The Leadership Paradox: Coveted Roles, Hidden Regrets

Ever wondered about the hidden truth of leadership roles? While they’re often seen as the pinnacle of professional success, the reality is that many leaders secretly wish they could step away. What’s causing this paradox, and how can we challenge the unspoken rules of business to address it? Let’s dive into the surprising dilemma faced by those at the top.

Isn’t it peculiar that the very roles folks strive for often become the ones they wish to escape? It’s the conundrum many in leadership find themselves in. They’ve climbed the ladder, gained the title, yet the reality of their positions is not as rosy as the image portrayed. Why’s this so?

The shared assumptions and beliefs within most businesses and societies paint leadership roles as the pinnacle of success. Yet, once in these positions, individuals often find them fraught with stress, long hours, a level of responsibility that can be overwhelming, and the implicit pressure to be mean to people. They’re bogged down by bureaucracy, and the freedom they envisaged is replaced with countless meetings, conflict resolution, and pressure to meet targets.

Yet, these same businesses’ cultures trap these individuals, creating a perception that stepping down or moving sideways would equate to failure. There’s a sense of being ‘stuck’, a lack of alternatives within the existing organisational structure. The irony is bitter: the very roles they once coveted have become ones they’d rather not hold, but the unwritten mores of business leave them feeling there’s no way out. It’s a dilemma that underscores the need for reimagining how we view success and leadership in our workplaces.

Leadership Lessons from ‘How to Train Your Dragon’​

“How to Train Your Dragon” is a 2010 animated film which tells the story of Hiccup, a young Viking, for whom dragons are seen as fearsome enemies.

Despite this, Hiccup eventually befriends a dragon named Toothless. Through his journey, Hiccup learns valuable lessons about leadership, teamwork, and the importance of understanding and accepting others.

One of the key themes in “How to Train Your Dragon” is the power of collaboration and teamwork. In the beginning of the film, Hiccup is a loner who is struggling to fit in with his peers and prove himself as a capable warrior. However, as he begins to work with Toothless and other dragons, he learns the value of cooperation and mutual respect.

This message is highly relevant to the business world, where collaboration and teamwork are essential to success.

Another important lesson from “How to Train Your Dragon” is the importance of understanding and acceptance. Throughout the film, Hiccup struggles to understand Toothless and other dragons, and initially sees them as threats to his community. However, as he gets to know Toothless and learns about the dragons’ behavior and needs, he realises that they are not as different from humans as he thought. He comes to see that dragons are intelligent and emotional creatures, and that they can be treated with respect and understanding.

This message is also applicable to the business world, where people can choose to understand and accept their colleagues, peers and customers, regardless of their differences. By creating an inclusive and welcoming workplace culture, companies can foster a sense of belonging and support. This leads to better communication and collaboration, as well as higher levels of morale, productivity and engagement.

In addition to collaboration and understanding, “How to Train Your Dragon” also touches on the importance of leadership and empowerment. Throughout the film, Hiccup takes on a leadership role, guiding Toothless and other dragons in their training and helping them to become more confident and capable. He encourages them to take risks and be independent, and trusts them to make their own decisions.

This type of leadership is conspicuous by its absence in most of the business world. By giving people the freedom to take ownership of their work and explore new ideas, companies can create a culture of innovation and excellence.

Overall, “How to Train Your Dragon” is a powerful and inspiring film that teaches valuable lessons about business culture. By highlighting the importance of collaboration, understanding, and leadership, the film encourages viewers to embrace diversity, communicate effectively, and work together towards a common goal.

A New Era for Workplace Dynamics?

💡 Are organisations ready to break free from the constraints of conventional leadership and embrace a future where everyone’s voice is heard? Consider the transformative potential of a collaborative work culture.

➡ As business organisations evolve, those in positions of influence may choose to reconsider traditional notions of directing and guiding work. Embracing a paradigm shift away from conventional hierarchical structures will foster a more collaborative and inclusive environment, wherein everyone contributes to the decision-making process.

