Plans and plannings are necessary. They help us align efforts and teamwork in the same direction. The most common problem is not usually in the plans themselves but in the way they are carried out.
As Hannibal Smith would say, “I love it when a plan comes together”. And who doesn’t! But unfortunately we all have faced plannings and plans that are never carried out or that, from the first moment, are doomed to failure. Who hasn’t ever lived a plan with dates set without taking into account the opinion of those who will actually carry it out? Or the moment when we are presented a weekly or quarterly planning and we agree, when everyone knows it is not feasible?
In this post I want to share with you our personal experience since we have also (and still) been here. I hope it can help you, at least, to avoid mistakes in which we have fallen.
Everything a good planning must take into account
In my opinion, and based on the problems we faced, there are some minimum aspects that all plannings must take into account. It doesn’t matter if it is to decide the focus of the work of the next sprint or to set the course of the organization’s strategy for this year.
First of all, we have to be aware that plans must change and be reviewed periodically. We live in an environment of constant change and uncertainty. It doesn’t make sense, at least if we want reliability, to make years away predictions. Everything around us changes continuously and new variables that we had not taken into account or results that are different than expected appear. That’s why we must review and adapt our plannings periodically. They have to be consistent with the context at all times.

On the other hand, they must have someone in charge. If a plan is left up in the air, there is a high probability that it will be forgotten or even not carried out. Does the situation of “we have to do… .X” or “we should do… X” but then X is never done because “I thought you would do it” sounds familiar to you? It is important that, when making plans, we set someone to be responsible for them (or the parts that compose them) to ensure compliance. Be careful, because here I am referring to watching over them, not having to carry out that part of the plan or “be above those who carry out that part”.
Specifically, we are still struggling with this problem. We had plans on the table that were then left in the air. Either because nobody checked them, or did it once a month, or because we were not even sure who had to keep an eye on them. Although we have already made a great leap and the improvements are remarkable, we still have a long way to go.
They also have to be ambitious, but realistic. That they do not make us fall into complacency or stagnation, that they lead us to give our best, but at the same time that they make sense. As advice, I think it is really important to, at least, take into account the opinion of the people who will carry out the plan when planning.
And last but not least, they have to be measurable. We have to know somehow how they progress. Whether the plan is going well or not. Setting metrics can be very complicated, especially at the beginning, but I encourage you to make the effort. It is better to have a bad metric, and aim to improve it, than to have none and go blind.
Our plannings
I’m going to tell you how we do plannings. Specifically, I am going to focus on the strategic part. That is to say: from the moment we set a course for the organization in a given period until the deployment and implementation of that strategy.
Although our case is that of a small organization, the principles are adaptable and applicable to other scales.
We work with a system of OKRs. I’m not going to explain it because a lot has already been said about it. For those who are not very familiar, it’s a model where we establish objectives (O), that is, what we want to achieve, and some key results (KRs) that will lead us to them, that is, how.

In our case, we start by establishing a common guide and direction for the entire organization. We do it on an annual basis. At the beginning of the year we met and, taking into account the Kypseli context, the key success factors and our mission and vision, we set an annual goal or direction to follow. For example: getting visibility in the startup environment in Madrid.
Then, at the beginning of each quarter, we hold a session where we establish the objectives and the ideal path (remember that it will change!) for each of the Kypseli areas (marketing, financial, sales, etc.) during the following months . These objectives are always set taking into account the annual objective as well as our mission, vision and values.
For each objective, we also set a series of key results that, if met, would result in the achievement of the objective. Each of these key results is associated with some type of metric that allows us to know its status and a person in charge of ensuring its progress and compliance.
In addition to the objectives derived from the organization, each of us sets a series of personal objectives, also aligned, that contribute to the overall result. In organizations with a stronger hierarchy it’s a very powerful way to ensure that not all objectives go “top down” and allow the people who know best the organization’s day-to-day to also start their own initiatives.
Once a month we conduct a follow-up session. In it we review progress and make adjustments that may be necessary. In addition, and most importantly, we discuss potential blockers and problems and coordinate the next steps to ensure that we meet the objectives together.
And on a day-to-day basis, team members, and particularly those responsible for each key result, monitor and ensure their progress and carry out the necessary adaptations.

Let’s summarize
Plans are very important to align everyone’s efforts in the right direction. Planning often results in unrealistic plans or other’s that are put in place and become diluted as time goes by. That’s why it’s important to pay attention to them and take the time to define and implement them properly. At least, to make sure that they have a person in charge to ensure their compliance, that there is a way to measure them to know their progress and that they are reviewed and adapted periodically.
And for this time, I leave it here. If anyone is especially interested in knowing more in detail how we implement the OKRs system, please let me know and I’ll be happy to do a more detailed post. And as always, I’ll be glad to hear about your experiences and I encourage you to share them to help others!