4 Ways to Improve Your Strategic Thinking Skills (2023)

If you’ve ever received feedback that you “need to be more strategic,” you know how frustrating it can feel. To add insult to injury, the feedback rarely comes with any concrete guidance on what to do about it. One of my coaching clients, Lisa, a vice president of HR, was in this situation and explains, “I was just told to think bigger picture and to be more strategic. It felt like I had been given the definition of a word by using the same word. It just wasn’t helpful.”

So what specific steps can you take to be more strategic in your current role?

Start by changing your mindset. If you believe that strategic thinking is only for senior executives, think again. It can, and must, happen at every level of the organization; it’s one of those unwritten parts of all job descriptions. Ignore this fact and you risk getting passed over for a promotion, or having your budget cut because your department’s strategic contribution is unclear.

Once you’ve accepted that it’s part of your job, focus on developing four key abilities that demonstrate your strategic prowess.

Know: Observe and Seek Trends

Lisa wasn’t seeing the big picture. Because of the amount of work she had and the pace at which she needed to get it done, she often took a “heads down” approach to her job and failed to “lift up” and observe both internal and external trends. She was missing key information that could help her focus, prioritize, and be proactive in addressing talent issues for her fast-growing company. Because Lisa approached her job in a transactional manner, simply getting the next hire, she didn’t recognize that she needed a completely new approach to recruitment and retention.

In order to be strategic, you need a solid understanding of the industry context, trends, and business drivers. An intellectual appreciation of the importance of bringing in current data and seeking trends isn’t enough. You also have to:

• Make it a routine exercise to explore and synthesize the internal trends in your day-to-day work. For example, pay attention to the issues that get raised over and over in your organization and synthesize the common obstacles your colleagues face.
• Be proactive about connecting with peers both in your organization and in your industry to understand their observations of the marketplace. Then, share your findings across your network.
• Understand the unique information and perspective that your function provides and define its impact on the corporate level strategy.

Think: Ask the Tough Questions

With a fresh understanding of trends and issues, you can practice using strategic thinking by asking yourself, “How do I broaden what I consider?” Questions are the language of strategy. Lisa came to appreciate that her life and prior experience gave her a unique, yet myopic, strategic lens. So she pushed herself to ramp up her perspective-taking and inquiry skills. By becoming more curious, and looking at information from different points of view, she was able to reduce her myopia and see different possibilities, different approaches, and different potential outcomes.

For example, when working on an employee retention project she asked herself, “What does success look like in Year 1?” “What does it look like in Year 3?” “What could impact the outcome in a negative way?” “What are the early signs of success/failure?” “What do business partners need to understand to ensure its success?” and “Do the outcomes support the broader goals of the organization?” By asking these tough questions first, she recognized that she could better engage with colleagues and senior executives early on in ways that would benefit the project — and would help shape the perception that she was thoughtful and strategic.

Speak: Sound Strategic

Strategic thinkers also know how to speak the language. They prioritize and sequence their thoughts. They structure their verbal and written communication in a way that helps their audience focus on their core message. They challenge the status quo and get people talking about underlying assumptions. Those that are really skilled walk people through the process of identifying issues, shaping common understanding, and framing strategic choices.

If this sounds complex, that’s because it is. But there are ways you can start honing these skills:

• Add more structure to your written and verbal communication. Group and logically order your main points, and keep things as succinct as possible.
• Prime your audience by giving them a heads up on the overarching topics you want to address so they are prepared to engage in a higher level conversation, not just the tactical details.
• Practice giving the answer first, instead of building up to your main point.

Lisa didn’t realize that the way she spoke created the perception that she was not strategic. She set about changing that. First by focusing her one-on-ones with her CHRO on higher level discussions and leaving tactical issues to email. She chose one or two strategic areas to focus on. and made sure to frame issues in the context of the CHRO’s and the CEO’s top priorities.

Act: Make Time for Thinking and Embrace Conflict

In the early phase of our work together, Lisa kept a jam-packed schedule, running from meeting to meeting. She found it difficult to contribute strategically without the time to reflect on the issues and to ponder options. Recognizing that she was not bringing her full value to the table, she started to evaluate her tasks based on urgency and importance as outlined in Stephen Covey’s 2 x 2 matrix. She stopped going to meetings she didn’t need to be at. She blocked out thinking time on her calendar and honored it, just as she would for other meetings. And she fought back the initial guilt of “Am I doing real work when I’m just sitting at my desk thinking?”

Lisa also practiced other key skills. She learned to embrace debate and to invite challenge, without letting it get personal so that she could ask tough questions. To do this, she focused on issues, not people, and used neutral peers to challenge her thinking. To manage the inevitable ambiguity that arises when you ask more questions, Lisa also learned to clarify her decision-making criteria, allowing her to better act in the face of imperfect information.

The quest to build your strategic skills can be uncomfortable. At first, you might feel like you’re kicking up sand in the ocean. Your vision will be blurred as you manage through the unsettling feelings that come with challenging your own assumptions and gaining comfort with conflict and curiosity. Once the dust settles, however, and you’re able to contribute at a higher level, you’ll be glad you took the risk.