Supporting High Stakes Decision Making

Sarah Marshall
8 min readJan 25, 2024

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A few years ago, I was discussing the company’s OKR tracking with one of the technical leads. For those of you unfamiliar with OKRs, OKR is an acronym for Objectives & Key Results. It is a process for making periodic strategic commitments. Once the commitment is approved, teams build projects and programs to meet those commitments. Once the programs and projects are in motion, progress is tracked with updates on a regular cycle. Often these OKRs are set annually and tracked at least quarterly.

The technical lead asked me what happens with the updates. He had been making updates for years, but never heard anything back. I realized that underlying his question was an expectation that there was a one-to-one relationship with update and executive response/action. That one-to-one interaction works well at the team lead level. Both the update provider and that team decision maker are in parity about the details of the effort. They have the same language, considerations, and ultimately the same stakes in the decision. This is not the case for executive leadership. Executive leadership concerns are ‘holistic’. By that, I mean an executive leader is considering all of the organization’s commitments, projects and programs, major risks and issues, health of the folks, long term bets, and interactions with both development partners and customers.

Typically, executive leaders are incredibly intelligent, subject matter competent, and deeply passionate about their area of responsibility. They are also human. Just like everyone else, they have capacity limitations and blind spots. Yet, they need to be on top of a complex, diverse and fluid remit. The decisions they make have broad, deep and reverberating impact on customers, business performance, and the people executing on the organizations commitments. They have to make sense of and compartmentalize the thousands of inputs that they receive on a weekly basis. The technical lead thought that his update should inspire a direct response when his and everyone else’s OKRs updates are one major input for an executive leader among many others that she will receive that week.

Crawling Inside an Executive’s Brain

An executive at a mid to large sized enterprise is tasked with delivering on a strategically critical aspect of the enterprise products/services, [making and selling], or backend operations. These executives represent either a function, such as sales, engineering, supply chain, or other corporate functions, or they are responsible for a strategic cross functional initiative. Regardless, the pressure to deliver, deliver, deliver is continuous and unrelenting.

They may have both internal and external customers to please, development partner executives to align with, and continuous shifts in market trends, industry trends, technology disruptions, regulatory changes to address, and operational failures to understand, integrate and contend with. Every decision they make, communication they deliver, and inadvertent faux pax they make directly impacts the hundreds to thousands of employees that work in their organization, with indirect impacts to thousands more. The pressure is real and the stakes are high.

Given the complex tapestry of activities, issues and trends that they need to juggle and their very human capacity limitations, where they spend their time and the type of intelligence that they take in needs to be choreographed and orchestrated. During any given week an executive will participate in multiple reviews daily, perhaps an offsite planning session or two, many aligning one-on-ones, need time to get personal work done, and perhaps need family time at some point. This Amazon River flood-volume of information flow and the executives capacity to take it in is the challenge we face when designing a structure that delivers critical intelligence.

Curating Executive Intelligence

Shaping the flood of information and transforming it into high value intelligence requires narrowing the feed and transforming the input. Narrowing the feed requires culling the most critical information from the vast possibilities. Transforming the input means packaging the selected information in a way that maximizes insight. Let’s consider the culling effort first.

Answering the Big Questions

To build a filter for executive feed, I like to address the questions an executive needs the answers for on a regular basis. These questions vary by industry and function but there are some common threads that give us a place to start: This generic, non-exhaustive set of questions below give us a place to start. Industry and function specific questions can be added to sharpen your information capture.

The Generic Big Questions that Executives Must Track and Answer

Note that while the list is neither exhaustive or customized to your needs, it is a long list with many questions to unpack and many sources to consider. Wait! That’s not all. Simply having the information at hand is insufficient. The information must be shaped to provide rapid, instant if possible, insight. The massive information available and the need to shape it points to the potential for a lot of behind the scenes effort to pull it all together.

Most organizations do not have a mountain of analysts lying about to sort through the information swamp. So a bit of upfront architectural work goes a long way. Carefully selecting the information sets and crafting template views for maximum insight will reduce the transformation lift, make the effort better understood, and perhaps make the capture and transformation effort a bit more repetitive. All of these business operations architectural design activities can reduce the ongoing effort to deliver answers to these important questions.

Spinning Gold from Hay

It’s important to provide excellent, well curated intelligence. It is at least as critical to have that intelligence fresh and access ready as decision points approach. Additionally, that intelligence becomes richer when scrutinized and debated with leaders and experts weighing in from their unique points of view. Planning in these points of constructive dissonance is key to elevating executive understanding. We have orchestrated our intelligence presentation. Now we have to choreograph value elevation and presentation timing.

