I spend my working life inside two kinds of documents: management accounts and strategies. And after enough years of both, a pattern becomes impossible to ignore. When a business stalls, the explanation is almost never missing from the numbers or the plan. It is sitting in the leader: something unexamined, unsaid, or unfaced, quietly reproducing itself through every decision, every meeting, and eventually every line of the income statement.
The numbers are the vital signs. The strategy is the map. But the leader is the system that produces both, and most leaders have never turned their considerable analytical firepower on themselves.
The spark: a list worth sitting with
The coach Joe Hudson, whose Art of Accomplishment work I rate highly, recently published a list of what he calls 21 highly psychoactive questions: three decades of self-inquiry distilled into prompts designed not to be answered quickly but to be sat with until they open something. One of them has followed me around since I read it: "What are you pretending to not know?"
His warning applies to everything that follows here: skim the questions and nothing will happen. Slow down with one, in writing, and you will find things. I will not reproduce his list; it is his work, and it deserves to be read whole on his page. What I want to do instead is bring that style of inquiry to the specific territory where I work: the leadership of a real business, with payroll, customers, funders, and a family depending on it.
Why questions, and not advice
Because advice bounces off a leader who has not yet seen the thing the advice is about. Every experienced advisor learns this the hard way: you can hand someone the right answer for two years and watch nothing change, then watch them transform in a month once they finally ask themselves the right question. Self-awareness is not a soft skill bolted onto leadership. It is the control panel. How a leader sees themselves determines what they can see in their people, and what the two of them together can see in the strategy.
That is the logic of the triad I build all my work around: Self, Selves, Strategy. So here are fifteen questions, five for each, written for owners and executives of real businesses. Treat them the way Hudson prescribes: one at a time, slowly, ideally in a journal. Not all fifteen in one sitting.
- Which number in your business do you avoid looking at, and what is the avoidance costing you?
- What decision have you already made that you are still pretending to weigh?
- If you could not blame the economy, the government, or your team, what would be left to explain your results?
- What are you busiest with that you know, quietly, is not the real work?
- Which of your strengths has become the business's bottleneck?
- What conversation are you not having, and what is it costing the people who can feel you not having it?
- Who in your business knows something important that you have made it unsafe to say?
- If your team described what it feels like to bring you bad news, what word would they use?
- What do you keep doing yourself because explaining it feels slower, and what has that trained your team to believe about themselves?
- Whose growth are you blocking by being too good at their job?
- If you started again today, knowing everything you know, which parts of this business would you not rebuild?
- Which customers would you not take on again, and why are you still serving them?
- What would have to be true for your biggest bet to be wrong, and how would you know it had happened?
- Where does the money say your strategy is, regardless of what the slide deck says?
- What are you measuring because it is easy to measure, instead of what actually matters?
What this has to do with effectiveness
Everything, and measurably so. Question 1 is why management accounts go unread and problems compound for two extra quarters. Question 6 is why strategies die in the gap between the executive team's meeting and the floor. Question 12 is usually worth more margin than any cost-cutting exercise. These are not philosophical luxuries for the week after year-end; they are the shortest known route to the operational problems underneath the operational problems.
Hudson's deeper point, and the reason his work resonates with mine, is that what a leader refuses to look at does not stay private. It becomes culture, then it becomes process, then it becomes the numbers. The discipline of honest self-inquiry is to a leader what monthly management accounts are to a business: an unglamorous practice of looking, regularly, before looking becomes unavoidable.
Questions are better with a witness
There is a limit to solo inquiry, and every honest practitioner admits it: we are all fluent in deceiving ourselves. The questions that would change your business most are precisely the ones your own mind is best organised to avoid. That is not a flaw in you; it is how minds work. It is also why the leaders I most admire all have some version of the same thing: a person outside the org chart who can hold the spreadsheet, the room, and the person at the same time, and who has permission to ask the question you have been circling.
Work the questions with a thinking partner
My Thinking Partner sessions are exactly this: structured, confidential 1:1 work on the decisions only you can make, from R12,500 per month, covered by the net-gain guarantee. Or start smaller with a free 30-minute conversation.
Book your free intro callIdeas that shaped this piece: Joe Hudson's "21 highly psychoactive questions" and the wider Art of Accomplishment body of work, which I recommend reading in full. The fifteen questions above, their business framing, and any errors, are my own.