Asher's Blog

One of my core leaders at Eazipay asked me a question that made me think: what goes on in my mind that enables me to be so decisive?

The simplest answer is that I believe you are, to a significant extent, the decisions you make and the outcomes those decisions repeatedly produce. If I do not like an outcome, I have to decide to do something differently. If I try an approach and it does not work, I need to decide what to try next. If an important matter has remained pending for too long, the question I ask is not merely why it is difficult, but what decision has not yet been made.

This does not mean that every outcome is within our control. Markets change, people disappoint us, currencies move, regulations arrive and unexpected events can overturn a well-reasoned plan. It also does not mean that every unsuccessful outcome proves that the decision-maker was foolish. A good decision can produce a poor result because probability and uncertainty are real.

The deeper point is that a leader cannot surrender the responsibility to respond. We may not control what happened, but we still have to decide what happens next.

Every unresolved problem contains a delayed decision

When something important is not happening, I try to locate the decision hidden inside the delay. Why has this role not been filled? Why has the product not launched? Why has the customer not signed? Why is performance still weak? Why is an unproductive project consuming money? Why is an agreement waiting on someone’s desk?

Sometimes the answer is that more information is genuinely required. Sometimes the business is waiting on a regulator, customer or partner whose timeline it cannot control. But a surprising number of pending issues exist because nobody has decided who owns the next action, what standard will be used or when waiting must end.

A leader can say, “We are still considering it,” for months, while the organisation quietly pays the cost of uncertainty. Employees create their own interpretations, resources remain committed, opportunities expire and the people closest to the work stop believing that management will act. Indecision is not neutral. It is a decision to preserve the current situation, whether or not the leader admits it.

This is why I ask direct questions. What are we doing? What outcome are we pursuing? What information would change the decision? Who is responsible for obtaining it? By what date will we act? If we do nothing, what will it cost?

The purpose is not to make people anxious. It is to convert a vague problem into a choice the organisation can execute.

Decisiveness is not certainty

Some people delay because they believe a decisive leader must know that the answer is correct before acting. In business, that standard is impossible. Most consequential decisions concern a future that has not happened, and the information available will always be incomplete.

Decisiveness means forming the best judgement possible from the purpose, facts, experience, counsel and time available, then accepting responsibility for the choice. It is not pretending to possess certainty. In fact, a leader who recognises uncertainty can often act more intelligently because they define what the decision is intended to test.

Annie Duke, in Thinking in Bets, explains the importance of separating decision quality from outcome quality. If a carefully evaluated decision had an 80 per cent probability of success, failure does not retrospectively make it irrational; the 20 per cent possibility was always present. Conversely, a reckless decision can succeed through luck without becoming a sound process.

This distinction protects leaders from two errors. The first is becoming paralysed after one failure because they assume the failure proves they cannot judge. The second is becoming overconfident after one success because they assume the result validates everything they did.

I want to review both the decision and the outcome. What did we know at the time? Which assumptions were reasonable? What did we ignore? What happened that we could not have predicted? Which part of the process should be repeated, and which part should change?

That is how decisiveness becomes a learnable discipline rather than a personality trait.

I meditate, think and pray before consequential decisions

For me, decisiveness is not a celebration of speed for its own sake. When I need a better outcome, I meditate, think and pray. I try to remove the noise around the problem, face the facts and ask the Holy Spirit for wisdom. I read, seek counsel from people who understand the issue and give my mind enough space to see alternatives that pressure may have hidden.

Prayer does not remove my responsibility to investigate, calculate or act. It helps me bring the decision before God, examine my motives and develop the peace to proceed. Sometimes what appears to be a business problem is an emotional attachment, fear of disappointing somebody or reluctance to admit that a previous decision no longer works. Quiet reflection can expose that.

Thinking should lead to clarity, and clarity should eventually lead to action. Meditation can become another form of avoidance if I keep revisiting the same facts after the relevant answer has emerged. There is a point at which the leader must stop asking for a feeling of absolute certainty and move with the conviction available.

The biblical book of James says that if anyone lacks wisdom, they should ask God, who gives generously. I believe that. I also believe wisdom often arrives as a practical next step: speak to this person, examine this number, stop this project, apologise, hire differently, wait for a defined period or try another route.

The pace of intelligent retries matters

Sometimes a decision does not produce the desired outcome, even after serious thought and prayer. The next responsibility is to learn and try again. A founder’s advantage is often not that they avoid failure, but that the interval between one failed attempt and the next intelligent attempt is short.

If the pace of retries is too slow, failure becomes expensive and visible. The company continues paying salaries, rent, infrastructure and opportunity costs while leadership remains attached to an approach that has stopped producing evidence. By the time the team finally tries something different, cash, energy and trust may already be depleted.

