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Writer's pictureDimitris Adamidis

Rethinking Efficiency in Strategic Planning: Embracing Strategy as a Journey

Updated: Mar 14


Annual Planning Process is Painful

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The PMI organization found that 90% of organizations must execute their strategies successfully. This means that even if a startup has an excellent strategic plan, it is likely to fail if it executes it effectively. Another study by CB Insights found that the top reason why startups fail is due to a lack of market need. It is often a result of poor strategic planning, which can lead to a startup targeting the wrong market or developing a product that does not meet the needs of its target customers. A third study by Harvard Business Review found that 42% of startups fail due to a lack of focus. It is often a result of poor strategic planning, which can lead to a startup trying to do too much at once or spreading itself too thin across different markets.


So, reading these stats, you might think about the execs swarming in the conference room trying to figure out the strategy for their business. The reality is slightly different. Yes, these meetings happen and are conducted in a certain way, but there are other places where these strategies are formed or occur.


When you ask business leaders around the world where they make when strategy decisions, the answer is rarely "in the strategy room or the boardroom." You are more likely to hear "in the shower before I went to meet my senior team" or "over that drinking session in the hotel bar with one of my customers." Sometimes, the decisions might be made during the walk with the dog or golf play with a couple of friends as this helps them with alignment and direction setting and reduces anxiety and opposition. In other words, it's easier to remain disciplined by following a comfortable pace of thinking and a self-challenging process. Yeah, slowing down sometimes is your ally.


Then what's broken in the strategy room? There are a few suspects before I get to my conclusion.


  1. They are not challenging the assumptions. A set of assumptions about the future needs to be challenged more, as these assumptions can often be wrong. Departments are pushed to show their ice hockey sticks to please their investors and help their bosses to avoid unpleasant questions.

  2. Not considering the risks. Every strategic plan involves some degree of risk. Executives often need help identifying and assessing these risks before they approve the plan. Execs often don't ask questions or understand the assumptions that usually carry the most significant risk.

  3. Not setting clear goals and objectives. The strategic plan should be clear about the organization's goal. It should also set specific goals and objectives that can be measured.

  4. Not allocating resources effectively. The strategic plan should specify how the organization's resources will be allocated to achieve its goals. Executives need to ensure that these resources are given in a way consistent with the plan.

  5. Not communicating the plan effectively. The strategic plan should be communicated to all levels of the organization. It will help ensure everyone is on the same page and the plan is implemented effectively.


Last week I talked to my good friend who is preparing for his professional MMA fight.

(I apologize to those not into this sport; I'll try to keep it short and sweet on parallels I see between these two worlds). He told me that he had done extensive research about the opponent, knowing everything about his record, his history, the martial arts that he practiced, understanding his style, cardio endurance, weight, arms reach, etc. He must have learned a ton of information and data about him. Now the fact that he knows all of this information is only helpful if he can adjust his ongoing workout routine to fit the new fighting conditions he will end up with. For that, he needs to train with often different coaches that are helping him to understand the strengths and weaknesses of the opponent's background, learn how to prevent his go-to moves, learn how to counter, and start getting good at these elements, understanding the distance against the opponents reach and length of his limbs, etc. He must adjust for their age difference as he is much older than his opponent. It is not a minor adjustment from my experience. All these elements are trained for that fight while putting together the inputs along the hard coded and gathered information into one piece, planned and executed over several months and weeks before someone is ready for that event. In other words, he needed to create a process that assembles two things, helping him to learn and adjust while the strategic goals and objectives remained the same. All these goals were set similarly as we all do with annual planning, figuring out how our bookings, top line, and cost envelope will look for the next 12 months and 3 to 5 years. Often companies need to remember to create a framework around how they will execute, how they will learn from as they go through, and how they adjust their course of action to execute their operational or financial objectives. Whether in the boardroom or under the shower strategy is formed, it's almost irrelevant. The key is to figure out how to create a process around validating what you know and learning what is possible and impossible to do over the time you have left before the significant event or deadline.


Conclusion: Here is what I've learned from practicing sports for many years. Every situation on the field, regardless of sports, has its constraints. Some of us are stronger, taller, faster, or react quicker. However, we are only suited to thrive in some circumstances. If that is given, we have to plan our "optimistic future" carefully, understanding to what extent I can create more favorable conditions (or leverage existing ones) and match my organizational abilities to leverage them. Once we know them, we must focus on attributes we'll exploit to overcome these constraints or compensate for them. Limited resources are one of your constraints in running a startup, and overcommitting can put you in a tricky situation. The next step is to look at the time horizon that allows you to put all these actions in realistic timelines. Let's say you hinge on three months assumption for your new product feature lease while your head of product tells you nine (9) mo minimum. You don't need planning anymore at that point but a sweep to clean up your desk area before you leave the building.


