Charlie Gilkey on Start Finishing, Part 10

In his book, Start Finishing: How to go from idea to done, Charlie Gilkey discusses how we can follow a nine-step method to convert an idea into a project and get the project done via a reality-based schedule.

These are some of my favorite concepts and takeaways from reading the book.

Chapter 10, Finish Strong

In this chapter, Charlie discusses how to conclude a project before jumping into the next project properly. He offers the following recommendations for us to think about:

  • Run a victory lap after the project. It is an important social activity that can rejuvenate our supporters and us.
  • Make the necessary space and time to transition between projects. The more project matters to us, the greater the need for downtime and transition time after finishing it.
  • Give ourselves CAT time, and it will make the next project easier because we will not be fighting the messes of our last project.
    • Clean up: First, make sense of what is around us regarding environmental, digital, and social factors.
    • Archive: Organize our environmental and digital stuff and store them in a way that can be retrieved without too much effort.
    • Trash: Throw away or delete environmental or digital stuff we no longer need for our next project.
  • After-action reviews (AARs) make every project a learning experience at the same time that they set you up for tremendous success in future projects. Ask ourselves:
    • What went well?
    • What setbacks, challenges, and missteps did we experience?
    • What did we learn?
    • What habits, practices, or routines do we want to keep doing going forward?
    • Were there any crucial difference-makers to the project that we should consider for our future projects?
  • Finishing a best-work project can unlock new realities. When it comes to our best work, we start finishing before success and after success. That is all there is to it and all there can ever be. Days spent doing our work compound to create a thriving life.

Charlie Gilkey on Start Finishing, Part 9

In his book, Start Finishing: How to go from idea to done, Charlie Gilkey discusses how we can follow a nine-step method to convert an idea into a project and get the project done via a reality-based schedule.

These are some of my favorite concepts and takeaways from reading the book.

Chapter 9, Build Daily Momentum

In this chapter, Charlie discusses some tactics for building and maintaining momentum while we do our best work. He offers the following recommendations for us to think about:

  • Celebrate the small wins as we move things forward. Celebrating small chunks of progress can enable us to celebrate big finishes when we get there.
  • We should create habits and routines that make it easier to build and maintain momentum. Figure things out in advance can minimize decision fatigue and create more prolonged periods of flow.
  • Leaving crumb trails for projects makes getting back into projects more enjoyable and efficient. First, we need to leave ourselves enough time at the end of a focus block to leave breadcrumbs. Second, we need to be honest with ourselves that the momentum we have at the end of a focus block will not be there when we get back to the task.
  • We need to distinguish and minimize interruptions and distractions. Interruptions are external diversions that keep us from doing our best work, while distractions are internal diversions that we allow ourselves to experience.
  • There are three ways that a project gets stuck:
    • A project cascade happens when a project falling behind makes other projects fall behind.
    • A project logjam happens when we have too many concurrent projects.
    • A tarpit happens when a stuck project gets more stuck the longer it stays stuck.
  • The creative red zone is the last stretch of the project, where the closer we get to the finish line, the harder it is for us to cross the finish line. This feeling is the “Resistance” calling us. Here are some tactics for countering the “Resistance.”
    • Remind ourselves of the “why” of the project and double down on our effort to return to it.
    • Focus on getting the result good enough.
    • Remind ourselves that the more something matters, the better is it that we start finishing sooner.
    • Understand that toward the end; we are usually just working on our mindset.
    • Finally, do our work, then step away.

Charlie Gilkey on Start Finishing, Part 8

In his book, Start Finishing: How to go from idea to done, Charlie Gilkey discusses how we can follow a nine-step method to convert an idea into a project and get the project done via a reality-based schedule.

These are some of my favorite concepts and takeaways from reading the book.

