Elevate Your Company’s Planning: Strategies for a Productive Session
“You can’t operate at a higher level without consistency.” This insight resonated with me from the TV show The Bear. At FXStreet, we have established a consistent company cycle to set regularity in our planning and operations. By implementing this rhythm and maintaining uniform company tempos, we not only bring our focus on pressing issues but also enhance our communication efficacy. Over time, this consistency fosters a culture indispensable for setting higher goals. This consistency is also brought to lower levels, like planning sessions where predefined steps are clearly stated so everyone knows the objectives. Let’s review the main ideas around the planning sessions.
From Tech to Top: My Journey
Back in 2013, I kicked off a journey at FXStreet as the CTO. I held that role for nearly seven years until two years ago. During my time there, we revamped the software setup, bringing top-notch architecture and the best industry practices into the company. By June 2021, life was good. We bounced back from the pandemic stronger than before, with solid economic numbers and everything running smoothly. However, a sudden shift occurred when the former CEO and founder chose to step down. He presented the opportunity to assume the CEO role to the Head of Content and myself. Going for a co-CEO structure was risky but lined up with the company’s culture of promoting from within. This transition marked a complete turnaround in my career. No longer directly involved in technical decisions, we were now running a company pulling in around 8 million in revenue every year. In this article, I aim to reveal the strategies and practices we have refined over the past two years for organizing and executing short-term/mid-term objectives through practical quarterly planning sessions.
The Power Trio: OKRs, Agile, and Releases
At the heart of our quarterly approach are three fundamental principles: OKRs, Agile methods, and Tempos. To clarify our objectives, we started with OKRs. We then broke down our major plans into manageable “Releases.” Finally, we’ve embraced a faster and more efficient way of working, following Agile/Lean methodologies. These three elements define how our company operates:
- Three Releases that set the year tempo
- Dedicated set of OKRs for each.
- Commitment to a lean approach.
A Year in Releases: Our Approach
Following the relationship with food and chefs, consider our year a three-course meal. Each course represents what we call a “Release.” These Releases extend over 3 to 4 months, occasionally influenced by holidays.
- Release Planning: Much like selecting the best ingredients for a dish, this phase is where we strategize and decide on the components of our upcoming release.
- Release Kick-Off: Analogous to the chef introducing a new dish to the staff, this is when we unveil and lay the groundwork for the approaching release.
- Release Execution: Here, we’re deep in the kitchen, engaging in our dish’s daily cooking and refinement — ensuring everything progresses as planned.
- Release Celebration: This is dessert time! After all the hard work, we celebrate what we’ve accomplished with a company event.
By the time the year wraps up and our three-course meal is done, we’ve faced challenges and made achievements, giving us a satisfying “full meal” of memories, successes, and learnings.
The Planning week
Let’s dive into Release Planning phase, how we plan and execute the planning week. We always break this into three sessions, each session last one day, and each part has an objective.
- Session 1 — Strategy overview and previous release retrospective
- Session 2 — Objective’s discussion
- Session 3 — OKRs crafting and Team Workload planning
Session 1.1 — Strategy Overview
When we get together, it’s as essential to think about our next steps as it is to look back at what we’ve done. In our planning sessions, we first go over our main strategic lines. We kick off with a presentation, lasting around 15–20 minutes, to go over our main plans. Then, we dive into questions like:
- Are we focusing on the right things?
- Are we still on track with our goals from the start of the year?
- Have there been any significant changes outside or inside the company that made us change our plans?
The output of this meeting should be that everyone is aligned on where we are and where we want to go.
Session 1.2 — Retrospective
Once the first session is concluded, it’s time to reflect on the highlights and lowlights of the past release. As we usually do in tech teams, this is a secure space to express concerns, give kudos, and share ideas or learnings. It is important that people prepare this in advance, at least the main points they want to talk about.
When planning the type of retro, keep it simple. There are plenty of examples out there. Choose the one that fits the best to your purposes. We learned two lessons from the previous retrospectives. First, record previous ones and share them with the team in advance; this allows people to be prepared, and more feedback will come up during the meeting. Second, a retrospective should only be closed if the main pain point has been selected and a set of actions to tackle it agreed upon.

The output of this meeting should be that everyone has expressed their concerns, and the subsequent release should solve at least one problem.
Session 2 — Objectives discussion
It is time to review the last release OKRs and discuss whether you want to continue with them or change the focus. This session’s main objective is to examine the focus of the next release, so don’t fall into how the new OKRs will be written; just focus the discussion on the high-level objectives. Some examples of the high-level goals could be:
- To increase the acquisition of mobile app
- To increase internal satisfaction with tool X
One of the difficulties is jumping from one objective to another and not getting stuck into one for too long. We recommend splitting goals into strategic lines and discussing them together allocating time for specific strategic lines; at least reserve 120 minutes for each.

The output of this meeting should be to discover critical factors and design a way of coordinating and focusing actions.
Session 3.1 — OKRs crafting
Now that you have the objectives, it is time to craft the OKRs. First of all, ask yourself the following question:
Is my team familiar with OKRs and how to write them?
In case the response is a yes (as in our case), the best way is to create groups for each objective and give the responsibility to gather the data and do the writing of one objective.
In case your response is a no, I suggest that they are trained about OKRs before the session. Writing the OKRs could be a complex task that needs practice, and no one gets it right at the first attempt. So after the training session, devote some time to gathering the OKRs created by each team and try to improve their style and writing of them.
Once the OKRs are done, get together, present them, and discuss the last bits and pieces.
The output of this meeting should be a document where all OKRs are placed.

Session 3.2 — Team workload planning
Let’s be clear on this: humans are often poor estimators; 90% of the time, it takes more time than we initially estimated, but estimations give us an idea of the amount of work that needs to be done.
During this session, we place all the OKRs, teams, and weeks of the release and try to give a rough estimation (being super conservative) of the weeks per team for each Key Results.
The document should look like this one:

Give the responsibility of each team leader to make the estimations for each task in weeks, and once we have this, identify bottlenecks and prioritize which OKRs must be dismissed.
The output of this meeting should be a list of Objectives that have been dismissed due to insufficient resources.
Learnings from the trenches
After several iterations we have learned some tricks to make the session more productive and avoiding common mistakes.
Limit the session duration so it doesn’t last all day. These sessions requiere energy and it is important that everyone is full of it. Our recommendation is expend a maximum of 6 hours per day in these sessions, do breaks every 90 minutes and bring some food to them.
Start each session with an Ice breaker. It is important to start the meeting with a positive mindset, choose one of the hundred ice breakers out there and devote 10 minutes to do it, it will be a game changer.
Send a quick survey about the planning session. Once completed send a quick survey to gather insights around the planning sessions. Keep those results to compare between releases.
Force yourself to say no to things. During the workload session there will be bottlenecks, don’t fall into the trap “We will manage to do that”. Say no to things and prioritize.
Don’t involve too many people in the meetings. In the first iterations many people attended to our sessions, despite it is beneficial to get everyone aligned is not productive. Keep the sessions to a maximum of 6 people.
Conclusion
In the same way a chef needs the right rhythm in the kitchen to deliver a top-notch meal, at FXStreet, we’ve honed our processes for success. We’ve mixed our skills in technology with strategic planning to serve up solid results.
If you’re struggling to find this rhythm in your business, get in touch. We are happy to help.