Balancing Strategy and Execution

As an internal tools/platform product strategist, I feel like an entrepreneur at times. Entrepreneurs face significant challenges in starting businesses and making a product successful. There are many duties to do. The danger is getting lost in the details. Entreleadership describes this as “working in the business” as a treadmill operator. The next level is “working on the business” as a pathfinder. Now you might be asking yourself, “Why does this matter?”

Balancing your time between strategy and execution is critical because you can excel at executing and fail as a business. You need to step back from the day-to-day and confirm your approach still makes sense. I am asking myself if my focus should move away from my singular product, Dev.Lab. Each week I could execute solely on my product’s success and the incremental delivery of features. If I only do that, I will miss achieving a significant impact.

Manage Your Time

When I worked at Harris Ranch Steak House as a table busser, my impact was minuscule. An idle busser is not ideal. My duty was to stay busy and find work to do. As an entrepreneur, if I applied the same expectation to Dev.Lab my impact is constrained to the features of the product. In truth, my only limit is the ability to persuade the business to invest in my plans. The majority of my weekly activities must align with the business goals.

  • 90-120 minutes each morning to think/write and do my hardest daily goal.
  • One-on-ones to align with my team on direction, improvements, and strategy.
  • Meetings to make decisions or unblock work.
  • Unscheduled time to think, answer questions and assist users of the platform.
  • Writing narratives that describe potential plans that align and answer tough questions.

High leverage tasks are the best use of my time, which means I am ruthless with my schedule. Declining meetings, empowering engineers, and saying no to some opportunities. I could spend time helping with tasks and moving the iteration along. That is not where I provide leveraged value. If I did not leave room in my day, I would be much more harried and distracted. I would not be able to assist new customers and answer their questions. Give demos on the fly. Or seize opportunities at the moment. This focus on managing time comes from the talk Keith Rabois gives on “How to Operate” as described in this blog post.

“It’s actually really important to have empty space. If you don’t have a day or two every week in your calendar where you’re not always in meetings, and you’re not always busy, then you’re not going to be able to think. You’re not going to be able to have good ideas for your business. You’re not going to be able to make good judgments. I also encourage taking at least one day a week (preferably two, because if you budget two, you’ll end up with one) where you just have time to think. It’s only after you’re bored you have the great ideas. It’s never going to be when you’re stressed, or busy, running around or rushed. Make the time.” - Naval Ravikant

My purpose is to create a framework for my team to do great work. Incremental improvements are rarely transformative for a business. To pursue greater risk/reward, persuade the company to invest in a new initiative and resources to do it.

Plan the Roof Shots and Communicate the Obvious

A roof shot is a higher effort project that results in transformative value. Craft a plan that could succeed, track that plan, and course-correct based on what the market is telling you. The Amazon Six Page narrative paints the obnoxiously obvious picture around investing in a new initiative. Start with asking yourself, “What does success look like?” Every business wants to take on the right amount of risk that leads to an outsized reward. Executives want to know that we thought through all the risks and dangers of a plan. We can be misled and confuse our activity with progress and not connect our actions to the business priorities. Product Strategists in a business are entrepreneurs/intrapreneurs. They can drive massive delivery of value if they can tell the story of a transformative effort. Many of my plans never come to fruition. They inform my team of potential opportunities and why they might make sense. Working on the business means spending time thinking and communicating about new efforts that may drive value for my company. Leveraging executive input is key to that process.

Collaborate with the Executive Team

Reforge has a section on product strategy leadership and managing product work. It conveys there is a lot of work to convert company strategy into potential product work. Then iterating/communicating/aligning on a plan with the executive team. If I reflect on how we invested in the developer platform, I can see the same flow. My next step is to understand how to commoditize and repeat this model for other roof shots. Your executive team wants to help you make good decisions. Make it easy for them to help you. Make your roof shot obnoxiously obvious on how it could succeed while sharing all the potential flaws in the plan.


The fun part of product strategy is the amount of impact that is possible. The difficulty is knowing when you need to work on the business. Be proactive to find those roof shots that will make the difference. Product strategy is a role that builds an entrepreneurial muscle.

  • Measure how you spend your time and decide whether those activities tie into your business priorities.
  • Make the time to communicate possible roof shots, even if they may never happen.
  • Collaborate with your executive team to create a more effective roof shot plan.