Scheduling Constructive Dissonance

Anyone that has attended an executive review knows that initiating debate is not a problem. Everyone at the table has a strong point of view and none or afraid to share theirs. It is not if a debate will happen, the real question is how to maximize the value of the debates. Meeting time is expensive in any situation. It is particularly expensive when a group of executives are sitting around the table. I think of meeting time as expensive real estate that I use thoughtfully and judiciously. I will savagely cut out of meetings anything that does not require direct discussion or affirmative, hands-raised alignment. The more disciplined your executive team is, the easier it is to make those tough choices. In other words, any debates and queries that can be resolved offline via a collaborative document or one-on-one discussions are completed before either the executive session or the final summary document is completed. I arrange executive sessions to discuss unresolved debates, provide nuanced discussions around complex issues, and for the senior executive to provide direction.

Orchestrating the Answers

Putting the above preparations together defines a transformational process for intelligence gathering that requires establishing requirements, architectural design, capturing data and information, transforming that captured material into packaged intelligence, debating the contents, and then finalizing the messaging.

Filtering Criteria — Process architecture defining questions to be answered, specific information and/or data required, and presentation structure that highlights insights.

Capture — The effort to capture required information and data to develop findings.

Transform — Structuring the summary to highlight trends, outliers, excursions, emerging challenges and opportunities, and any other insights to be gleaned.

Debate — Establish a review and feedback effort that helps highlight areas requiring resolution.

Finalize — Summarize findings, perspectives and recommendations is a document and/or dashboard. Highlight unresolved topics and topics requiring discussion. If an executive review is still required, establish an agenda that covers those open topics.

While this process is necessary for answering each question, performing this process for each individual question would be tedious and the messaging would get lost in rigorous detail. So, finding ways to consolidate the efforts across multiple questions is key to reducing the workload.

Rhythm of Business

We have answered the ‘what’ [we need to know] and the ‘how’ [we are going to put it together]. The last question to answer is ‘when’ to provide it. Ideally, we drive the process of answering the questions to deliver the answers at decision points. What do I mean by decision points?

Decision Points

Some decision points are par for the course of executing organization efforts. Tweaking head count allocations, adjusting financial runrates, and shifting project support as plans meet reality are all standard decisions that must be made at some cadence. Other non-standard decisions also arise. When to shift priorities, restructure an organization, spin up a new effort, spin down a failing effort, or address operational failures may not have an obvious cadence, but need to be addressed.

Establishing a Cadence

Many companies have, or are in the process of establishing, a rhythm of business model. Microsoft is at the forefront of this effort. In essence, the rhythm of business model is a fancy term for establishing a review cadence that has specific goals for delivering:

  • Leadership strategy that provides vision and operating goals.
  • Organizational communications that drive awareness and alignment.
  • Cross-organizational alignment on the goals and clarity between departments and teams.
  • Establishing focus on priorities and accountability for all teams within the workflow.

Most organizations have an established cadence for finance and people disposition reporting, often, but not always, quarterly. Commitment reporting [OKR tracking] typically aligns with financial and resource reporting, to create a comprehensive reporting. Operational performance tracking [KPIs/metrics] may be ongoing. However, extracted insights may be set at a specific cadence, often aligned with the other cadence. If you are reporting out on these standard items on the same cadence, the picture painted is more comprehensive. However, the parallel efforts compound at reporting points. Because the same leaders and experts participate in most or all of these reviews, the efforts pile up and can overwhelm them. So creating an offset for reviews helps spread the load.

For the non standard items, a weekly placeholder review can be established and curated to pull in topics as needed for emerging operational, program, people, and external issues and other non-standard discussions. A condensed rhythm of business example might look like:

Mock Rhythm of Business Cadence

With your cadence established, you now have a continuous funnel for intelligence that is understood by the executive and reviewers, and the folks tasked with intelligence delivery.

What are the Takeaways?

The key takeaways from the intelligence packaging process discussion and mock schedule are:

  • Identify decision points wherever possible.
  • Provide reviews and updates to feed the decision points.
  • Leverage organizational cadence to support your rhythm of business planning.
  • Consolidate your question answer structure to focus the intelligence points and reduce workload.
  • Spread the reviews and efforts where possible to limit review cumulation and leadership overwhelm.
  • Have meeting real estate available to deal with emerging topics. And, curate the review requirements for clear outcomes and decisions.
  • Remember that each review point has an associated transformation process. Expectations for that process should be clear to all evolved and notification timing should take that process into account.

There is no perfect way to manage executive intelligence feeds. However, a comprehensive rhythm of business cadence with clear review development criteria can provide for a relatively effective executive feed that will support executive decisions. As pointed out in the beginning of the article, executive decisions are supported by multiple orchestrated feeds. The better the delivery of those feeds is choreographed the better the executive is supported.

Find more articles from Sarah at: www.operations-architect.com.

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Sarah Marshall

Sarah is a writer, mother, partner, tech industry professional, and transgender activist.