Your mom’s best friend’s project manager! Key skills for a successful career in project management and management

Your mom’s best friend’s project manager!

Key skills for a successful career in project management and management

Semyon Kolosov

In memory of a friend and like-minded person…

Dedicated to Dmitry Moroz.

Proofreader Irina Ignatyeva

Illustrator Dasha Shchegolyutina

© Semyon Kolosov, 2024

© Dasha Shchegolyutina, illustrations, 2024

ISBN 978-5-0064-3202-4

Created with Ridero smart publishing system

About the author

Before you start reading this book, I thought I’d write about my experience so you can better understand the context in which my thoughts and conclusions were formed.

My name is Semyon Kolosov. I am a management consultant in IT. I help founders, top managers and executives to organize effective management of strategy, projects, teams and business processes at all the stages: from idea generation to scaling. In addition as a mentor, I help people change their lives and careers for the better through developing soft skills and management development.

Prior to that, I was the COO of a design unit and center of expertise at a company that builds digital products and digital transformation for big tech companies. Even before that, I was there as a project manager and Head of Project Management Office in client projects for digital services development.

I was also engaged in developing and conducting internships and educational programs on people management, project and product approaches, problem-solving and change management, motivation and team management for IT-companies.

Overall, I have 10 years of experience managing projects and teams in digital products, education, consulting and marketing.

I consider project management a prioritized skill in today’s world, so I strive to ensure that everyone can implement a project approach in their lives to achieve the results they want.

To that end, I wrote my first book “System Life” about management for life and work, which has already helped many people. “Your mom’s best friend’s project manager!” – is my second book, and it’s already specifically for project managers and executives. I also run telegram channels about self and project management.

All links and contacts can be found at the end of the book. Subscribe, I will be glad to receive any feedback and new acquaintances.

Enjoy reading!

Prehistory

Inside the psychotherapy room, lost in the hustle and bustle of the city, was a comfortable leather couch filled with pastel colors and fluffy cushions. The room was dimly lit, bookshelves lined the walls, and sitting at a desk with books was Dr. Emily Milestone, a somewhat eccentric psychotherapist known for her unusual approaches.

Mr. Gregory Sprintsky, the CEO of a successful technology company, burst into the office, looking disheveled and agitated. He was breathing heavily, pouring sweat and radiating nervous energy.

Dr. Milestone, watching this show, raised her eyebrows and asked:

Doctor: Good afternoon, Mr. Gregory. What brings you here so urgently today?

Gregory: Doc, I had another dream last night. About the perfect project manager.

Please sit down and tell me more about it.

Gregory: Well, I dreamed of a project manager who could easily handle any project. He was riding a beautiful electric bike smoothly and silently on a quiet road surrounded by beautiful scenery. There was water all around and the people were transfixed with tranquility and harmony. He was organized, adaptable and had cool communication skills. He had a sense of humor. He knew how to make the team laugh and keep morale high even during stressful times. He was a creative problem solver, always coming up with innovative solutions to even the most difficult problems. And he wasn’t afraid to take risks and take responsibility.

Doctor: I understand. How did you feel after that dream?

Gregory: Encouragement. Hope. But also a little anxiety. Because I know that finding a project manager like that is like finding a needle in a haystack. His image is always with me. I can’t avoid him! He’s always there, like a ghost that won’t let me rest! When I walked into my office in the morning, it seemed to me that the furniture had become an exact replica of this perfect project manager’s workplace. My desk, my chair – everything was just as I envisioned it. I tried to change things around, moved furniture around, but nothing worked. That image always found me. In meetings with my employees, they would start talking exactly as I envisioned the ideal project manager in my head. They would say phrases that I had only heard in my mind. Even when I was resting, that image never left me. I saw his face in the clouds, in the fire of a campfire on the beach, even in the stars in the sky. It’s just crazy!

Doctor: Is this perfect project manager with us now, in this room?

Gregory: Yes!

Doctor: Gregory, I’m going to say a phrase that will make you feel better. Calm down, Gregory. Now that you’re calm, describe him more specifically. What does he do? What skills does he possess? What results does he achieve? What makes him the perfect project manager for you? What kind of image is that?

Session 1.

Self-management

Gregory started telling:

For me, the ideal project manager, or, as we tend to say, PM, is an independent part of the company. He achieves the result of the project in any understandable and incomprehensible situation. He is a team leader who broadcasts the rules of work. He sets the vector of movement, the right mood, the pace of work. He watches for deviations and corrects the direction. He is a project manager who chooses and applies the management technology. Keeps the situation under control, analyzes and makes decisions. Makes the process transparent and communicates decisions. Organizes a purposeful course of work and people to achieve the result. Simply put, this is the person to whom I voice a goal or say, “Do it right,” and he or she produces a predictable result. Without too much oversight, I’m always sure he knows what “right” means, that there won’t be any surprises before the deadline, and if conditions or the environment make the result unfeasible, everyone will know about it beforehand and the PM will come up with a solution to change those conditions. And sometimes we don’t even know the goal ourselves. We just want him to figure it out and do it himself. An ideal PM is not afraid of problems, does not whine, knows how to organize and negotiate, is responsible for the quality of the result and delivers everything on time.

