Right-sizing project management for early-stage startups
How do you keep aligned on projects without being bogged down in endless notifications and tasks?
After one too many meetings with a “we should do this” that floats off into the void, you realize that it’s time for your team to invest in a project management system. The tool options are endless, and you’re eager to grab the tool that all the others use, set up some templates, and get your team doing the work they say they’ll do. But suddenly, you find yourself avoiding the tool at all costs, fumbling around to find links to the right page and flush with a sea of notifications that leave you more lost than you started. Is this the organizational mecca that project management tools promised? Because it feels messier than when you started.
how DO you establish a project management system that is simple and effective, while making space for the shapeshifting course changes that occur in the early days?
Build project management as an agreements tool, and leave space for the rest.
Why This Works
It is all too easy to proclaim from the digital rooftops that your team will now start using a project management tool and all of its best practices without recognizing how complex managing projects can become. Consider how you manage your email inbox. The deep obligation to respond immediately – and apologize for the delay – is email etiquette 101.
We recently came across a post by Jake Kahana of Cave Day Slow Replies Don’t Also Need Apologies that resonated with us. These words encapsulate the reality of our behavior and shed light on the unnecessary burden we often place upon ourselves in this age of constant connectivity.
“Last week, a friend of mine shared a personal newsletter announcing his engagement. I wanted to wish him and his new fiancee a congratulations, but after a few days of limited work time, my inbox backed up and I had forgotten.
So about a week later, I sent a reply and started with “Sorry for the slow–“
wait.
Why am I sorry?
He wasn’t even expecting a response. It was just a work instinct.
We all do this.
We apologize for not being more available, not being fast enough to reply. As if there’s some sort of standard agreement between all humans that we need to be available to each other and responsive as soon as we get an email.
But there’s not an agreement.
It’s just an expectation– unspoken and assumed.”
Assumptions get us nowhere. All too often, our working operations are built on assumptions of what we think our colleagues will be doing, and when they’ll be able to do these things to support our work, but have we agreed to this together? This is where using project management as not a task manager, but rather a way to capture agreements of work you’ll commit to achieve together in a timely manner to achieve big goals, you’ll see org magic be made. We remove unrealistic and unknown expectations on the work we’re giving and receiving from one another and commit clearly to the work we’ll accomplish, the collaboration we’ll support, and the analysis that helps us work on the right things.
Why Do This Now
As your team grows, 1:1s become the breeding ground for duplicative conversations. “I told the head of engineering this last week. Did I tell you, the head of operations, this yet? Ok, let me tell you. And then you can tell our marketing coordinator. She’ll tell her marketing lead.” In this painful game of telephone, who is doing what when? No one knows and meetings simply become status updates. Add a few more people, and you’ll find that people are working hard, but no one’s sure what’s being worked on, or how, or when.
Overengineer this and it goes wrong too. “Did you update the tracker? Have you updated your tasks? This project is indicative of what’s going on. Why?” If you build an agreements-based instead of expectations-based culture, you’ll find that the autonomy, excitement, proactiveness, and exceptional work that you’re hoping for becomes part of the subconscious system you (intentionally) built as you manage projects with little effort and maximum efficacy.
Gena Gorlin's article How Builders Think encourages approaching life as a project and taking charge of shaping it according to personal vision and values. Embracing this builder mindset in project management practices enables startup founders to empower teams, foster ownership, and deliver exceptional results. By defining their own standards of excellence and carefully selecting suitable project management tools, founders can create a transparent and efficient workflow that aligns individual efforts with common goals.
how We Do: Aligning your project management systems to support an agreements-based culture
Tools 🛠️
Project management tool options are endless. It’s how you use the tools that make the difference.
Set up notifications before tool implementation.
Are they going to email? Slack? Neither? Are these going to all team members in the same way?
Define a place to “do the work”.
Start with templates to move quickly, but resist the urge to retain everything. Throw out what you don’t need so you’re left with the essentials. You can add it later.
Establish task management for individual contributors. If you require someone to review something, simply include it in their list of tasks. Don’t forget the invisible work that will bottleneck a project if not planned intentionally in advance.
Define a place to “review the work”.
