Mastering Active Management: Five Insights for Generating Value

April 15, 2025

X min read
Human Resources

Author

Joshua (Josh) Santiago, Managing Partner of Santiago & Company

Josh Santiago

Managing Partner

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Key Takeaways

Active portfolio management is the underutilized cornerstone of sustainable value creation. Companies that consistently refresh their business mix outperform peers by 3.5 percent in long-term Total Shareholder Return (TSR).

  • To accurately assess performance, benchmark each business against external market peers rather than internal metrics. Even if its market grows even faster, a high-growth unit may still be underperforming.
  • Overcome decision biases that prevent necessary divestitures by changing the burden of proof, categorizing businesses definitively, and prioritizing value creation over emotional attachments to business units.
  • Act decisively without delay, as postponing portfolio decisions has real costs ill-fitting assets rarely appreciate under continued ownership, while acquisition synergies require time to materialize.

The Secret of Visionary Executives: Active Portfolio Management

Visionary executives know a secret: active portfolio management isn't just another strategic option. It's the cornerstone of sustainable success. Organizations consistently refreshing their business mix outperform their peers in Total Shareholder Return by a compelling 3.5 percent over extended timeframes. These market leaders methodically cultivate, acquire, and divest businesses to bring their enterprise strategy to life. Their North Star isn't expansion for expansion's sake but maximizing returns accomplished through deliberate growth and investing precious capital in genuinely mission-critical priorities.

Strangely, despite its proven track record, the transformative power of active portfolio management often languishes in corporate blind spots, with a parade of excuses blocking necessary evolution. In boardrooms across industries, executives reflexively point to market headwinds and tailwinds as the primary drivers of financial performance, even when results spring more from strategy quality, execution discipline, and classic competitive dynamics at play.


As the post-pandemic economic surge recedes and cost-optimization initiatives reach their natural conclusion, visionary leaders are circling back to fundamentals. They relentlessly pursue maximum free cash flow from invested capital, ensuring every business aligns with their organization's unique capabilities and the trends reshaping their industries. Top-performing corporations perpetually question whether they remain the optimal stewards for each company in their portfolio. Then, they transform insight into action: shifting capital toward strategic imperatives, orchestrating acquisitions and divestitures to align with their vision, channeling proceeds into high-potential opportunities, and conquering decision biases to generate substantially enhanced shareholder value.

Markets don't stand still. They constantly dance, twist, and reinvent themselves. Competitors never pause in their pursuit of advantage. Expecting yesterday's perfectly calibrated portfolio to remain ideally positioned today, let alone tomorrow, defies business reality. With finite resources at your disposal (particularly regarding capital, talent, and leadership bandwidth), a rigid approach to resource allocation can't empower each business unit to capture and maintain leadership in their respective competitive arenas. Let's explore five essential insights for leaders embracing active portfolio management as their strategic weapon of choice.

1. Benchmark each asset's performance against external peers, not against each other

Consider this scenario: your corporation achieves an overall CAGR of 5 percent while a particular business unit delivers an impressive 25 percent. Should you treasure this apparent gem? The answer isn't straightforward. It hinges entirely on context. If the business unit's growth mirrors its industry peers, you've likely discovered an underappreciated value creator worthy of celebration. However, if the broader market surges at 40 percent annually, towering 15 percentage points above your unit's performance, the operation is falling behind, surrendering market share and potentially eroding value. Such an underperformer might require substantial investment to reclaim competitive footing. At a minimum, you should thoroughly diagnose the root causes of its underperformance. Rather than representing an investment opportunity, this business warrants consideration for divestiture.

2. Be pragmatic about real portfolio synergies that exist among your businesses and understand the upside that other owners could offer

Owning diverse businesses creates inevitable trade-offs regardless of individual earnings profiles. Every portfolio component competes for your organization's limited resources, not just financial capital but equally precious leadership attention and specialized talent. In the best cases, synergies across businesses justify these allocation costs many times over. Traditional value-creating connections include selling advantages (established customer relationships, efficient sales channels, privileged market access, powerful brand umbrella, and specialized marketing expertise), production efficiencies (optimized manufacturing footprint, integrated supply chain networks, shared engineering talent, and cross-pollinating R&D capabilities), and competitive insight (transferable management expertise and privileged market intelligence).

Conversely, certain business combinations generate troublesome "dis-synergies" that destroy value rather than create it. A generic pharmaceutical operation demands fundamentally different capabilities from businesses focused on proprietary medications or cutting-edge biotechnology innovations. Similarly, commodity chemicals operations follow entirely different success formulas than specialty chemicals businesses. Your portfolio companies might require vastly different SG&A structures to thrive in their respective markets.

