Boost Your Product Management Skills Through Strategy, Planning, and OKRs

Are you using OKRs to measure the effectiveness of your strategy, or just to plan your tasks?

Mike Goitein

Aug 02, 2023

The retro-modern Product Manager of the Future — Designing Strategy, Planning, and Setting Goals. Image via Midjourney from an author prompt.

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The Product role is often referred to as the most “strategic” role.

Product Managers are expected to have a firm grasp of strategy, and use strategic thinking to guide their choices. At the same time, they’re expected to be able to negotiate and plan with UX and Engineering to understand how long things will take, and when they can make commitments for releases.

Added into this mix is the increasing emphasis on setting goals through Objectives and Key Results (“OKRs”). How do you set them effectively? How do OKRs relate to strategy and planning?

Many people speak of Strategy, Planning, and OKRs interchangeably, but after reading this piece, you’ll understand the key differences between the three, and how to use each appropriately.

The Biggest Shift — Strategy is Not a Plan

Often confused even by senior, experienced leaders, perhaps the biggest mindset shift for Product Managers to understand is the fundamental difference between Strategy and Planning.

While the two words are used together, as in “strategic planning,” we’ll dig into how, at their core, these are very different things.

Strategy

Strategy is a fundamentally creative approach focused on solving a client-centric problem.

The Strategy Choice Structuring Process is used to design a set of choices that will allow you to positively influence your end-user clients to change their behavior in ways that mean success for them, and for your business.

Outcomes

The results of this behavior change, the new sets of actions clients take produce what we call Outcomes.

One of the main points underlying strategy is to understand you’re trying to create an alternate future where you’re attempting to influence something that’s outside of your control.

Ultimately, you can’t force clients to do anything — you can only create great experiences for them, and they’ll come, stay, and be happy to hand over their money.

The two moments of truth

Strategy involves recognizing you don’t control the two key leading moments of truth –

Will your prospective client choose your solution from among other available options (and continue to choose it)?
Will your desired end-user client respond in the ways you hope as they use your product?

If our Strategy is designed well, this will lead to our desired lagging measures:

How will their habits and sentiment change over time as a result of using your product?
What actions will they take as a result of those changed habits & sentiments?

Being aware of these “moments of truth” and designing our strategic choices to influence them effectively can’t come from analyzing data from the past — we require creative thinking to design an alternate future.

Strategic Product Managers spend their time speaking with clients, collaborating with their broader team and leadership, and maintaining a close watch on the “What Would Have to be True” conditions for their strategic choices to remain valid.

Four key Strategy takeaways

It’s a set of choices
You work backwards from a client-centric problem
It’s fundamentally creative
You seek to influence, but recognize you don’t control the Outcome

Planning

Planning, by contrast, is a fundamentally analytical and internal-centric approach to laying out a series of activities.

Planning involves sequencing how you will bring certain internal organizational resources (people, time, software, knowledge, money) to bear in ways you hope will accomplish a seemingly-sensible set of “initiatives.”

Outputs

The result of these planning activities are known as “Outputs” — lines of software code written, interfaces designed, software upgrades implemented, platforms “lifted and shifted.”

The important contrast with Strategy is to recognize Planning is always within your control. Perhaps this is what makes it preferred by many in business — there’s a great sense of comfort in focusing on only that which you can control.

If you have a Product Manager title, yet spend all your time in meetings with stakeholders, planning activities, and creating Roadmaps and budgets, you’re really a Project Manager.

Four key Planning takeaways:

It’s a sequence of activities
It’s Internal-centric
It’s fundamentally analytical
You are in full control the Outputs you create

The need for both Strategy and Planning

The main takeaway isn’t that Strategy isn’t inherently “better” than Planning. You need both to create successful outcomes.

Unfortunately, as organizations mature, their focus tends to shift to prioritizing internal problems, as client concerns get pushed into the background over increasingly heavy “yearly planning” cycles. This is compounded as creative approaches to strategy are rarely taught or encouraged, and people who use analytically-focused, planning-based thinking tend to be rewarded and promoted.

