Developing a One-Year Execution Strategy

Problem

We had recently announced a brand new company mission followed by a new strategic direction. The long-term vision was comprehensible and well-communicated within the organization, but the one-year execution strategy was somewhat ambiguous.  

That was a bit alarming from a planning point of view. It seemed that the prospect of misalignment among different teams and departments on what we were trying to achieve in the upcoming year was a risk worth taking seriously. It was closely knit to overcommitment and dispersed focus, which threatened to impede our progress long term too.

Actions taken

My actions were founded on two main assumptions: the existence of long-term strategy and abundant research and analysis we had at our disposal. We researched the market and industry thoroughly, had plenty of user insights, were cognizant of macro trends, and had a solid understanding of our internal capabilities.

Yet, we lacked the direction and focus for the upcoming year.

First off, I communicated to the CEO and executive leadership what I identified as a gap -- we were without a streamlined focus for the upcoming year, which made the teams misaligned. My intention was to remedy the situation by creating a one-year execution strategy. After hearing my proposal, they welcomed and greenlighted my plan.

I started off by creating a centralized document and writing down things I knew or thought to be true. I wanted to document all the current assumptions and questions in a comprehensive list that could serve as a beginning point for any future discussion. Next, I restated the company mission and vision for the future, captured the company goals, and -- through a series of intensive conversations with the CEO -- added their non-negotiables as well. I didn’t want to get too much into the weeds and list concrete projects or features as much as I wanted to identify large-scale problems our CEO thought we should be working on. I tried to extract their perspective and blend it with the already existing strategic documents.

I also spent significant time with our CFO to better understand key assumptions embedded in our financial plan and what was driving our business success for the upcoming year. Again, I looked at their non-negotiables; for example, we had to hit a five percent margin, among other things. But I also identified assumptions that could be changed in the financial plan. Throughout the process, I tried to differentiate what were a-musts and what were changeable assumptions. The idea was to project ourselves in the future context to see how that would affect our decisions of this year. Though it may not be something that we would address at the moment, the team should know about it because it may impact the solutions they were building. Furthermore, I meticulously captured key assumptions about our users, industry trends, and our competitive advantages. Critical problems I was hoping we could tackle were also included alongside some open questions.

Then I had the cross-functional team involved. Through a series of conversations with representatives of different departments, I learned about their assumptions and had them question and comment on mine. In the end, I would inquire to see whether some questions were not covered and were blocking them to plan and implement their part of the strategy. I covered most seniors from all the departments, but I also wanted to mix levels a bit and brought in some ICs whose perspective I thought would be enriching.

By bringing more people in, many open questions became easily resolvable. Through an honest and engaging discussion, we were able to agree on most assumptions and move forward. All items that we could agree on, I moved into a separate document. While many of the remaining open questions were resolvable through a comment or suggestion left directly in the document, some required additional examination. If I gauged that it was something quickly resolvable, I would hop on a phone call or block time for a discussion if that matter required more serious deliberation.

After cleaning up the assumptions and open questions, I realized that there were still too many comments or suggestions that were perplexing the team. So I worked with my PMs, each of whom owned one of the strategic pillars, to create a list of high-level things we could do this year. We first came up with six to eight objectives, which we narrowed down to three, and made recommendations on the most important and reasonable to do first. Then I had a conversation with the CEO and executive team and set the expectations right from the start. Next, I explained how we came to prioritize the three most important objectives in each strategic pillar and what the trade-offs were to be made. It is worth noting that I sent out the pre-read on the expectations before the actual meeting, which clarified my intention beforehand and provided the other side enough time to study our proposal and make an informed decision.

By that time, I collected all the input needed to create a one-year strategy that would set the focus for the year and make sure everyone was working off the same assumptions. I also sprinkled some context for the future where I thought it would have an impact on the decisions we were making. I kept the whole document to a couple of pages without getting into the weeds because it was meant to be a guiding document and not a directive.

Once the strategy was finalized, we socialized it extensively. We presented it at All-hands, I circulated it through emails, and the CEO recorded their talk on the company strategy for the upcoming year. At Product, we used it as a foundational document for quarterly planning; everyone would refer to it to delineate ownership and decide on priorities.

Lessons learned

• Include various people and include them early. I kicked off the process by a series of engaging conversations with the CEO but had those complemented by different perspectives coming across the organization. That helped me understand the extent of misalignment as well as foundational assumptions and open questions. Constructive conversations with multiple stakeholders allowed for agreement on trade-offs.
• Make sure that things stay outside of the weeds. It is a strategic document, not a roadmap. From the beginning, I was very clear about the intent and did a lot of advocacy on the document’s purpose. I wanted to make sure that teams were empowered, knew where we were heading, and had guardrails that would enable them to make informed decisions. However, they were not micromanaged or told what to do. The document equipped them to make better on-the-ground project decisions, but they were the ones to make those decisions.
• Address focus issues head-on. Though it may imply some uncomfortable conversations, I didn’t want to shy away from it, regardless if it meant disagreeing with the CEO. I knew that it would save us all from touh conversations later if I had those tough conversations early on. If you don’t address them timely, they will come back to you at some point.
• There is no such thing as overcommunication. While we had the document being presented in All-hands and through emails, people would forget or not listen. The process of communicating decisions and explaining why they were made is a never-ending one.
• As Product, we took this document and embedded it in our processes, but that was not true for other departments. So the lesson I learned from this experience was to understand better how different departments would use the strategy in their planning. That included learning about how they communicated it within their teams and how they shared it because the way they did it didn’t always take hold.
• Creating the strategy wasn’t a job done. It was step one. Communication and its consistent use in the planning one quarter after another had to be reinforced. Also, one needs to understand that some of the assumptions will be discarded in the light of new information, but that is a natural consequence of an iterative process.