When retries are fast, the organisation can test several plausible routes before one unsuccessful assumption threatens the company. The first sales message may not work, so the team changes the segment or proposition. A product flow may confuse users, so the company observes them and redesigns it. A partnership may stall, so leadership pursues alternatives rather than waiting indefinitely for one powerful person to respond.

Speed should come from reducing the size and cost of each test, not from repeatedly gambling the whole company. A fast retry is valuable when it incorporates what the previous attempt taught us. Repeating the same action with more emotion is not perseverance; it is refusing to learn.

The military strategist John Boyd’s Observe–Orient–Decide–Act loop offers a useful way to think about this. The organisation observes reality, interprets it in context, makes a decision, acts and then returns to observation as new information appears. The advantage belongs not merely to the person who moves fastest, but to the one who completes this learning cycle more effectively than the environment changes.

Make reversible decisions quickly

Not every decision deserves the same amount of time. Jeff Bezos has written about distinguishing between decisions that are difficult to reverse and those that can be changed. The principle is useful because organisations often subject reversible choices to the same process as decisions that can permanently damage the company.

A reversible decision might include testing a marketing message, changing the order of an onboarding flow, running a small pilot, trying a new meeting format or using a limited budget to test a sales channel. These decisions should usually be made close to the work and reviewed through results. Waiting for perfect consensus destroys the advantage of experimentation.

An irreversible or difficult-to-reverse decision deserves more scrutiny. Issuing a large amount of equity, taking debt secured by critical assets, entering a co-founder relationship, selling the company, handling customer funds, making a senior leadership appointment or signing a long-term exclusive agreement can alter the company’s future. These decisions require due diligence, independent counsel, downside analysis and appropriate governance.

Even here, decisiveness remains important. Careful does not have to mean endless. The leader should define the information needed, the people who must be consulted and the date on which the decision will be made. Otherwise, “This is important” becomes an excuse for permanent delay.

Decide the downside before you decide the action

One practice that helps me move is thinking about the worst credible outcome. If this decision goes wrong, what happens? Can the company recover? How much money, time or trust is at risk? What early warning would tell us to stop? What action can limit the loss?

When the downside is small and reversible, it becomes easier to act quickly. When the downside could threaten the company, the decision can be redesigned. We can reduce the initial commitment, run a pilot, add a termination clause, require milestones, split the investment into stages or protect the most important asset.

This is not pessimism. It is how ambition becomes survivable. A founder can pursue a large opportunity while structuring the first step so that one wrong assumption does not end the journey.

Scenario planning also prevents the team from being shocked by outcomes that were entirely foreseeable. What will we do if sales take twice as long? What happens if the currency depreciates? What if the new leader does not perform? What if the investor delays? The answer does not have to be perfect, but considering it creates options before pressure narrows them.

Put a deadline on waiting

Some decisions involve another person whose answer we cannot force. An investor may promise a cheque, a customer may say procurement is almost complete, or a partner may keep asking for another week. Waiting can be reasonable, but dependence on one uncertain answer is dangerous.

I have learned to put a deadline on waiting and pursue alternatives in parallel. If the preferred route works, that is good. If it does not, the company has not surrendered months of momentum. A person who has promised support cannot become the only means through which the business survives.

This applies inside the company too. When an employee is struggling, the leader should provide feedback, support and a defined period for improvement. When a project is uncertain, the team should agree on the milestone that earns further investment. When a product is not gaining traction, the company should define what evidence would justify continuing, changing or stopping it.

A deadline changes hope into a decision process.

Decisive leaders need people who can disagree

There is a danger in becoming known as a decisive leader: people may stop challenging you. They may assume your confidence means the discussion is over, or they may bring only information that supports what they think you already want.

That makes the leader weaker. Decisiveness should not eliminate debate; it should give debate a purpose and an end. Before a significant decision, I want capable people to present facts, alternatives, risks and disagreements. I want the person closest to the problem to speak, and I want leaders to interrogate one another’s assumptions.

Once the appropriate decision-maker acts, the team should understand the choice, the reasoning and the conditions under which it will be revisited. People can disagree and still commit to execution. If the decision later proves wrong, the organisation should not punish the person who raised the concern or pretend the earlier debate never happened.

Ray Dalio’s Principles discusses the value of thoughtful disagreement and an environment in which ideas are tested against reality. I do not believe every company must copy Bridgewater’s culture, but the underlying lesson is useful: strong decisions improve when truth can travel towards the leader without fear.

