Success through planning — a wakeup call for “startup snobs”

  • Jonas 

“Startups are about speed of execution…. getting shit done… ‘blitzscaling’ … speed wins!”

Planning has a bad reputation in startup circles. In order to achieve breakthrough results though, both efficiency and effectiveness are required. Individuals and companies must work on what matters most first and they have to do so achieving the largest possible output given the smallest possible input. And this is exactly where (very detailed) plans traditionally were made to help navigate our work and serve exactly this purpose.

In a world of growing complexity and accelerating change, planning cycles have (rightfully!) increasingly been shortened often even to the point where many of us have de facto abolished any form of proper planning.

Instead, broad and vague goals are picked up from somewhere (“redefine healthcare”, “build a modern retail chain”, “disrupt XYZ”, “build a unicorn” …) and then off we go and hustle. So much work to do, so little time — best to make every second count and not get stuck in planning paralysis!

This shift from making plans even seems to be endorsed by one of the godfather’s of strategy — General Clausewitz — who famously said that no (battle) plan survives the first contact with the enemy, even though that did not lead him to believe the activity of planning to be worthless.

And definitely, there are plenty of poor plans, often even bordering on the comical (e.g.. Soviet 5-year economic plans). Especially the startup world though seems to be stuck in a self-imposed downward spiral where the quality of plans I see from entrepreneurs and startups seems to keep decreasing, ultimately becoming little more than random bullet points (hint: “influencer marketing” is not a go-to-market plan).

It is high time to reverse this ongoing demotion and trivialisation of plans and planning. Whether a pleasant or painful process, or whether the outcome is success or failure.

I have not seen any other tool that comes even close to allowing organisations to reliably and cheaply increase the chances of their efforts yielding breakthrough results. From my observations, planning becomes so valuable to organisations because it enforces at least these three distinct high-leverage activities which directly drive organisational success:

1. Defining and mapping lower-level activities to high-level goals force a deeper understanding of what the goal actually is.

Teams typically have far more ideas and tasks that they could undertake than things that really will matter and should be undertaken (as reflected in the 80/20 principle).

Mapping between what one could do and then critically assessing how exactly that would (or would not) advance the overall mission is a crucial step in allocating resources to whatever activity promises the greatest return.

For such linking, however, clarity of the goal will be required first in order to properly evaluate if and how certain tasks would serve such higher purpose.

For example, if the stated goal is to increase sales, there are a myriad of potential tactics. But are we actually talking about any kind of sales or is it units sold, total revenue, total customers, online sales vs offline sales, sales at X per cent margin or even something else?

Maybe it is truly just any kind of sales, but more often than not, there are some further qualifications of the definition.  Hence, there will be a lot of going back and forth between activities; the goal helps sharpen that understanding and forces further clarification and definition.

2. Increasing the overall resilience and robustness of the business by deepening the understanding of how different activities interact and why the matter.

As part of the planning process, naturally, the various components of such a plan will be assessed to understand which ones actually must be successfully delivered in order for the overall goal to be achieved. How do things relate to each other, which parts are interdependent and which ones are independent?

If different parts of the organization are responsible for different parts of the plan, it only makes sense for each team to keep pushing their portion as long as the related parts of the plan also hold true.

A retailer may want to push sales as the overall goal and identifies online as the new focus channel for the next quarter. Such push will naturally include tech development, online marketing, legal reviewing T&Cs and many other activities.

But if there’s a major delay on the tech front, then it does not make sense for the remaining organization to spend the bulk of their efforts on the other components of this original online plan.

Instead, as part of the planning process, the organization should have identified that, for example, preparing online ads are merely a supporting activity for an overall online push of online sales to increase overall sales, but if the tech backbone gets delayed then resources should temporarily be spent elsewhere.

By properly analysing such interdependencies during the planning process each team gives themselves a good chance of realising how different changes may impact their priorities and then shift their work accordingly.

Tweaking plans appropriately, therefore, can happen semi-autonomously at different organization levels instead of relying exclusively on the overall company leadership, which increases organisational agility and speed.

Further, when breaking tasks down into smaller components it allows for a more granular understanding of what some of the underlying assumptions are behind how each activity may support the overall goal. Through such improved understanding of (often implicit) business assumptions, risk can be managed much better.

Inevitably over time, some assumptions will prove to be wrong. But when assumptions are invalidated, the impact is much clearer understood, hence, can actively be mitigated. Compared with this, when assumptions are not properly identified, then new insights and data points may not be mapped back correctly. Ultimately companies then may not even realise how such new insights completely change the assumptions the entire business was based upon.

3. Producing comprehensive plans requires and enforces alignment among stakeholders.

Reaching any form of a challenging goal inevitably will require the collaboration of different people and teams. In a proper planning process, this will, therefore, mean that these stakeholders will have to come together and discuss how such a goal will be achieved as described in the above two points.

Afterwards, they should be forced to put their names onto such a plan. In any organization where members have even the slightest bit of professional pride and ethos (i.e. every single organization I have ever dealt with), the act of putting one’s name onto a certain document does not come lightly. Instead, linking plans with the individual’s names and reputations immediately bolsters the prominence of the process.

This can definitely create levels of planning paralysis or even deadlock among teams as obviously nobody can ultimately predict the future with certainty or how certain activities may pan out.

Therefore, individuals and organisations may struggle to reach an agreed-upon compromise on the best way forward. However, it is exactly this process — given appropriate moderation/facilitation — that is at the core of planning’s potential for providing organisations with significant leverage.

Being forced to argue one’s position leads to significant context and perspectives being shared during discussions, establishing a common understanding. People increasingly “see the same thing” which reduces the risk of misalignment and individuals & teams intentionally or unintentionally pursuing local vs. global optimisation.

It may take time for people to agree upon what matters and what does not — but this is far faster, cheaper and easier when done while speaking hypothetically about the future (i.e. planning) instead of later when various real-world activities have been implemented and any changes and course corrections for a poorly conceived and half-implemented plan are much more painful to undertake.

Ultimately, as part of that process, healthy discussion cultures can also emerge including principles to break through such impasses like disagree and commit.


The above three outcomes of (1) increased clarity of goals, (2) increased organisational resilience, and, (3) robust alignment among stakeholders are crucial to the ongoing company success. Achieving these should be at the forefront of every leader’s mind. The art and act of planning hereby are uniquely qualified to produce these outcomes.

In the startup community, we take great pride in “disrupting things”, moving at supposed high speeds, dealing with extreme levels of uncertainty etc. — all of these mental frames can be useful in trying to overall advance where we are today. Yet, entrepreneurs’ tendency to ignore or even look down on any serious planning is not something to be celebrated but rather is highly reckless.

Taking out as little as one to two full days with key stakeholders every few months to actually engage in meaningful planning with documented outcomes that are constantly measured against and updated where required would serve almost every company well. And maybe, just maybe, bolstering planning can be one of the keys to finally improve startups’ generally abysmal success rates – which would be a great outcome for everybody!

Leave a Reply

Your email address will not be published. Required fields are marked *