be balanced against the rest.
Track the Right Few Things
When the audience was polled on their biggest execution challenge, most answered "too many priorities." For Whynde, that's where the work starts. People track too many things, she said, and in many cases the wrong ones. They track activity over business value, and the outcomes of single teams over collective outcomes.
Alex sees the same pattern when clients adopt a new platform.
"They go, okay, we're going to use this platform. Well, let's put in everything we're working on. In practice, everyone still has to do these things, but the need to track it in your strategy and put it in a system is not necessary. I don't have to tell you that I'm coming into the office every day and turning on the lights. That's what's going to happen regardless." - Alex
Asked which metrics she would drop, Whynde named most counts of activity. She doesn't care how many things a team has, she said, and a high number of projects can even be a bad sign. Alex agreed, especially when a count carries a target nobody can explain, since a high volume of work says little about its quality.
What she keeps is the golden thread that runs from goal to objective, metric, course of action, capability, and project. Objectives also cascade into other objectives, with causal links between them, so the first job is understanding what drives what. Once you know what drives experience or revenue in your organization, you know which levers to pull. From there, she focuses hard on value and outcomes, checks capability maturity several times a year, and keeps it simple.
Alex suggested the year-end review should also look at the friction in reporting. Was it painful to integrate data for KPIs? Were people writing updates that helped anyone? Does a given item really need a monthly update, or would less often be enough?
For a baseline before the 2027 cycle begins, Cascade's strategy maturity assessment takes about 10 minutes. It's the same assessment Cascade uses with clients to see where they sit on the maturity spectrum, from how they think about strategy to how they track it.
Give Shared Work a Shared Owner
A common year-end discovery is that projects and initiatives had owners, but the workstream they belonged to didn't. Whynde's best-case answer came from another Fortune 500 company, which built a customer experience leadership council over time. It brought together the head of every customer-facing business unit plus the CIO, organized around every customer-facing capability, from insights and preferences to payments and communications.
The council governed three layers: the future state of customer experience, the strategic roadmap for how those capabilities would mature, and the projects that delivered the details. In one case, the group went as far as setting enterprise-wide principles for how customer experience should work.
Its cadence followed the work. The council met often while it defined the future state and agreed on investment, then moved to quarterly reviews against the capability roadmap to check whether those capabilities were actually maturing. It also became the place where any team planning a new investment that didn't fit the roadmap had to bring it for discussion. Either the roadmap changed or that team changed course.
None of these companies had an unusual setup to start from.
"In all these examples I'm giving, they were structured like every other organization. Portfolios aren't set up to do this. Executive motivation isn't set up to do this. But if you get the right group of leaders that sees the benefit of thinking enterprise and doing what's really best for the organization and customers, you'll start to make change and set a pattern." - Whynde
Her advice for getting started is deliberately small. Know your top priorities, pick a capability or set of capabilities, get the relevant leaders together, and gather the projects that touch it. Then ask whether those projects should be working together, and whether everyone shares a view of the future. She has also seen three separately funded efforts make a much stronger case once they were pulled together.
Take the Ego Out of It
When a leadership group agrees on direction but each leader runs their own department, shared work slides into the familiar trap where everyone owns it and nobody does. Leaders hesitate to tell peers what to do in their own area. Whynde's answer has two parts, mindset and process.
On mindset, she described a Fortune 500 CEO who started telling the organization that everybody needed to become a good enterprise citizen. With that message coming from the top, people could raise a concern as a question of direction ("this isn't aligned with where we're going") without it landing as personal criticism. Principles, mantras, or goals shared across executives can do the same job by giving people something to hang on to.
On process, the capability lens does a lot of the work.
"At least having this capability lens, it's not personal. There's no name on it. There's no department on it. You can just say, hey, we have this many million dollars going towards customer information. Does that make sense? You're not pointing fingers." - Whynde
A bigger why also brings leaders together. Whynde has seen the customer rally an entire organization, along with cross-cutting themes like sustainability. One government organization made sustainability part of its strategy, let every group pursue it separately, and lost track of whether it was on course. Urgent risk or compliance issues can rally executives quickly too, because if they don't all succeed, none of them do.
Advocates matter as well. Whynde described a C-suite leader who put this to his peers:
"I would gladly give up my investment in XYZ because I know we're not doing all the right things for the organization. How can we come together as a group of leaders to have the hard conversations about trade-offs in an objective way?" - A C-suite leader, as recounted by Whynde
By putting himself out there, he got the rest of the leadership team to have that conversation. Whynde added one caution: not everything has to be enterprise. Some initiatives are rightly local, and the shared effort belongs on the global ones.