Delegation is part of decisiveness

A company cannot become decisive if every decision requires the founder. The founder may move quickly personally while the organisation becomes slow around them. This often happens when decision rights are unclear or when employees fear being blamed for a reasonable choice that produces an imperfect outcome.

Leaders should specify which decisions belong to which roles, the limits within which people can act and the circumstances that require escalation. A marketing leader should not need the chief executive’s permission for every experiment within an approved budget. An engineering leader should be able to resolve technical trade-offs within agreed reliability and security standards. A customer-success leader should know what remedies can be offered without seeking approval each time.

The founder should remain close to decisions that shape purpose, capital allocation, senior leadership, major risks and the product’s most consequential direction. Other decisions should move towards the people with the best information.

This requires tolerance for responsible mistakes. If employees are criticised whenever an experiment fails, they will return every choice to the founder. The standard should be whether the decision followed the agreed process, respected the limits, used the available evidence and produced learning—not whether every uncertain action succeeded.

Measure decision velocity, not performative urgency

A fast organisation is not one in which everybody appears busy or every request is labelled urgent. Performative urgency exhausts people and makes priorities indistinguishable. Decision velocity is the speed with which important uncertainty is converted into responsible action and learning.

I would examine how long major issues remain open, how many approvals ordinary work requires, how quickly experiments produce usable evidence, and whether teams revisit decisions when the underlying assumptions change. If the same issue appears in five consecutive leadership meetings without a named owner and deadline, the organisation is not being careful; it is avoiding responsibility.

Written decision records can help. For a consequential choice, record the objective, facts, assumptions, options, decision-maker, expected outcome, risks and review date. This prevents the company from rewriting history and allows leadership to improve its judgement over time.

It also separates a decision from the ego of the person who made it. When evidence changes, updating the decision becomes evidence of intelligence rather than an admission of weakness.

Your life reflects accumulated decisions

The principle extends beyond business. If something important has not happened in our lives, we should ask whether we have truly decided to pursue it. Desire is not the same as decision. A decision rearranges time, attention, money and behaviour.

If I decide to become healthier, the decision should appear in what I eat, how I exercise and what I permit in my schedule. If I decide to deepen my relationship with God, it should appear in prayer, meditation, study and obedience. If I decide to build a great company, the decision should appear in the people I hire, the customers I listen to, the capital I protect and the difficult actions I stop postponing.

This does not mean that effort guarantees every dream. It means that our repeated choices are among the strongest forces shaping the outcomes available to us. We become decisive when we stop treating decisions as statements and begin treating them as commitments expressed through action.

The goal is not to hide failure

When I say the pace of retries should be fast enough that failure is not evident, I do not mean founders should conceal mistakes, manipulate reports or create the appearance that nothing went wrong. Transparency matters, especially with employees, investors, customers and regulators whose interests are affected.

What I mean is that the organisation should respond so quickly and intelligently that one unsuccessful attempt does not become its defining condition. Customers may see that a feature needed improvement, but they also see the company fix it. Investors may see that a channel failed, but they see disciplined capital allocation towards a better one. Employees may see leadership reverse a decision, but they also see that facts matter more than pride.

Failure becomes dangerous when it remains unexamined, unfunded or uncorrected for too long. A strong company does not pretend failure never happened; it metabolises failure into learning before the loss consumes the resources required for another attempt.

Decide, learn and decide again

What enables me to be decisive is not the belief that I will always be right. It is the belief that remaining passive will not create the outcome I want, and that I can seek wisdom, make the best decision available, observe the result and decide again.

When the decision is reversible, I prefer to test it quickly. When it is consequential and difficult to reverse, I slow down enough to examine the downside, obtain counsel and protect the company. In both cases, I put a limit on waiting and accept responsibility for moving the matter forward.

The founder’s job is not to eliminate uncertainty. It is to prevent uncertainty from becoming permanent paralysis. We think, pray, meditate, ask questions, confront the facts and act. When reality gives us new information, we do not defend yesterday’s decision as though our identity depends on it. We learn and try something better.

Over time, this creates a company that can survive its mistakes because it notices them early, responds without ego and preserves enough time and cash to continue. The individual decisions matter, but the larger advantage is the system: a disciplined rhythm of seeking wisdom, acting responsibly and retrying intelligently.

You are not only the decisions that worked. You are also what you chose to do after the decisions that did not.

Further reading

• Annie Duke, Thinking in Bets, on decision quality, probability and learning without hindsight bias.
• Jeff Bezos’s 2015 shareholder letter, on distinguishing reversible decisions from decisions that require greater care.
• Robert Coram, Boyd, on John Boyd’s thinking and the Observe–Orient–Decide–Act loop.
• Ray Dalio, Principles, on thoughtful disagreement, decision systems and learning from reality.