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The Radical and Stress-Free Guide to Strategic Planning

The Radical and Stress-Free Guide to Strategic Planning

‘Tis the season! For yearly planning that is… As Q4 approaches, it’s time to take stock of the year gone by, what went well or didn’t, and start to plant the seeds for the new year.

This period of strategic planning is often a stressful one. You may feel like you’re asked to commit to arbitrary targets. And just as you give in, you’re told about stretch goals that seem to distend a mile past the signpost marked “Unfettered Ambition”.

Often the focus on targets and goal-setting detracts from the feeling of being in it together. You may see individual agendas rear their heads in these discussions and, if your work environment is particularly difficult, you may see political wranglings that make agitated rattlesnakes look tame.

All of this is happening at a time when employees are feeling a higher rate of burnout and quitting at a higher rate. If it wasn’t already clear that we needed a new approach, now is especially an important time to change how we engage in strategic planning.

Strategic planning doesn’t have to be stressful, instead, it can feel like a bonding experience across the organization. This article gives you concrete steps on what you can do differently to reduce the stress as you plan for the upcoming year and make your discussions more productive.

Taking stock of the past year

We typically look to numbers such as revenues and user acquisition to decide how the year has gone. This year, in addition to those numbers, take some time to talk about product diseases - these are the unquantifiable barriers that may be endangering your products. Your product can be sick for years before it succumbs to the disease - open discussions on whether you’re seeing the 7 most common diseases will help you with early diagnosis. I describe these diseases in my book, Radical Product Thinking, but here’s a summary:

  1. Hero Syndrome strikes when we focus on external recognition and scale instead of solving the problem that we’re inspired to.
  2. Strategic Swelling means building a wide range of capabilities but lacking the focus to develop any one to a breakthrough level.
  3. Obsessive Sales Disorder means borrowing against the long-term vision to close short-term deals.
  4. Hypermetricemia is an obsession with metrics to determine success, irrespective of whether those are the right ones to measure.
  5. Locked-In Syndrome means overly committing to a specific technology or approach because it has been successful in the past.
  6. Pivotitis means changing direction whenever things get tough and leads to exhausted, confused, and demoralized teams.
  7. Narcissus Complex is an inward focus on your own goals to such an extent that you lose focus on the customer and the change you’re trying to bring about for them.

Planning for the next year

Typically in planning for the next year, we focus on goal-setting and more recently on setting OKRs. The rationale behind OKRs is that they help us convey the narrative of the impact we want to have. Our vision statements for the company are almost always broad slogans that sound like a tagline without conveying a meaningful purpose. According to Gallup’s workplace research, only 22% of employees strongly agree their leaders have a clear direction for their organization. The statistics are even more dismal when it comes to strategy: 95% of employees say that they don’t understand the company’s strategy.

We often use OKRs as a band-aid to address the gap left by the lack of a clear vision and strategy. Research has found that goal-setting has significant downsides and often harms innovation. While OKRs can help convey the desired direction, they also cause collateral damage. Setting OKRs to address the fundamental lack of alignment in vision and strategy is like using band-aids to hold together the cracks in the foundation.

Here are three things you can do to address the fundamentals before you resort to goal-setting:

1. Articulate your vision

Instead, take some time to work through a detailed vision for each product in your product portfolio. A broad vision statement such as “To be the leader in XYZ” or “Reinventing ABC” doesn’t give clear direction on what problem you’re setting out to solve together or the end-state you envision. Instead, you provide a clear narrative of the impact you want to have when you have a shared picture of what the world looks like when you can say “mission accomplished.” I’ve found that it’s hard to write such a vision statement when starting with a blank sheet of paper. Instead, you can download the free Radical Product Thinking Toolkit to craft a detailed vision.

2. Craft a clear strategy

You then need a RDCL (pronounced “radical”) Strategy to translate your vision into an actionable set of steps. RDCL is a mnemonic for a comprehensive set of questions that help you define your strategy and communicate it to your team:

  • Real Pain Point: What’s the pain that makes someone engage with your product?
  • Design: What’s the design or solution that solves this pain for them? What’s the functionality, and look and feel?
  • Capabilities: What special sauce helps us power the solution (e.g. IP, technology, partnerships, relationships)
  • Logistics: How do we deliver the solution to the customer? What are the Logistics of our solution, i.e. pricing model, customer support, sales plan, etc?

3. Measure what matters

With a clear vision and strategy, you can finally measure what matters - your metrics validate whether your strategy is working and if you’re on the right track to achieving the vision that you set out to.

To measure what matters, derive your metrics from your strategy, i.e. for each element of your Design in your RDCL Strategy, what metric(s) will tell you if it’s working? While it’s tempting to measure popular metrics including revenues, daily active users, and time spent on site, the reality is each of these metrics comes with assumptions that may not be right for your business.

Kickoff a discussion

You can use the Radical Product Thinking book in a book club discussion to introduce this new approach to strategic planning in your organization. If you’re organizing such a book club discussion, I may be able to join (schedule permitting) for a Q&A session and to share a behind-the-scenes look at how the book came to be. Feel free to email me at