Build a dashboard for the doers of the work, as well as a dashboard for the reviewers of the work. Put it all in one and the form doesn’t meet the function. Clarity of communication will win the day here.
If you’re stuck in a creative planning rut, leverage ChatGPT and other AI tools to assist with project planning, time estimation, and prioritization. Seek out opportunities to leverage AI within your tool stack to offboard menial tasks.
Rules (Process) 📝
Systems and cycles matter. There are three key steps to managing projects in the early days. Every other in-depth tracking mechanism has the potential to derail you. Start simple, and focus on these three pillars for team success. Notice that the focus is to “agree upon” an operating system. Master this so you can focus on working on the work that matters.
Agree upon how and when projects are getting added.
Use space in 1:1s and team meetings to add projects, and prioritize against existing work.
When new projects come up within the week, take care to not add them immediately. Add them to a Project Queue. Review the queue each week against the existing list to reprioritize as needed. This review will also help you catch redundant projects that come out of 1:1s. If multiple team members are interested in tackling the same challenge, you may have a natural opportunity to encourage cross-functional collaboration.
To avoid scope creep, regularly review how a project’s direction is moving relative to its initial goal. If it’s shifted, was it intentional to reflect new information or lessons learned from experiments? If unintentional, does the new scope warrant a whole new project?
Agree upon time frames of when projects are getting updated.
When is the team responsible for updating project tasks and progress?
How are we making space for team members to stop executing, just for a moment, to analyze the work, and effectively plan the next crucial moves?
Agree upon time frames of when project progress is getting reviewed.
It’s essential for a founder, manager, or leader to determine the appropriate times to assess project progress and when to refrain from adding comments and questions that may impede the team's workflow. By establishing clear guidelines in this regard, the team can focus on their strengths and carry out their tasks efficiently.
Review for prioritization, bottlenecks, efficiency, and exceptional work. Are we doing the right things at the right time? What is holding us back? Are we using our limited time and resources the best we can? Are we doing work we’re proud of?
People 🫶
Empower team members to embrace a culture of project management both independently and collectively. Each team member should take ownership of their assigned tasks and be accountable for their timely completion. By taking responsibility for their role in the project, individuals contribute to meeting project timelines and achieving project goals.
Fostering a collaborative environment encourages effective project management. Team members should work together, share knowledge, and provide support to ensure tasks are completed efficiently and dependencies are addressed.
Establish clear guidelines with your executive team to ensure project-management implementation is viewed as a net positive to support efficiency and organization, as opposed to a big brother tool.
Leverage project management experts to implement tool stacks that support your team, while being mindful to meet them where they are.
Embed incentives at the team level for engagement and success to support adoption.
Actually Actionable
Nice article. Now what?
We’ve taken the ideas above and created an action plan for you and your team.
Objective 1: Introduce project management adoption and establish the foundation for an effective system as an agreements tool.
Meeting 1: Discuss project management challenges and the need for streamlined processes with your executive team (1 Hour).
Meeting 2: Narrow solutions to identify which accomplish the needs of your team (2 Hours).
Objective 2: Define specific processes and guidelines for effective project management.
Meeting 1: Implement an agreements-based approach to PM tool management (30 minutes).
Meeting 2: Establish time frames for updating project tasks and progress (30 minutes).
Objective 3: Onboard the new tool
Meeting 1: Meet with the executive team to establish employee-supportive policies and expectations (30 minutes).
Meeting 2: Onboard the new tool with your team (1 Hour).
Wrap-Up
In the fast-paced world of early-stage startups, striking the right balance between efficient project management and avoiding administrative burdens is crucial. Implementing processes that prioritize agreements over mere task management ensures alignment and commitment to common goals. But truly, it’s about no longer working on remembering what work is happening and making space for extraordinary work to take shape.
The goal is to provide clarity and structure, transforming collaboration into effective decision-making without burdening the team with administrative tasks. Embracing right-sized project management practices allows founders to ensure clarity and guide teams from opaque collaboration to clear, decisive action.
Writer: Britt
Collaborators: Caleigh & Scott
Thoughts on a topic that you would like us to cover in a future issue - we would love to hear from you: founder@weofalltrades.com