Not Every Business Challenge Is the Right One to Take On
By Stephan Engelen ยท 2026-10-26
What experience has taught me about leadership, transformation and the willingness to change.
Throughout my career as an entrepreneur and executive, I've always been attracted to complex business challenges, particularly when companies were facing rapid growth, strategic uncertainty or significant organizational change.
I enjoyed understanding the underlying issues, exploring possible solutions and working with people to move the business forward. In fact, the more complex the situation, the more appealing I often found the challenge.
Looking back, however, I realize that this enthusiasm sometimes led me to underestimate an equally important consideration: whether the leadership and the organization were genuinely prepared to embrace the changes required.
It's a distinction that has increasingly influenced how I look at business transformation.
Understanding What Needs to Change Is Only the Beginning
Coming from an operational background, it's often relatively easy to identify areas where a business could improve. Perhaps the strategy needs reconsidering, the organization has outgrown its existing processes, or the management team is struggling to assume greater responsibility.
Once you recognize these patterns, you naturally start thinking about what could be done differently.
Yet identifying the right course of action and creating the conditions to implement it are two very different challenges.
I've been involved in situations where the business opportunities were clear, but where the organizational environment, governance structure or leadership dynamics made progress considerably more difficult than anticipated.
This wasn't necessarily a question of competence or ambition. More often, it reflected a gap between the desire to achieve better results and the willingness to reconsider established ways of working.
Over time, I've learned that this gap deserves at least as much attention as the business challenge itself.
When the CEO Becomes Part of the Transformation
This becomes particularly relevant in founder-led companies, where the qualities that contributed to early success can gradually become constraints as the organization grows.
A founder's close involvement in daily decisions, direct relationships with customers and personal control over execution can be extremely valuable in the early stages. As the business becomes more complex, however, that same approach may prevent the management team from developing the autonomy and accountability required for further growth.
Introducing better processes or clearer responsibilities can certainly help, but these changes will have limited impact if the CEO continues to intervene in every important decision.
The challenge is therefore not only organizational. It also involves the founder's willingness to reconsider their own role, which can be particularly difficult when the behaviors that need to evolve were instrumental in building the company.
The next phase of a company often requires a different version of the leader who built it.
Strategy, Organization and Leadership Are Interconnected
Of course, not every obstacle to growth originates in leadership or organizational structure. Sometimes the underlying strategy needs to be questioned, particularly when companies attempt to scale before their commercial model is sufficiently proven or pursue opportunities that stretch their resources and management capacity too far.
In such circumstances, improving operational efficiency may have little effect on the fundamental challenge. An organization can become increasingly effective at executing a strategy that is no longer appropriate.
The reverse is equally true. Even a well-considered strategy can fail when the organization lacks the leadership capabilities, decision-making structures or management discipline needed to execute it.
This is why I increasingly see strategy, organization and leadership as inseparable elements of business transformation. Progress in one area often depends on changes in the others, and the willingness to reconsider existing assumptions becomes essential.
What Experience Has Changed for Me
These experiences have gradually changed how I evaluate potential engagements.
I'm still attracted to ambitious businesses and challenging situations, but I no longer consider the complexity of the challenge or the potential of the company sufficient reasons to become involved.
I also want to understand how the CEO and management team view their own role in the transformation. Are they open to questioning strategic assumptions, distributing responsibility differently and accepting that their own leadership approach may need to evolve?
These aren't questions to which I expect immediate or perfect answers. Transformation inevitably involves uncertainty, resistance and difficult decisions, even among highly capable leaders.
What matters to me is the willingness to engage in that process with openness and a genuine desire to learn.
It also reflects how I see my own contribution today. Rather than taking operational responsibility or concentrating primarily on process improvements, I'm more interested in helping CEOs and their leadership teams navigate the strategic, organizational and leadership challenges that come with the next stage of their company's development.
That requires challenging assumptions, bringing perspective to difficult decisions and helping create the conditions in which both the CEO and the organization can evolve.
A Question Worth Asking
One of the most important lessons I've taken from my career is that an attractive business challenge and the right leadership engagement are not necessarily the same thing.
Successful transformation depends on many factors, including market conditions, strategic choices, financial resources and execution capabilities. But experience has taught me to pay particular attention to the willingness of those leading the organization to reconsider their own role.
Because ultimately, transformation is not simply something a CEO asks others to undertake. It is a process in which the CEO must be prepared to participate.
If the next phase of your company requires you to change the way you lead, are you genuinely prepared to do so?