Dear Lewis, how can I become more strategic?
I reveal how an executive coaching client transformed his career by moving from tactical execution to strategic thinking. What began as a daunting challenge soon became second nature.
Welcome back to another edition of Dear Lewis, where we tackle the thorny issues of corporate life with a dash of humor and a heap of practical advice.
Today, we're diving into a common conundrum: "My boss thinks I'm not strategic enough. What do I do?" This feedback is as common as stale coffee in the break room, but fear not! I'm here to offer some guidance, including:
Decoding what "being strategic" really means in the corporate jungle
Analyzing why your boss might think you're tactically terrific but strategically challenged
Recommending specific actions to boost your strategic street cred
Keep your eyes on the prize (and maybe the C-suite),
Lewis C. Lin
CEO, ManageBetter
🤔 How can I become more strategic?
Meet Tom, my coaching client. (It’s not his real name, but let's be honest, there's probably a Tom somewhere facing this exact issue). Tom's a rock star front-line manager at a Fortune 500 company. He's been there for five years, consistently hitting deadlines and making his team purr like a well-oiled machine. His colleagues think he's the bee's knees, but his boss keeps dropping the S-bomb: "You need to be more strategic, Tom."
Tom comes to me, bewildered and a bit miffed. "Lewis," he says, "I'm doing everything right. What gives?"
I tell Tom that being strategic isn't about doing things right; it's about doing the right things. It's like he's been expertly arranging deck chairs on the Titanic when he should be figuring out how to avoid the iceberg altogether.
Tom's current approach sounds something like this:
"So, we've got this project, right? And we're going to optimize our workflow, maximize efficiency, and deliver on time and under budget. We'll use agile methodologies, have daily stand-ups, and create a detailed Gantt chart. It's going to be great!"
I explain to Tom that while this sounds impressive, it's all tactics, no strategy. It's like having a map but no destination. We need to elevate his thinking from "how" to "why" and "what if."
Here are the exercises we start working on to help Tom flex his strategic muscles:
1. The 30,000-foot view: We practice looking at his projects from a higher perspective. Instead of diving into the details, we ask questions like: How does this project align with the company's overall goals? What market trends could impact its success? What are our competitors doing in this space?
2. The "So What?" test: For every decision or action, we ask, "So what?" at least three times. This forces Tom to connect his work to broader impacts and outcomes. For example:
We're launching a new product feature. So what?
It'll increase user engagement. So what?
Higher engagement leads to better retention. So what?
Better retention means higher lifetime value and lower acquisition costs, improving our overall profitability and market position.
3. The Future-Back approach: Instead of planning from the present forward, we start with envisioning the desired future state and work backwards. This helps Tom think more long-term and identify the critical steps needed to achieve big-picture goals.
Tom finds these exercises challenging at first. He's used to being in the weeds, but that's the point. Strategic thinking is like a muscle – it needs consistent exercise to grow stronger.
As we continue our work, Tom's language starts to shift. He begins to sound less like a project manager and more like a business leader:
"Our latest initiative isn't just about launching a new feature. It's about positioning ourselves as the go-to platform in an increasingly competitive market. By focusing on user engagement, we're not only improving our retention rates but also setting the stage for expansion into adjacent markets in the next 18-24 months. This aligns perfectly with our CEO's vision of doubling our market share by 2025."
The transformation in Tom's thinking is palpable. He's no longer just executing tasks; he's connecting dots, anticipating challenges, and seeing opportunities. His boss notices the change, commenting on Tom's improved ability to see the bigger picture and contribute to high-level discussions.
Remember, becoming more strategic isn't about abandoning your tactical skills – it's about adding another dimension to your thinking. It's like upgrading from checkers to chess; the board is the same, but the game is infinitely more complex and rewarding.
So, the next time your boss says you need to be more strategic, don't panic. Take a step back, look at the big picture, and ask yourself: "Am I playing checkers when I should be playing chess?" Your move, strategist.
Simple, right? Well, not always
I'm here to help. Email me if you have any management or employee challenges. I've got your back, and your identity will remain anonymous.
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