Asher's Blog

Leadership can slowly turn one person into an answer desk. Everyone comes into the office looking for something; someone needs a decision about the product. Another person wants approval for an expense. A team member wants to know how to handle a customer. One department wants clarity about a target, while another wants the founder to settle a disagreement. Outside the office, visibility creates another kind of demand. People invite you to speak, send you personal questions and assume that because they have seen your work publicly, you must also possess the answer to whatever they are facing privately.

If you are not careful, you can begin to believe that leadership means always knowing what to say.

I do not personally feel a strong pressure to have an answer to everything, but I know many leaders do. They feel that saying “I don’t know” will weaken their authority. They worry that silence will make them appear unprepared or that asking the team for ideas will suggest they are no longer needed.

I think the opposite is often true. A leader’s responsibility is not to provide every answer. It is to ensure that the right questions are being asked, the right people are thinking and a sound decision is eventually made.

Visibility Creates an Illusion of Omniscience

When people encounter you mainly through public appearances, articles, interviews or social media, they see a compressed version of your life. They hear the conclusions after years of trial and do not see all the uncertainty that preceded them. They see the confidence required to communicate an idea, and they may mistake that confidence for universal expertise.

As your visibility grows, people will ask for opinions on subjects far beyond your competence. Some questions will be thoughtful. Some will be vague. Some will be questions the person could have answered with a small amount of effort. Others will involve decisions so personal that nobody should make them on the person’s behalf.

You have to become comfortable saying:

• I do not know.
• I am not the right person to answer this.
• I need more information before I can form an opinion.
• Speak to someone with the relevant expertise.
• Let me think about it and return to you.

These are not weak answers; they are honest answers. The dangerous leader is not the one who sometimes lacks an answer. It is the one who cannot admit the limits of their knowledge and therefore gives confident direction without sufficient understanding.

Daniel Kahneman’s work in Thinking, Fast and Slow reminds us that confidence and accuracy are not the same thing. Human beings can construct coherent explanations from incomplete information and then feel certain because the story sounds convincing. The phrase he uses is “What you see is all there is.” Good leadership requires resisting that false completeness. Sometimes the wisest answer is a question.

You Do Not Need a Mentor Before You Can Ask a Question

One request I receive regularly is, “Can you mentor me?” The question is understandable, but it is often too broad to produce anything useful. Mentorship is not a magical relationship that transfers wisdom simply because two people have adopted the label. It grows through specific questions, relevant opportunities, repeated conversations and evidence that the person receiving guidance is acting on what they learn.

Instead of beginning with “Will you mentor me?”, ask the question you actually need answered.

Explain what you are working on, what you have already tried and where you are stuck. If you are asking for an opportunity, make the request clearly. Show why the opportunity makes sense and what you can contribute. Make it easy for the other person to understand the decision you want them to make.

A useful request might sound like this:

I am building a payroll product for companies with 50 to 200 employees. We have interviewed 20 employers and found that compliance reporting is their biggest problem. I am deciding whether to build the reporting module first or focus on payments. You have experience in this market; could I ask how you would evaluate that trade-off?

That is more answerable than, “Please mentor me.” It shows preparation, creates a focused conversation and allows a relationship to develop naturally.

You may not need a mentor in the formal sense. You may need one honest answer, one introduction, one opportunity or one piece of feedback—and the courage to ask for it properly.

Learn to Say No Before You Say Yes

One of the most valuable habits I developed from a mentor was the habit of saying no.

I learnt to say no consistently enough that a person asking me to say yes must explain why the request deserves my time, attention or resources. This is not hostility, and it is not a performance of power. It is a method of protecting focus.

Every yes creates an obligation; a meeting occupies time that cannot be recovered. A new product request competes with work already in progress. A speaking engagement consumes preparation, travel and mental energy. A partnership creates follow-up. Even a helpful conversation can become expensive when hundreds of people request it.

Greg McKeown writes in Essentialism, “If you don’t prioritise your life, someone else will.” The same is true of a founder’s calendar and a company’s roadmap. If you do not decide which requests matter most, urgency, visibility and other people’s preferences will make that decision for you.

However, “no” should be a starting position for evaluation, not a permanent refusal to listen. The other person should be able to change your mind with evidence. A thoughtful proposal may reveal an opportunity you had not considered. A team member may understand a customer problem better than you do. The point of saying no first is to prevent a casual yes, not to protect the leader’s ego from being persuaded.

A useful no can sound like this:

I am not convinced yet. Show me the customer evidence, the expected impact, the resources required, the main risks and what we would stop doing to make room for this.