Organized and systematic

This is the base. A systematic approach to tasks and problem solving is the foundation in work. An unorganized person will not be able to organize others. The ideal PM effectively plans and organizes his time and workspace. He has his own self-organization system with his favorite tools from calendar to task manager. It’s without flaw, without cheating, as reliable as a couch spring. It evolves and adapts so that it never wastes time on uselessness. That doesn’t mean he’s obsessed with systematization like a maniac. When needed, he can unfocus or go into creative mode. But systematically managing your life, time and tasks is a masterstroke. It is always said about the ideal PM that he is a systematic person who has everything in order.

Punctuality and compliance to agreements

The ideal PM performs tasks on time, does not allow delays, does not break agreements and promises. The team and clients can rely on him because he always keeps his word. When he says what will be done, it really happens. And if he didn’t give us a heads-up and he didn’t show up for the meeting or he didn’t send us the paperwork, something really bad happened. The perfect PM exemplifies its punctuality and discipline to other team members. It sets high standards and ensures that all employees are accountable and comply with agreements. It helps create an atmosphere where everyone knows that their work is appreciated.

Working under conditions of uncertainty

Systemic does not mean bureaucracy and unconditional adherence to algorithms. The ideal PM is flexible, able to work in a changing environment, and able to develop solutions in the face of uncertainty. He knows that certainty exists only in mediocre projects. And not always. He is not afraid of uncertainty, he knows that projects can be subject to change, sudden shifts and surprises. He is ready to adapt coolly to new circumstances, to eliminate uncertainty or turn it into risks with all his actions. When it’s unclear what to do, there are many inputs or interdependent connections, he doesn’t panic, lose direction or call his mom in tears. The ideal PM is creative and goes beyond traditional methods and solutions. He is especially adept at communicating with the team and stakeholders to ensure that the situation is understood and changes are agreed to. Uncertainty for him is an everyday occurrence. No matter what happens, he will change the system to suit the conditions, just as sailors change course and sail position simultaneously when the wind changes.

Responsibility and reliability

In almost every job opening for a project manager you will find the requirement “to be responsible”. You don’t know the goals, conditions, team and atmosphere yet, but they already say that you will start working and you will be responsible. In short, the ideal PM is a responsible PM. But what does it mean to be responsible? I thought about this question for a very long time and decided that “taking responsibility” means making a decision and being prepared to experience negative emotions, suffering and pain if something goes wrong. To experience failure on one’s own, rather than being scared of it in the beginning and inaction. And if everything is clear with a person’s personal life, because there the consequences will inevitably come and it will be painful, where does responsibility at work come from?

In the workplace, it is commonly believed that to be “responsible” is to have a vested interest in the business, the project, the outcome, etc. But how should an employee have a vested interest in someone else’s business? Cultures of “ownership positions” are invented and “shared missions and values” are created, but it doesn’t work. Because the business owner, partner and employees have different goals. And they use their work in the company for their own purposes, not for shared ones. They don’t care no matter what they tell them in the interview. The interests of the employees conflict with the interests of the owner at every turn. The business owner risks everything every day, the workers risk nothing. Where would the consequences that the worker would fear come from in such an arrangement? There is no accountability. Even to fire an employee for a joint is very difficult, if he is employed by law. And even if there is such leverage, the employee will simply change jobs. For some people this is scary, so they tolerate, do not dare to change and do their job responsibly. And some do it irresponsibly, but take advantage of the unprofessionalism or softness of management. Spent someone else’s investment, sitting on a salary, and no result – oh, well, it happens, sent the payment to the wrong place – sorry, promised cosmic goals and did not do it – so the world has changed, we are not to blame. It won’t be a big deal, the money and resources are not spent by the employee. And an employee will not agree to risk something personal and his own. Why should he go out of his comfort zone for a paycheck? There is no accountability, just a line in the mission and in the dreams of the manager. Even if the owner thinks he’s paying fairly. We know we never have enough and we work like wolves. It’s always unfair by default.

