This is more of an open discussion than my usual posts, as I don’t have a definitive answer. Lately, I’ve been reflecting on when optimism and cheerfulness are most effective in managing projects and leading large teams. Before diving into this, let’s establish some definitions—at least as I interpret them when it comes to a project. Even these are open to debate, but they serve as a foundation for the discussion.
Key Definitions
Determination:
Determination is the unwavering desire to contribute and work through a project. It’s about sheer resolve—nothing will stop you from completing the task. Key point: Determination is neither emotional nor time sensitive. It’s not about the future or the success of the project. It’s about the here and now: getting things done.
Optimism:
Optimism builds on determination by adding hope for a better future. It’s the belief that, despite challenges, there’s a goal worth striving for. Key point: You might not be happy about the present situation, but you’re confident it will improve. Optimism is forward looking and success oriented.
Cheerfulness:
Cheerfulness is optimism combined with happiness. It’s an outward expression of positivity—not just believing in a better future, but also radiating joy and enthusiasm in the present. Key point: Cheerfulness is upbeat, engaging, and contagious, making it a powerful tool for boosting morale.
Application to Management Styles Now we have definitions, how do these traits translate into leadership and project management?
The Cynical Optimist
A cynical optimist maintains hope for the future but is realistic and grounded. They don’t sugarcoat challenges or pretend everything is fine. Instead, they acknowledge the hard work ahead while believing in the eventual outcome.
The Cheerful Optimist
A cheerful optimist is not only hopeful but also exudes enthusiasm and positivity. They inspire others by creating an energetic, uplifting environment, making challenges seem less daunting and the goal more attainable. At first glance, you might assume that a cheerful optimist would naturally be a better leader—someone who motivates and energizes their team. However, the effectiveness of either style depends on the audience.
Audience Matters
The best leadership style is often dictated by the needs and expectations of your team or stakeholders.
Technical Teams, such as Information Technology or Business Analysts:
These individuals are typically pragmatic and focused on the realities of their work. They’re not easily swayed by cheerfulness and can see through superficial positivity. What resonates with them is honesty and a grounded no nonsense approach. For these teams, cynical optimism works best:
Acknowledge the challenges.
Communicate that success is possible with effort.
Avoid overly cheerful reassurances that might come across as dismissive of their workload. Example: “Yes, this will be a grind, and it’s going to be tough. But with persistence, we’ll get there.”
Non-Technical Stakeholders such as Customers or Senior Managers:
Stakeholders often value reassurance and confidence. They’re less concerned with the technical details and more with the perception of progress. Cheerful optimism can prevent unnecessary panic or doubt, making it easier to keep projects on track. For these groups, cheerfulness is more effective:
Inspire confidence in your ability to deliver.
Reassure them that challenges are under control.
Create a sense of enthusiasm about the project’s future. Example: “We’re making great progress, and while there are challenges, I’m confident we’ll deliver excellent results.”
The Importance of Adaptability Ultimately, the best managers are adaptable. They adjust their style based on their audience and the situation.
Be honest and pragmatic when dealing with teams that value transparency and realism.
Be cheerful and reassuring when dealing with stakeholders who need confidence and enthusiasm to stay engaged.
It’s all about balance: conveying optimism without dismissing reality and bringing energy without losing credibility.
Does anyone else have thoughts on this? How do you balance cynicism, optimism, and cheerfulness in your leadership style? Disclaimer: As always these posts are not aimed at anyone client or employer and are just my personal observations over a lifetime of dealing with both management and frontline associates.
Project managers generally fall into two distinct types: facilitators and demanders. As someone who has worked for project managers as well as having them work for me, I feel confident making this distinction.
Facilitators
Facilitators actively contribute to getting tasks done. They play a hands on role in delivering results and often get involved in the finer details of the project. Their effectiveness is apparent when they go on holiday: productivity may slow or even halt because their direct involvement is crucial to progress.
However, facilitators have a notable weakness—they are often too immersed in the process. This closeness to the “coalface” can make it difficult for them to maintain an overarching view of the project. It can also hinder their ability to transition seamlessly between projects since they are deeply embedded in the operational details.
Demanders
Demanders, on the other hand, take a more removed approach. They don’t do much hands on work themselves; instead, they push, chase, and pressure others to deliver. Their value lies in their ability to maintain momentum, as they often accelerate delivery timelines by holding team members accountable.
Interestingly, when demanders go on holiday, tasks may still get done—albeit at a slower pace—because their presence primarily serves to keep pressure on the team. Their absence gives the team a breather but doesn’t stop progress entirely.