In this new landscape, individuals who previously held supervisory roles may choose to focus on cultivating collective intelligence and facilitating open communication. This will be achieved by encouraging people to share ideas, opinions, and feedback openly, while also being receptive to diverse perspectives. By fostering a culture of trust, respect, and empathy, those in influential positions can create a more empowering and dynamic work atmosphere.

To successfully navigate this transformation, those who once held command may choose to develop and promote skills in active listening, conflict resolution, and emotional intelligence. These capabilities will allow people to support and guide without exerting authority or control. They may also choose to embrace and promote continuous learning and adaptability, as these traits are crucial for thriving in a rapidly changing world.

Ultimately, the transition away from traditional management and leadership roles necessitates a shift in mindset and culture, wherein individuals focus on empowering others, fostering collaboration, and nurturing a culture of shared ownership and responsibility. By embracing these changes, organisations can unlock the full potential of their people, driving innovation and success.


Transitioning Mindsets

Unlocking the true potential of organisations requires more than just developing individual leaders. It takes a deeper level of engagement and a transformative approach to shifting collective assumptions and beliefs. Discover the key differences between leadership development programs and organisational psychotherapy interventions, and which one is right for your organisation.

Leadership development programs and organisational psychotherapy interventions are two distinct approaches to improving the functioning and performance of organisations. While both aim to enhance organisational effectiveness, they differ in their focus and methods.

Leadership development programs are typically focused on developing the skills and capabilities of individuals within an organisation who are in leadership roles. The goal is to improve their ability to lead and manage teams, communicate effectively, make decisions, and navigate complex organisational dynamics. Leadership development programs can include training, coaching, mentoring, and other forms of development activities. These programs often emphasize the importance of self-awareness, emotional intelligence, and interpersonal skills.

Organisational psychotherapy, on the other hand, focuses on shifting the collective assumptions and beliefs that underlie an organisation’s culture and behaviours. These interventions typically involve a deeper level of engagement with the organisation, including the identification of underlying assumptions and beliefs, the exploration of underlying dynamics, and the creation of a shared sense of purpose. Organisational psychotherapy interventions can include a range of methods, such as group facilitation, dialogue, reflection, and other forms of participatory engagement.

While leadership development programs focus on developing the skills of individual leaders, organisational psychotherapy interventions aim to transform the organisation as a whole. Both approaches can be effective in improving organisational effectiveness, but they require different levels of engagement and investment.

Leadership development programs may be more suitable for organisations that have a well-defined leadership structure and a relatively stable culture, while organisational psychotherapy interventions may be more appropriate for organisations that are undergoing significant change or facing systemic issues.

In summary, while both leadership development programs and organisational psychotherapy aim to improve organisational effectiveness, they differ in their focus and methods. Leadership development programs are focused on developing the skills and capabilities of individual leaders (who may move on), while organisational psychotherapy is focused on shifting the collective assumptions and beliefs that underlie an organisation’s culture and behaviors. Both approaches can be effective, but require different levels of engagement.

This is my DeLonghi four slice toaster. It’s been doing sterling service in my kitchen for the past seven years. If you’re looking for a toaster, you could do a lot worse.

Only last week I (finally!) discovered the “bagel” button. Which turns off one element in each slot so as to toast only one side of a bagel, burger bun, etc.

What’s this anything to do with employees?

It strikes me we often treat employees like I have treaded my toaster. We overlook some of the things they can do, really useful things, through familiarity and/or lack of attention. Their talents in some areas go begging because we’re habituated to seeing them in only one light. We succumb to the functional fixedness bias (not limited to objects, methinks).

Aside: FWIW I’ve never used the “defrost” or “reheat” buttons either. I guess my toaster is currently quietly looking for a new, more appreciative boss.

