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Eating the Elephant: Tackling Big Projects One Bite at a Time

We've all been there. Your boss or client invites you to a meeting—you walk in with a sense of foreboding, and you walk out with what feels like the biggest, most impossible project you've ever been assigned. This project is enormous, multifaceted, highly visible, and you're terrified of failing. Your mind races as you frantically open a new tab in your OneNote to begin a to-do list. The assignment haunts you all day and follows you through the night. You even wake up in a cold sweat, rushing to jot down the bullet points that haunted your dreams. I've been there many times, and I've had my fair share of fever dreams and nonsensical midnight voice memos.

But here's the good news: you can get through it and even succeed. Here are my lessons learned from handling such gigantic projects.

Mapping the Madness

This might seem trivial, but it's crucial: you have to start with the process. Invest in tools like Lucidchart or Visio, or even buy a large whiteboard with multiple colored dry-erase markers, and map out the entire process. Do whatever you need to do to get a full picture of the process at play: conduct informational interviews, shadowing sessions, test runs, customer interviews, or scour forums if available. Gather as much information as you can.

  • How does the process start?

  • What are the triggers?

  • Who are the key players?

  • What are the key functions?

  • What is the desired outcome?

  • Where are the pain points?

  • Where are the opportunities for improvements?

  • Who is the beneficiary?

  • What are the by-products?

  • What data points are collected along the way?

When you start with the process, you identify key players and the proponents and opponents for driving the change. You understand what data to collect and which visualizations will be helpful. You spot the "gotchas" and ensure your solution is robust enough to handle the necessary outliers and problem cases. Most importantly, and this is why this feels like such a cheat code, you can pinpoint where changes need to occur, and your project plan will practically write itself.

Embrace Iteration

Another lesson I've learned is that if you miss something (honestly, it's 'when you miss something'), it's rarely the end of the world. If requirements change or are added later, you can tackle these iteratively. Call it "Day 2", "Subsequent Release," or "Post Launch." It all basically means that your product or project doesn't have to be perfect out of the gate—although this is what we aim for, things don't always work out this way. But I've found that bosses and clients are always more receptive of your work product's shortcomings when you have a concrete plan to address them.

Maintain Trust

The final lesson is that relationships will make or break any project. A strong relationship with your client, built on trust, is essential. One of the best ways to maintain trust is clear communication. This helps in managing expectations and reducing misunderstandings. Ensure the client feels heard and maintain this feeling with weekly check-ins, progress reports, demos, and/or shared documentation. All of this would be overkill, but again, listen to your client and understand what would most help them feel a sense of transparency and mutual trust.

I recall a time at Wells Fargo when my boss marched me over to our head of operations to deliver the news that her project would be delayed due to resource constraints. My relationship with her cushioned the blow—since I had already built a strong rapport with her and she trusted that I was doing everything possible to advance her project, her reaction wasn't as bad as anticipated. This experience underscored the value of having a solid relationship with your clients—trust can mitigate even the most challenging situations.

However, I do want to note that trust goes both ways. As the project manager or service provider, you need to feel confident that your client has provided all necessary points of contact and information for your success and isn't waiting for you to discover any major traps that could affect timeline, feasibility, or the resources you initially scoped for the project.

Rolling with the Punches 

Be adaptable. Projects can change, and flexibility allows you to pivot when necessary without losing sight of the end goal. Earlier in my career, one missed requirement would often throw me into a spiral of disappointment and panic. But I've since learned that taking things as they come, and understanding that projects evolve in phases, with each phase offering an opportunity for improvement, makes management much easier.

The MVP Mindset

Prioritization is the bread and butter of product management. It's crucial to break down tasks and prioritize them to effectively manage large projects. Start by identifying your end goal and then determine the "Minimum Viable Product" (MVP)—the essential components needed to kick off the project. This approach, sometimes referred to as vertical slicing, helps by tackling the most critical elements first.

For example, instead of attempting to complete the entire UI in one phase, each phase should focus on implementing the necessary UI changes that advance the project incrementally. By prioritizing tasks in this way, you ensure steady progress, provide room for flexibility, and keep the project on track, step by step.

Mini Milestones Matter

Recognize and celebrate progress, no matter how small. This keeps morale high and maintains momentum. Celebrating mini milestones motivates your team and reinforces the value of each member's contributions, fostering a positive work environment and better collaboration. It also strengthens team cohesion and keeps the ultimate goal in sight, reminding everyone that each of their own little successes plays into the larger objective. By making these celebrations a regular practice, you build a culture that values progress and maintains motivation throughout any big project.


Handling big projects can be daunting, but with the right approach and mindset, they

become manageable.

  1. Start by getting a full picture of the process. This is the best place to start and ensures a holistic solution.

  2. Embrace iteration, knowing that missing something isn't the end of the world and that you can always refine your project in subsequent phases.

  3. Maintain trust through clear communication and strong relationships.

  4. Be flexible and ready to pivot when necessary, keeping sight of your end goal.

  5. Prioritize tasks and break down the project into manageable phases.

  6. Celebrate the little successes to maintain positive momentum.

And always remember the wisdom my little brother shares when we're feeling overwhelmed.

How do you eat an elephant? One bite at a time.

You don't need to eat your elephant alone. Let’s tackle your biggest projects and CRM challenges together. Schedule a consultation with me today and discover how we can transform your CRM strategy, one bite at a time.

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