Strategic Thinking

How Can Strategic Thinking Take Your Life and Leadership to the Next Level?

Let me ask you… what makes a strategic thinker?

A strategic thinker is someone who is intentional in their decisions and continuously aligns themselves and their actions with a big picture vision. That may sound simple, but being an actively strategic thinker takes planning, focus, commitment and a willingness to acknowledge mishaps and learn from them.

I have many clients tell me that they want to be more strategic in their approach, but they just don’t have time for it. They feel they’re always being pulled into the weeds of life. The last minute meetings, the urgent tasks, the constant pings of emails and messages, the household tasks, the errands… how are we supposed to be strategic in all that? How do we create space for ourselves to be creative and intentional?

The truth is, being strategic in your thinking will give you back your time. Yes, it takes an initial commitment that may feel out of reach, but once you start rolling with it, you’ll start to notice your time being used far more efficiently, and in ways that genuinely fuel you.

In this article, we’ll explore:

How Do You Define Strategic Thinking?

A strategy is, “A general plan or set of plans intended to achieve something, especially over a long period.” 

Building on that, we can define strategic thinking as an approach to thinking that is deeply intentional, analytical, and focused on bringing big picture objectives to fruition. It’s an approach to thinking that isn’t just about next steps, but about understanding how those steps fit within the larger picture, including values, purpose, strengths, challenges, resources, overall objectives and so on.

Strategic thinking is considered one of the highly sought-out soft skills. It is deeply connected to intuition, creativity and curiosity, and demands a willingness to truly look within.

Why is Strategic Thinking important?

In both our personal and professional lives, we have things we want to accomplish, shift or create. We may be actively working towards those things, but if we aren’t taking time to examine all areas and aspects of the situation, and our own bigger picture, we may not be using all our resources in the best way. We may even go way off course without realizing it. If you’ve ever had an experience of setting out to accomplish something, but getting sidetracked by all the distractions of life, you know how easily this can happen.

Strategic thinking uses a three-phase framework that empowers you to make more confident decisions that move you away from what you don’t want, and towards the things you do want.

In this way, a strategic thinking approach can help you:

  • Anticipate potential roadblocks and have a plan in place should they come up;
  • Stay focused on efforts that actively move you in the direction you want to go;
  • Quickly highlight distractions or anything that may pull you off course;
  • Keep your mind open to new perspectives and possibilities;
  • Keep you aware of the impact you want to have and how you’re bringing that forward;
  • Continually align your decisions with your values and purpose.

In your personal life, this can help you create the meaningful relationships and experiences you deserve. 

In your professional life, this can help you create maps for yourself that will make goal-achievement clearer, more measurable, and smoother to work toward. 

Overall, strategic thinking can be a powerful tool in preventing burnout, cultivating self-management, practicing genuine self care, and creating a life for yourself that is engaging, fulfilling and joyful.

What Are the Three Phases of Strategic Thinking?

In terms of how to think strategically, there are different tactics you can take, depending on what works well for you. However, those tactics should all work within the three phase framework of strategic thinking:

  • Where are we now / Where am I now
  • Where do we want to be / Where do I want to be
  • How will we get there / How will I get there

It’s a simple framework that keeps you aligned with what you want to create, grounded in the moment, and realistic about what you’re working with. 

Let’s say, for example, you want to pay off a credit card. With just that goal in mind, your thoughts and emotions can spiral into overwhelm, or you may end up accidentally sabotaging yourself. However, if you take the time to fully dive into where you are now, and a clear picture of what your ideal future will look like, you empower yourself to plan realistic, actionable steps, including realistic tactics to keep yourself on track.

This approach is also hugely beneficial with more complex goals. For example, if you’re tasked with increasing your team’s productivity by 20%, you absolutely need to do a deep dive into where your team is at today and why, what a 20% productivity increase would look like in practice and the full impact it could have, and what factors genuinely motivate and engage your team members. Going through these three phases would not be easy, but it would massively streamline that endeavor.

As you go through the three phases – whether in a personal or professional context – here are some questions you could ask yourself:

  • Where am I now?

