Why Strategic Thinking Is So Hard for Project Managers

Advice for project managers looking to improve strategic thinking skills

“Making sure the trains run on time.” I once heard project management described this way. Sure, project managers are responsible for timely delivery. But succeeding in the role requires more than merely keeping teammates on schedule. The best project managers also bring a strategic mindset when making decisions and allocating resources.

Strategic thinking is the first step to successfully delivering any project.

The day-to-day reality can make this tough. After all, “project manager” is a bit of a misnomer — you are not focused on only one thing at a time. You should be called a “projects manager” since you are juggling multiple workstreams with many teammates and deadlines. And there is always the pressure to deliver more at a faster pace (and often with fewer resources). When you are doing so much, it can be challenging to see beyond today’s to-do list.

Now, some organizations handle this by creating program or portfolio manager roles. These folks oversee a collection of many projects and are typically responsible for setting a vision for the group that supports business goals. But everyone benefits from thinking through work in a more strategic way.

When you know where you are headed and why, you are better equipped to add value and make an impact.

That is because strategy illuminates what is most important. As a project manager it is imperative that you can make good judgement calls and prioritize work. So you have to understand the broader context — the high-level company vision and how a given project supports it. Here is how you can strengthen your own strategic thinking skills every day:

Look big
It might seem difficult to see the big picture when you are mired in the details. But it is important to think holistically about how each effort you oversee supports the overarching business goals. Of course, ideally you are regularly reviewing company strategy. But ongoing check-ins with cross-functional teams will help you gain a better understanding of overall objectives.

Get super curious
Looking is not the same as knowing. So constantly look to understand why and then question your assumptions. Has your team gone through a project like this in the past — so maybe you assume that the same stakeholders, timelines, and criteria apply? Do you really understand that success criteria?

Notice patterns
All that noticing should be revealing. For example, you might note repeated failure points — where teammates consistently miss deadlines, the same bottlenecks occur, or handoffs between teams dead-end. Once you identify these patterns, create a visual that highlights the issues. Look for signs that you (or others) can improve how you deliver projects.

Be consistent
Carve out time for regular retrospectives after each project. Of course this requires discipline and diligence — but reflection is necessary and worthwhile. It can be helpful to start a project log to jot down any revelations as you go. Review the original timeline and actual delivery velocity. Look at those reports and capture what went well and what you want to improve for next time. Ask colleagues for feedback while the experience is still fresh.

Strengthening your strategic thinking skills makes it easier to succeed in any role.

Ultimately, the cross-functional teams you work with depend on you to deliver the project on schedule and within budget. Applying analytical yet flexible thinking to everything you do is essential. So everyone can be confident that the trains will not only run on schedule — they will also reach the correct destination.

How do you bring a strategic mindset to your daily project work?

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About Brian and Aha!

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 roadmap software — and the author of the bestseller Lovability. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

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