Starting Smarter: 5 Practical Tips to Up Your Strategic Thinking Game 

If you’ve ever found yourself wanting to become “more strategic” at work or wished your team could sharpen their strategic thinking skills, this post is for you.  

As Tip #1 will spell out, knowing what you’re (really) trying to accomplish is the first step, so let’s start with that. (And if you want to implement it more rigorously in your organization, download our “DRIVE” strategic planning workbook.)

What does it even mean to be “strategic?” 

Dictionary definitions of “strategic” read like, well, dictionaries: “Relating to the identification of long-term or overall aims and interests and the means of achieving them.” Or “carefully designed or planned to serve a particular purpose or advantage.” 

In the worlds of business, PR and marketing, the definition of “strategic” can be simpler: a focus on outcomes over outputs. 

It’s all-too-easy to get sucked into activity-based approaches measured in output, but strategic thinkers resist that mindset. They understand and can clearly articulate the business goal of everything they work on, giving them the power to go beyond the original assignment and devise new or unexpected ways to impact those business goals. Because in the end, nothing matters more to the true strategist than whether the effort – whatever it may be – produces the intended outcome. 

If that doesn’t describe you or your team yet, how do you get there?  

5 Ways to Be More Strategic Right Now

For most people, it’s a lot easier to follow a few rules of thumb than to change how their brains work, so here are five practical tips you can put to work right now. Sure, there are lots of other ways to grow as a strategic thinker, but employ these five regularly and your colleagues will notice your growth as a strategist. 

1. The 3 Whys + The KPIs 

There’s a great quote that’s made the internet rounds (dubiously attributed but relevant here): “Progress has little to do with speed, but much to do with direction.” How true. Yet, in most businesses, everyone feels enormous pressure to produce more work more quickly. They rarely ask: But what if it’s the wrong work? 

In our business, we often hear things like, “We need a PR plan to announce XYZ,” or “We’d like to run an ad campaign for this new product,” or even more tactical requests like, “We want to make a video.” It’s not a knock on our clients. It’s just how the brain naturally works. We prefer the concrete, tangible and familiar over the intangible or unfamiliar. But that can be a fast track to “outputs over outcomes” when true strategists pursue the exact opposite.  

Here’s a way to sidestep those scenarios and make everything you do more strategic from the start (part of what we call the “Diagnosis” stage in our downloadable “DRIVE” strategic planning workbook). 

The 3 Whys:

The strategist starts every assignment by identifying the true purpose of the work, starting with the most valuable outcomes that can be achieved. Use three simple questions to get started: 

1. Why are we taking action at all? What outcome are we seeking if we’re successful? 

2. Why is that outcome important (to our goals and/or to the business)? 

3. Why is that outcome important (to the business)? 

The KPIs (Key Performance Indicators): 

Once you’ve asked (and answered) the Three Whys and established one or more critical outcomes you’re pursuing, it’s time to establish how you’re going to measure success. These two questions will get you there:  

• How will we measure our success in achieving the desired outcome(s)?  

• Do we have a way to measure it already or do we need to create one (or find a proxy measure)? 

(Note: no matter what the answers to the Three Whys were, the first question often tells you what the purpose of the work really is, so be prepared to revise your stated goals accordingly.) 

2. Be a “heads up” player 

The “heads down” doer rarely stands out as a strategist compared to the person who naturally looks “up and out” for new inputs, insights and inspiration. Context matters, so don’t operate in a vacuum, especially when we live in a golden age of information. Here are a few areas to explore, and remember, any research-informed insights are better than none.  

• What does the internet/AI say about it? This is the most basic step. It’s so fast and easy that skipping it is almost irresponsible.  

• What are competitors doing? In the business world, you’re rarely the only one trying to do what you’re doing.  

• What data would help you better understand the problem or reveal new insights that might lead to unexpected solutions? Imagine a chart, table, graph or even a spreadsheet that might tell you something useful. Where might you find it?  

• Who else in the organization (agency or client) might have valuable insights here? I’m always amazed by two things: 1) How rarely people ask others in their same organization for advice, and 2) how much people like being asked by others in their organization for advice. 

3. Consider the trade-offs  

There’s a difference between a smart approach and a wise approach. The wise approach recognizes that every strategy comes with trade-offs and weighs them carefully. Here are a few thought-starter questions to ask yourself and your team as you pursue a wise plan.  

• Will this effort take resources away from something else? Should it? All businesses have limited resources, so investing in one place almost always means taking from somewhere else.  

• If it would pull resources from other valuable efforts, does it have to happen now? Is there a way to sequence your strategies so they don’t compete with each other or require more resources at any one time? 

• Is there a shorter path to the desired outcome? Often the most elegant solutions are the simplest ones, so if the strategy is starting to feel complicated, pause. Is there a simpler way to achieve the same end, even partially? 

4. Be a test pilot

In business (and corporate America in particular) there’s a paradox: everyone lauds innovation while insisting on proof that something will work before they try it. You can’t have both. Or can you? 

A skilled strategist won’t let a good idea die because it’s unproven. The unproven ideas are the innovative ones. But a good strategist doesn’t force their team, clients or organization to take unnecessary risks, either.  

The right approach isn’t “all or nothing.” It’s “test and learn.” With any unproven strategy, find a way to pilot it on a small scale (there are whole books dedicated to this; Little Bets by Peter Sims is a good one). You will learn a lot that will make a bigger initiative – if scaling up makes sense – far more successful. 

5. Prepare to be wrong 

For years I’ve taken strategic inspiration from the book Decisive by Chip & Dan Heath, which is about avoiding biases and fallacies in decision-making. This last tip comes directly from their guidance, which in turn is based on extensive research by psychologists and behavioral economists. 

• Conduct a “pre-mortem” – Coined by research psychologist Gary Klein, this exercise asks you to imagine it’s a year from now and your plan (which feels smart at the moment) has turned out to be a total failure. What went wrong? You’ll be surprised how easy it is to come up with answers, so make a list and adjust your strategy accordingly. 

• Set tripwires – Don’t wait until the end of the project to find out if it’s successful. By then it’s too late. Instead, calendar specific outcomes you’d like to see by specific dates (so-called “tripwires”), such that being off-target would trigger a mid-stream pivot. Then make it one person’s job to monitor these outcomes on these dates and report back to the team so you course-correct before the clock runs out. 

The Next Step 

While there are many more ways to become more strategic, these five practical actions – if performed regularly – will make an immediate impact on your team’s strategic thinking capabilities, the quality of the work, and most important of all, the outcomes you can achieve. 

If you’re ready to take the next step to a more rigorous and strategic planning approach in your organization, download our “DRIVE” strategic planning workbook.