    • What are the facts, as I know them?
    • What are my core values and purpose? (if you’re doing this as a team, consider the values and purpose of the organization)
    • What’s working for me now?
    • What isn’t working for me now?
    • What obstacles or challenges are in my way?
    • If other people are involved, what mental models might be at play?
    • What resources do I have available?

Many people find it helpful to conduct a SWOT analysis as part of this phase.

  • Where do I want to be?
    • What does the ideal future look like?
    • If nothing were standing in my way, what would I create?
    • What would that ideal future feel like? (visualization techniques can help you develop full clarity around your goal)
    • How will this goal impact all areas of my life?
    • Is this ideal outcome in alignment with my purpose and values?
    • By when do I want to achieve this?
  • How will I get there?

    • Is this a goal that can be broken down into steps, or is it a more complex goal that needs to be broken down into chunks (or sub-goals), then into steps?
    • How will I measure success?
    • How will I practice time ownership to make this happen?
    • How will I manage the obstacles I identified in phase 1?
    • How will I manage my inner Saboteurs?
    • How will I hold myself accountable?
    • Do I have someone who can act as an accountability partner?
    • If others are impacted, when and where do I need to involve them?
    • When will I check in on my progress and reassess, if needed?
    • What steps will I take today/this week to start building momentum?

How long each phase takes really depends on what it is you want to accomplish, but be aware that this can be a time consuming process when it comes to complex goals, or when you’re working in a team where different perspectives need to be heard.

As you go through the phases, record everything. Write down the steps you will take and when. Write down what you uncovered and your vision for the future. A significant aspect of this approach is having regular check-ins on progress. You need a record to refer to.

The Importance of Space

If you, like my clients, feel that you’re always being pulled into the weeds of life, I cannot stress enough the importance of space. Not just physical space, but the space within you.

In the techniques and practices below, I mention making time to set up your environment and get yourself in the right headspace for being strategic. I encourage you to really focus on what your ideal needs are. When you invest in this element of strategizing, you empower yourself to lead from your highest brain – that part of you that sees clearly, is naturally creative and resourceful, and accepts what comes up with curiosity.

What do you need in your physical environment? Do you need quiet, or the background buzz of a café? Do you need music? Brown noise? Do you focus best when sitting, standing, laying on the ground? Does your creativity flow best when typing, or when putting pen to paper? What about lighting? Aroma? A beverage? Personally, I like to start a session with a steaming cup of chai or matcha latte.

What do you need for your inner environment? What activities seem to open up your creativity and focus? Meditation, yoga, a hot shower, a run or walk outside, grounding, holding a handstand, reciting affirmations, spending time with a vision board, watching a motivating Ted Talk. Some people find that doing a “mindless” task like washing dishes or giving their desk surface a good scrub helps calm their mind and open up the flow of ideas.

Leading from your highest brain makes a difference, and being intentional about your inner and outer environment will support that.

How Do You Use Strategic Thinking in the Workplace?

As a leader – and in many other roles – you likely have multiple areas to consider. There’s yourself, your team, the organization, possibly specific projects, or any other wide scale elements that are under your purview.

Break out your strategic thinking needs into the categories that make sense for you. Then, set aside – actually book it into your calendar – a recurring block of time each week to engage in strategic thinking. This type of thinking is not passive. It’s active, engaged, creative thinking that demands your full, undivided focus, and produces concrete plans.

Break down the strategic thinking you need to do for yourself, your team, your higher ups, and write questions you need to think of for each one. Then, on the creative day you’ve chosen, see which one is calling you to work on and lead from there.

