The strategic planning process, and the working rhythm underneath it: Anna Elwood of Cascade

A strategic planning process usually produces a plan. Anna Elwood's argument is that the plan is the easy half, and what determines whether anything happens is something less glamorous: the working rhythm underneath it.

Elwood is COO at Cascade, the strategy and execution platform. She previously helped scale Zocdoc into a unicorn and ran operations across continents at Nomad Health during a period of rapid growth.

From an equity card to operations

Elwood did not go to business school and did not grow up wanting to be in business or technology. She went to school for the arts, moved to New York with her equity card, and started auditioning.

What she loved about theater is instructive about what she does now: the diversity of experiences, the different stories, teams and people, the need to build relationships very quickly, and going deep on whatever topic a play required.

What she discovered is the other half. She is type A, and found it unfulfilling to put her heart into something with no control over the outcome, which is the nature of auditioning.

Working various jobs to pay rent, she was introduced to a small company with the word beta in the corner of its website, and asked what that meant. The company was Zocdoc. She joined as an operations associate, doing everything, and stayed nearly ten years.

Her explanation for staying so long is the same instinct: there were always more different challenges to solve.

The generalist question

Michael raises the tension anyone with a varied background will recognize. Companies hiring leaders usually want someone who has done it in that industry.

Elwood's answer is that her identity was never in healthcare, despite a decade there. She followed problems rather than sectors, on the basis that the challenges she is drawn to are not unique to any industry.

What that has produced, she thinks, is the ability to learn a sector quickly and stay nimble.

And her position on playbooks is the useful part. When you join an early-stage company, bring your playbook, and do not marry it. The balance is between coming to things with fresh eyes and applying the universal learnings.

Her method for holding that balance has two components. Pattern recognition, which requires observing for a period first. And a distinction between decisions you can reverse easily and decisions you cannot, so that applying parts of your playbook quickly to the reversible ones stays low risk.

What she changed first

Elwood's initial focus at Cascade was retention. The company had recently launched a new version of the product, it took time to reach feature parity with the old one, and some customers were caught in between. So the immediate work was the adoption challenges around the new product.

But within three or four months she made a more consequential change, and it is the heart of the episode.

The company was fully remote and scattered globally. Managing time zones while staying nimble and making quick decisions felt, in her words, impossible.

The working rhythm

Her framing is one every operator should borrow.

Every organization needs a working rhythm. It is part of what people might call culture, and she considers it part of a company's operating system: the thing you do not have to think about, because it is simply how you work.

The reason it matters is what it frees up. What the company should be focused on at all times is driving customer value, which is hard when everyone is distracted by the mechanics of running a global business remotely.

Asked to break it down, she names two components.

Meeting cadences, where information gets reviewed, decisions get made, and information is communicated.

Communication practices, meaning where different conversations happen, which she describes as the digital office. Chat versus email, and the conventions around each.

Her admission about Cascade's own state is candid, and will be familiar. When she joined there was no weekly leadership meeting, and they were not reviewing business metrics. For a company selling strategic maturity, they were not eating their own cooking.

Her diagnosis of why: a lot of leadership change and moving quickly, which is exactly when these disciplines get dropped.

And the reason to fix it: those practices create a governance model where accountability can attach to specific projects, initiatives or deliverables. Without meeting rhythms where information gets reviewed and things get discussed, holding people accountable is very hard.

The hybrid decision

The other change she made within a year was investing in in-person time and moving to a hybrid model.

Cascade signed its New York office in October of the previous year, roughly a year after she joined, and hires from it. She notes it is typically half a dozen to a dozen people on a given day, and empty on the Friday of the recording, which is the honest version of how hybrid actually works.

Governance without red tape

Michael raises the obvious risk: governance brings accountability and it brings red tape.

Elwood's answer starts by noting the governance model differs by maturity and size. Cascade at post-Series A does not have a concrete three-to-five-year plan. A large public automotive manufacturer does, and has to be held to it.

Her observation about who can self-correct is worth noting: it is hard for a large organization to reflect and work out whether things could go faster and whether all its process is necessary. For a smaller company that should be a constant question.

The five pillars of strategic maturity

The framework Cascade uses to assess where a company sits, and the most portable content in the episode.

Visibility. A strategically mature organization has high visibility across the organization.

Alignment. Everyone's work contributes to the goals the organization has set.

Focus. Not being distracted by things that are not critical to those goals.