Even if the dynamics in the strategy room were perfect, the world unfolds differently than in nice, neat, annual increments. Things change constantly, both in your business and the markets around you. Unlike my friend, many organizations have a greater responsibility going beyond an individual's sports career (although I root for him). Often these decisions impact hundreds and often thousands of people around the world. For the same reason, we must focus our planning efforts on the tactical elements within the planning framework that allow us to adjust as we learn while your organizational goals remain the same. The key is understanding your constraints with the typical strategic planning package, your ability to overcome them, and the time remaining while everything else might change it. Life is too complex to assume you can handle it through static thinking. The goal is a cohesive plan, including an execution path, not avoiding changes. There is always room for incremental adjustments as you learn, regardless of your constraints; that is the way to go with your planning.


Here are some additional helpful thoughts about structuring the Strategy as a Journey without only settling with the typical annual plan.


Hold regular strategy dialogues. Refrain from assuming your annual planning is over, and you keep going with other stuff. Your volumes and frequency around strategic planning are changing, but your yearly process should continue. Instead of abandoning the planning element, launch more regular incisive strategy conversations with your team. The adequate approach could be as a fixed space on your monthly management team meeting. You start plain. You are training a "live" list of the most critical strategic issues, your big moves, and a pipeline of initiatives for executing them. The goal is to get closer to achieving continuous engagement on strategy. Every time you meet as a team, you update each other quickly on the state of the market and your business, then reflect on your issues, big moves, and initiatives. You consider whether they remain appropriate, should be modified, or should be stopped. You also profoundly dive into one or a few opportunity topics every meeting or concern. Don't overload it.

Track your portfolio of initiatives - the strategy will evolve with the pipeline of initiatives working through different stage gates. You must take a loose list of ideas, topics, and initiatives that look more like a wish list this idea and create stages you will be tracking them. It should be different from what you use for sales opportunities management. Remember that every long-term-oriented idea must go through varying levels of familiarity. You must understand a lot before you get into the deployment phase.

On the other hand, you will have to scale growth initiatives that must have a 3-year horizon at maximum. Here the emphasis will be on managing capital investments, achieving milestones, and showing strong user acceptance. It might be overkill initially, but remember you are getting ready for the marathon, not a sprint. It goes back to my point about urgency awareness point. It should help you avoid creating 200 slides deck for the board meeting where only three (3) are used, making strategic planning a tedious work forgotten after surface-level discussions missing many essential talks. You're fixing a lot of other things with that.


Monitor a rolling plan. Every significant move leads to an update on the expected trajectory of the business. You are moving all the time, just like the world around you. To monitor the progress, you need a 12 months rolling plan. Again, this differs from your budget exercise or the 3-5 years plan you submitted during the last board meeting. These are primarily around financials only. I'm referring to several selected metrics that help you to reflect the impact of your strategic decisions. It's less about being formulaic and more adapted to the needs of businesses at any given point. It will be a journey of almost continuous checks of whether the assumptions made in a strategy still hold, whether the plan needs a refresh, or whether the context has moved so much that new approaches are required. Start with your assumptions to understand whether they still hold; if not, you will know why. That should give you plenty of good reasons to take corrective action. They help to navigate highly competitive industries and fast-moving trends. Your company has to have a broad strategic direction toward developing its platform, product, or service and new elements to help you re-establish fundamentals. Change due to continuing dialogue among the management team and in reaction to changes in their business context.


Create a mid-year planning window. Every goal or plan has its controls, as essential as a regular planning cycle for ensuring that all important questions are being surfaced and that budget processes are being informed. Each year will bring unexpected decisions you can't predict for 12, 24, and 36 months. If this is not statistically possible with human abilities (not AI or quantum computing), why would you expect your plan to remain the same after closing your second quarter? A regular, standardized cycle is not well suited to the dynamic nature of today's business environment. Set the expectations with all teams that staying on track is essential and that you have a planned revision mid-year. That should help the team to focus on execution instead of kicking cans down the road towards the fourth quarter without room to react to internal and external trends.


Evaluate urgency. There are a lot of fake signals popping up throughout the fiscal year. Tracking the urgency of these critical highlights should be part of your strategic journey meeting. Your leaders will make suggestions based on their professional experience and their ego. Let's face it. We all have it, so we need someone with a suitable skill set to evaluate the urgency. Trying to solve your big strategic questions and simultaneously lock down an agreed plan can be challenging. You must ensure that the urgent will not dominate the important and that those big questions won't be sidelined. Besides, those messy non-linear, and uncertain strategic issues need to fit into the linear world of the 3 to 5-year plan. This is your tool to link them together, keep them for the next cycle, or ignore them. Having criteria that help you to decide which items should alternate the latest 3-5 years plan but also often showing valleys instead of peaks you had before with the months ahead.



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