When portfolio businesses contribute minimally to each other's success or when promising growth opportunities remain beyond reach because stretched teams struggle with execution, another industry player or a seasoned private equity investor could unleash more excellent value and pay a premium for the privilege. These proceeds could fuel investments in businesses where your company maintains genuine competitive advantages or directly flows to shareholders. Remember, the ultimate objective isn't building an empire but maximizing returns on the capital your shareholders have entrusted to your stewardship.

3. Recognize and mitigate your own biases

Value creation frequently derails due to stubborn decision biases regarding sunk costs, particularly (though not exclusively). Executives who built their careers and reputations developing particular divisions face extraordinary psychological barriers when those businesses plateau. Yet perpetually optimistic hockey stick projections prove just as unlikely to materialize this year as they did in previous years, and confronting disappointed investors becomes no easier with time. For better or worse, activist investors approach your portfolio without these emotional anchors. Leaders who cling to suboptimal business combinations too long effectively extend an invitation to activist intervention. Typically, carefully considering activist perspectives represents a prudent course of action.

Executives frequently hesitate to pursue necessary divestitures, citing operational complexity, perceived scarcity of interested buyers, and deep-seated concerns about diminished enterprise scale and reduced earnings. Though intellectually recognizing the superiority of leading a smaller but more value-generating organization, the prestige and influence of managing a larger enterprise remains powerfully seductive.

To overcome these decision biases affecting business mix, forward-thinking leaders implement practical countermeasures: inverting the burden of proof (establishing, as a thought-provoking exercise, that divestiture represents the default outcome unless managers convincingly demonstrate retention value), rigorously categorizing businesses into clear "grow, maintain, or dispose" buckets, and enforcing transparent rankings of companies by value creation potential. As always, nothing replaces a meticulously constructed discounted cash flow analysis with results candidly presented. Emotional attachments must never override tangible returns.

4. There's a cost to waiting, so get moving now

Attempting to perfectly time market cycles presents formidable challenges. Consider divestitures: an ill-fitting or non-core asset rarely appreciates significantly under continued ownership and inevitably becomes increasingly peripheral to strategic priorities with each passing month, further eroding its value compared to peers receiving appropriate resources and attention. Yet research reveals a startling statistic: 77 percent of executives acknowledge divestiture decisions that management teams or boards delayed. These findings align perfectly with our frontline experience. Managers consistently wait too long to divest underperforming assets, watching helplessly as these businesses hemorrhage value. By contrast, leaders who liberate capital promptly gain precious flexibility to invest in growth priorities where they possess genuine competitive advantages.

Fighting organizational inertia proves equally challenging regarding acquisitions that strengthen your strategic portfolio. The temptation to hold out for marginally improved pricing should be balanced against opportunity costs from delayed integration and the very real possibility that sellers pursue alternative options, particularly with your direct competitors. Moreover, capturing synergies demands time; even exceptionally well-managed integrations typically require 18-24 months to realize the most potential benefits. We've observed that programmatic acquirers commit to pursuing strategically aligned acquisitions, even at premium valuations, provided transactions create long-term value. While overpayment risks deserve serious consideration and can generate substantial costs, positive outcomes invariably begin with a commitment to the strategic thesis; when a transaction creates genuine strategic sense, immediate action coupled with ongoing flexibility yields optimal results.

5. Executing a divestiture is frequently more complicated than anticipated.

Most executives naturally wish to "move on" swiftly from the asset following divestiture decisions. However, not all separations follow the same playbook, and many demand meticulous management. Our research reveals that 45 percent of separation programs exceed expected timelines. Leaders consistently identify greater-than-anticipated business complexity and insufficient dedicated resources as primary delay factors. Regulatory timelines introduce additional unpredictability, often unexpected, further amplifying variability and uncertainty.

These challenges underscore a fundamental truth:

While portfolio management represents a fundamentally strategic undertaking, execution shortfalls undermine the most brilliant plans, while tactical excellence can become the decisive difference-maker. Active portfolio management demands continuous attention in determining the optimal business mix and providing the resources and engagement required to bring this vision to life. Creating substantial shareholder value requires both penetrating insight and disciplined execution. These lessons remain evergreen. With market experts forecasting increased buy-side opportunities, there's never been a better moment for executives to reexamine their portfolios and transform conceptual improvements into value-creating reality.

The most successful companies continuously evolve their business mix year after year. Many renowned CEOs built their legacies precisely through relentless portfolio renewal, particularly through balanced acquisition and divestiture programs. Waiting too long to refresh your business mix inevitably invites disappointing outcomes. Markets transform continuously, and your competitors certainly aren't standing still. The ideal moment to begin is right now.

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