(Credit: Joseph Emmi)

What does success look like?

One of my go-to questions, but not everyone seems to get it

Published in
4 min readNov 5, 2018

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What does success look like? Think about it…

If there were no constrains, or challenges, how do you see things working in an ideal world?

This is a question I usually ask, because it allows to elevate the conversation (with a stakeholder, user, customer or client) in a different way, one that remove us from the linear thinking that tends to focus merely on the issues and pain points.

It’s about not focusing just on the limitations of today and why “X” cannot be done, instead, we start to think what could be achieved.

It’s about better understanding the aspirations and desires, but also, what it’s actually needed, which in many cases is significantly different from what it is wanted.

But most importantly, it allows us to see beyond the obvious. Yes, there will always be a budget to meet and time constrains to battle against, but if these variables will solely determine the future of a project or a solution, we are already limiting ourselves to the least great thing that we can come up with, one only sitting in the present and hardly difficult to be meet in the future.

Thinking about that ideal scenario, is thinking about the future, but also about overcoming the challenges it might require to get there.

The problem with just focusing in the linear present, is that it is conditional. Many people won’t allow themselves to think about the future until they get the past and present fixed, hoping that once these are overcome, the rest will work for the better.

They will be playing catchup forever.

For me this question is not about forgetting the present or neglecting real and tangible challenges mitigating it with fluffy clouds of possibilities and nice-to-haves, “an ideal world utopia”. Instead is a bout finding a middle ground between both. It is about getting a sense of direction that many organisations lack due to their continuous reactiveness.

It’s about how you continue doing what you are currently doing (or have to do) while keeping on sight where it would be great to be.

I always prefer and believe in doing it backwards

We all have heard that in order to arrive somewhere, we first need to know where are you going. This is exactly the same.

Think about how things should work in the ideal world.

How you see them working?

Now think about what, from that vision, can be done today with what we have?

A great example of this type of approach at a great scale can be found in this episode of Reid Hoffman’s Masters of Scale podcast. As he speaks with AirBnB’s Brian Chesky, Chesky explains an approach he calls the “11 stars experience”, how this has helped his company to position where they are right now, and why they keep doing it.

For Chesky, this is like a roadmap of possibilities, where he knows that they might never reach to 11, and they don’t have to or can, because some things change and others are simply not feasible; but having them present help him and his company to at least try to get close to them, or in some cases even lead to unconsidered possibilities.

There’s a catch

Expectations can be a killer…

There’s a reason though, for why some people sometimes don’t like to ask this question, or say they need to be cautious about it, and that is because it seems for them, to set high expectations for those they talk to.

In my experience, that is because they are not asking a question, they are painting (by themselves) a picture of the future, rather than looking to understand it. Clearly is not the same, nor are the outcomes.

They portray the possibilities of that future, what can be done with X, what can be achieved if Z, and by doing so, intrinsically skyrocketing the expectations

Don’t complicate things

If it’s a question, treat it like so. Wait for the answer, listen carefully and use it to inform your work and decisions, to help those who answer, to remove their own barriers and allow them to explore new avenues without feeling the risk of having to invest or commit, while actually envisioning the possibilities.

Don’t sell an idea, look for it and maybe even show them the way.

Never forget that it is about obtaining information. That’s what questions are for.

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