Question What's Carrying Over
Every new cycle starts with a portfolio from the last one, and some of those items are large, long-running, and expensive. Whynde didn't soften her view on them.
"I'm going to say something that I know is really hard, but every cycle gives us an opportunity to relook at what we're doing. Sometimes it's not the right decision to keep funding the big thing they're doing, even if they've sunk a lot of money in it. If you think about it, we have a finite set of resources. How do we spend those on the right things?" - Whynde
Her practical starting point is to map everything carrying over to a one-page view of the organization's capabilities and see where it clusters. Then compare that with the capabilities the new strategy needs, like two heat maps side by side.
To judge whether an initiative is done or needs more time, she asks whether the organization has a picture of the future state the work is meant to deliver. She compared it to building a house: you know you're finished because the result matches the blueprint. For an initiative, that picture covers people, process, and technology, and it goes beyond the KPI. Does the result match the picture from both the customer and the business perspective, or does it need more iterations?
Then there's the initiative you want to stop that the CFO loves. Whynde's advice is to tie the decision back to a bigger why, so it stops being about anyone's personal project. If one focus matters most right now, and critical work can't be funded because of something else, the trade-off becomes concrete for everyone in the room. She was frank that it's still hard, and that this is exactly why strategy execution is hard: it means dealing with people's thoughts, feelings, and opinions.
Start AI at the Value Question
Whynde was upfront that her best example of AI in strategy isn't the typical case. The organizations getting it right start with leaders asking what AI means for how their organization creates value. Skip that step, she warned, and you risk optimizing an organization that may not be relevant tomorrow.
Finding that kind of opening asks executives to think hard about value creation, products, and services first, and only then translate it into capabilities.
Working from the other end, more organizations are noticing that their AI use cases are fragmented. Pilots don't add up to business value, and some have already been abandoned. Whynde is seeing companies assess whether each pilot drives a capability tied back to strategy, which any organization can start doing now. It's the same disconnect from earlier, with everyone running at the problem separately and no shared focus on what the business needs.
On what organizations lose by not using AI, she named two things. The first is rationalizing the many-to-many relationships between objectives, which are almost impossible to manage without a tool and which AI handles brilliantly. The second is generating strategic options, with a caveat.
"Everybody has access to AI models. So the real human part is what choices are you going to make, and how do you rally the organization around those choices and move fast." - Whynde
Alex added a warning from what he's seen. Some organizations used AI to generate their whole year of to-dos from their objectives and didn't review the first pass closely enough. They ended up with KPIs that couldn't be tracked and milestones that sounded logical but had nothing to do with the business.
AI can get you a decent way up the hill, he said, and someone still has to do the rest. Leaders still need to form a view with enough conviction to bring the rest of the organization along. Whynde agreed, and added that strategy and execution are only speeding up. Organizations need to sense and respond faster, and AI can help with that too.
Ask What It's Worth
Tracking happens in a lot of places: strategy and planning teams, transformation offices, product management, PMOs, and a few value management offices. Whynde sees the same gap across all of them.
"I hear a lot of talk about value, value management, value realization, benefits realization. But at the end of the day, I see very little. I think this is one of the top challenges with strategy execution that I see. Organizations just can't really get to 'did we deliver the final value?' But we can tell you, did we deliver the thing." - Whynde
So her one question for every leader heading into 2027 is about value.
"Do you know the value of what you're planning to fund to the organization?"
Alex agreed that it's the right question to keep asking.
"I've seen enough strategies where it's just, that's just how we've tracked it for a while. And maybe it's also true in organizations where it's very hierarchical and compliance-driven. Are we actually tracking strategy, or are we just tracking numbers?" - Alex
Asked every week or every month, the value question keeps the plan honest. It also gives leaders something to work through together, since what counts as value tends to get diluted as it moves through the hierarchy. When executives rethink their business model, Whynde takes them back to how they create, deliver, and capture value. For a portfolio, she ties each item to the organization's strategic objectives and its shared model of capabilities, value streams, and customer experiences.
That's a good way into the 2027 plan. Start with the fewest things that will get the best result, and make sure each one has a value someone can name.
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This article is based on a Cascade webinar on planning for 2027 with Whynde Kuehn, founder and managing director of S2E Transformation, hosted by Alex Lee, Cascade's Chief Customer Officer. Watch the full recording.
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