Here are questions to ask yourself to engage a strategic thinking approach in the workplace:

  • Do others need to be involved?
    If you need to strategize for a team, you may need to involve team members in weekly thinking sessions where you go through the three phases and check-ins together. If so, it would be a good idea to include your team in choosing time, duration, location, and so on. Make it a co-creative venture.
    If you’ll be having team sessions, be sure to also book yourself weekly solo sessions. You need to prioritize all aspects of yourself and your life, not just your team.
  • What duration will you start with?
    There’s no way to know how much time you’ll really need until you get started. In the beginning, you may find you need more time, or even less if you’re building a new habit of focus. Decide on a length of time, book it, and adjust as needed once you’re in it. I recommend keeping sessions as short as possible so that the sessions don’t become draining.
  • Where will you do this?
    Will your strategic planning take place at home or in the office? At your desk, or in another room? It’s a good idea to always use the same environment as your brain will adjust to it and naturally begin to prepare itself for active thinking.
  • Does your zone need prep time?
    Do you work best if your zone is tidied up first? Do you need to set up a screen share? What tools will you need on hand? Do you need a hot beverage ready? Do you work best if you open a window? Do you need noise canceling headphones or music playing? Make a plan to handle all of this before you start your session so that you are set to focus.
  • Do YOU need prep time?
    Are you able to sit down and dive right in, or do you need to take a brisk walk, play a meditation, or dance to your favorite playlist? Plan it and do it.
  • What tools do you need?
    I mentioned tools in a previous point, but you may need to consider this more broadly, especially if you’re working with a team. For example, would your team benefit from some kind of project management software to keep track of tasks and achievements? If so, plan for it in advance, and plan how you’ll familiarize everyone with it.
  • What is likely to distract you?
    Try a dry run. Get your environment and self prepped, sit down, and try to focus on something like a quick to-do list. What’s distracting you? Write down anything that pulls at your focus.
  • What will you do to limit distractions?
    Now that you know what will distract you, what will you do about it?
  • What will you do if a session goes over or under time?
    If you get to the end of your time block and still have work to do, how will you handle that? Will you simply continue on, or will you book yourself another session for later? Have a plan.
    If you finish earlier than planned, how will you use that time? Maybe for you, that’s a great time to use your momentum to get to work. Or maybe you want to use it for other things that fuel you. Time is a gift. Don’t let your gift fizzle away with mindless scrolling or tasks that drain you. Have a plan.
  • What will you do at the end of a session?
    Strategic planning takes a great deal of focus and energy. How will you replenish that energy? How will you encourage your team to replenish their energy? A great thing to do is to get outside and moving in some way. If you’ve gone through all three phases, you have a plan with next steps spelled out. Those steps will be waiting for you and your team after you’ve had time to move, get your eyes off of screens, take deep breaths, and remind yourselves that there is a bigger picture you’re all working towards.

Tips for Strategic Thinking As a Team

It’s one thing to practice this approach for yourself, but when you’re working in a group, there are multiple perspectives that deserve to be heard and considered. How do you handle that?

Here are tips for leading strategic thinking sessions with a team:

  • Involve the team from the start
    When you use this approach as a team, the whole idea is that you’re working together to make something happen. Involve the team in setting up the sessions, learning about how and why you’re doing this, creating the right environment and so on. Doing that not only gets people engaged and feeling some ownership, it’s also practice for working together. Once you start having sessions, you’re starting from a point of having already created together.
  • Prioritize facts and tasks
    Emotions can run high in situations where accountability comes into play. That’s normal, human and worthy, but also a common cause of derailment in strategy sessions. When you see a conversation starting to veer off track, bring it back to the solid facts and/or tasks being discussed.
    If it looks like there’s a larger issue that needs attention, acknowledge it, commit to setting up time to discuss the issue (or appoint someone to lead that), then bring the focus back to strategy.
  • But also “woo” creativity
    If facts and tasks keep you on track, creativity is what fuels the engine. In his book, The Genius Zone, Gay Hendricks writes about the importance of wooing creativity, meaning showing genuine appreciation for our creative selves. No judgment, just full love, respect and admiration.
    Encourage your team – and yourself – to really open up to their own creativity. There truly are no bad ideas. Even if an idea isn’t put into practice, it still has the potential to inspire, and to encourage more ideas to come forward. Always, always, always recognize creativity. Make it feel welcome and wanted.
  • Be conscious of who you’re hearing, and who you’re not
    One of the key benefits of strategic thinking is how it pushes you to be open to all possibilities. That benefit increases when you get curious about what perspectives you’re truly hearing. Inclusive leadership is an approach that keeps you accountable for who you’re truly hearing, who you aren’t and what to do about it.
    For strategic thinking to work as a team, everyone needs to be engaged with the process. Actively listening to everyone enables that engagement.
  • Rotate seating
    It may seem silly to do this, but it can really open up people’s creativity, help broaden the relationships within your team, and help people drop some of the self-protective masks they’ve been holding up.
    When you prep your meeting space, use Post Its to assign seating randomly and rotate the seating regularly. You’ll be amazed at the difference such a simple change can have.
  • Ask better questions
    Another benefit of strategic thinking is the opportunity to co-create as a team. Getting people to create with you works best when you know how to ask questions in a way that opens up people’s curiosity and creativity. Here’s how to ask questions that get people working with you, and bringing their best selves to the table.
  • Make truth safe
    Everyone has to feel that it’s safe to say what they’re thinking and ask the questions they need to ask. As a leader, it is your responsibility to cultivate an environment where truth is safe. Here’s how to empower truth in your team.

