When to give up on waiting for someone. A leaders’ dilemma.

I was having a whole ship full of anger after I met Ruben1, one of my coachees. Instead of revolting the room like a child in the throes of a tantrum, I decided to call my coach. The coach listened to my ranting and answered: “It’s up to you to decide when it’s worth wasting time with someone. As a leader, you are not supposed to wait forever.”

I stood quiet for a while. I don’t remember the rest of the conversation, but the hypothesis that I could be enabled to decide whether to insist or not on someone’s growth has been haunting me since then.

I have always considered myself a leader capable of seeing latent potential in others. And I chose as my mission to empower people to make the world a better place. 

I could have seen right or wrong in Ruben, and I could have chosen a good mission or not. In any case, it was not working.


What is leadership about?

Being a leader is the transparent act of giving myself to a cause. That is to care about the success of the people whom I lead. 

The concept of a leader’s total dedication to other people could appear as a self-elimination act. Indeed, it has a utilitarian purpose: the leader’s success depends on how many people one can engage in the same direction2

To a self-centered person (and everyone is), shifting the entire focus to others is controversial. And it may seem like a heavy lift. However, it could be split into a succession of small steps. These steps are experiments on how people learn because learning equals improvement. 

Learning the wrong way leads to improvement in the wrong direction. 

As a matter of fact, leadership is all about:

  • Setting the right direction for a group of people
  • Observing how people fit in this direction
  • Sharing the goals tailor-made for each one.
  • Negotiating on the circumstances that would lead to meeting the goal
  • Doing a succession of experimentations in short periods that would narrow your people to your great direction.

While the succession of steps is simple, I experienced in the pores of my skin how challenging it could be to act as a leader every day. 

So here is what I learned, how to resolve a leader’s issues with productivity and why it is crucial.


It’s all up to you

Back to the day of our story, this coachee wasn’t delivering what we expected—for the third day in a row.

In coaching, the coachee is the main responsible for setting and meeting the goal. The purpose of the process is to take action for the proper goal outside of the person you are working with. 

Ruben set his own goal. To meet it, he chose the next experiment: creating, printing, and attaching a simple Excel table to our coaching board. 

I prefer in-person coaching meetings by far because we can use our bodies to be involved. The coaching method I apply is based on Toyota Kata3: it requires an A0 paper board to track our experiments, which always brings to mind the final goal. Those days we were working to grasp the current situation deeper. 

The first day he missed it because of some issues.

The day after, he said he was not having enough time. “Is it important to you?” I asked. The closed question, closed answer: “Yes”. “So you said you didn’t have time. But how much time would you need for this task?”—I urged. “Mmh. Maybe something around 10 minutes.” was the answer. I resisted the temptation to lift my tone of voice. If it was important for him and for the company, why is it so hard to protect just 10 minutes to complete this one task?

He declared he wouldn’t miss it again. And he did it.

On the third day, I couldn’t cope with it in a calm way. I closed the coaching session, asking Ruben specifically to deliver the action, and I left the room to call my coach. Do you see the vicious cycle?

Then my coach (the so-called “second coach”) told me something unexpected: that I can decide if someone is worth my attention as a leader if it is not committed. Back in time, this concept made me feel a burden to carry. I relied a lot upon my “why” to make decisions. Because I wanted to activate Ruben’s potential, it was logical for me to wait for him, as it is that the sun rises in the sky every day.

Having to “decide” to go against my way of acting was inefficient and outside of my expectations.

If it was the duty of a leader to set goals, define roles, ask for commitment, and verify how and how much a goal is met, how can I step down and let chaos reign as the master of bad results?


How to resolve leaders’ productivity issue

My coach was right: the decision to insist or not was up to me. After some days had passed, I understood that while it was certainly my role to define goals and evaluate the commitment, it was my fault for misjudging the people I was leading.

Indeed, I made a mistake. I had the wrong expectations when I started this leadership journey with Ruben. And look, he decided to apply in the same journey, so we share the fault of having set expectations that were too high. But I can only guarantee for myself, and as a leader and entrepreneur, I am the one who is, by definition, the most committed to the final result.

