connecteddale

Strategy Coach — Clarity + Alignment

About Dale Williams

Strategy Coach

I'm Dale Williams, a Strategy Coach who helps business leaders discover clarity in their strategy and alignment in their teams.

This isn't consulting where I hand you a report and walk away. I work with you to surface what's already there—the strategy your team knows but hasn't articulated, the alignment that's possible but hasn't happened yet.

I've been doing this for nearly 20 years. Since 2006.

Professional Background

My path to strategy coaching wasn't linear. It rarely is for the best coaches.

The Journey

Entrepreneur & Programmer (1987-1998) — Started writing software as a teenager. Built and sold businesses during the first wave of internet innovation—including South Africa's first Unit Trust comparison website and the software behind the country's first internet-only listing (E*Data, 1997).

Director, Global Technology Services (1998-2001) — Ran software development operations. Founding member of Rocketseed.

CIO at Standard Chartered / 20twenty (2001-2004) — Built and managed technology and banking operations for what became Standard Chartered's Retail Bank in South Africa. Team of approximately 70 people across technical, banking, and risk management disciplines.

Head of Consumer Bank, Standard Chartered South Africa (2005-2006) — Bottom-line responsibility for retail banking in South Africa. Led through major restructuring and strategic pivots. Team of approximately 150 people.

Strategy Coach (2006-Present) — Nearly 20 years helping leaders get clear on strategy and aligned on execution.

President, COMENSA (2007-2008) — Led the professional body for coaches and mentors in South Africa.

Strategic Thinking Lecturer, UCT (2007-2022) — Convened and taught the Business Strategy course (BUS4050W) for final year Business Science students at the University of Cape Town. 16 years. Approximately 500 students per year.

Leadership Solutions Associate, Center for Creative Leadership (2011-Present) — Over 14 years developing and delivering leadership programmes across Africa with CCL, a top-ranked global provider of leadership development.

COO at GetSmarter (2017-2018) — Operations leadership at one of Africa's fastest-growing edtech companies.

SVP International Partners, 2U (2018) — Oversaw global partner relationships post-acquisition of GetSmarter.

The thread through all of it? Every role taught me that strategy fails when alignment is missing, and alignment fails when clarity is missing.

My Approach

Clarity + Alignment

Most strategy work focuses on analysis and planning. Mine focuses on two things:

Clarity — Can you explain your strategy at 3am, half-asleep, to a skeptical board member? If not, it's not clear enough. I use what I call the 3am test —a simple but brutal filter.

Alignment — Does your team tell the same story about where you're going? Not just intellectually agree, but own it? Alignment isn't consensus; it's shared conviction.

How I Work

I don't bring pre-packaged frameworks and force them onto your reality. Instead:

The result isn't my strategy imposed on your business. It's your strategy, finally clear enough to execute.

Core Beliefs

People support what they create. When your team shapes the strategy, they own it. When they own it, they execute it.

Alignment means shared stories. If your leadership team tells different stories about where you're going, you don't have alignment. You have tolerance.

Brevity beats verbosity. If it takes 50 slides to explain your strategy, you don't have a strategy. You have a deck.

Want the Full Story?

Review my LinkedIn profile for detailed career history, qualifications, and recommendations from people I've worked with.

Ready to Talk?

I don't do sales calls. I do conversations. If something here resonated, let's chat .

Not sure yet? That's fine too. Browse the Strategy Tools —the Whole Earth Strategy Catalogue—to see how I think about strategy. It's free, and it might answer questions you haven't asked yet.