The System Is Unethical

Or at least, it’s “the system” that sits at the root of the unethical behaviours costing software delivery organisations £££millions annually. And it’s the culture of an organisation that defines that system.

Many years ago I wrote a White Paper titled “All Executives Are Unethical”. This paper riffed on a theme from Seth Godin – “All Marketers are Liars”. And channeled the ethical arguments of William Kingdon Clifford:

…whatever someone chooses to believe cannot be exempt from the ethical judgement of others.

In the aforementioned White Paper, I spoke of the ethics of executives, and in particular the folks that make the decisions about committing to improvements (or maintaining the status quo) in software delivery.

It’s been my experience over the course of thirty-plus years, that said executives act as if they believe their software delivery capability has little need, or scope, for improvement. Acting as if investing in improving said capability has little to no payback, and little to no impact on the organisation’ top line or bottom line.

It’s The System

Bill Deming famously wrote:

The fact is that the system that people work in and the interaction with people may account for 90 or 95 percent of performance.

~ W.E. Deming quoted in Scholtes, PR 1998 ‘The leader’s handbook: making things happen, getting things done’ McGraw-Hill, London p 296

Some readers of my aforementioned White Paper may have inferred I was criticising individual executives for their shortfall in ethics. Not at all. These folks work in “systems” as much as everyone else. It’s the system that drives their behaviours. Behaviours such as:

  • Failing to dig into the effectiveness of their organisation’s software delivery capabilities.
  • Indifference to the waste involved (wasted time, money, opportunities, human potential,…).
  • Ignorance of just how much more effective things could be, with e.g. a change in perspective.
  • Bravado and denial when questioned about such matters.

And it’s not limited to executives. Most advisors and practitioners (coaches, developers, middle managers, etc.) are equally ignorant, indifferent, flippant and slow to inquire.

Organisational Psychotherapy – and in particular, Memeology – offers a means to being addressing the shortcomings of the system, and thus bring about changes in folks’ behaviours.

– Bob

Further Reading

Marshall, R.W. (2021). All Agilists Are Unethical. [online] Think Different. Available at: [Accessed 30 May 2022].
Seddon, J. (2015). 95% of Performance Is Governed By The System. [online] Vanguard Consulting Ltd. Available at: [Accessed 30 May 2022].

An Exec’s Guide To Achieving Mission-critical Software Delivery

Nowadays, every business is a software business. Your enterprise needs to prioritise software delivery, be that deploying off-the-shelf solutions, commissioning bespoke software development, or a mixture of both.

Digital transformation: The term has been bandied about since it was coined more than a decade ago. I think we can all agree, though, that the “use of technology to radically improve performance or reach of enterprises” really gained momentum when the COVID-19 pandemic set in.

As we remember all too well, the entire world went digital within a matter of weeks, and companies raced to fulfil the soaring consumer demand for digital products and services. In fact, according to McKinsey, global businesses accelerated the adoption of digital offerings by an average rate of seven years — in a matter of just seven months. Some companies describe how they had to enable tens of thousands of home workers in just a few days!

The same McKinsey report shows that most business leaders see society’s digital shift as permanent. JPMorgan Chase’s CEO certainly thinks the increased use of digital apps and services is here to stay. He recently announced a 26% increase to Chase’s technology budget, focusing the $12 billion investment on further growing Chase’s portfolio of digital apps and services.

Providing innovative technologies is just half the job, though. There’s a lurking problem for business leaders: They can’t afford to let the delivery and integration of software into their businesses suffer delays and poor quality.

Just one schedule slippage in a key system can cause a cascade of problems. And when one of these slippages delays the deployment or upgrade of a key app or service, companies risk disrupted revenue streams, disgruntled customers, interrupted supply chains, lost productivity and frustrated staff.

Maintaining flow of software into the business is imperative to business continuity, but ensuring a steady, reliable flow is difficult. As businesses digitally transform and move their key processes to the cloud, and consumers utilise more digital innovations, their software estate grows in scale, complexity and fragility.