That response does more than reject an idea; it raises the quality of thinking.

Pushback Is Not the Same as Having the Answer

I often push back during discussions. If someone says a goal is impossible, I may ask, “Why is it impossible?” If someone says we can achieve an ambitious target, I may respond, “Why do you believe we can achieve it?” In either case, I am testing the reasoning rather than automatically accepting the conclusion.

This is important because a team can arrive at the correct answer for the wrong reason. It can also reject a valuable idea simply because the first version appears difficult. The founder’s role is not always to choose one side immediately. Sometimes the role is to make both sides think more deeply.

Peter Drucker wrote in The Effective Executive that important decisions are not made well by acclamation, but through the clash of conflicting views. He went as far as arguing that one should not make a decision without disagreement.

Disagreement reveals assumptions; it forces people to provide evidence. It exposes risks that enthusiasm may conceal and possibilities that pessimism may dismiss. A room in which everybody immediately agrees with the leader may feel efficient, but it can be intellectually weak.

The leader has to be careful, though. If every question sounds like a verdict, people will stop contributing. If “Why do you think that?” is delivered with irritation, employees may hear, “You should not have spoken.” Pushback works only when people believe that their ideas are being examined rather than their intelligence being attacked. Challenge the argument while preserving the dignity of the person making it.

Brainstorming Requires a Storm Before It Requires Order

I like the word brainstorming because a storm is not immediately neat. It moves in several directions; it is energetic, unsettled and difficult to control.

That is often how ideas emerge. You explore several possibilities without knowing which one will survive. You allow people to make unusual connections, suggest incomplete thoughts and question assumptions. At that stage, judging every idea too quickly can prevent the group from discovering anything new.

But a storm cannot continue forever. After generating possibilities, the team must move into evaluation. We examine the advantages and disadvantages, customer evidence, cost, timing, strategic fit, operational risk and likely impact. We ask what would have to be true for each idea to work. We identify the assumptions that can be tested and the decisions that can be reversed.

Good brainstorming therefore has two distinct movements:

1. Divergence: produce many possibilities without prematurely narrowing the conversation.
2. Convergence: evaluate the possibilities and choose a defensible course of action.

Teams often damage innovation by mixing these stages. If criticism dominates during idea generation, people offer only safe suggestions. If enthusiasm continues during evaluation, the company may pursue exciting ideas without discipline.

The leader should make the stage clear. Are we expanding the possibilities, or are we deciding? Are we trying to imagine what could work, or are we now testing what should be funded?

When that distinction is understood, brainstorming becomes more than a noisy meeting. It becomes a structured way of turning collective imagination into sound judgement.

Sometimes the Leader Should Speak Last

When you have smart people in the room, one of the most powerful things you can do is refuse to give your opinion too early.

The founder’s view carries weight, even when the founder does not intend to dominate. Once the most senior person says, “I think Option A is best,” the conversation can become an exercise in supporting Option A. People begin editing their thoughts before speaking. Some assume the decision has already been made. Others do not want to appear difficult or disloyal.

By speaking last, the leader gives the team space to develop its own reasoning.

You can begin by asking each person to write down their view before the discussion. You can ask the people closest to the problem to speak first. You can invite the most junior participant before the executives. You can ask for the strongest case against the popular option. You can assign someone to identify what everybody may be missing.

This is not leadership by silence. It is leadership through the design of the conversation.

Ed Catmull describes a related practice in Creativity, Inc. through Pixar’s Braintrust: a group gives candid feedback on work in progress, but the director is not compelled to follow every suggestion. The purpose is not for the group to seize ownership of the solution. It is to expose weaknesses and help the person responsible see the problem more clearly.

That distinction matters. Advice should improve the decision-maker’s vision, not remove the decision-maker’s responsibility.

Build Psychological Safety Without Lowering Standards

If you want people to contribute ideas, they must believe it is safe to speak.

Google’s Project Aristotle studied 180 teams and found that team effectiveness depended less on who was on the team than on how the team worked together. Psychological safety—the belief that a person can take an interpersonal risk without being punished or humiliated—was identified as the most important of the five dynamics associated with effective teams.

Amy Edmondson, whose research established the concept, describes psychological safety as an environment in which people can speak up with ideas, questions, concerns and mistakes. It does not mean that everybody must be agreeable or that poor performance has no consequences. In The Fearless Organization, she writes, “Psychological safety is not about being nice.”

