Leadership Conversation is a five-part series. Though each post in the series stands alone, please refer to the first and second topics below on Fearlessness and Authenticity if you want to go in order.
Happy New Year, finally! This particular topic in the Leadership Conversation Series was the most refreshing to write! The previous two leadership traits, Fearlessness and Authenticity, seemed very innate to my personality. They only took further development, experience, and personal confidence in these abilities. However, I can confidently say that Strategy Thinking is a trait that I've exercised in the least amount of time, but spent the most effort to develop. As I sit writing this, I couldn't help but feel proud of myself. You'll see why as I delve into this topic.
Enjoy reading, people!
What is My Definition of Strategic Thinking?
Strategic thinking is the act of looking ahead based on a vision or direction and aligning people, personal capabilities, and environmental forces to bring that vision to fruition. Strategic thinking can incorporate, but is not limited to the following elements: 1) Establishing a vision or mission statement 2) Setting goals or objectives to accomplish the vision or measure success 3) Gathering buy-in, agreement and approval 4) Using foresight to predict what could happen 5) Concentrating on environmental elements through research 6) Connecting with people in the know 7) Leveraging all of the prior points to prepare or adjust your objectives for the strategy's benefit.
In accomplishing a vision, the timeframe makes no difference. It could be 5 years ahead, 10 years ahead or even just 6 months ahead. The vision, however, must be expansive to personnel other than yourself. Thus, it must be inspiring, motivational and forward thinking to get stakeholders (i.e. investors, future employees, teammates, volunteers) bought in, aligned, and executing based on it.
There is no limit to ambition when it comes to strategic thinking.
Strategic thinking doesn't have to be based in the reality of today. If so, more than likely, it's already been done. It can be as small as a tactical vision for a team and as large as a strategic vision for the Earth (cue Amazon's leadership principle, Strive to Be Earth's Best Employer"). Overall, the subject and scope is irrelevant. All that matters is that you're using some of the elements described above. Then, you're strategically thinking!
Strategic thinking lays the foundation for project management and execution to actually happen. The vision or objectives is like the northstar and presents the "why" for a project. Think of Simon Sinek's concept, the Golden Circle. Creating a vision reinforces the "why" from the top down. If you have never heard of the Golden Circle concept, please refer to the Ted Talk clip below.
Okay let's talking about what it's not.
Strategic thinking doesn't mean you're the smartest person in the room or that you have all the answers.
Strategic thinking isn't about you being the all-knowing omniprescent resource that has all the answers. That becomes a burden to you and your mental health. Ultimately, if you're doing all that thinking by yourself, what's the point of having a vision that others can follow? Also, people can build upon your vision or your objectives, make these concepts better, and bring in diverse perspectives that you never thought of before. You can be the smartest person in the room but that also might mean you would be going it alone. You might've thought of everything in your domain, but without consulting others, you might be missing the very thing that determines your success or your failure. Besides without people, we wouldn't be really discussing leadership, now would we? This is a leadership conversation series, you know! If you're looking for an example, look no further than one of my favorite scenes in The Princess Bride. Let's just say dude thinks he's the smartest in the world, gets twisted up in his own logic, and then...you'll see.
Strategic thinking isn't about thinking strategically because you can. It actually needs to make sense.
Everyone has that friend. The friend with the big idea that you still have no clue what he's really talking about. He's talking and talking, draws a map, and gesticulates with his hands, but you're still shaking your head because you still don't get the point. Eventually, you might even give up and nod along just to get to the end (at least that's what I do). Strategic thinking on paper, ultimately, has to translate to others and actually make sense. It doesn't mean you have to dumb down the size and scope of your ambitions, but it does mean you have to take the time to simplify and distill it for the widest and most effective audience. If not, you're fully lost in the sauce, like our old pal, Charlie Day here in this scene from It's Always Sunny in Philadelphia.
Why is Strategic Thinking Important?
At a macro level, strategic thinking literally inspires and creates companies. Most modern companies operate under a vision, mission statement an objectives that have been iterated on over the years. However, strategic thinking contributes to the classic corporate comparison. Netflix vs. Blockbuster. Apple vs. Blackberry. Ernst & Young vs. Arthur Andersen. Live Nation vs. Fire Festival. Target vs. K-Mart. I hope I'm not speaking too soon once this post is published, but these are classic comparisons of companies that have pivoted effectively or outlasted disaster vs. their now declining counterparts. Without looking around the corner, adjusting either minimally or drastically, a lot of the companies that we think of in a long-standing capacity would cease to exist.
At a micro level, strategic thinking is integral to establishing, motivating and guiding teams towards success. I have to credit my wonderful friend, Terra Cooke, for this analogy. You can tell a team to develop a product without a direction or purpose. 9 times out of 10, you're going to get 10 different products based on purely personal motivations. You can tell a group of people to plan a vacation. You're going to get 10 different destinations, 15 different activities, and 30 different restaurant choices. Without a strategy, the team has no anchor, operates in silos, and moves at a various conflicting beats. A strategy not only provides a direction, but also reduces resourcing to non-essential activities. Additionally, people are better motivated if there is that northstar that all can point to.