Consequently, maintaining the necessary software quality and delivery schedules must be a primary business objective. While leaders traditionally farmed out these responsibilities solely to their IT departments, technology has become so critical to business success that quality and delivery schedules can no longer hide in the opaque IT silo. It must – and has – become a culture and leadership issue.

Here are five steps executives can take to start embracing software quality, predictable schedules and steady flow:

Elevate Quality To Priority #1

When considering an enterprise’s numerous priorities, executives should take stock of the critical importance of quality. Does the company employ a virtual or hybrid workforce? Does the company interact or transact with customers online? Is revenue generated from online transactions? The questions can continue based on your industry, but chances are that most modern enterprises would agree they rely on a suite of software apps and software-based services for desired business outcomes.

Given the critical nature of digital apps and services — and their ability to provide a seamless experience for customers — executives should consider creating a culture of quality as a key performance indicator. Practically speaking, executives can and should treat quality numbers similarly to sales figures or other revered business metrics. One senior leader should be held accountable to the quality metrics and deemed responsible for relentlessly scrutinising and reporting on these figures alongside the business’s other KPIs.

If executives really want to underscore the importance of quality, they can walk the talk for their workforces. Business leaders can make quality a compensation-affecting business objective, like profit or sales targets. And they can tie these quality metrics back to the bottom line.

Focus On The People

In the era of “every business is a software business,” enterprises can no longer tuck away tech talent out of sight, removed from customer interaction. In fact, they should do the exact opposite, moving software folks to the front line and making them part of the business’s core value proposition. Actively marketing a company’s tech and nerd credentials will drive confidence in the brand’s digital presence. And enhance employer branding at the same time.

Naturally, redeploying the software folks goes both ways. Executives must also show genuine trust and respect for these key people. Even without extensive technical knowledge, business leaders can provide the kind of environment, and culture, that makes teams’ lives easier by reducing the cognitive load imposed by traditional management approaches. And they can give them the freedom to use modern paradigms like DevOps and CI/CD pipelines. Software teams with respect, resources and support will have a foot up on delivering innovations and protecting the quality of their deliveries.

Treat Unceasing Innovation As Standard

As most executives know, today’s world of digital business demands continuous innovation as a minimum requirement for keeping pace with competitors. This unceasing innovation requires executives to drop risk-averse postures and embrace reinvention and the concomitant continuous change.

Of course, amidst digital innovation, reinvention and even failure, quality remains a top priority. Executives need a business culture that allows their organisation to experiment, and sometimes falter, with the least amount of negative impact. After all, stagnation is no longer an attractive option.

Open The Chequebook and Invest!

If an enterprise relies on various digital apps and services for business performance, executives should guarantee the entire software delivery pipeline is exemplary.

While only the lucky few have an extra $12 billion on hand to invest in software delivery and the associated spend, executives should advocate for a big piece of the pie to go toward technology investment. And technology investment shouldn’t stop at commissioning delivery projects. Forward-thinking enterprises invest in next-generation delivery methods like Quintessence, alongside talent, training and time to innovate.

Make Technical Know-how A Leadership Must-Have

Executives should ask themselves a simple question: does anyone on the most senior team have “SDLC” or software delivery experience in their past or even present core competencies? While leadership teams are usually stacked with impressive qualifications — CPAs, MBAs and JDs — few include software people with practical SDLC experience. But given the importance of technology, executives should surround themselves with true technology practitioners.

A chief digital officer (CDO) can become a business leader’s quality czar. With a depth of SDLC experience, this role can help executives understand and benchmark their companies’ digital performance and balance digital transformation efforts with operations management.

Following these steps sends a clear message both internally and externally: innovating is no longer enough — changing the culture to remove the shackles of outmoded assumptions and beliefs is also necessary. If executives want to maximize their digital investments and thrive in a digital-first world, they must embrace quality and the culture that enables it.