Employees aren’t bad, they just have their own goals and motivations. That’s the way it should be. This needs to be recognized and understood, then the picture of what to do about it will become clearer. You just need to recognize that there is no premise for the birth of responsibility at work. Come down from the turquoise skies and stop imposing responsibility. Responsibility comes from within. And in the perfect PM, and in any human being. No matter where I’ve worked – from shanty towns to cool companies – there have been non-ideal processes, non-ideal salaries and non-ideal teams, but my employees have always been accountable. They may have complained and been disgruntled, but no one ever let me down. They were reliable. Their accountability came from not wanting to let me down specifically or let anyone down in principle. But in the beginning there was a desire to accomplish the goal, to be committed to achieving the goal and meeting the needs of the stakeholders, and to implement all necessary measures to achieve a successful bottom line. This is the kind of attitude that is valued in an ideal PM. It is always easier to quit than to change your attitude to that of a business owner. But it is this transformation that affects the application of all the skills of the ideal PM. Whatever he does, he will put his best effort to make the result. I mention this at the beginning because without an understanding of responsibility, the other skills are meaningless.

Ability to recognize and reflect on mistakes

A perfect PM knows that no one is perfect. Everyone is strong and weak at the same time. That is why he is not afraid to admit his mistakes, realize them and learn from past experiences. He knows that mistakes are inevitable, and instead of hiding them or denying them, he openly admits to them rather than turning the tables or holing up in Zoom without a camera. He accepts responsibility for mistakes, looks for ways to correct them, and never repeats them again. He may step on new rakes, but never on old ones. I have seen people who will deny their mistake and blame everyone around them until the end. I have seen managers who would rather find someone to blame and make him a scapegoat than draw conclusions and support the team. Therefore, it is equally important to understand the culture and management styles of the company to avoid being the one who just takes everything on himself and destroys his reputation. The ideal PM knows when to admit mistakes publicly, and when to admit them in the small circle of the team or in his or her own mind.

Session 2.

Planning

Planning for the ideal PM is not just a Gantt chart. First and foremost, for him, it’s a process. A thought process. When planning, he looks at the entire project from analyzing the current situation to the ideal end result. This allows him to assemble a plan of action that will lead to the outcome with the highest probability. That is, to sign up for a plan that is impossible not to execute. Or realize on the shore that you need to change the terms or not do the project. You’ll never hear from the perfect PM, “Why bother planning? Things change so fast” or “There are too many inputs and scenarios, you can’t plan here.” He will consider all aspects of the situation and prioritize scenarios. He will choose the best plan of action and how to work with the plan to adapt when it is implemented.

Evaluation and verification

In a perfect world, the ideal PM is involved in sales, preparing a project estimate and a commercial proposal that leaves no chance to the client. He takes into account all factors related to the project and creates accurate estimates that help in planning and decision making. In the real world, a job estimate can be passed to the PM from sales department, another PM, etc. The project may be new, obscure, or have specific requirements. In such a case, I want the PM to know how to prepare a detailed estimate. Verify the functionality, cost and team, consider the risks and not overpromise. And if there is no experience, could organize the estimate using methodologies or with the help of other team members and experts that allow to make a realistic estimate in different scenarios, highlight assumptions and constraints. I think a 20% deviation from the initial estimate is acceptable, but you still want everything to be perfect. Often novice project managers can’t understand what to estimate because the scope is unclear or there are a lot of inputs. An ideal PM in such a situation fixes the project boundaries himself and describes the constraints. In his evaluation, it is always clear what scope or result is being evaluated, what can affect the evaluation and what needs to be clarified for a more detailed evaluation.

Goal setting

The ideal PM knows that goals need to be real and clear, and then SMART and other tools that help you move organically toward the goal and revise them as needed. Real goals means actually leading to the desired result in the shortest path. I often see aspiring project managers perfectly articulate framework goals, but can’t explain why this is our goal. Or because of insecurity, they make a big list of goals and can’t prioritize them. Especially if the right goal is ambitious and the degree of responsibility rises. An ideal PM doesn’t set goals like “for all good and against all bad” or “because they said so”. He knows how to distinguish fake goals from real ones and communicate this to the team in clear language. Moreover, he tries to make sure that his goals in the project are achieved by all parties: the client, the company and all team members. Therefore, he can organize communication and find an approach to help formulate the goals of each side of the project. Needless to say, this is an agile process and the goals are not carved in stone. Let’s not forget the times we live in.

Planning horizons

As the big goal is broken down into a chain of smaller goals, short-, medium-, and long-term planning emerges. Our handsome PM lives and thrives in these horizons. He effectively does short-term planning based on medium-term plans. Everyone understands the weekly and daily plan and keeps the project plan up to date. He does medium-term planning competently, assessing risks and timelines correctly. Informs the team of key milestones and mid-term project plans. He can plan a long-term project plan. For long-term projects, he uses the “surging wave” method, when the plan for the immediate period is as detailed as possible, and further on it is quite top-level. Even if it is the realization of a new project from scratch and a long-term roadmap is needed. He works out plans without fanaticism. The depth and detail of the plan is always directly proportional to the incomprehensibility and complexity. This skill is a good basis for strategic thinking, which is very useful for career development.

