2 People and 2 Perspectives on the Art and Science of Projects
Updated: Aug 28
Navigating Project Management Across Books, Silicon, Entertainment, And SaaS
I’m sure you have heard of project management. My friends and colleagues have a love-hate relationship with project management. Sometimes managing a project is fun, other times tedious. Project managers can either save you from heartache or be the cause of it.
In this post, Liam and I co-write about project management. We share our first brush with project management and how we learned it.
Have you seen friends use structured task-planning approaches in the sanctuary of their homes? We are both those kinds of friends, although with varied approaches.
Yet, why co-write an article?
Whenever I meet someone interesting, I am drawn to understand more about their journey. When I met Liam, I was curious to hear about his journey. At first glance, Liam's career was the polar opposite of mine. Liam and my stories span different industries — from book publishing to semiconductor engineering. But, to my surprise, we are both solo consultants. We had gone through similar challenges in setting up our businesses. Even more surprising was our mutual expertise in project management and planning.
I hope this post shows how personal experiences can shape our professional paths.
Here Are The Questions We Discussed
What Brought You To Project Management?
What Are Your Operating Principles?
Which Skill Was Crucial For Success In Introducing Or Implementing A Project Management Process?
Project management techniques as a solopreneur?
Have these techniques also spilled into your personal life?
Snapshot Of Liam And Harshal
I’m a creative consultant through my company Castle Stream, where I work with organisations to manage their creative projects. Apart from acting as a project manager, I also contribute scripts, audio and video recording, and design. Before this I was a lecturer in Publishing Studies at the University of Pretoria. You can read about more of my work and my journey into UX here.
I run Spark Creative Technologies, where I provide product consulting to B2B SaaS companies to improve their customer experience. Before this, I worked in Product Management and engineering, including at Cisco and Qualcomm. Most recently, I was a Staff Product Manager at Twilio.
What Brought You To Project Management?
I initially trained for the book publishing industry where my goal was to be a production co-ordinator. This is sort of the book equivalent of an engineering manager. As production co-ordinator you oversee the transformation of an edited typescript into a finished book. So you’re a generalist whose job it is to bring together materials, designers, illustrators, photographers, editors, and printers to create something beautiful. It’s a marrying of technical, social, and creative skills, and being part of a process like that still excites me.
During my first year working as an engineer at Qualcomm, I had the opportunity to change my role to a verification lead. The leadership role included project management to keep 40+ engineers on track with verification as part of their project delivery. This leadership role introduced me to project management principles. I realized the continued value of managing a project well when doing case competitions, validating startup ideas, and participating in 50+ group activities during my MBA at UCLA Anderson. The numerous activities made MBA a crash course in learning people and task management.
I consider project management one important skill of a Product Manager. As a solopreneur, I work with freelance contributors. This working relationship needs project management due to the numerous moving parts.
Our journeys, though in different industries, converge on the importance of project management.
What Are Your Operating Principles?
I have two guiding principles.
1) Clear communication: Everyone involved should be able to access the necessary materials, and feel free to ask questions. The more transparent the workings the better. Everyone needs to see where they fit into the project and feel like a valued team member.
2) Plenty of time: I like to start work early and progress at a steady pace. I strongly believe that doing a job well is always better than doing it quickly. If there are specific deadlines that need to be met, then it’s important to get in touch with people early, get a reasonable estimate and (if possible) double it.
Liam and I seem to resonate with the importance of clear communication in our operations. However, while Liam emphasizes starting early and allocating generous timelines, I lean more toward being wary of estimations, largely influenced by my readings and experiences.
Here are some tenants I follow:
1) Projects will never complete in the timeframe you plan. I limit the time spent on estimations. My observations on the job shape this. My feeling of not relying on estimations intensified after reading Nasim Taleb’s Black Swan. I wrote more about the book’s influence on me here. I don’t prefer building Gantt charts to show the waterfall development. I prefer to know the sequence of tasks and relative priorities. It helps me keep an eye out for scope creep. But I also realize people love to see a plan, so I build that to satisfy stakeholders.
2) Communication brings clarity to colleagues. It helps bring stakeholders on the same page as your team. I communicate project updates as soon as possible. Early communication helps keep a surprise small. A later surprise is a bigger surprise.
3) I follow the Checklist Manifesto approach. I create checklists of research, execution, and launch of any project.
4) When communicating, I aim to communicate in multiple mediums. For example, when hiring freelancers, I provide a summary of the task, write a document, provide a template or example of the output, and create a Loom video walking through the details.
5) When managing freelance projects, I aim for a gradually increasing scope of delivery across milestones. I do this by 1) milestoning a project, and 2) looking at the smallest increments of work possible that are deliverable and can be reviewed.
Although I consider project management a crucial skill in Product Management, I also find many more PMs who can manage projects, but not own a product. I wrote my perspective on the different components of a PM role here and here.
Which Skill Was Crucial For Success In Introducing Or Implementing A Project Management Process?
