Rebuilding From the Inside Out: Helping Companies Navigate Transformational Change with Clarity, Courage, and Conviction

In a business world awash with digital promises and platform noise, Joseph Flesch, President & Co-Founder of Fermata Strategic Ventures, is a rare voice of pragmatism. Equal parts advisor and advocate, his leadership in organizational transformation is not about adopting the flashiest tool or the most disruptive trend. It's about knowing when to move, how to lead, and who needs to be at the table to make it happen.

Over the course of two decades, Joseph has advised companies ranging from mid-market manufacturers to Fortune 100 giants. But his focus is clear: transformation that works for people, not just systems. In this conversation with Dialectica’s Executive Community, Flesch opens up about the foundational moments that led him to co-found his current firm, the patterns he sees across struggling organizations, and the brutal truths executives need to face to build transformation strategies that last.

Starting With the Why

For the strategic advisor, the decision to step into the world of independent strategic advisory work was less about entrepreneurship and more about alignment. “Having worked for both large enterprises and small businesses”, he reflects, “my wife and I began to realize that the success and failure of working with Fortune 100s left behind a lot of clues. There was a clear opportunity to apply what worked; tailored strategy, structured governance, leadership accountability into environments that often lacked those tools”.

His early work began before the term “fractional executive” became fashionable. As a Vistage Chair supporting small business leaders, Flesch was already operating in hybrid roles that blurred the line between executive coach and embedded transformation partner. “It gave me the space to grow professionally without being tied down to any one organization”, he says. “But more importantly, it gave me the freedom to show up where I was needed most: guiding leadership through the complexity of change”.

Why Most Modernization Efforts Stall Before They Begin

No matter the sector, Joseph has come to recognize a set of common failure points that derail transformation efforts. These are not sector-specific; they show up whether the organization is manufacturing automotive parts, running wholesale distribution, or providing professional services. At the core is an overcomplication of what modernization should look like.

“There are too many choices now”, he explains. “Companies are sold massive ERP systems - Oracle, NetSuite, Dynamics 365 - when in reality, they don’t need 80% of the functionality – especially right away. They’re not ready for it, and frankly,it distracts from the fundamentals”. 

This misalignment of need and capability leads to cascading confusion, especially when it comes to the concept Flesch believes is deeply misunderstood “fit to standard”. “People think it means sacrifice. But it’s not about giving up capability; it’s about understanding what enables your team, what makes sense for your workflows. Fit to standard is a leadership and education process long before it becomes a technical decision”.

Even before a configuration attribute is updated or a single line of code is implemented, he says, most organizations have already made critical missteps.-.

The Myth of Speed

In Joseph’s view, one of the most persistent executive fallacies is the false dichotomy between speed and sustainability. Leaders often seek rapid results while overlooking the foundational steps required to make transformation endure.

“Speed and sustainability are not mutually exclusive”, he argues. “It comes down to how you mobilize. Planning isn’t a formality; it’s the beginning of change management. You have to understand how people will be impacted, how they can contribute, and how to keep them engaged across multiple sprints of execution”.

He frequently finds himself coaching teams through a crucial mindset shift: transformation is not a “lift and shift”. It is not about replacing spreadsheets with platforms or chasing features for the sake of innovation. “You have to define what ‘a day in the life’ looks like for your future state. If that’s not clear, then everything else - tools, timelines, vendors -is just noise”.

In one recent engagement, Flesch had to challenge the very premise of a client’s vision. “They were excited about becoming more digitally mature. But I had to ask: ‘Do you realize this strategy makes you less of a manufacturer and more of an IT company? Is that really the direction you want to go?’ It was a moment of pause they hadn’t considered”.

Navigating Investor Pressure

Transformation becomes even more complex when external stakeholders, particularly private equity firms, enter the picture. The advisor acknowledges that these relationships can create tension between long-term functional leadership and short-term financial priorities.

“Let’s be honest”, he says. “When a PE firm is involved, the CFO is often balancing two masters. That makes clarity absolutely critical. You need open channels of communication, defined success criteria, and frequent touchpoints that allow you to course-correct before things go sideways”.

But more than that, executive teams need someone who’s walked the road before. “In my last two major projects, the client asked me to act as their advocate, not just during vendor selection, but across the whole lifecycle. Because most of their team, even at senior levels, had never been through a transformation before”.

That level of trust, Joseph notes, only comes with brutal honesty.

The Power of Advocacy

It’s easy to talk about transparency and visibility, but it’s much harder to embody it, especially when you're not on the payroll. “Every company has internal politics”, Joseph says. “But as an external advisor, I have the freedom, and the obligation, to tell the truth”.

This often means saying what others won’t. “Sometimes I’ll start with: ‘Look, I’m going to be brutally honest with you, and it might not be what you want to hear.’ But that’s the job. It’s not about being liked. It’s about being trusted”.

In one engagement with a large enterprise, the advisor encountered a transformation project that had stretched from six months to 18 due to endless decision-making by committee. “I had to tell them flat-out: this isn’t working. You need to make changes in how decisions are made, or this will never move forward”. To their credit, the leadership team acted quickly, restructuring roles and responsibilities to accelerate progress.

On the other end of the spectrum, with a founder-led company, Flesch’s role became almost daily. “The owner was silent but influential, and we had to manage that dynamic carefully. Because without his buy-in, or at least his absence, the project would have stalled”.

Leading When Stakes Are High

When asked about leading in highly regulated environments, Joseph doesn’t offer cookie-cutter advice. “Every sector has its own version of the 80/20 risk rule. In food manufacturing, for example, it’s quality assurance and FDA oversight. In investment and financial services sectors, it’s AML and KYC (anti-money laundering and know-your-customer) considerations. You have to bring those risk owners to the table early. Because when things go wrong, they’re the ones who are accountable”.

The lesson, again, comes back to stakeholder alignment. Not every department has the same transformation lens, and that’s the point. “Success means finding common ground between compliance, operations, finance, and IT. That’s where your governance model earns its keep”.

Three Lessons for the C-Suite

Finally, Flesch distilled his approach into three imperatives for senior leaders, regardless of company size or sector.

First, be present. “You can’t delegate transformation. Even the smallest decisions will come back to you. So, show up early and stay involved”.

Second, plan for reality. “Transformation doesn’t pause your business. Your team still must keep the lights on. So, you need to understand the burden you’re putting on them and allocate time, not just resources”.

Third, find the right advocate. “Someone needs to translate your vision into execution, especially when third parties are involved. That person must understand your business and be willing to challenge vendors, internal leaders, and even you; respectfully, but firmly”.

Beyond the Buzzwords

The advisor is quick to remind clients that transformation is not about trends. It’s about knowing your culture, defining your outcomes, and building the right team to get you there. “You don’t need to chase shiny objects”, he says. “You need to be honest about what works, what doesn’t, and who’s willing to lead from the front”.

That kind of leadership is rare, and perhaps more valuable than ever in a business landscape where change is constant, but clarity is not.