How Do You Apply Strategic Thinking in Daily Life?

In our day-to-day lives, strategic thinking can be useful for specific situations, or as an overall approach to creating the life we want for ourselves.

Just as you would in the workplace, I recommend setting aside time each week for strategic thinking. In fact, I highly recommend doing your personal and professional strategizing at the same time because what happens in one area of your life will impact other areas. You are one whole person living one whole life. It makes sense to strategize with the full picture in view.

For me, I’ve started a routine of taking time every Wednesday morning for a strategic planning session for myself. As an entrepreneur, this naturally includes business objectives, but I also include objectives in my personal life. I do this because I strive not to see a “work self” and “home self”, but my whole self, who is impacted by the ebbs and flows in all areas of my life. 

During this planning time, I take a look at all the objectives I have in play at the moment. These can be financial goals, things I’m working on in my relationships, fitness objectives, parenting goals and so on. Sometimes, I may only look at one of those goals if it’s currently taking a lot of my energy. 

So far, I’m finding that having this weekly, structured check-in with myself is helping me make better use of my time overall. I’ve been able to identify the ways I’m causing myself to be “time poor”, how I can reclaim that time, and how I can use that time to take better care of myself and the things that are truly meaningful to me… not just to jam in more work hours.

How can you do this for yourself? Here are some ways:

  • Having done it myself, I recommend identifying a weekly time slot, booking it into your calendar, and holding yourself accountable for actually taking that time to plan, using the three phase approach.
  • Take stock of the boundaries you currently hold in all areas of your life, and where you might need to implement new ones, or strengthen existing ones. Though this isn’t directly related to strategic planning, poor boundaries are one of the biggest culprits of lost time in our lives.
  • Try visualizing your whole life as one full picture with many moving parts, rather than strategizing in silos. This will empower you to clearly see how the different moving parts impact each other, and strategize with that in mind.
  • Practice non-attachment in thinking about where you want to be. This may seem counterintuitive in goal-setting, but non-attachment is about letting go of the idea that your worth is defined by what you achieve. Non-attachment is liberating and actually fuels you to create.
  • Consider how guilt may be getting in the way of what you want for yourself, and what you can do to take guilt out of the equation.
  • Having a life purpose can be beneficial when it comes to strategic thinking, but if this doesn’t really resonate with you, the concept of Ikigai may be helpful.
  • Woo your own creativity in how you set up your environment by including reminders of what you’ve already created. Sure, it could be artwork, but our creative endeavors are also in our hobbies, our parenting, our relationships, our passions, and even our appreciation of the creativity in others. When do you feel your creativity really shines and what reminders of that can you bring into your space?
  • Get really clear on where you are and where you want to be. Physically write it or create an actual picture in some way. This can be a lot harder to do when it comes to personal goals, but it can also have the greatest impact on our overall satisfaction in life.

If you would like guidance in adopting a strategic thinking approach for yourself, your team or your organization, I invite you to connect with me.