Accountability. Which is partly what the governance model delivers.

Speed. And this is where she connects it back. If things are moving slowly, if objectives and initiatives are not being met, that belongs in a regular strategic review, where the executive team recalibrates on what is genuinely necessary to achieve the goals and what is simply in the way.

Where the performance half comes in

Michael asks how strategy and tactics relate in a strategy-led performance platform, and specifically where performance enters.

Elwood's answer is that performance is the execution.

Her description of the failure mode is the one everyone recognizes. Organizations think of strategy as a vision and a plan that gets set, and then sits on a shelf, unreferenced until the board meeting or the end of the fiscal year.

The elements that make a plan executable: a broad objective describing what you want to achieve, and then the specific tactics or key results, the things you can measure, whether that is metrics, projects or actions.

Her ambition for what the tool is: a strategic command center for the C-suite.

Which comes with a definition of the C-suite's job worth quoting in substance. Ideally they are not firefighting, though at some sizes they will be, and they still have a responsibility to think about the future and about external factors.

She calls it a first team mentality. Executives manage functions and are responsible for them, and the first team is the peer group responsible for the ultimate success of the business.

So the question the command center answers is not whether you sold the widgets this week or hit the gross margin this month. It is whether you are set up to achieve everything you committed to over the next three to five years, with the business-as-usual data integrated alongside it to give the full picture.

When the strategy itself is wrong

Michael's best question: what if you miss the targets and the problem is not execution but the strategy?

Elwood's answer starts where she starts on any problem, with data on what is actually happening. And with the prerequisite that a leadership team has to reserve the time to reflect on that data at all, which is the thing that quietly does not happen.

The 5 things I took away from this conversation

1. The working rhythm is part of the operating system. Meeting cadences where decisions actually get made, and clear conventions for where conversations happen. Anna's point that it should be the thing you do not have to think about is the test: if people are deliberating about how to work, they are not working on customers.

2. A plan without a review cadence is a document. Cascade sells strategic maturity and, by Anna's own account, had no weekly leadership meeting and was not reviewing business metrics when she arrived. That is not hypocrisy, it is what happens to everyone during leadership change, which is exactly when it costs the most.

3. Sort decisions by reversibility before applying your playbook. Her method for entering a new industry is pattern recognition plus a reversibility test: move fast on what you can undo, observe longer on what you cannot. That is how you bring a playbook without being married to it.

4. Five pillars give you a diagnosis rather than a verdict. Visibility, alignment, focus, accountability, speed. When execution is slow, the useful question is which pillar is failing, because the fix for a focus problem is nothing like the fix for an accountability problem.

5. Reserve the time to look at the data. Anna's answer to whether a miss is tactical or strategic starts with a prerequisite most leadership teams skip. You cannot diagnose either without a standing slot where the numbers actually get examined.

FAQ

What is a strategic planning process? The process by which an organization sets its objectives and the measurable results and initiatives that will achieve them. Elwood's emphasis is that the plan is only half of it, and the other half is the review cadence and governance that keep it from becoming a document nobody revisits.

What is an operating rhythm? The recurring meeting cadences where information is reviewed and decisions are made, combined with the conventions about where different conversations happen. Elwood treats it as part of a company's operating system, meaning it should be automatic enough that nobody spends attention on it.

How do you know whether a missed goal is a strategy problem or an execution problem? Start with data on what is actually happening, and ensure the leadership team has reserved time to examine it. Elwood's five pillars, visibility, alignment, focus, accountability and speed, give a way to locate which part of the system is failing.

How much governance does a startup need? Enough to attach accountability to specific initiatives and deliverables, and no more. Elwood notes the appropriate model varies by size and maturity, and that smaller organizations should constantly ask whether their process is excessive, because larger ones find that self-reflection much harder.

Should a remote company go hybrid? Elwood's decision at Cascade was to invest in in-person time within months of joining, because managing a global startup across time zones made nimble decision-making feel impossible. The office runs at partial occupancy, which is the realistic version of what hybrid looks like.

Also mentioned

• Cascade, the strategy-led performance platform and its five pillars of strategic maturity
• Zocdoc, where Elwood spent close to a decade and started as an operations associate
• Nomad Health, where she ran operations across continents during rapid growth
• The first team mentality, and what a C-suite is collectively responsible for
• Superstorm Sandy, and the day half of Manhattan lost power while the Scottsdale office kept working

Listen to the full episode

Anna Elwood on Between Two COO's

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