What Amazonian Leadership Principle Does Strategic Thinking Tie To?
Strategic thinking aligns to a lot of the following Amazonian leadership principles. There's an intentional encouragement to plan ahead, think creatively, and be resourceful.
Customer Obsession: Leaders start with the customer and work backwards. They work vigorously to earn and keep customer trust. Although leaders pay attention to competitors, they obsess over customers.
Think Big: Thinking small is a self-fulfilling prophecy. Leaders create and communicate a bold direction that inspires results. They think differently and look around corners for ways to serve customers.
Frugality: Accomplish more with less. Constraints breed resourcefulness, self-sufficiency, and invention. There are no extra points for growing headcount, budget size, or fixed expense.
Ownership: Leaders are owners. They think long term and don’t sacrifice long-term value for short-term results. They act on behalf of the entire company, beyond just their own team. They never say “that’s not my job."
How Did Strategic Thinking Manifest For Me?
As mentioned before, strategic thinking was the leadership topic that took me the longest to develop. From my early days of consulting to the first year as an Amazonian, I was frustrated by virtually anything that would imply developing a strategy. I would roll my eyes when someone would say triggering phrases like, "What's the bigger picture?", "Let's have a brainstorming meeting!", "What's the 5-year plan?" or "What's the Way Forward?" I considered these efforts a waste of time, especially since I had a lot of executing and tasks that were on my plate to do. To be honest, there weren't many examples of people that looked like me doing it. It felt like it wasn't my place to be in these discussions and I felt uncomfortable. Ultimately, I wasn't a salt and peppered hair gentleman of a certain age in a suit that had legions of people working for them while they could sit in a room for 2 hours drawing on walls. Or at least, that's what I thought strategic thinking was.
It wasn't until I went to Amazon that I saw strategy planning in a real and tangible way. In the first year, I recognized that even though I was making strides in my job, I felt like I was woefully unprepared for the next-level things that I was being asked to do. How do I increase productivity by 50%? How do I reach a wider audience? Where should AWS invest when it comes to FedRAMP? I truly couldn't answer any of these questions without gathering data, having brainstorming sessions with my teams, writing down in an organized way, and presenting the docs to leadership for buy-in. After talking to my executive coach, Laurie Patton (Yes I got an executive coach. I told you I felt woefully unprepared right?), I realized that I needed to transition from a tactical thinker to a strategic thinker. There were elements in what I was doing that was already in the strategic domain, but I fully didn't realize it. Deep down, I hated being out of control of my destiny and my career than I hated brainstorming strategy sessions. I learned through my discussions with her that I could actually control the narrative by coming up with a strategy first. It started with a doc based on a high-level escalation aimed to increase FedRAMP authorizations and progressed to more and more docs outside of my immediate domain. Then, it progressed to not being prompted by escalations or asks from leadership, but my own proactive gumption and intuition based on what was needed. It then led to me being invited to review strategic docs of others and providing feedback based on my perspective.
As I sit here and write today, I've finished a proactive strategy doc for my team that I intend to iterate on every year and circulate to key personnel to understand the strategic direction of the U.S. Government Security and Compliance (UGSC) Program. When I look back on my journey to be a strategic thinker, I think back on all the times I would research a topic to understand the long-term impact on my current department or focus area, the times when I would write down thoughts absentmindedly that I would incorporate into a later doc, the times I would identify a point made in a meeting that would influence the direction of the organization later on. Over time, these things became easier and easier and going into these mode of thinking became more natural.
What is an Example of Successful Strategic Thinking in Others?
My first inspiration for Strategic Thinking takes me back to my EY days. I remember a late night session in an EY building writing workpapers. Back then, I refused to take work home because I would get distracted by videogames. I was wandering along the partner wing of the offices when I noticed familiar writing across one of the whiteboard walls in a Partner's office. I passed by it a few times that night before I got the courage to step into his office with assurances that no one would notice me. As I read through the words, there were branches of the military, dates, people, and visual diagrams etched out. It was confusing at first because there was a lot shorthand writing. So I stood in the office for a couple more minutes trying to make sense of it. Then a light bulb went off in my head!
This was a strategic plan to expand EY's audit presence for the government.
Now I was just like every EY IT Audit Senior at the time. I received the direction from the company through All-Hands meetings like everyone else but I wasn't really absorbing it. This was the first time seeing strategic thinking in action. I didn't take note of who's office this was until the next day. I walked by and I noticed a partner adding more to the whiteboard and I quickly checked the outside of the office. It was John Short. At the time, he had just recently joined the company and I didn't know him that well. However, as I saw his vision manifest in expanded audits, I started to get close to the people in his inner circle and start to ask him more questions. He probably doesn't know what I was getting at to this day and I probably stumbled through my questions. I couldn't articulate then that I wanted to know how he had the foresight to plan so far ahead and confidence to be so ambitious so early on at EY. As my career progressed, I started to piece together how he did it and how every minor step that he took to connect with someone, to win a contract, was another foothold towards completing of his strategy. No doubt now, his strategy has morphed into something much grander, but to this day, I would love to just sneak back into his office and see where he's planning to take the practice next.
To be honest, I was in awe of John Short. Still am.
