The three questions

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Tagged under leadership.

Around 3 min read.

What is the most important quality for a leader? I would vote for the ability to visualize a system or business and its surroundings. In order to thrive, you need to take action, but what actions do you take?


I’ve gone to a training session on leadership and team management with João Gilsanz Magalhães. He is currently the strategy director of a local brand consulting agency called Super. With over 20 years in business under hisbelt, João is remarkably experienced when it comes to dealing with people and leading them towards an objective. His stories were the most valuable pieces of the whole two days because I got to understand real-life scenarios on which leadership skills were put to the test. One of the things he taught us was the three questions every leader needs to ask when faced with any challenge:

  1. Where are we now?
  2. Where do we want to go?
  3. What do we need to do?

It feels weird to wonder why doesn’t everyone ask this question to themselves? Why would a leader stand out from the pack just by asking these three simple questions? Much like a game of chess, perspective is the answer he/she holds, offering vision and purpose to the pieces: groups of specialists in either digital product development, consulting experts, creatives and artists, among others.

Let’s dissect all three questions and draw insight as to their importance and as to what a leader brings to the table when asking them. I’ll use chess as an analogy but don’t be discouraged if you don’t know how to play the game. The game is known to be a metaphor to life so I’ll hang onto that very notion.

Where are we now?

Understanding the current position in the game is crucial to the overall strategy to employ. There are so many questions that can be thrown out. For instance, how are the pieces laid out on the board? What are their strengths and weaknesses? Are there any opportunities to gain an advantage and progress further in the battlefield of intellect and cunning? Are there imminent threats that they have to defend from the opposing player?

Usually, a leader has a more generalist point of view of an entire system and its interconnecting parts, aware of its surroundings and on alert to potential stimuli. Experience normally prepares the leader to be responsive to unusual scenarios and mitigate (or perhaps avoid entirely) more dramatic outcomes. It is the leader’s job to step away from detail and minutia in order to give room to the bigger picture and its overall stance.

Where do we want to go?

Having a long-term objective is the ultimate guiding light. In many cases, it makes or breaks our decision making process as leaders. In chess, checkmate is usually the only successful victory condition. However, I’ve come to learn that while I aim to checkmate my opponent in the long run, there is more to winning than that. More often than not my objective is to go for small wins: forcing and exchange to win a piece, even if a single pawn; pinning a knight to the queen or king; bursting a file open where my rook can sit and take control of.

Knowing where to go is sometimes tricky. Sure, most people know what it is they want to see in the end but they fail to see where it is and where to go, there is no clear view of the road to get there. Most of the time the endgame is crystal clear, unlike the early and midgame checkpoints. A leader has the ability to tap into the big picture, split it into smaller, SMARTer (specific, measurable, achievable, realistic and time-bound) milestones and lift the fog that covers the road to follow.

What do we need to do?

How is it that competent chess players move their pieces the way they do? Because they know where they have to go on the board, they conjure a plan to achieve that end. They employ a strategy with a set of tactics to progress through the different files, columns and diagonals of the battlefield. Each piece is carefully positioned, protected by other pieces, attacking the adversary or weakening their ability to move such as with a pin. Each piece is close to worthless on its own, but all of them together and organized, they pose a devastating threat.

The leader coordinates the team. He/she leverages its strengths and maneuvers its weaknesses with proper care. Each person adds little value when alone. However, when the team is aware of where they are, what the goal is, where the road leads them, what the obstacles are and how it can leverage its attributes in order to overcome those obstacles, it succeeds and grows.

Note that leader is not necessarily the most technically skilled person in the group, the odds of it being true are slimmer than you think. His/her true value comes from acknowledging the team’s potential, evaluating the challenges at hand, asking the right questions and support decision making.


I was surprised by how simple this coach-like approach can bring so much value. Most of the times the leader does not have the answers but rather the right questions. It enables the team to think better.

This is the process of growth: to have individuals and teams gather insight, vision and inspiration, generate meaningful discussion, take action, fail and learn, and achieve new heights; step after step, challenge after challenge, question after question.