At that precise moment, I learned something that obsesses me: leaders have a productivity issue because they don’t apply systems to how they lead.

There is a more efficient way of leading people, and unfortunately, it is not meant to be easy: when you are managing someone, you have to set rules, expectations, and a cultural system that fits with you. That could be resonant with you.

Teaching moment - The best system to lead.

I have experienced a specific succession of actions that have made me more efficient (and effective) in leading people.

The main duty of a leader is to set goals and build a reliable system to meet them.

Look around and observe how the goals fit the current 4M+E framework, thus, men, methods, materials, machines, and the environment. About people, who they are, and how they act to meet their goals.

Define the specific expectations you have for each person. When it comes to people, make it clear, reachable, and right for them. 

Share your expectations with everyone, get feedback, and negotiate. This process is called catchball. You are exchanging information like a father launching the ball on the grass field to his kids.

Schedule an experiment and verify the outcome. Here an experiment is a person doing a task. Focus with a spyglass on what went differently from your expectations. After setting goals, understanding why and learning it is your main task as a leader.

Repeat the cycle or abandon it.

I sorted out what went wrong with Ruben: we shared ideas, but we didn’t engage to the level of our expectations. And because of not sharing expectations, we didn’t open a negotiation on these expectations, and eventually, we didn’t engage in the same direction. 

We were looking, apparently, for the same problem. But with a perspective that was as different as the panorama from a mountain rather than a beach. 

I knew what I expected from an associate to meet goals on an executive level. Ruben knew his expectations from a line manager. The effect was catastrophic.

As a leader, I often experience sinking problems, things that happened and in which I feel I have to act here and now. Each time, I choose between extinguishing the fire in the first person or calling for the firemen. 

Have you ever tried to dial the emergency number? It’s annoying that you have to provide detailed data. It appears that you are losing a vast number of seconds, which could lead to saving the situation. We don’t want to lose time. But we are speaking with someone who ignores what we know and needs us to be fast and efficient to clarify the facts. Without good preparation, you risk completely missing the goal. 

Well, the same applies to me. I prepared something, but I didn’t dedicate the right amount of time to negotiating expectations, letting problems emerge first. Imagine avoiding mentioning to the emergency number that your house is engulfed in flames, but there is no space for the fire truck to pass.

We assume the others are on the same page with us. But in fact our mind tricks us, filling the gap after the threshold of knowledge4. We assume that we understand everything behind this threshold and that others have the same perspective.

Long story short, we know nothing behind the threshold, nor do people have the same perspective we have.

From the book Toyota Kata Dojo, by Tylo Schwarz.

Leaders are not exempted from this bias. On the contrary, from their comfortable perspective on the golden seat of power they are probably the category that most easily misjudges people. Leaders have the possibility to see a broader verson of the world and it’s always hard to understand how far are your backyards. 

Once one of my academic mentors told me: “I have a problem with students. Every year I do a further step in knowledge. But new students are always at the same level.”

It is never people’s fault if they are not as we imagine they would have been. 

They are not wrong. Instead, we had the (always) wrong expectations.

The most effective way of leading people is to make a continuous loop of understanding how far we are from the reality about a specific person as fast as possible. We ate the apple, and we are the sinners. But we never regret it, so we don’t learn.

The more we don’t learn this lesson, the more we will continue to blame others for our missed milestones. And we will never reach the destination.

The supreme art of war is to subdue the enemy without fighting.”
—Sun Tzu, The Art of War

You can’t control everything, but it’s better to force mistakes because they are the fastest way to discover the problematic area that reduces your performance.


Rules are not what you expect

Rules are necessary for society to function properly. They help us avoid harmful behaviors and promote creativity and knowledge sharing. However, breaking rules can be addictive and lead to negative consequences. So, why is it so important to use them to lead people?

Rules are a booster for creativity, aid diagnosis, and facilitate knowledge sharing. 