Distinguishing the Two:
At first glance, it can be hard to tell facilitators and demanders apart. However, their behavior and approach reveal key differences:
Facilitators:
Provide actionable solutions.
Offer hands on help to overcome obstacles.
Criticize constructively by identifying steps to resolve issues, e.g., “This can be done if we contact X and Y to address these dependencies.”.
Demanders:
Focus on dates and deadlines, and how this effects perceptions of the project by the wider company.
Use corporate jargon like “root cause analysis” often without direct knowledge of the production process.
Sometimes use blanket statements: “We’re missing deadlines, This isn’t acceptable”.
Ultimately, facilitators are deeply engaged in the delivery process, while demanders rely on oversight and pressure to drive results. Recognising these distinctions can help organisations understand how to better utilise their project managers for different challenges.
This is just a silly little post, but enough people found it amusing that I thought I’d cross post it here.
I was asked to do a reading at a friend’s wedding and was presented with a poem that’s often used for such occasions. However, considering that at least the groom was a serious warhammer nerd — I decided to make a slight alteration.
Just for fun, I recorded the altered version and sent it through. It sounded so good that I was actually tempted to really read it out during the ceremony. However, since the bride was wearing Converse, I figured she might catch me halfway down the aisle and kick me to death if I did! Better safe than sorry, I suppose.
I present it here for your amusement.
The Original:
The Magic of Love by Helen Steiner Rice Love is like magic, and it always will be, For love still remains life’s sweet mystery. Love works in ways that are wondrous and strange, And there’s nothing in life that love cannot change. Love can transform the most commonplace Into beauty and splendour and sweetness and grace. Love is unselfish, understanding and kind, For it sees with its heart, and not with its mind. Love is the answer that everyone seeks; Love is the language that every heart speaks. Love can’t be bought, it is priceless and free. Love, like pure magic, is life’s sweet mystery.
And my alternative:
The Magic of the Emperor by Ciaphas Cain The Emperor is like magic, and he always will be, For the Emperor still remains life’s sweetest mystery. The Emperor works in ways that are wondrous and strange, And there’s nothing in life that the Emperor cannot change. The Emperor can transform the most commonplace, Into beauty and splendour and sweetness and grace. The Emperor is unselfish, understanding and kind, For he sees with his faith, and not with its mind. The Emperor is the answer that everyone seeks; The Emperor is the language that every heart speaks. The Emperor can’t be bought, he is priceless and free. The Emperor, like pure magic, is life’s sweet mystery.
The Contractor or Consultant “Green Zone” is a semi-informal pricing range on quotations that normally avoids raising concerns or objections from a client.
Explanation:
The contractor or consultant “Green Zone” is the ideal place to quote if you want repeat business with a client, prices that fall below the “zone” can raise suspicions, while prices above it often provoke frustration and indicate greed. This range becomes especially evident when multiple vendors are quoting together on the same project even if they are quoting for different parts.
Quoting within this range can be challenging, as it often requires estimation. The Green Zone varies between projects and even more so between different clients, some clients are actually quite open about such things, and you can even ask for their “rate card” to see if you can match it and make everybody’s life much easier.
Disclaimer: As always these posts are not aimed at anyone client or employer and are just my personal observations over a lifetime of dealing with both management and frontline associates.
This is something that I personally find drives me crackers, and has done all the way through my professional career, it is also one of the golden rules that I apply now that I spend more time doing management stuff than I do doing technical or support stuff. It is to not inappropriately delegate. What do I mean by inappropriate? In this case, I mean to delegate items that do not have clear owners and therefore, often, managers delegate to anybody they can find rather than just doing it them selves. The worst case for this is to delegate administration tasks to subject matter experts. The classical one is, if you are running a project and you are running a lot of meetings within that project, but have no project office member, or scrum master or general admin, you ask technical specialists or Business Analysts to do admin tasks such as minute the meeting or raise requests Unless there is a hard dependency on a skill set they use, do not waste the time of specialists on such things. I personally believe all minor admin actions fail back on the project manager in the absence of anyone else. If you feel that you are ill equipped to do such administration items because you do not understand the subject matter. For example, to raise a ticket that you don’t know the process for or that requires complex technical details to fill in, you initially take it as your job. Then you ask one of your fellow managers to assist, to see if they can help you. If that fails, then you go and ask one of the subject matter experts if they can guide you through the process the first time so you can learn. In summary, if in doubt, all boring and dirty jobs become the project managers responsibility.Disclaimer: As always these posts are not aimed at anyone client or employer and are just my personal observations over a lifetime of dealing with both management and frontline associates.
