I have earned a rather questionable reputation with my wife that I sometimes choose books purely by judging their covers. I won’t deny it entirely. There is something thrilling about wandering through a bookstore, randomly pulling a book off the shelf, and heading straight to the checkout counter.
Admittedly, some of these bold decisions have backfired. Yet, despite those disappointments, I continue this habit because it adds a sense of adventure and also helps to get some great books. The First 90 Days by Michael D. Watkins was one such fortunate discovery.
I came across the book shortly after transitioning into a new role, following nearly 20 eventful years in my previous organization. Naturally, the title struck a chord. Having already stepped into my new position, I was hoping the book would offer practical guidance to navigate the early phase of this journey. It certainly did.
One particular theme resonated deeply with me: why capable leaders often struggle or even fail when they take on new executive roles. Then I thought to write a article on this topic bleding some inspiration from the book and my real experience in life:
Not able to identify the supportive group
When you join a new organization, the welcome can be overwhelming. Smiles are generous, handshakes are firm, and promises of support flow freely. However, as time passes, reality begins to surface.
Some people who initially appear supportive may gradually distance themselves. The reason behind such attitude is those people have been waiting for the certain position for many years which is filled up by you suddenly. So, you can’t blame them for their frustration to some extent. On the contrary, there is another group of people from the same organization who want to support you genuinely to achieve your goals. Therefore, one of the key strategies to be succeeded in leadership position, is to identify the right group of protagonist people from the organization so that as newly entrant leader, you can align people from supportive group with your strategic priorities while setting right action plan to bring the other group from resistant zone to supportive zone. If anyone fails to address the mindset of the people around them, possibly high chance to slip from their leadership position with getting a tag that you are not top executive element.
Ignoring Small Wins in Pursuit of Big Success
No matter how impressive a leader’s experience or skill set may be, impact is measured by actions, not intentions. Many leaders fall into the trap of aiming for big, transformational wins right away. However, such initiatives often require deep-rooted structural or cultural change that rarely happens quickly.
Organizations develop their cultures over years, and people naturally resist abrupt change. As a result, large initiatives may face pushback, delays, or even outright failure.
Each organization holds some unique dynamics
Every organization has its own culture, people, systems, and unwritten rules. What worked brilliantly in one environment may not work at all in another. A common leadership mistake is attempting to replicate previous methods without adapting them to the new context. When leaders impose familiar ways of working without sufficient explanation or cultural sensitivity, both resistance & frustration of people grow rapidly.
Perhaps right leader at wrong time in Organizational Life Cycle
Beyond individual leadership behavior, organizational context plays a decisive role in success or failure. Michael Watkins introduces the STARS model (Startup, Turnaroun, Accelerated Growth, Realignment, Sustaining Success). Each stage demands a different leadership approach. A leader who excels in sustaining success may struggle in a startup or turnaround environment, where uncertainty, pressure, and ambiguity dominate.
Moreover in some cases, organizations bring in external leaders during particularly turbulent phases, expecting immediate stabilization. Without a clear alignment between leadership capability and organizational stage, even strong leaders can falter.
Final words, Leadership failure in a new role is rarely due to a lack of talent or intelligence. More often, it stems from misreading people, culture, timing, or context.
The writer is Chief Business officer, Dhakacolo Data Center