– Bob

If Putin Ran A Software Development Business

Or a tech business in which software development was a core capability – much like military forces are a core capability for any nation, including Russia.

If Putin ran a business where software development was a core capability, he’d:

  • Ask for estimates and rail against his project managers and middle-managers when those estimates proved unreliable.
  • Wonder why new features were stuck in a long queue of undelivered features.
  • Not notice that developers were so demoralised that they were just going through the motions, not caring a hoot about requirements or deliverables or even customers’ need.
  • Ask regularly and bitterly “why can’t they (developers) just do as they’re told?”.
  • Have little clue about the state of his tools and hardware, the skills – or lack of them – of his developers.
  • Apply huge resources to bludgeon through problems and delays, only to find that doesn’t work.
  • Discount the importance of morale and motivation in his employees.
  • Be secretly embarrassed about the quality and accuracy of his employees’ work.
  • Not understand the importance of learning, skills development, training and senior staff.
  • Underestimate the difficulties inherent in all software development endeavours.
  • Blame competitors and market conditions for his people’s failures.
  • Belatedly hire external contractors in the naïve and forlorn hope that they might accelerate progress.

Maybe you know of some other CEOs that make the same choices?

Yayy for Ukraine! Ukraine-Flag-PNG-File

– Bob

Further Reading

Marshall, R. W. (2013). Product Aikido. [online] Available at:

My favourite quote this week:

What distinguishes exemplary boards is that they are robust, effective social systems … The highest performing companies have extremely contentious boards that regard dissent as an obligation and that treat no subject as undiscussable.

Perhaps the most important…is the capacity to challenge one another’s assumptions and beliefs. Respect and trust do not imply endless affability or absence of disagreement. Rather, they imply bonds among board members that are strong enough to withstand clashing viewpoints and challenging questions.

~ Jeffrey A. Sonnenfeld

It’s About Time

It’s about time we moved beyond Agile. It’s only sensible to abandon what twenty years of failure has proved almost entirely useless. 


Ironically, moving beyond Agile means retracing our steps, the steps that have led us into the Agile cul-de-sac. We cannot move beyond Agile by building on Agile. Its multiple flaws disqualify it as the basis for moving forward. We must not only seek a new path, a new game, and learn new things, but unlearn a whole passel of Agile-related ideas that just tie us to the dysfunctional past.


It’s about time we recognise that any approach that addresses the needs of only one constituency – i.e. the software developers – disqualifies that approach from serious consideration. 

It’s about time we considered approaches that embrace the needs of all constituencies – of all the Folks That Matter™️. Approaches that design-in means to “prepare the soil” – means to effect the socio-technical environment necessary for effective development and learning to take place.


I offer Quintessence as one such approach.

It’s about time we started talking about the Quintessential organisation. And building it. Again.

– Bob

The Unemployables

There’s a saying in recruitment that the best jobs are never advertised.

There’s another idea, not quite a saying as yet, that the best candidates are unemployable. Allow me to explain. 

Most vacancies as advertised are shaped to fit the mediocre candidate. Any candidate with outstanding skills, experience, capabilities and insight is such a poor match for the position as advertised – with job description, education, certification and experience requirements, and all – they’ll never get past the first filters / gatekeepers (people with no understanding of what it really takes to excel in the job).

The outstandingly capable candidates are thus, for all intents and purposes, practically unemployable.

This leads to my regular refrain – the recruitment / hiring market is irredeemably broken.

Irredeemably broken? Yup. At least until those who unknowingly suffer the consequences of their organisations’ hiring mediocre candidates (CxOs, particularly) go to the gemba and begin to see what’s ACTUALLY happening in their name.

– Bob

Golden Insights From the Gemba

A recent video (57 minutes) exploring the long-term experiences in Portsmouth City Council with the Vanguard Method. Golden.

Also applies to software development (and other functions) within tech organisations. Can you see the parallels?

– Bob


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