Blog
Questions to Begin 2026: Leading When the World Offers No Respite
por Alfredo Carrasquillo

Every new year begins with a familiar ritual: fresh planners, renewed promises, and the ever-legitimate hope that this time we will do things differently. Yet the world with which we welcome 2026 seems unwilling to grant us the calm we often associate with new beginnings. Persistent geopolitical tensions, fragile economies, exhausted organizations, technological advances that challenge our certainties, and a growing sense of emotional overload all shape a context in which leadership has become more complex—and more human.
In such a landscape, focusing exclusively on goals, metrics, and resolutions risks becoming another form of denial. Not because planning is useless, but because planning without self-inquiry often reinforces automatisms that no longer serve us. Perhaps, rather than adding more items to our agendas, the real challenge in starting 2026 lies in asking better questions.
Through my work accompanying leaders and teams across different countries and sectors, I have learned that honest inquiry remains one of the most powerful tools for removing obstacles, broadening perspective, and regaining room to maneuver. Questions that unsettle us, that shake our internal narratives, and that force us to revisit how we are interpreting—and inhabiting—our role.
Some of those questions might be the following.
From what emotional place am I leading today?
It is not enough to speak of emotional intelligence as a concept. We need to ask ourselves, candidly, whether we are leading from calm, from a state of permanent urgency, from fear of losing relevance, or from a need for control. Under sustained pressure, many decisions are made not from strategy, but from exhaustion. What impact does this have on the quality of our decisions and on the climate we create?
Which conversations am I avoiding, and at what cost?
In tired organizations, postponement becomes a silent strategy: issues left unnamed, tensions swept under the rug, mediocre performance tolerated out of convenience or fear of conflict. Which difficult conversations are we delaying, and how does that delay erode trust, credibility, and results?
Am I adapting my leadership to the real diversity of my team or am I still leading as I learned ten or twenty years ago?
Generational, cultural, and expectation-based diversity is no longer an “emerging issue”; it is the everyday terrain of leadership. Are we adjusting how we communicate, delegate, inspire, and give feedback, or are we clinging to formulas that worked in a different context with different people?
What place do learning, and error truly have in our culture—beyond the rhetoric?
Many organizations claim to value learning yet penalize mistakes explicitly or implicitly. What concrete signals do we send when someone gets it wrong? Do we invite reflection and improvement, or do we activate defensive mechanisms that inhibit initiative?
What are we doing to protect attention and focus on an environment designed to fragment them?
The hijacking of attention is not merely an individual problem; it is an organizational one. Endless meetings, artificial emergencies, permanent hyperconnectivity. Are we deliberately designing spaces for concentration, reflection, and deep work, or are we normalizing distraction as if it were inevitable?
How are we building a “we” in contexts of fragmentation?
Collaboration does not arise by decree. It requires spaces, clear rules, and leadership that convenes. Are we creating opportunities to think together, review how we work, and redefine agreements, or are we simply complaining about silos while reinforcing them through our practices?
Am I devoting enough time to developing people, or only to putting out fires?
When everything feels urgent, development is pushed aside. Are we differentiating between operational spaces and spaces for coaching and growth, or are we still expecting what truly matters to happen in the margins of the day?
What kind of example do I set regarding the balance between work and life?
Beyond well-being rhetoric, what do we model through our agendas, schedules, and availability? Are we enabling other ways of working without sacrificing results?
Am I leading through presence in the business, or through confinement to indicators?
Data is indispensable, but it does not replace contact with customers, partners, and teams. How much space does our agenda allow for relationship-building and for a living reading of the environment?
What am I willing to let go of in order to lead better in 2026?
Perhaps this is the most uncomfortable question of all: letting go of practices, beliefs, roles, or even identities that once gave us security, but now constrain us.
A new year does not guarantee a new beginning. That only happens when we dare to question ourselves honestly and choose, again and again, to walk a different path. I hope some of these questions accompany you as you begin 2026—not as a checklist, but as a compass.
Because in complex times, leadership is not about having all the answers, but about daring to hold the right questions.