Work Breakdown Structures

The ideal PM breaks down complex project plans into smaller, manageable elements, making it easier to plan, allocate resources, and control tasks. Work Breakdown Structure or WBS is the organization of project tasks and activities in a hierarchy where each larger task is divided into smaller subtasks and activities. This structure provides a clear view of the order in which work is performed and its interrelationships and dependencies. The point is to break the project down into subtasks until a level is reached where each subtask becomes manageable. The ideal PM doesn’t crush the entire project down to the smallest tasks by instruction. He uses the world’s most effective tool – common sense. If the decomposition covers the whole project, has a clear hierarchy and interrelationships are logical and clear to the whole team, then there is no need to go further into detail. As always, everything depends on the team and the complexity of the project. First of all, WBS is done to get clarity of planning. This way, at the start it is possible to notice unobvious risks, actualize the necessary resources and blind spots of the project.

Risk management

The credo of the ideal PM is that risks cannot be eliminated, but they can be managed. He is not afraid of risks. He assesses the probability of risks and the effect of the consequences, prioritizes them and puts their treatment in the plan. In short, he identifies, plans, minimizes or eliminates risks on a project on time. Without giving cognitive distortions a chance. The cooler person is not the one who sees more risks in advance, but the one who sees the most devastating risks he can influence. The greater the ambition, the greater the risks. This has a direct impact on responsibility. That is why it is very important to work with risks in a focused way. Otherwise, you can make up so many ideas that you may not even be able to start the project. Working with risks is one of the foundations of planning. An ideal PM has a lot of experience and knowledge. Therefore, his head is full of cases with the most common risks and strategies for responding to them. If you don’t have enough cases of your own, you can always find those who do. They can suggest new risks and help with the assessment of current ones. The main thing is to soberly add them to the risk matrix and not add fuel to the fire of anxiety. In any communication, the ideal PM always uses the word “risks” along with a suggestion of what can be done about them. Sometimes you need to take a risk, but if the risk works, it is important to have an experience, not a total fiasco and psychological trauma.

Priority management

Priorities are linked to goals and are also subject to change. Priorities are a matter of choice. The ideal PM knows how to make the right choice at each point in time to maximize value. He or she not only knows prioritization techniques, but can describe the logical process of why a particular choice was made and what can change. Working with priorities affects the customer, the team, and task completion. That’s why it’s important to communicate the mechanics of prioritization in advance and transparently communicate why they have changed. So that everyone on the team prioritizes based on team principles or project goals, rather than on a whim. A cool PM knows that the word “priorities” didn’t exist before and if you have to choose one of the three most important priorities, he knows how to consciously do it. With all information and data, the ideal PM uses a visual hierarchy. He places the most important tasks or figures at the top so that everyone always knows what is most important right now.

Strategic thinking

I’m probably nuts, but the ideal PM knows how to live from the future to the present. For him, the word “strategy” is not “understanding where we want to go, what plan and approaches to use” and certainly not a document with a written strategy. It is a process of managing strategic tasks and decisions. It requires an understanding of the place and role of yourself, your company or project in the future. Understanding what should be done now, what decisions should be made in order to have a favorable position and competitive advantage there, in the future. No matter how ideal a PM is, he cannot predict the future and accurately determine the end point. It’s about working with the future on different horizons to understand how it’s changing and what you need to focus on in the here and now. What balance to choose between strategic actions and operational actions. So first the strategic process, then the strategy, and then the planning and approaches that need to change with the changing future. Often aspiring PM confuse planning with strategic process, but not our ideal PM. After all, he always thinks with a sequence of “Why?”, “How?”, “What?”. By the way, with these skills, he can build a personal life strategy. Therefore, he will always grow in all areas faster than others.

Session 3.

Managing the project

In fact, it doesn’t matter how a PM manages a project, as long as the result is done on time and on budget, the team is happy and demands continuation, the case is getting likes, the company has earned money, and the client is already filling the case with money to continue working with you. You can read as much as you want about methodologies, get smart with quotes from PMBOK and cross Scrum with anything, but project management is a constant problem solving to make results. Knowledge of classic project management and modern frameworks gives you a base, but no project goes perfectly according to the plan. Not even the perfect PM’a. If the client, team, events or uncertainty make adjustments to the actual process, the ideal PM always remembers that the team is not working for the sake of following the process, but for the result. The process can change, and for a great PM’a this is not a problem!