I'm also really impressed with entrepreneurs who have their visions come to fruition through their companies. There have been many friends who have done this over the years, including my own mother. Crystal Brown and AJ Yawn are two individuals that I have had the pleasure to see grow from afar and build upon their natural talents to the creation and success of their own companies. Whether it's career coaching or cybersecurity, seeing two people of color use their platforms to inspire others to take the leap into entrepreneurship or think strategically about their field has been a joy.
I've seen Strategic Thinking really manifest in the non-profit space. Though I've been involved in some capacity in the space for many years. 2021 was the first year that I was on the Board or a founding contributor for 3 non-profits. Watching Tim Fields from BESN X Community is a masterclass of persistence, realness, and focus as he executes his vision for underrepresented creatives in the eSports and gaming community. Witnessing Dr. Natalie Maggitt's drive and empathy for underrepresented minority women to thrive and succeed in their communities puts IThriveHer on the map. And of course, being brought into Tia Hopkins epic vision for workforce development of minority women in cybersecurity seeking to be established in the field is unparalleled. Through her, Empow(H)er Cybersecurity is building status in the cybersecurity community as a haven and a source for women switching fields.
How Do Leaders Develop Strategic Thinking?
The following suggestions are for leaders that are looking to develop strategic thinking:
1. Network With Other Big Thinkers
It's increasingly difficult to think big without building a circle of other personnel that think big. It could be entrepreneurs, innovators, or finding a company where the core principle is thinking bigger (in my case). Once you have these enablers around you, you can't help but getting into strategic thinking mode. You can bring your ideas to them and they can help build on them, challenge your assumptions, and hone your tactics or data points. There's a few people in and outside of Amazon that I go to automatically when I have a new idea or want to float my solution to a problem. They are invaluable.
2. Identify the Problem, Work Backwards
It's not always easy to do strategic thinking just for strategic thinking's sake. It's good to have a problem or issue to work backwards from. It could even be something that has already been solved, but the exercise is helpful for you to think of the solution in a new way. As soon as you have a problem and a solution brimming in your head, you must do the next step...
3. WITx3 = Write it Down, Write it Down, Write it Down
This step is so crucial to strategic thinking. It's so nice, I'm saying it thrice. Write it down. Write it down. Write it down. Figure out whatever method works for you, be it a computer, a notepad, a tissue paper (seriously, it can start off on a tissue paper, but it can't stay that way). There's nothing like writing your idea down for the first time. Reading it back to yourself makes you your first and safest critique. There are many styles for a strategic doc. For vision and mission statements there are many enablers online to help you create it online. For an innovative idea, I tend to use the Amazonian method, Press Release Frequently Asked Questions (PRFAQ). It's a style meant to force the writer to put the end result product or concept up front simulating a press release followed by a prospective customer's frequently asked questions. Once you've written it down...
4. Socialize, Get Feedback
Get the word out! The reason why I encourage people to write it down is because it's easier to socialize and gain feedback of a realized concept instead of someone attempting to talk it through. When going through a doc review or presentation of your idea, you should recognize that the entire point is to make your vision or idea better. You should ask questions that really help you understand if you have the bases covered. Here are a few examples:
Would a new person off the street understand this vision?
Do you have any personal data points validating my problem?
Is there a risk that I'm not thinking of that I need to address?
Am I thinking of all the resources that are needed to solve this?
Will the strategy yield the expected outcomes?
Am I missing anything in my recommended solution, goals or objectives?
Are my timelines realistic?
5. Execute, Fail, and Try, Try, and Try Again
Now what are you waiting for? Go forth! Oops, you hit a snag. What does that mean? Try new angles and keep going. Your strategy will further refine based on trial and error. You can't get discouraged. You must use the failure as a new data point for what your new objectives, goals and solutions must be. Reconsult your trusted network of big thinkers. What advice can they give you? Soon enough, you'll start executing and the initial phase of your plan is over.
6. Always Be Iterating a.k.a Don't Drink Your Own Kool-Aid
Don't think it's over. Even if you[re successful, it doesn't mean that you shouldn't revisit your strategy with fresh eyes and see what tweaks could be made. As soon you think your shit doesn't stink or you start drinking your own kool-aid, you might be missing a crucial factor that could take your strategy to the next level or save it from a failure. Iterating takes on multiple meanings. It could be as simple as making edits or rewriting your strategy. You could change the format altogether and resocialize for various groups for feedback. Either way, take another look on a periodic basis to make sure that you're still going in the right direction. Take a look to make sure it represents the best version of you and your priorities.
That's it! That's my leadership conversation on Strategic Thinking! Like many of my colleagues, strategic thinking was seen as a definite mark of a leader but the most abstract to execute especially when transitioning from a transactional or tactical mindset. But as most leaders encouraged me, I'm going to encourage you as a reader and a fellow leader. There's no better way to make the switch than jumping into the waters headfirst and playing in the land of a big thinker. It will make you smarter and more capable of leading the people that you care about into the future.
Before I leave you, please check out a sketch below representing my initial thoughts about Brainstorming Sessions. It's pretty hilarious but I want you to think about role you might play in this kind of meeting.
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