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3 Lessons I Learned Leading Strategy in a Complex Industry

August 5, 2026 · 2 min read · Tola Oladiji

Working in strategy has taught me that the neat version of strategy we learn from frameworks rarely survives contact with a real organization.

The slides may look structured.

The business usually is not.

There are competing priorities, resource constraints, legacy decisions, stakeholder interests, regulatory realities, market uncertainty, and the simple challenge of getting different teams to move in the same direction.

Over time, three lessons have shaped how I think about strategy work.

1. A good strategy needs organizational reality

It is easy to design an ambitious strategy.

The harder question is whether the organization can execute it.

A company may want to launch several new products, enter new markets, transform operations, and reduce costs at the same time.

Each initiative may make sense independently.

Together, they may exceed the organization's capacity.

Strategy therefore has to account for people, systems, funding, leadership bandwidth, capabilities, and existing commitments.

Sometimes the smartest strategic decision is sequencing.

Do this first.

Build this capability next.

Enter that market later.

Ambition matters, but execution capacity matters too.

2. Stakeholder management is part of strategy

I used to think stakeholder management sat around the strategy.

Experience has taught me that it sits inside it.

Strategic decisions affect different groups differently.

A restructuring may improve efficiency while changing someone's span of control.

A new technology may improve productivity while creating uncertainty for employees.

A pricing decision may strengthen margins while creating pressure for commercial teams.

Ignoring these dynamics does not make them disappear.

Strong strategy leaders understand who will be affected, where resistance may come from, what concerns are legitimate, and where alignment needs to happen early.

A technically sound strategy can still fail when the people responsible for executing it do not support it.

3. Execution discipline matters more than excitement

Strategy launches often have energy.

People are enthusiastic. Leadership is aligned. Presentations look impressive.

Six months later, reality looks different.

Urgent operational issues have taken over. Some initiatives are behind schedule. Others have lost executive attention.

This is why strategy requires governance.

  • Clear owners.
  • Measurable outcomes.
  • Regular reviews.
  • Visible accountability.
  • Fast escalation of blockers.

And sometimes the discipline to stop initiatives that no longer make sense.

I have come to see strategy less as an annual event and more as a continuous management process.

You make choices, execute them, learn, adjust, and make new choices.

The frameworks help.

The harder work is building an organization capable of turning those frameworks into results.