I remember sitting in a management meeting early in my career while the finance department presented its debtors book. The familiar complaints followed. Customers were taking too long to pay. Collections were difficult. Outstanding invoices were becoming a problem.

For reasons I could not understand, the finance team seemed reluctant to engage directly with the accounts departments of our clients. Instead, department heads were being asked to help with collections. I was expected to chase money that finance said our clients owed us.

I reluctantly took on the task. I started calling clients, working my way to the people who handled their accounts, asking for statements and requesting remittance slips so we could establish which invoices were still outstanding.

What happened next was embarrassing. The clients I contacted told me the invoices I was chasing had already been paid.

I went back to finance. Had they reconciled the accounts? Had anyone checked the bank statements against the invoices listed as unpaid?

I asked them to pull out their files. We went through the statements line by line, matching payments to the corresponding invoices. The money had come in. Our records did not accurately reflect the position.

I was furious. I never took up that collections responsibility again.

Mistakes happen in accounting. Payments can be misallocated, references can be unclear and reconciliation can uncover genuine discrepancies. What bothered me was how far this issue had travelled before anyone checked the underlying records. We had taken a debtor listing into management meetings, assigned work on the strength of it and involved customers before establishing whether the claims were correct.

The questions that should have come first were basic. Were the invoices actually unpaid? If the records disagreed, where was the discrepancy? And why were we asking clients to help us resolve a problem that might have been sitting in our own books?

I had seen what competent work looked like

Before university, I had worked as an accounts assistant. It was my first formal employment, and the accounts department was a well-oiled machine. That experience gave me a benchmark for what I considered ordinary professional diligence.

So when I encountered the situation I have described, I struggled to understand how a department could repeatedly discuss a problem without first doing the work needed to establish what the problem actually was. Why were we relying on customers to answer questions that might have been resolved by reconciling our own books? Why did it take someone from another department to insist on checking the bank statements?

I saw versions of the same pattern elsewhere. Details went unchecked. People waited for instructions when a first investigation was possible. A problem was identified, explained and escalated, but nobody seemed especially compelled to work through it. The comfort with leaving things unresolved baffled me.

I have also had to consider my own part in those experiences. I was early in my career. I had a great deal to learn about managing people, setting expectations and motivating colleagues. Perhaps I sometimes assumed that what seemed obvious to me would be obvious to others. Perhaps I could have explained the purpose of a task better, taught a process more patiently or found a more effective way to encourage initiative.

Those are fair questions, and I cannot rule out shortcomings in my management style. But I had also seen colleagues come to me voluntarily for advice or ask me to show them how I approached a task. They would take the advice, try it and put what they had learnt into practice. That did not prove my management was beyond criticism, but it made it difficult to explain every frustrating encounter as a failure to teach or motivate.

The contrast I was trying to understand was between people who engaged with a problem, asked questions and applied what they learnt, and people who appeared to stop at describing the problem. I could not work out why that difference was so pronounced.

The school subject that came back to me

During my British-curriculum education, I studied a subject called Thinking Skills. The name has stayed with me because the work was about something fundamental: examining information, testing arguments, identifying assumptions and solving problems when the answer was not immediately obvious.

Cambridge International's AS & A Level Thinking Skills syllabus is one formal example of the subject. It combines critical thinking with problem-solving. Students learn to evaluate reasoning and evidence, analyse unfamiliar problems and make informed decisions. I cannot say from the name alone that Cambridge 9694 was the exact syllabus I studied, but it is a useful reference point for what Thinking Skills is intended to develop.

In the finance example, critical thinking meant questioning the claim that customers owed money. Problem-solving meant gathering the available evidence, checking the transactions and tracing the discrepancy. The records had to be tested rather than accepted simply because they appeared in a report from the department responsible for them.

That sounds elementary when written down. But it brought me to a distinction I have been turning over for years: knowing how to think and choosing to apply that ability are not the same thing.

Doing the task is not always the same as owning the problem

My work as a business intelligence analyst put that distinction in front of me repeatedly. Business intelligence is supposed to turn information into insight that can inform decisions. Producing a technically correct report is important, but it is not the whole job. An analyst also needs to notice when a number does not make sense, ask what is missing, test alternative explanations and understand the decision the analysis is meant to support.

There is a difference between receiving a request for a report and understanding the decision behind it. There is a difference between repeating a figure and checking whether it is meaningful. And there is a difference between identifying a problem and investigating it until you can explain the cause and suggest what to do next.

These differences are not reducible to intelligence. Someone can be bright but passive, energetic but careless, or curious but short on the technical skills required to make progress. Some people need better training or clearer authority. Others have the necessary skills but prefer to wait for instructions. From the outside, those situations can look similar. They do not call for the same response.

What frustrated me was the repeated failure to take responsibility for the thinking that a task already required. I was not expecting everyone to behave like a business founder or to donate their personal time to an employer's ambitions. I was expecting people to check their work, investigate discrepancies and use the judgment appropriate to their roles.

Then I started paying attention to entrepreneurs

One reason I remained interested in business intelligence was my exposure to entrepreneurs and businesspeople. I was fascinated by how many of them approached problems. They looked for information, asked questions, noticed opportunities and kept working at an issue without waiting for somebody to assign every next step.

My impression was that the commercial consequences of a decision made some things harder to ignore. A missed opportunity might disappear. A mistake could cost real money. An unanswered question could prevent a deal from moving forward. There was often a direct connection between noticing something and having a reason to act on it.