Rules and expectations are two faces of the same coin. While rules set policies not to be trespassed, expectations are the thresholds based on these rules. In jargon, they are called “standards” to refer to a broader meaning, thus the shared best-known method to be followed to do a specific action, procedure, or process. 


Rules boost creativity

Not many people know that Creativity, as we intend it, is a concept that was born only after the Enlightenment.

The first person to define it was Henry Poincaré, a French mathematician and philosopher known for his work on the foundations of mathematics and the theory of dynamical systems. Poincaré, in his “Science and Method” emphasizes the importance of the unconscious mind in making novel connections between disparate ideas.

Like many other things, Creativity is an actor in a dualism5. Creativity couldn’t exist without the State of the Art. 

“Be regular and orderly in your life, so that you may be violent and original in your work.”6

—Gustave Flaubert, commonly attributed

When we set a standard way of doing things, we leverage people’s power to build new things and exploit divergent thinking. Standards reduce the effort required to perform an action because they reduce the number of brain cells that need to understand how to make something, leaving space for them to work on creative things.

For example, consider the standardization of computer programming languages. By establishing standard syntax and rules for coding, developers can spend less time figuring out how to write basic functions and can instead focus on innovative problem-solving and creating new software applications. This allows for greater creativity and exploration of different approaches to programming challenges, leading to a wide range of diverse and inventive software solutions.

That’s why you can’t change the rules, because the rules make it fun!
—Coco from Bluey, S01E05 “Shadowlands”


Rules aid diagnosis

Imagine you’re a part of a team, and your manager has set clear standards for how they communicate with you, provide feedback, assign tasks, and conduct meetings. You know exactly what to expect from your manager and what is expected of you in return. This approach makes you feel empowered, and you feel confident in your ability to address any issues that may arise.

I used this technique when transforming the deal development process. When we transformed the process, I was the final filter, the one approving prices, and conditions, and doing the final check before sending the proposal to the customer. In the first interaction of our reengineered process, I was receiving over 70% of deals processed with mistakes. I used the rule to never let crap be shipped to customers. But instead of fixing myself the issues, something that would have reduced the effort and time I was obliged to place into the tasks, I shipped the job to the previous phases. 

By sending back to the previous phases the wrong deals means worse time management and upset customers in the beginning. But ultimately it helped to create a muscle to check the standards for my team, and to build a smoother interaction after the setup period, freeing up time for everyon

Establishing clear standards for managers’ relationships with their employees, reduces anxiety and minimizes unproductive meetings and frustrations that arise from individuals not adhering to expected behavioral norms. This approach fosters a more proactive and empowered workforce that is capable of addressing challenges as they arise.

A powerful example is to set clear expectations and standards for your team’s relationships. Show them what it looks like to communicate effectively, provide constructive feedback, assign tasks fairly, and conduct productive meetings. By doing so, you’ll create a culture of trust, transparency, and accountability, where everyone feels valued and empowered to do their best work.


Rules facilitate knowledge sharing

“Wax on, Wax off”. Mr Myiagi in “The Karate Kid”

Setting standards is also good for sharing knowledge and building on best practices, which can improve general performance. Standards are expectations that the leaders share with their associates. 

Just like the iconic ‘wax on, wax off’ technique in The Karate Kid, mastering the basics can lead to extraordinary results. The concept of ‘wax on, wax off’ beautifully illustrates the idea that seemingly mundane tasks can lay the foundation for greatness. In the movie, the main character is initially puzzled by the seemingly unrelated and repetitive chores assigned to him by his mentor. 

However, as he progresses, he realizes that these seemingly mundane tasks were actually building muscle memory and fundamental skills that were essential to his development as a martial artist. Similarly, setting and adhering to standards may initially seem tedious or unrelated to immediate success, but they form the bedrock of excellence. Embracing these standards and consistently adhering to them can lead to remarkable growth and success, just as mastering the basic karate moves paved the way for the protagonist’s triumph in the movie. 

Start with the fundamentals, and watch as your skills and abilities grow beyond your wildest expectations.