Chapter 8, Weave Your Project into Your Schedule

In this chapter, Charlie discusses the techniques to integrate our environments with the daily requirements demanded by our best work. He offers the following recommendations for us to think about:

  • Make sure our environment is working for us. Pay attention to these seven environmental factors and determine how they might affect us:
    • Sound
    • Smell
    • Sunlight
    • Clothing
    • Clutter/Organization
    • Amount of space
    • Music.
  • Batching and stacking are two techniques that can improve our efficiency.
    • Batching work is the process of doing similar kinds of work in a contiguous period.
    • Stacking work is the process of doing different but compatible kinds of work at the same time.
  • Keep the dread-to-work ratio down by dealing with the “Frogs.” Frogs are the tasks and chunks of projects that we do not want to do. However, we should consider addressing them early and often as necessary.
  • Focus more on the “when” rather than the “what.” Decide upfront when it is best to do particular work and stick to the schedule/plan.
  • First in priority doesn’t always mean first in the sequence. The key idea is to get to those high-priority tasks at the right time to complete the tasks in the most effective manner possible.
  • Use the 5/10/15 split to build daily momentum. We use our five projects to create and update our daily plan for ten minutes before we start and fifteen minutes at the end of our day.
  • Do not plan too far in advance. Doing so can create frustration and resignation because the further out we plan, the less likely our plan will be correct or practical.

Charlie Gilkey on Start Finishing, Part 4

In his book, Start Finishing: How to go from idea to done, Charlie Gilkey discusses how we can follow a nine-step method to convert an idea into a project and get the project done via a reality-based schedule.

These are some of my favorite concepts and takeaways from reading the book.

Chapter 4, Convert Your Idea into a Project

In this chapter, Charlie discusses the steps to convert our chosen idea into a project. He offers the following views for us to think about:

  • A SMART goal is:
    • Simple: A simple goal is not necessarily an easy thing to do, but a goal is simple when we can look at it without wondering.
    • Meaningful: A goal is meaningful when we understand the importance of completing that goal.
    • Actionable: A goal is actionable when it is immediately clear what we need to do to accomplish the goal.
    • Realistic: A goal is realistic when we know we can achieve it with the available resources.
    • Trackable: A goal is trackable when it is apparent to us what progress means, either quantitatively or qualitatively.
  • There are three levels of success:
    • Small: A string of small successes done with coherence and intention can still lead to greater success down the road.
    • Moderate: Moderate success is the highest state we can achieve with just our own effort, resources, and advantages.
    • Epic: Epic success always requires us to build a team to help us achieve it.
    • Each level of success requires a corresponding amount of effort and focus, and we cannot do everything at the epic level.
  • Our success pack consists of four groups of people: guides, peers, supporters, and beneficiaries.
  • Steps for leveraging the success pack to go from idea to action:
    • List the three to five people who are a part of each group.
    • For each person, brainstorm at least three specific ways they can help us or we can help them.
    • Determine the frequency of communication that would be most supportive of the project.
    • Let each person know they are a part of our success pack.
    • Proactively communicate with and show our work per the agreed-upon communication frequency.
  • If a project does not have start and completion dates, it is not likely that it will get done.

Project Management, A Process or Practice?

Is the work of project management a process or practice?

I think project management is both a work of process and practice, so what is the distinction?

A process focuses on being consistent and repeatable – you should be able to get predictable results from a process.

PMBOK has five process groups with ten knowledge areas intersecting those process groups for various project management stages.

Practice focuses on applying knowledge, judgment, and wisdom to achieve the desired outcome and dealing with changes. All project managers need to produce results by balancing the triple constraints: scope, time, and cost. Those constraints can often change during project execution.

A good project management practice established and executed by qualified personnel will bring the desired results, even with those limitations.

These days, just about everything we do requires a mix of process and practice. For example, implementing just the ITIL processes verbatim from the framework without applying the necessary effort on building an ITSM practice will just yield generalized, paper processes.

With the pace of changes picking up and the predictability of our environment shrinking, developing a practice is just as important as developing the required processes.

What I learned about Managing IT Projects from Playing Online Games


Time flies when you’re having fun. It seems like just yesterday I grew up playing video games on Atari and Nintendo, and now we have many more gaming choices available to us. To this day, I still enjoy playing video games on computers. Gaming for me is not merely entertainment – I enjoy learning and understanding the design and mechanics behind a particular game. I also enjoy the socializing and friendship-building aspects of the online games.

Many computer games clearly were built to provide entertain value, but there is a surprising amount of wisdom to pick up from some of today’s more sophisticated online games. One aspect of playing those online games involving social activities of organizing a group of players to accomplish a common objective, usually involve slaying a dragon or a boss monster. It is fascinating to me that one often can find some intriguing parallels between organizing a raid and organizing a project team within an organization. Whether it is organizing a 25-player, 6-hour long raid or organizing a 25-member, 6-month long project, some leadership and management principles seem to apply for both cases.