That contrasted with some of the workplace behaviour I had experienced. I would watch a business owner chase down information, challenge assumptions or try a different approach, while other colleagues seemed content to report a problem and wait for someone else to solve it. I found the difference intriguing, and it helped keep me interested in the work.

Still, I would not conclude that entrepreneurs are inherently more capable or more hardworking than employees. Business ownership selects for certain kinds of risk-taking and puts different pressures on people, but it does not guarantee good judgment. Plenty of entrepreneurs make avoidable mistakes. Plenty of employees show outstanding initiative and ingenuity. My observations were not a representative study of either group.

The question that interested me was narrower: what made some people more likely to investigate, learn and act, while others seemed comfortable passing the problem along?

A Stanford seminar asks a related question

That question came back to me when I read The Stanford Daily's 21 May 2026 report on “So You Think You Can Rule the World?”, an informal seminar run by Stanford alumnus Justin Lewis-Weber.

The article describes a selective, ten-week group in which a dozen students discuss topics including money, power and what makes a life worthwhile. The reported teaching format starts with a short presentation and moves into a Socratic-style debate. Lewis-Weber describes the course as an effort to understand the incentive structures and frameworks that govern how the world works.

Students interviewed by the newspaper talked about mental models, selecting important problems and finding ways to generate results that compound over time. The report also mentions entrepreneurship, guest speakers on negotiation and startup law, and the idea of multipolar traps: situations in which individuals or organisations follow their own incentives but collectively produce a worse outcome than cooperation would have produced.

The seminar's exclusivity and emphasis on influential networks have drawn criticism, and some students characterised its approach to power and opportunity as overly opportunistic. It is worth keeping that tension in view. The reporting does not provide a full public syllabus, and the existence of an elite seminar is not evidence that its participants have discovered a superior formula for life.

What interested me was the broader focus on seeing the systems behind the immediate problem. Who has an incentive to act? What behaviour does the existing arrangement reward? Which problem is actually worth solving? What would change if you addressed the cause rather than treating the symptoms?

In the finance department, the immediate problem was supposedly late payment. A more careful look showed that at least some of the supposed debts had already been settled. We were trying to solve the wrong problem because the records had not been tested against the evidence.

Initiative is affected by more than personality

Personality is one possible lens on these differences. The Big Five model describes five broad dimensions of individual variation: openness to experience, conscientiousness, extraversion, agreeableness and neuroticism. Some facets may sound familiar in the behaviours I was noticing. Conscientiousness, for example, is associated with dependability and orderly follow-through, while openness is associated with curiosity and receptiveness to ideas. But personality traits do not neatly divide people into proactive and passive camps, and they cannot explain a particular workplace incident on their own.

Research finds associations between personality traits and different measures of performance, but the strength of those relationships varies by trait and outcome. A synthesis of 54 meta-analyses found conscientiousness had the strongest overall association in the review, while also documenting variation across performance categories. That is a useful reminder to take personality seriously without treating it as destiny.

Research on proactive behaviour at work adds another useful angle. A meta-analysis published online in 2025 and included in the Journal of Organizational Behavior's 2026 volume examined 308 independent studies involving 107,084 participants. It looked at motivational conditions associated with people taking action at work, including whether they believe they can act effectively, have a reason to act and feel energised to act.

The research does not mean that every instance of passivity can be blamed on management or workplace design. Individual differences matter. So do skills and habits. But the findings are a reminder that initiative is influenced by context, not just by a person's presumed character.

Consider an employee who identifies a problem but has learnt that raising it brings extra work without recognition, or that proposing a new approach is treated as insubordination. They may eventually stop speaking up. A manager can demand initiative while creating conditions that make initiative feel unwise.

There is another side to this. Sometimes an employee has adequate support and a clear responsibility, but still does not check the work or follow an issue through. Management has to distinguish between a skill gap, unclear expectations, weak incentives and unwillingness to do the required work. Calling everyone lazy may express frustration, but it is a poor diagnosis.

Three things that should not be confused

I have come to think about this as three related but separate questions. Can someone reason through the problem? Will they take the initiative to act on it? And can they follow through carefully enough to produce a reliable result?

Thinking Skills gave me a way to approach evidence and arguments. My early work managing people exposed the difficulty of getting others to apply that discipline consistently. Business intelligence showed me how much depends on asking the next question rather than stopping once a task has technically been completed. The entrepreneurs I encountered made me curious about how incentives and personal responsibility shape that willingness to continue.

It also left me with some questions about my own role as a manager. Could I have communicated expectations better? Could I have made it easier for people to take initiative, taught certain tasks differently or offered more useful feedback? Probably, in some situations. I do not think that possibility explains everything I observed, particularly when other colleagues sought advice, learnt the method and acted on it. But it is a reminder that managers should examine the environment they create as well as the performance they criticise.

What kind of entrepreneur are you, and how do you respond to problems?

At BizInfo Africa, we explore how people build businesses, make decisions and navigate the realities of running them. If these questions have made you curious about your own tendencies, take our free Entrepreneur Type Test. Treat it as a prompt for reflection rather than a verdict on your potential. A test can help you examine patterns, but it cannot replace experience, feedback or the hard work of changing a habit.

I still think about that debtors book. What frustrated me was not simply that mistakes had been made. It was the willingness to let an unverified claim travel through the organisation, become a management problem and reach customers before anyone checked it. I also think about the people who did ask questions, learnt a new approach and applied it, because they showed me that the alternative was entirely possible.

Perhaps the most useful question is not whether people are naturally proactive or passive. It is what they do when they encounter a problem, what prevents them from doing more, and how much responsibility they believe they have for the outcome.