Orientation in strategic situations.
Better decisions under uncertainty
Rebbelib is my independent practice, focused on orientation in strategic situations. I’m Benjamin Wittorf. I work with entrepreneurs, founders, leaders and others responsible for decisions with significant consequences.
The focus is on our ability to orient ourselves. Through conversation and joint inquiry into specific questions, we work to develop that ability: examining familiar explanations, discovering new connections and shaping our actions accordingly.
When we might work together
Our orientation shapes what we observe, how we decide and how we act. New observations and the consequences of our actions can change it. We might work together on very different kinds of questions:
-
- Experienced people involved in the same situation see it differently. Each explanation seems plausible, yet the proposed next steps are at odds with one another.
-
- An initiative looks sound on paper. In practice, it repeatedly stalls, and it remains unclear which conditions are actually holding it back.
-
- Changed circumstances call established answers into question. It is not yet clear which parts of past experience still apply and what needs to be understood anew.
-
- A plan needs to be tested against the strongest objections before a decision is made. Its objective and the way the problem has been defined so far may also come into question.
We also examine what information is missing, which interests are at work and what material conditions shape the situation. New explanations must hold up against observations and the consequences of action. It may also turn out that a decision originally under consideration is no longer relevant. The ability to recognise contradictions and revise our own judgement remains important beyond any single engagement.
Working together
Strategic orientation
An open question, a contradiction or an initiative can be the subject of a single working conversation. I contribute knowledge and my own interpretations. Together, we develop explanations and examine what they reveal and what they overlook.
The conversation can stand on its own. Meeting regularly as thinking partners gives us space to reflect on your experience of taking a next step and to develop your orientation in light of it.
Testing assumptions
You bring a plan or a recommendation. I examine sources and underlying assumptions, looking for counterevidence and alternative explanations. Together, we clarify how we could tell that a key assumption is wrong, and which conditions make the initiative possible or limit it.
The examination may change a plan, suggest further work or provide grounds for keeping it. The reasoning behind the judgement becomes clear, including what is not yet known.
Investigating a situation together
When a question calls for additional sources and perspectives, we investigate the situation within a defined engagement. This may involve research, close reading and conversations with other people involved. I explore sources, analyse connections and develop a reasoned judgement.
In our work together, we connect the findings with the courses of action available to those involved. We clarify responsibilities, interests and the specialist contributions needed, identify a possible next attempt and pay attention to what its consequences reveal. An assessment of the situation or a written basis for further work emerges when the work calls for it. Here, too, there is room for what we do not know and for later revision.
When the situation is ‘AI’
AI can analyse data, automate tasks and suggest new explanations. When its ready-made answers replace our own work of observing, explaining and testing, they can hinder reorientation.
One reason to work together might be that AI is being used, yet it remains unclear why its outputs are not helping. We then examine the source material, overlooked clues and the conditions under which the outputs are produced and used. This includes who can recognise a discrepancy and ensure that an objection has an effect. Whether AI is helpful, and for what, is something we establish in relation to the specific question. This may also lead us to decide not to use it for that question.
Benjamin Wittorf
My experience brings together technical and organisational responsibility with the investigation of information and decisions.
At Self Trade’s Paris headquarters, I was jointly responsible as Co-Head of IT for a department of around 100 people. This included Europe-wide reporting and handling operational incidents. For DHL, I automated reporting for the executive board as part of a small external team. I was active in the US Intelligence Community and worked on security audits in China. For a European self-defence provider, I examined a planned entry into the German market, down to the economics of individual locations, and recommended not pursuing the expansion.
I have translated John Boyd’s writings and briefings into German, have maintained the German-language compendium since 2021 and am a member of the John Boyd Gesellschaft. Boyd’s work on orientation and continual reorientation is an important point of reference for my practice.
A Short Book on Orientation
A sound insight may have no effect. In A Short Book on Orientation, I explore how people and organisations orient themselves with incomplete knowledge, what stabilises these orientations, how they can fail and what it takes to change them.
Concrete cases make it possible to trace how perception, attachments, power and material conditions interact. They offer distinctions to use in our own questions and decisions: When does additional information help? When do objectives, rules or responsibilities need to be examined? And how can we tell whether a new explanation holds up? The book offers points of reference for developing our own judgement, recognising other possible courses of action and testing action against its consequences.
Coming in 2027 Request an advance copy
Other work
In my other work, I also pursue questions through essays, brief statements and selections with commentary:
-
- Uneven Present: Essays on digital power, vulnerable infrastructures and the fault lines between familiar orders and changed conditions of life, with a foreword by Patrick Riedl.
Read the essays → · View the book →
- Uneven Present: Essays on digital power, vulnerable infrastructures and the fault lines between familiar orders and changed conditions of life, with a foreword by Patrick Riedl.
-
- ÜBERSCHRIFTEN (in German): Prompts for thought in hypermodernity, at the intersection of text and public space. Observations on habits, relationships and self-images.
View the project → · View the book →
- ÜBERSCHRIFTEN (in German): Prompts for thought in hypermodernity, at the intersection of text and public space. Observations on habits, relationships and self-images.
-
- Dilep (in German): Selected links with my own commentary on technology, society and the conditions for action.
Visit Dilep →
- Dilep (in German): Selected links with my own commentary on technology, society and the conditions for action.
Contact
Write me a few sentences about what is involved and the question or decision you are facing. The question need not be fully formed. A document may help make the situation tangible.
In our initial contact, we clarify what you need and whether we are a good fit. Before any commissioned work, we agree on the subject, scope, remuneration, confidentiality and how the engagement will conclude. This also applies to a single working conversation. I am responsible for my professional contribution; the decision remains with the people responsible for it. We agree on further work separately if needed.