The Cheshire Cat Prioritization Method

Hernan Garcia
6 min readOct 7, 2016

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Alice and The Cheshire Cat talking

Alice: Would you tell me, please, which way I ought to go from here?
The Cheshire Cat: That depends a good deal on where you want to get to. Alice: I don’t much care where.
The Cheshire Cat: Then it doesn’t much matter which way you go.

As Alice, when it comes to creating a product we need to know where are we going. I am sure that most of the times we think we do know, but instead, we are just defining what it comes next to do without taking into account the desired outcome, and that lead us to a wrong prioritization of our efforts.

Doing prioritization right is crucial for the simple reason that ALWAYS our resources are limited, we do not have all, the time, the money, the knowledge, and the energy we want, so is crucial to allocate our resources in the best possible way. Also, in my opinion, the biggest problem to prioritize is that many times we get lost in the sea, we have too many objectives, they are not clear enough, or they are just too complicated to create an appropriate list of things to do.

Now we know the overwhelming situation we all have to face at the moment of set priorities in our backlogs or projects. To help with this, I want to introduce a five steps process I follow to make my product prioritization more efficient, clear, and most of all, with the outcome at sight view all the time.

The five steps:

  1. State the business needs
  2. Discover the desired situation gap
  3. Order the problems in terms of business impact
  4. Define what is the look of the problem solved
  5. Create the problem-solution roadmap

1. State the business needs

Before ordering the different activities you are going to make, you have to state CLEARLY your desired outcome. In my experience, this kind of knowledge used to exists within the organization, but for some strange reason, it is not communicated to everybody. So working with your stakeholders, you have to discover what are the organization objectives. This is probably the most simple step in the process, because when you ask “What are our objectives? Or What do we have to achieve?” you are going to have a simple and straightforward answer, and most of the time the answer is going to have the symbol of money.

2. Discover the desired-situation gap

Now we have the, apparently, impossible to tackle objective, we have to disaggregate the numbers into something more actionable and understandable by digging into the why’s we want to achieve that.

For doing this all we need to do is ask Why or Why not. For instance, if the organization objective is to reduce by 50% the operating cost, we could ask, why we are spending the double in our operation, and that will lead us to a list of reasons. For example, we over dimensioned the sales department; we hired more people because we do not have automatization in our processes, or we need a very big support team because people can not understand our product, etc. So if you keep asking "why" you are going to find the root of the problem and that is a good place to start working. You have to repeat this for each objective your company has, and you will finally end up with a list of problems.

Now the former “Impossible to tackle” has a face and a name so that we can act on that. It is important to acknowledge that not always this process works because your stakeholders could not know why something is happening or worst they could be wrong on the reasons for why something is happening. This happens most frequently when you are facing any problem related to the outside of the company. If the problem is internal probably is easier to know the root-cause.

As I said in my post "User research, the not-so-secret weapon for startups" is important to rely on more than just the gut feeling or what you think you know. When trying to define the reasons why you are not in your desired state is extremely helpful to have real data about your problem.

3. Order the problems in terms of business impact

At this point, you already know what are the organization objectives, and the problems that are creating that desired-situation gap. So now, you have to face the first challenge in prioritization. With the list of problems in your hands (or a whiteboard) you have to assign them weight, this is the economic value that each of the problems has for the company. If you are working with business stakeholders they can probably have a gut feeling about the value of each of them, but if you do not have that information it is time to put your hands on a spreadsheet and do the math. This calculation does not have to be perfect, but they have to be done with consciousness so you can jump to valid conclusions. Once you did the math, your are going to have the list of problems to solve in order of business priority.

At this point, it is important to mention that because you are not working in a solution space, you are not going to skip on solving a problem just because is too complicated or expensive to fix. You only have a list of problems, and its business impact but there is no complexity involved because you have not started thinking about solutions.

4. Define what is the look of the problem solved

As important as is knowing your problems, and what are the impact they have in the business, is to know when your problem is solved, what KPI's are impacted and in how much.

For instance, if your problem is something related to your conversion rate then when you solve that problem your conversion rate should change by X%, this point is probably the hardest to nail because in may situation a KPI is not affected by an isolated problem, in fact, is affected by a series of problems and situations.

No matter how accurate or inaccurate you be when defining your targets, you have to set them upfront so you know how bold you have to be with your initiatives. Imagine that is not the same try to change something by a 1% than by a 50%

You can adjust the targets in the future when you learn more about the situation. I recommend you to read the book "Lean Analytics" that gives you a comprehensive explanation about setting KPI's and assigning them targets even when you do not have information about the context.

5. Create the problem-solution roadmap

At the last step of this process you have to do two things, first working with your team and with some stakeholders, to create a list of possibles solution to your problem, probably and ideation workshop or some design thinking tools are going to be your best friends. The output of this is going to be the list of features that aim to solve the biggest problems within the organization. The second thing you are going to do is to use any framework you like to prioritize the different initiatives you come up to in your ideation process. I particularly like the R.I.C.E. framework from the guys of Intercom.

The most important thing in this “method” is that detach the problems from the solutions, so there is no way you do not focus on solving the most important problem because a matter of a solution is beeing too complicated or expensive. Once you framed the right problem to tackle you can focus, with the resources you have, in finding a way to do it.

Following this approach, beyond helping you to prioritize, will help your organization in two different, but really meaningful ways.

Bonus track 1

When you stop thinking about solutions and open your mind, you will find that what it was a problem that needed help from your engineering team now is something that you can solve in other way or that maybe, it does not worth solving it at all.

Bonus track 2

Probably, the best side effect ever in a process is that when you have such straightforward, clear and easy-to-communicate way of prioritization you can stop saying NO to your folks. Because when everybody can understand what happens in the so-many-times called product-black-box, now is open, is understandable and make sense, so nobody else will come to you to ask for things that have nothing to do with the company objectives.

Some ideas for creating this model were based on the “impact mapping” technique.

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Hernan Garcia

I'm a product-making lover, user-centered enthusiast, and full-time learner.