Build A Winning Project Strategy & Stay Organized Like A Pro

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Let’s face it, no matter what job you have, we’ve all been subject to the high demands in this fast-paced world and have found ourselves overwhelmed or near burnout. Not a great place to be in. But, with a little preparation, strategy and organization, you can stay ahead of that “buried” feeling, crush those deadlines, streamline workflows and deliver killer results.

Whether you’re running a project completely solo or have a team right there with you, getting a project plan in place is KEY to success. Let me help you map out a winning project strategy and give you some tips to stay organized like a pro.

1. Define clear objectives and goals

First things first: What the heck is the point of it all? Every successful project starts out will well-defined (and communicated) objective(s). Here are some key things you should be able to answer before getting started:

• • What is the desired outcome?
  • Who are the key stakeholders?
  • What does success look like?

Make sure you set or obtain very clear goals (search: “S.M.A.R.T. criteria”). That way, everyone involved can understand the vision and direction of the project. People will be more mindful when making independent decisions – whether small or big – to help achieve success.

2. Build a detailed project plan

Off to the races! Now that you know what the heck the point of it all is … it’s time to grab that stick and draw out the attack plan in the sand for your troops (JK, write it down somewhere more permanent). Miscommunication can be frustrating for anyone, so breaking down a project into key phases and assigning tasks with clear deadlines helps avoid crossing wires. One of the project management tools we use and love to help keep our teams organized is Basecamp, but there are so many out there – find what works best for you.

3. Prioritize (and re-prioritize) tasks frequently

Even if you’re managing just one project, it can have a lot of moving parts day-to-day that can get chaotic if you’re not well-organized. Knowing deadlines is key here so you can re-prioritize your focus and tackle what’s most important first. A few techniques that are widely used include:

• • Eisenhower Matrix: Categorize tasks based on urgency and importance.
  • Kanban Method: Visualize tasks in different stages (To-Do, In Progress, Completed).
  • Time Blocking: Allocate specific time slots for each project to maintain focus.

Personally, time blocking has been a lifesaver for me. At the end of each day, I write down the top three tasks I want to complete for the next day and then I intentionally time-block my calendar for focus work to git ’er done (if you don’t, people will always need more of your time on other work and you’ll never have enough time!).

Worth a read: How CEOs Manage Time (Harvard Business) / One CEO’s Approach to Managing His Calendar (Harvard Business)

Bonus tip: Keep and update all of your tasks in one single place. If you’re like me and find yourself with notes or action items all over the place (sticky notes, scribbles in a notebook, lengthy email chains, chat threads, Notes iPhone app, etc.), make sure to take time at the end of the day or even end of the week to consolidate in one place (you can choose better, but my go-to place has always been a running list in a draft email to myself 😅). 

4. Set up progress checkpoints

If the only milestone you set for yourself is the finish line, it can feel like it’s too far away and like you’ll never get there (I’m a shite runner, but in marathon terms, I would need those cheering lads and water stands at each mile to know I’m at least making headway). Break down the project into bite-sized phases for better progress tracking. Set up regular check-ins with yourself or your team to provide updates and ensure everything is on track to reach that finish line on time. And celebrate all those little wins, too!

Communicating with stakeholders is key in this phase to keep everyone informed and aligned. A few tools we use daily to do this include:

• Microsoft Teams for daily chats and quick calls/check-ins
• Zoom for more formal stakeholder calls
• SharePoint or Basecamp for document sharing

Again, there’s an endless list of options out there. Regardless, find the time to keep open communication with your key stakeholders throughout the project (I still love an old-fashioned phone call myself ☎️).

5. Stay flexible

Us Type 1 personalities have a rough time with this one, but not everything will go as planned and you might have to pivot, adjust or completely change up plans. Unexpected events are inevitable – so if you just [mentally] prepare for the inevitable to pop up at any moment, you’ll be in a better mindset to make adjustments when called to do so.

6. Be self-aware

Even the best-laid plans have room for improvement. Take a moment to look back earnestly at how everything went from inception to execution and make note of what went really well, as well as what could have been done better. This will help you and your team make advancements to future projects. “Excellence is not a destination but a continuous journey.”

Final Thoughts

Building a winning project strategy and staying organized doesn’t have to be daunting. With clear objectives, detailed planning and the right tools, you can successfully manage multiple projects without feeling bogged down by the weight of it all. Simply implement these best practices and you’re well on your way to adding project management pro to your resume!

What are your favorite strategies for staying organized and managing projects effectively? Let me know if you have any tips!