Alex Ostwerwalder – Apprentice CEO

Alex Osterwalder is probably best known as the creator of the Business Model Canvas and is undoubtably one of the world’s leading thinkers, experts and practitioners on business strategy and innovation. You might not think of him as an apprentice CEO.

One of the defining characteristics of the most successful entrepreneurs is their commitment to learning and growth and Alex is no exception.

In this online session, Alex spoke about his journey from well known author and speaker to what he describes as being a ‘real’ entrepreneur over the past 10 years.

He discussed what he feels are the most important aspects of his leadership journey and the five things he consider most important in his path to becoming the leader of a self-funded, fully remote, software company employing over 50 people. He discussed:

  • Coaching
  • Emotional Literacy
  • Three Books That Shaped Alex Osterwalder’s Approach to Leadership
  • Organisation Structure
  • Explore and Exploit – OKRs vs AKIs

We’re sharing some notes below but if you want to watch the talk when it is published, you need to get on the BoS newsletter and you will be the first to know.

Meanwhile, you can watch Alex Osterwalder’s talks from previous BoS Conferences.


You need experienced people who hold you to account and one of the best ways of achieving this goal as you develop as a leader is by finding great coaches.

Great coaching is not technical, it is about breaking through your own leadership barriers.

Traditional coaching is often technical and can focus on helping solve challenges. Coaches however should be concerned if their suggestions become orders.

Breakthrough coaching is about becoming a better leader by understanding yourself better. It is not about fixing things that are wrong, it is about growth and improvement. The best coaching should focus on the best people in the org, not the worst. We are all a little broken and all have ample room to grow as people and ultimately leaders. What could we be? We are the same person at work and at home.

As an entrepreneur, Alex wanted to work with the best breakthrough executive coach in the world. He worked out he could get an intro to Marshall Goldsmith through Professor Rita Gunther McGrath and joined Marshall’s first coaching programme which had an enormous impact on his thinking and approach to leadership.

Today, everybody at Strategyzer gets a $2,500 budget for coaching to work on professional and personal challenges.

Emotional Literacy

One example of the impact of his coaching experience has been a focus on developing emotional literacy, something that he subsequently worked on with another coach, Shani Ospina, to develop an emotional literacy scale that can ultimately help you operate in an environment where decisions and interactions are less clouded by emotions.

The Emotional Literacy Scale.

  • Avoid feeling emotions. Not possible!
  • Observe my emotions and recognise when I am in their grip.
  • Accept and label my emotions without judgement.
  • Explore how my beliefs give rise to my emotions. What I believe about others that is leading me to feel X.
  • Shift my beliefs to change my emotional state. What would I have to believe about myself, others, the situation that makes me feel a desired emotion.
  • Choose my beliefs to create my desired emotional state.

Three Books That Shaped Alex Osterwalder’s Approach to Leadership

The No Asshole Rule, Bob Sutton

  • Hire Relentlessly for Culture 
  • Do not compromise.
  • Stress test candidates before running hiring ‘test’

Radical Candor, Kim Scott

  • Challenge people directly because you care. 
  • Brutal honesty kindly delivered
  • The fish rots from the head. The more you love each other the more you should share the hard truths. If you don’t have that open culture, either people fear you or they don’t care.
  • Lead by constantly asking for feedback.

Principles, Ray Dallio

  • Governance, transparency and creating an idea meritocracy.
  • Alan Mulally turned around Ford, not by firing people, but by changing the culture. If we’re losing $17 billion we can’t have a dashboard where everything is in green.

Organisation Structure

Working on your organisational structure can make a big difference.

Strategyzer Strategy Implementation

  • Every organisation needs a structure and hierarchy but Strategyzer has developed a cell like structure that contains multiple hierarchies.
  • Value Proposition and support functions exist in cells.
  • Where company decisions are made, we have decision forums.
  • Where company-level alignments take place that don’t require decisions, we create alignment huddles.
  • Resources are allocated in an investment forum.
  • Hiring driven by the hiring forum. 
  • Each forum has online canvas for managing progress.
  • Meetings in sessions are recorded for future reference.

Strategyzer Operating System OS

Strategyzer Strategy Implementation

Product Portfolios are formed around sales, customer success, pricing, product etc.

Strategyzer doesn’t have one hierarchy. It has hierarchies.

The one place Strategyzer doesn’t have transparency is in making people resource allocation. It becomes too confusing for people in a decision making process.

Explore and Exploit – OKRs and AKIs

Fundamentally different processes and using different language for the elements of each. For example, planning is a part of exploitation, too much planning in exploration constrains the exploration process.

OKRs are useful for directing and measuring Exploitation.

Exploration is different. In 2023, Strategyzer have adopted AKIs – Aspirations and Key Insights. What do we want to do and what do we need to know to understand the potential?

The concept of using AKIs rather than OKRs as a core part of the exploration and innovation processes at Strategyzer is a work in progress. It has been developed over several years but 2023 is the first year that the concept has been implemented. You can find out more here, and we look forward to welcoming Alex back to BoS to go into more detail about how they are working out.

Life is a journey. Onwards and upwards.

Working On It

A final thought from Alex:

You need to work on leadership. Start today. You cannot put it off. It takes time to change and too often it is put off, nothing changes in people, and things get worse.

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You can watch Alex Osterwalder’s talks from previous BoS Conferences here.