Patience, empathy, and a willingness to compromise. These are traits rather than skills but I think they’re more important. Time-management is a skill, but if you’re not a patient person you won’t appreciate it.
For me, time management isn’t about having something to do every hour. Rather it’s about allocating time to stimulate, focus, and recover.
Clear communication I think is often mentioned as a skill as well, but I think it stems from empathy. I don’t think anyone likes feeling out of depth or confused, and that people enjoy feeling like they’re part of something, and that their work matters. The last thing you want to hear from someone in your team is, “I don’t know what’s going on.”
You also need to be adaptable, and encourage the same among your team members. As Harshal says about “gradually increasing the scope of delivery”, you need to take your team’s input to heart when you do that and be very clear on expectations.
Entertainment is fundamentally a waterfall workflow. In a production you need to complete script work, costuming, effects, sound, lighting, blocking, and get them to a relatively immutable stage. Planning is key to make sure you don’t waste anyone’s time, because it is expensive and logistically difficult to get a group of people together.
So you can still use a Jira board, but because your project (sometimes your entire company) is temporary and has a fixed budget , once you have your jobs-to-be-done ready, you don’t want to be adding to it.
I like to start planning by reviewing all the stages and jobs-to-be-done. Take in estimates and review them. Then each job gets assigned to a person with a reviewer. The reviewer assignment guarantees everyone knows whom to share their work with for review. That person might often be me, but in a review stage I will have to report back to them and maybe the client.
This review system is part of ensuring regular communication.There’s always at least two people involved in every job, and everyone can see at what stage we’re at.
I try to make a job for everything. There’s a job to write the first draft of a script. A job to review it (QA). We iterate to, usually, three drafts. Once the writer, producer, director, and client are happy, we can consider the script done. Lines may be cut later on, but a script gives you all the requirements for a production (number of actors, locations, FX) which affects the budget, so it needs to have a level of fixidity.
When it comes to time management. Let's say we’re doing a short content video. Say 1 minute long to market a service. This isn’t a long script to write. But I assign 6 weeks to get all the drafts and reviews done. If we get it done quicker great, but it often takes 2 to 3 days to hear back from a client while they pass a draft around. We might have to do extra research, we may have to organise another meeting… so giving plenty of time is really helpful.
Collaboration, gradual changes, and reasoning. I’ll share an example where I worked with a client to implement a project management process for content marketing.
I made incremental suggestions. I suggested we understand our customers’ needs and gradually learn how customers discover our product. I aimed for low-fidelity research in my first week. The lo-fi approach meant I wasn’t tied to the research, nor did I spend too much time in the wrong direction. It turned out I was in the wrong direction because of issues in their product analytics. I took another gradual step of taking one content piece through an experimental process, before recommending to scale up the process.
I presented my research, my recommendation, and the reasoning behind them. Providing explanations was vital as it provided transparency. It made it easier for the client to point out gaps in my understanding of the client’s context. These built more trust and helped them accept and implement the recommendations. My approach aligns with Liam’s recommendation of communicating clearly because no one likes feeling out of depth or confused.
Like Liam’s observation that people enjoy feeling they are part of something, I make the changes collaborative. Chip Heath and Dan Heath mention in Made to Stick and Switch, that involving your stakeholders helps make them changemakers. They are more likely to follow the new process if they are part of the decision. I shortlisted some freelancers we wanted to work with, then asked the client team to decide on a hire. See illustrated summary of Switch from Rachel Smith.
Before my project with this client, they created a content piece once in six months. Their content was vague, so it did not help prospects discover their product. I built a customer research tool, project brief template, freelancer hiring questionnaire, and content quality criteria. After my project of establishing this content pipeline, the client went from 1 to 25 content pieces in six months. They occasionally ranked on page-1 of search results. I will write more about this case study in another article.
What Project Management Techniques Do You Use As A Solopreneur?
The main tool for me is a Kanban board. Since I work on a project basis this is very helpful for me to see at a glance what I’m working on, and how far along in the process it is. Most of my work tends to follow a waterfall flow so I list all my jobs in a checklist and keep notes on the work I’ve done along with the time spent.
The time tracking is quite useful to me, not so much for direct billing but for estimating how much time I need to set aside for different tasks. For example, if I take on a job that “should” only be a day’s worth of work, then I strive to get that job done within 8 hours. I might spread that out over a week, but timing myself helps me gauge the difficulty of the work.
Other than that, my calendar is my best friend. If there’s an event, it goes in the calendar. Day to day I find I can monitor my productivity pretty well with paper notes, but if I don’t make formal, scheduled calendar appointments I will miss them.
Day to day I tend to work in 50 minute bursts, then give myself a 10 minute break. I usually have a focused task in the morning, a mid-morning email session, and set different tasks for the afternoon. I find it’s helpful to divide the type of work I’m doing. So for example, if I was working on designing in the morning, then I would focus on writing in the afternoon.
