Originally aired May 28, 2026 on Extropy On AIr.
Most transformation strategies don’t fail because they’re wrong. They fail in execution, when small breakdowns in communication, ownership and planning pile up until the plan no longer matches daily work. In this episode, Mike Jasper and Cecile Brown-Smith of Extropy Advisors explain where that execution gap comes from and how finance teams can close it.
Listen to the full episode on the Extropy On AIr podcast page or on Spotify.
Key takeaways
- Strategy is aspirational, execution is operational. A plan only becomes real when people understand how it changes their daily work.
- Execution rarely fails all at once. Small gaps like an unclear owner, duplicate work or knowledge that lives in one person’s head pile up until the project drifts.
- A North Star needs numbers. Define qualitative and quantitative success criteria and connect them to what each person and team actually does.
- Planning is not a phase. Revisit the plan and realign people throughout the project as availability and priorities change.
- Invite the right people from day one, including the people doing the work and groups like legal, tax, InfoSec, IT and audit that often show up late.
What is the execution gap?
It’s the distance between a strategy leaders can describe and what actually happens on the front line. The vision is clear in the boardroom, but the people doing the work don’t know what it means for them.
Cecile sees the same pattern across industries. Leadership is excited and can articulate a clear strategy, but without frontline input, priorities shift and expectations blur. A plan can look great in a slide deck, yet if people don’t understand how it affects their daily work, execution starts drifting almost immediately.
Mike pointed out why: a transformation asks people to change what they do every day, often before they know what the future state looks like. “We’re automating accounts receivable” is a strategy. It doesn’t tell anyone what their job looks like next month.
Why do good strategies fall apart in execution?
Usually not because of one big failure, but because of many small ones that build up over time. At Extropy we call that drift toward disorder entropy, and it happens on every project unless someone works against it.
Mike explained that entropy is the natural tendency of any process to break down without effort. Its opposite, extropy, is intentional order, and it takes ongoing structure and attention to maintain. On transformation projects, entropy tends to show up in a few familiar ways:
- Tribal knowledge. Someone who has been there 25 years knows a step nobody documented, and nobody thought to ask them.
- Duplicate work. When ownership is unclear, two people complete the same task. One deliverable goes unused, and the person who made it starts to feel their input doesn’t matter.
- Ambiguity. Send a request to 10 people and each assumes one of the other nine has it covered, so nobody answers.
- No North Star. Teams hear what the project is trying to accomplish, but it’s never turned into specific goals they can measure against.
What does strategic planning usually leave out?
The how and the who. As Mike put it, strategic planning tends to focus on the why and the what, while execution depends on how the work gets done and who does it. When that gap isn’t filled, entropy sets in.
Cecile described two very different kickoffs. In one, the call includes only a CFO, an AP supervisor and an IT supervisor. Everyone understands the vision, but nobody in the room knows the real workflows or who needs training. In the other, 30 people join from four departments, including the AP team members who process invoices all day. By the time design workshops and training arrive, those people have already shared everything the project needs to know.
Mike added the groups that are most often left out of the plan: finance, supply chain, InfoSec, IT, legal, audit, compliance and tax. Cecile shared what happens when they show up late. On one project, the legal contact changed, and the new person raised requirements nobody knew about, the week before go-live.
How do you close the execution gap?
Build execution systems that turn the strategy into daily behavior, then keep reinforcing them. Mike and Cecile shared the practices they lean on most:
- Define success criteria. Set qualitative and quantitative goals and translate them into what they mean for each team and role.
- Run a gap analysis on who’s affected. Include anyone who reviews the process, relies on its data or has to sign off, even if it isn’t part of their daily job.
- Keep planning. Revisit the plan and realign resources as people go out of office, new work competes for their time and priorities shift.
- Make every ask specific. Name who you need, what you need, when you need it and why. Explaining the why gets you better, more complete answers.
- Set a communication rhythm and stick to it. Consistency and daily reinforcement keep the strategy visible long after kickoff.
In their words
“Strategy is aspirational, but execution is operational.”
Cecile Brown-Smith, Project Manager, Extropy Advisors
“Strategic planning, a lot of times, focuses on the why and the what. But the execution infrastructure has the how and the who.”
Mike Jasper, VP of Finance Transformation, Extropy Advisors
About the speakers
Mike Jasper is VP of Finance Transformation at Extropy Advisors, where he leads digital transformation and client success, working hands-on with clients to set success criteria, optimize their people, process and technology, and measure the results. He is also a regular host of Extropy On AIr. Cecile Brown-Smith is a project manager at Extropy Advisors, where she guides client teams from kickoff through design workshops, training and go-live.
Frequently asked questions
What is the execution gap in strategy?
The execution gap is the distance between a strategy leadership can describe and what actually happens in daily work. It opens when the people doing the work do not know how the plan changes their job, who owns each decision, or what success looks like.
Why do transformation projects fail?
Most fail in execution, not strategy. Small breakdowns like unclear ownership, duplicate work, undocumented knowledge and late input from groups such as legal or tax pile up over time until the project misses its goals.
How do you close the gap between strategy and execution?
Define measurable success criteria, involve frontline users and supporting groups like legal, tax and IT from the start, keep revisiting the plan as people and priorities change, and communicate on a steady, specific rhythm.
Keep exploring
- More episodes of Extropy On AIr
- Previous in the series: The Speed Trap: When Growth Outpaces Your Systems
- Related: AP Is Not an Afterthought: Why ERP Transformations Keep Leaving Accounts Payable Behind
- How we approach transformation: Why Extropy
Working through a transformation of your own? Book a discovery call to talk through where your strategy and execution might be drifting apart.