Ideally, you wouldn’t start planning until you were first aligned on a client-centric set of strategic choices, and then use planning to turn that simple, clearly-articulated strategy into reality.

How OKRs Work with Strategy and Planning

Which approach will you bring to your OKRs?

OKRs in place of strategy

Many people who jump on the Objectives and Key Results bandwagon see it as a remedy for their organization’s inability to focus or get things done.

They believe that by simply setting aspirational Objectives, and pairing them with Key Results, they’ll somehow rally and magically achieve previously-unimaginable levels of progress.

But to quote Roger L. Martin, simply wishing for things to happen won’t make them happen:

“But desire (as with hope) is simply not a strategy. The desire to achieve the named key results won’t cause those key results to happen. You may desire the substantial rise in your NPS, but if you are serving customers that your key competitor serves better than you do, your NPS is unlikely to rise — even though you really want it to.”

Roger L. Martin, Stop Letting OKRs Masquerade as Strategy

If your “Where to Play” choices are not supported by the necessary “How to Win,” “Must-Have Capabilities,” or “Enabling Management Systems,” no amount of “wishing” in any goal-setting framework will get you there.

OKRs for Planning

When planning-focused people start using OKRs, they inevitably start from their analytical, project- and internally-focused perspective, and end up using OKRs as a planning tool.

They simply take their existing Gantt charts, and rewrite them as OKRs:

Their Objective represents the Initiatives they’ve already decided to do
Their Key Results are the series of tasks they believe will accomplish them

What’s missing?

The alternate future they’re trying to create
The client-focused problem to work back from
The integrated set of strategic choices necessary to uniquely solve that problem

Ask any leading OKR expert — Christina Wodtke, Ben LaMorte — and they’ll both be the first to tell you that you can’t set OKRs without first being clear on your Strategy.

OKRs to Activate Strategy

Alternatively, OKRs can be used as an “Enabling Management System” to measure the effectiveness of a strategy.

In a strategy-focused approach to OKRs:

The Objective represents the aspirational vision of what “winning” looks like
Your Key Results become the measures of how your chosen clients (your “Where to Play”) will be doing things differently as a result of your strategic choices

Rather than representing lists of things to do, Key Results in a strategy-focused OKR approach measure the winning the “moments of truth,” and the positive client behavior changes you believe will happen as a result of the strategic choices you’ve designed.

True Strategy involves everything necessary to win

In keeping with a strategy-focused approach to OKRs, beyond your “Winning Aspiration” qualitative statement, and the one small part of your “Enabling Management System” your sets of Key Results metrics represent, you’ll need three other critical components:

Where to Play
How to Win
Must-Have Capabilities

You can read more about the process of identifying and refining an integrated set of these strategic choices here, and here.

Strategy is the ultimate upstream intervention point

For Product Managers who haven’t thought about strategy, or feel it’s above their “pay grade,” I invite you to not be intimidated by the word.

For too long, strategy has been thought of as a complex, intimidating area of expertise reserved only for MBA graduates and the highest-paid executives in your organization.

Or worse, as some complex, boring, obtuse, inaccessible corporate-speak.

A more applicable strategy framework for Product Managers

But there’s another way to approach Strategy.

The advantage of using a simple framework like “Playing to Win” is how it can help democratize strategy, and finally make it simple, interesting, clear, fun, and easily accessible in plain language.

Instead of spending your time solving the problems created by heavily-upfront-planned Initiatives, you can go upstream to intervene, answer the important questions of Strategy, and align to improve the plans so the Outputs will support those client-focused Outcomes.

And with more diverse perspectives participating in the strategy creation process, you can both make it stronger as well as roll it out more easily, by designing it collaboratively with the people who’ll be doing the actual work.

TL:dr; & Takeaways

Understanding the difference between Strategy, Planning, and the different ways OKRs can be used (or misused) will help you understand what you’re currently doing now, and how you can gain an advantage over more than 95% of the organizations out there.

Always work backwards from client needs

Given that many organizations tend to shift to focusing internally, how can you and your leadership, management, and teams start to work backwards from client problems?

Understand the two moments of truth