Here are some lessons I believe many younger IT colleagues might be able to learn from spending some time in the virtual world.

What are we trying to accomplish and why?

In the game world, we ask which dragon do we want to slay tonight? Announce the final objective up-front and let people know what is in it for them. Players come to a particular raid for many of their own reasons. Some will come for a specific loot or reward. Some players come to the raid to experience a particular portion of the game content. Some players will come to a raid to learn more leading a particular raid. Some will come just for fun and sight-seeing.

In the real world, people band together to form a project team for a variety of reasons. Those reasons could be driven by organizational, political, or other factors. The why factor always should be aligned to a business goal. Helping others to understand the end state up-front can help to build commitment and to foster positive motivation.

How are we going to accomplish the objective?

In the game world, we need to understand the details of the encounter as much as possible before you can have a successful raid. “Know the fight” is a common phrase used in online gaming. Today’s online game raids can be quite sophisticated and involve many stages or phases. Everyone participating in the raid should have a basic understanding of the raid and what to expect during each phase. However, knowing the fight at a high-level is just half of the battle. Each segment of the raid will have certain activity requirements that need to be met, often under some time constraints. If the requirements are not met in a timely fashion, it is quite possible the raid will fail. To plan ahead, the raid team needs to translate the requirements into workable tasks and assign a time line.

In the real world, it works pretty much the same for a project. The project team should have a common understanding of how the project should be executed at a high, summary level. The project team then breaks down the work into tasks and assigns deadlines or timing dependencies to those tasks.

Whom do we need for this effort?

In the game world, a raid will require a collection of players to fulfill a variety of roles. In online games, the roles can also be referred as jobs or classes. To complete a raid successfully, it will require a proper combination of roles all working together and executing the tasks along the way. In addition to having the proper roles, the raid team will also need skillful players in order to succeed. The skillful players know their jobs/classes well and understand how their roles fit into the raid encounter. The more skillful players can also provide valuable input into the raid and support everyone else to get the job done. Very often, the most time-consuming aspect of organizing the raid is to find and recruit the classes/players you need for the raid.

In the real world, we also need people with the proper skillsets and competency level to execute a project. Staffing a project team with a perfect combination of the skillsets and personalities can be a difficult task. Sometimes, the staff choices are given or established by the organization beforehand or is not entirely negotiable for some reasons. When those things happen, the project team will work with what it has. Sometimes the project team might need to recruit additional people or to replace individuals in order to cover the skill or competency gaps created by the project team make-up.

Which tools will we need to manage the effort?

In the game world, the game client application serves as the foundational tool for all raid team members. Having access to the same information by everyone is critical to the successful execution of any raid. Many raid teams rely on websites or in-game chats to communicate pertinent information about the raid. Very often, critical information also must be delivered quickly. Many raids today are also supplemented by another communication tool, such as voice conferencing. The game world can be unforgiving, and unwanted things can happen extremely quickly. A few poorly-timed missteps by the raid members can easily add up to a deficiency that is too severe for a raid team to overcome, leading to a wipe.

In the real word, consistent execution of a project requires all project team members to have access to the same project information via a set of common tools. Information can be communicated in written form or in verbal form. Project plans, meetings, memos and minutes are just a few tools we often use. The real world can be just as unforgiving as the virtual one. Poor communication can add up to either severely delay a project or sink one.

When Games Mimic Life

Even with the proactive planning in place, many things can still go wrong. Risk management most also be practiced when operating in both worlds. In the game world, risk management takes the form of having a robust combination of roles and solid communication channels. In the real world, we often have a lot more risk management options available to us if we put in the proper level of planning. There is no reason why we cannot do what we can to be properly prepared and well organized for any project.

Whether in the game world or in the real world, producing positive results with a group of people takes leadership, management, collaboration, and communication.

Footnote: Wall Street Journal reported that a new study reveals that adults who played a video game helped their mental agility more than adults who did crossword puzzles. Just saying.

Image Credit: Courtesy and Property of Blizzard Entertainment, Inc.