Common pitfalls in rule-setting

Rule are important. But you don’t want to set them incorrectly. Here are the most important points to consider.

Faking your rules, not splitting desiderata from reality. . It’s easy to say that you’re going to do something, but it’s much harder to actually follow through with it. This is why it’s important to be honest with yourself and others about what you’re capable of. If you set unrealistic goals for yourself or your team, you’re more likely to fail. People will see through your facade, and you’ll lose their trust and respect.

Being too vague or too strict. Be specific about what you can achieve, while still striving for your ultimate goal. If you’re too vague, you won’t be able to make progress, and if you’re too strict, you’ll end up alienating your team or blocking them in a cul de sac

Focus on outcomes, not processes. Getting caught up in the details of how you’re going to achieve something is important, as it ensures that you are on the right track and making progress. Instead of focusing solely on what you want to achieve, pay attention to the steps you need to take to get there. This will allow you to develop a well-defined and effective plan. And leave people learning something more impactful.

Not negotiating. It’s rare that you’ll be able to get everything you want without making any compromises. Negotiating you have a golden opportunity to check if everything is clear. Never leave an important task without verifying it is well understood and accepted.

Setting unrealistic expectations without appropriate resources. If you set goals that are impossible to achieve without the appropriate resources, you’re setting yourself up for failure. Make sure you have everything you need to succeed before you start working towards your goal. This includes things like time, money, and support from your team.


When you are managing someone, you have to set rules, expectations, and a cultural system that fits with you. That could be resonant with you.

It’s up to you to decide when it’s worth wasting time with someone. As a leader, you are not supposed to wait forever.

It is never people’s fault if they are not as we imagine they would have been. 

Be empathetic, at least you will come out as a better leader.


Cover picture by Raphael Koh on Unsplash

  1. Ruben is a fictitious name ↩︎
  2. The leadership style I am pointing out as a good standard is indeed a combination of a series of separate behaviors. Daniel Goleman spots 6 different leadership styles: cohercitive, authoritative, affiliative, democratic, pacesetting, coaching. I find it hard to use the coercive style, it is an emergency situation, but I developed my style as a mix of the other 5s.

    Read more about it here: https://hbr.org/2000/03/leadership-that-gets-results 
    ↩︎
  3. My Coaching Method is Toyota Kata.Toyota Kata is a methodology that embodies a pattern of continuous improvement through coaching and practice. It instills a culture of ongoing learning and problem-solving based on the scientific method of hypothesis and experiment. 

    Central to this approach are two primary patterns: the Improvement Kata, which focuses on achieving specific goals through iterative learning cycles (observe, hypothesize, experiment, learn); and the Coaching Kata, which enhances this learning through a structured coaching dialogue. 

    This methodology transforms the traditional managerial role into that of a coach who guides and supports teams in navigating challenges. It encourages a deep understanding of current conditions and fosters an environment where decisions are based on evidence and collaborative effort. The methodology’s goal is to create a sustainable culture of continuous improvement and problem-solving capabilities within an organization.

    To read more about it:
    https://www.cuoaspace.it/2021/02/toyota-kata-come-nuovo-modo-di-pensare-e-di-agire-in-azienda.html [Italian source]
    – Introduction to Toyota Kata[Mike Rother traveled to Japan to grasp how Toyota built a learning organization and figured out this coaching method was the golden nugget. In this video, he summarized the whole method in 40 minutes]
    ↩︎
  4. This bias is called: “False consensus effect.” This cognitive bias leads us to overestimate the extent to which our own opinions, beliefs, preferences, values, and habits are normal and typical of those of others. Essentially, it causes us to assume that our own views are more common than they actually are.
    ↩︎
  5. Heraclitus, Greek Philosopher, found in dualism the manifestation of the logos. ↩︎
  6. H/T to Hugo Lebarrois for editing this essay and giving me the idea to add this quote ↩︎

Published by Matteo Cervelli

🎯 My "Why" is to Trigger Talents to Create a Better World 📝 Writing on strategy, innovation, leadership and growth

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