Laura Famularo: President, Co-Founder at Famular LLC
Why do capable, accomplished leaders sometimes struggle to make decisions?
It’s a question I’ve found myself reflecting upon.
After all, these are leaders with strong track records. They are intelligent, experienced, competent, and have demonstrated sound judgment throughout their careers. They have earned the increase in responsibility because of their ability to solve problems and deliver results.
Yet as they move into more senior leadership roles, hesitation or “second-guessing” may begin to creep in.
Interestingly, the issue is often not a lack of capability. More often, it is a combination of two factors:
First, they begin to doubt their own judgment.
The higher one rises, the more complex decisions become. There is rarely complete information, and every option has an element of risk. Highly thoughtful leaders see nuance and consider unintended consequences, which can sometimes make decision-making feel heavier and more uncertain.
Second, they struggle with the reality that leadership decisions inevitably disappoint someone. It is the old adage, “you can’t please everyone.”
Many successful leaders are relationship oriented. They value collaboration, seek consensus, and genuinely care about the people around them. These qualities help them advance. However, at senior levels, leadership often requires choosing between competing priorities, allocating limited resources, and saying “no” to good ideas and good people.
The challenge becomes less about making the decision and more about developing a comfort with the discomfort that follows it.
One of the most important shifts in leadership development is recognizing that decisiveness is not primarily an intellectual skill—it is an emotional one.
Leadership requires trusting your judgment, accepting that certainty is rarely available, and understanding that disappointing others does not mean you have failed them.
In fact, avoiding difficult decisions often creates more uncertainty and frustration than the decision itself.
This is where coaching can be particularly valuable. Many leaders don’t need help understanding what the right decision is. They need support building confidence in their own judgment, reframing difficult conversations, and developing the courage to act despite discomfort.
At the highest levels of leadership, the challenge is often not knowing what to do.
It’s having the confidence and conviction to do it. What have you found to be the biggest obstacle to decisiveness in leadership—lack of information, fear of being wrong, or concern about disappointing others?