That distinction is essential. A psychologically safe company can still have demanding targets, direct feedback and strong accountability. In fact, high standards require honest information. If employees are afraid to say that a deadline is unrealistic, a customer is unhappy or a product has a serious weakness, the leader may feel respected while the company moves towards failure.

Safety without accountability creates comfort. Accountability without safety creates fear. Growing businesses need both candour and performance.

Hire People Whose Thinking You Intend to Use

There is no point hiring brilliant people and then requiring them to wait for the founder’s answer to every question.

A company does not become stronger merely by placing impressive names on an organisational chart. It becomes stronger when capable people are given context, authority and room to exercise judgement.

This is especially important for growing companies in Africa. The environment is too complex for the founder to become the single point through which every decision must pass. Customers behave differently across markets. Regulation changes. Infrastructure creates unusual constraints. Currency movements affect planning. Products need to work under conditions that may not exist in the markets from which many management ideas were imported.

No founder can understand all of this alone. You need excellent people in product, engineering, sales, customer success, finance, compliance and operations. Then you need to let those people think. Give them the outcome, the constraints and the relevant information. Ask them to return with options, evidence, risks and a recommendation—not merely a problem for you to solve.

A useful delegation framework is:

• Here is the outcome we need.
• Here are the non-negotiable constraints.
• Here is the information currently available.
• Tell me what you recommend and why.
• Tell me what you need from me.

This moves the team from permission-seeking to responsible ownership.

Replace Answer Dependency With Decision Capacity

If everybody comes to the founder for answers, the problem may not be that the employees lack initiative. The organisation may have trained them to depend on the founder.

Perhaps previous decisions were reversed without explanation. Perhaps people were punished for taking reasonable risks. Perhaps responsibilities are unclear. Perhaps the founder insists on approving every detail and then complains that nobody takes ownership.

The solution is not simply to tell people, “Think for yourselves.” The company must build decision capacity.

Start by clarifying which decisions employees can make independently, which require consultation and which must be escalated. Explain the principles behind previous decisions so that people can apply them to new situations. After important decisions, conduct reviews that examine the reasoning and result without turning every mistake into blame.

You can also change the questions you ask when someone brings a problem:

• What do you think is happening?
• What options have you considered?
• What does the evidence suggest?
• What would you recommend if I were unavailable?
• What is reversible, and what would be difficult to reverse?
• What is the downside if your recommendation is wrong?

Over time, people learn that bringing a problem means participating in the solution.

The objective is not to make the founder unnecessary. It is to ensure that the founder’s attention is reserved for decisions that genuinely require it.

Knowing When the Leader Must Answer

There are moments when “I want the team to decide” becomes an avoidance of leadership.

Some decisions belong to the leader. Questions involving values, existential risk, major capital allocation, senior appointments, legal exposure or the fundamental direction of the company cannot always be delegated. After listening to the relevant experts and hearing disagreement, somebody must take responsibility. The leader may not possess certainty, but must still provide clarity.

This is the difference between having every answer and owning the final decision. You can say:

I do not know with certainty which option will succeed. I have listened to the evidence, understood the risks and decided that this is the direction we will take. Here is why, here is what we will monitor and here is what would cause us to reconsider.

That is not pretending to know the future; it is responsible leadership under uncertainty.

Once the decision is made, the team should execute with unity, even if reasonable people preferred another option. Debate should be open before the decision and commitment should be clear afterwards. Otherwise, endless discussion becomes another way to avoid action.

The Freedom of Not Knowing

The pressure to always have an answer can turn leadership into performance. You begin speaking because silence feels dangerous; you say yes because disappointing people feels uncomfortable. You offer advice because visibility has created an expectation of wisdom. You solve problems your employees should learn to solve and eventually become the bottleneck in the company you are trying to grow.

There is another way. Say no when a request has not earned a yes. Allow evidence to change your mind. Ask questions that force ideas to become clearer. Separate brainstorming from evaluation. Speak last when your early opinion would distort the room. Hire brilliant people and create enough safety for them to disagree with you. Give them authority that matches their responsibility. Admit when you do not know, and consult people who do.

Then, when a decision truly belongs to you, make it. The strongest leader in the room is not necessarily the person with the quickest answer. It may be the person secure enough to create space for a better answer to emerge.

References

• Amy C. Edmondson, The Fearless Organization
• Daniel Kahneman, Thinking, Fast and Slow
• Ed Catmull with Amy Wallace, Creativity, Inc.
• Greg McKeown, Essentialism: The Disciplined Pursuit of Less
• Peter F. Drucker, The Effective Executive
• Google re, Understand Team Effectiveness