In my early solopreneur journey, I started off by using a 2-D to-do backlog. It was my to-do backlog. This allowed me to list my tasks and check each one's urgency and importance. Yet, this method had limitations - it could not divide specific time or scope to each task. So, it was not effective for planning.
I then switched to using my calendar to plan my weeks. But, this approach didn't prove to be the silver bullet either. The calendar-based approach brought in its own complexities. I created artificial time blocks and underestimated the effort for tasks. I went low-tech, experimenting with handwritten weekly plans. Using it made tracking progress difficult, even though it helped me focus and manage my backlog.
Looking for a more holistic solution, I went to project management software. I used Asana for my content calendar, Zoho projects for my resume parser backlog. I tried out Trello and settled on Linear.app for my weekly planning.
I created a few habits to help me plan and stick to my plan.
1) I start each day by first reviewing my weekly priorities and that day’s calendar. I want my daily calendar agenda to reflect my weekly priorities.
2) I keep one or two most important items to complete in the day. The meat of the day. Rest everything is ancillary. Like salad dressing. I write this focus on my chrome new tab in Momentum.
3) I work in 25 mins work and 5 mins break sprints.
4) I workout every morning. I follow a measured diet of whole foods. More about being a Fitness Fanatic here.
Each day I update my table with goals vs accomplishments. By the end of the week, it gets filled.
The process of weekly planning as a solopreneur is not static. I strive to fine-tune this process.
Have These Techniques Also Spilled Into Your Personal Life?
I don’t keep a board for my everyday activities but I do keep lists. Usually the first thing I do on a Monday is start a to-do list. I start by adding things left over from the previous week, and then I add tasks as I think of them. Sometimes I add things as I do them to make me feel more productive.
I started telling myself a little while ago that if I can achieve one thing everyday, then I’m doing ok. Sometimes that one thing is sitting in the park and reading my book. Other times it’s making a dent in a large task. Doesn’t matter what it is, but it’s a goal to be met. And reaching a goal, and crossing something off a list is immensely satisfying.
I do the same thing on holidays now. There are no full itineraries, there’s just one thing to make it to each day, and everything else is a bonus. I find that that opens up life for adventure, and gives you the excuse to do things you hadn’t planned for.
It’s about balance really. The organised approach I bring to my work has one main goal: to make time valuable.
Something I’ve experienced in both the performing arts and education is that people working in these industries tend to push themselves too hard, and undervalue their time.So I encourage people to work smart, rather than working long because I want to save people’s time to let them spend with their families or hobbies. Rewarding work to me is work that you enjoy doing while you’re doing it, and then are able to put it out of your mind when you’re not. It allows you to approach life at a pace that you dictate.
I apply this to myself because while I may be my own boss, I still need to keep my employee happy.
My spouse and I started our household planning, a.k.a Life Ops, on Whatsapp. Then emails. Even scheduled emails. We used the calendar to remind us of to-do. But we faced the same problem as mentioned earlier - the calendar created an artificial time block for a to-do.
We found better success by creating a unidimensional list, using OurGroceries. Its integration with Alexa and Google Assistant helped us add items to it whenever we remembered.
OurGroceries was great to create a backlog. Yet, we struggled to remember when to do a to-do. Is there a deadline for some, like e-commerce returns?
We created a habit of reviewing our to-do occasionally, but that system was not robust enough. We tried out enterprise-level software with trepidation. Reading Family Firm bolstered my motivation to try it out. We used Zoho Projects and created a custom Kanban board. We aimed to keep minimum items in “Doing” or “Scope” status, but it was ok to have more in “Spouse Review”.
Liam’s Takeaway From Discussing Project Management
“There’s more than one way to build a bridge”, as they say.
I think Harshal and I both have this desire to do things better. To improve, to grow. As facilitators, it is difficult to turn this desire off, because we’re always looking at how we can do things better the next time.
Something I’ve learnt from Harshal is the benefit of deep-dive experimentation. He reads constantly and immediately puts new ideas into practice to test them out. It’s an incredibly detailed approach, which – combined with rigorous testing – allows for an objective view of different methods.
I think this approach is highly valuable in an organisation where protocols and procedures function as the circuits that keep the machine running.
What I also see though is a commonality:
Whatever process you choose, however you decide to divide a job, however you manage your work… you need to do the work without work management getting in the way..
My own way of working has come from a whittling down of everything I find distracting so that starting my day is as simple as writing a line on a notepad, or writing a one-line card in Trello.
Harshal is on a similar path. He’s looking for those silver bullets that will cut-down on admin time and let people get on with their day. Give people a space to talk, and a way to visualise progress, and you’ll have a happy team.
My Takeaway From Discussing Project Management
Drawing from Liam and my tales, it's evident that the beauty of project management doesn't lie merely in its methodologies. It lies in the way you can weave it into your lives. The beauty lies in using it in both professional and personal lives. There is no one approach, but there is a right approach for you. When we found the right approach, we found it easier to work towards our goals. Our approach also created pockets of time to relish life's spontaneous adventures.