Strategic Leadership

Michael Clark, current Conference of Consulting Actuaries (CCA) President has been sharing articles on what it means to be strategic during February on LinkedIn. I haven’t had a chance to read them all and since the goal of GoActuary is to focus on networking/professionalism type stuff I thought I would try to consolidate them here for easy reference later.

February 4, 2020

Are you strategic? I think we all know if someone is a strategic thinker or good at strategizing. These people inspire and motivate us, provide a vision for a successful path forward, and lead without micromanaging. So how do they do it and can we learn to be strategic too?

The Golden Circle

Being strategic is a skill that absolutely can be learned - for some it comes easier than for others though. I recently finished reading Start With Why by Simon Sinek. I love the premise of this book and think that it relates perfectly to what it means to be strategic. In the book, Sinek lays out the concept for what he calls The Golden Circle. The circle has three levels, two of which are fairly ubiquitous. Most people know what they are doing and how they are doing it. People that are strategic though know why they are doing what they are doing.

Take a minute and think about the “why’s” in your life:

  • Why do you spend your time on the things you do?
  • Why do you get excited about your passions?
  • Why is your company in business?

Without a clear understanding of “why,” the how and what are anchorless. Sure we can keep doing what we are doing but without the why we lose something, our teams lose something, our company loses something. That something is at the core of being strategic.

So how can you learn to be strategic?

A dictionary definition of “strategic” is

relating to the identification of long-term or overall aims and interests and the means of achieving them.

Being strategic requires us to think and act differently. It requires us to not only provide a vision for the future and a path for getting there, but it also requires the ability to assess, reassess, and make adjustments to move ourselves, our teams, and our businesses towards successful outcomes. Are you strategic? Do you aspire to be strategic? I’d love to hear what’s worked for you and even what hasn’t.


Pretty comparable to studying for exams as well. What and how are mechanical, Why gets the understanding.
Last week I started working with a tutor for a stats course I’m taking and he starts with "let me start with the story of what we’re doing here’ - which is the why. If you know the why, you understand the rest of it, and problem solving becomes much easier.

4 Ways to Improve Your Strategic Thinking Skills

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.

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Strategic Thinkers Are Found to Be the Most Highly Effective Leaders

When you think of the word “strategy,” it’s natural to think about rigid military postures and phalanxes of soldiers. But strategy is really nothing more than thinking a handful of moves ahead. It could be on a battlefield somewhere, certainly. But even zipper-merging onto a highway requires strategy.

And the workplace is no different. If you haven’t yet learned what separates strategic thinkers from the pack and made this sort of talent an important part of your workplace, here’s what you need to know.

How to Think Strategically Daily

Again, conjuring up ideas of strategy as it applies to military life is natural. Consequently, you might believe applying strategy is best for one-off events or something that happens a couple of times per year, such as planning for events you already know are approaching. But strategic thinking can and must happen daily — and it equips you to react to changes you don’t know about in advance.

According to multiple studies, people said strategic thinking was the leadership quality that correlated best with perceptions of “success” and “effectiveness” in the workplace — far more so even than communication skills and innovation. In other words, employees respect and value leaders who are mindful of the future and always seem prepared for it.

Why do people put such a high value on strategy? Perhaps because strategic thinkers appear surprised far less often than people who do not think strategically.

Why? Because strategy requires you to take the long view of life. It’s not just about solving today’s problems — it’s about planning for tomorrow and next week and making sure these problems don’t recur again then. Being strategic in your thinking isn’t about anticipating everything out into infinity. Rather, it requires you to divide your thinking into time frames. You know what has to happen today, tomorrow and three years from today, and you can adjust your timetable based on what’s happening right now.

Strategic thinking is a skill, to be sure. But like any skill, you can cultivate it. If you’d like to build your workforce into a team of long-term strategic thinkers, here are some points to get you started.

  1. Encourage Employees to Plan Their Work Strategically

Have your team or teams sit down for 15 minutes at the beginning of the work week to think about everything they need to do in the next five days. Encourage them to break their time into manageable, modular chunks of time. This practice encourages deadline-mindedness, but you’ll find it also serves as a segue into even longer-term planning. Plotting a week’s worth of work and responsibilities will smoothly turn into monthly and then quarterly planning, and so on.

  1. Recognize Ongoing Learning Is Required

Provide “contextual” information for your company, including events in your industry and market as well as the national and international economies. Even if you already have a broad knowledge base to draw from, and regularly educate yourself about new developments in the world that concern your business model, the rest of your team can’t engage in strategizing unless you share what you know.

You can also set up ongoing learning programs to encourage employees to maintain and add to their current knowledge to keep their strategic planning fresh and on-point.

  1. Get Serious About Mentorship

Whether formal or a little more laid-back, mentorships are incredibly important. The global economy is in transition, so if nothing else, pairing experienced team members with less experienced ones is important as you plan for a smooth transition into an economy and workforce run by millennials.

But mentorships also take the previous idea of ongoing learning and make it even more practical. Mentorships ensure nobody within your organization has unanswered questions or is making do with an incomplete understanding of their role. Strategic planning can’t happen if your employees are flying by the seat of their pants or don’t fully understand their role within the company.

  1. Make Strategy a Part of Culture

It’s commonly said real leaders reveal themselves in a crisis. But isn’t that reactionary thinking?

Your culture should spend less time talking about crisis management and a little more time on training managers and other process owners to anticipate both opportunities and problems. Identify and show appreciation for strategic thinkers who identify multiple solutions to a given problem and mobilize the one that shows the most merit — not necessarily the manager who’s quickest with a knee-jerk response.

If you really value strategic thinking, you can even fold it right into your hiring process and make it a part of your culture literally from day one. Talk to your applicants about times in their professional lives where they had to react to problems as they emerged, or where they assembled a plan of action even before difficulties started. You might be able to learn a lot about how they think.

Strategy Means Working Mindfully and Finding Balance

Think about it like this while you’re at it: In an organization with 10,000 individuals, does it make sense to enshrine strategy as something that occurs only in the management suite?

Your organization’s ultimate trajectory, and its daily successes, depend a little less on five-year plans your seven managers put together and a little more on the daily, weekly and monthly changes that occur — both anticipated and unseen — and how well your 9,993 “regular” employees react to them.

To borrow a phrase, high-quality strategic thinking is what happens when the work on your business meshes effectively with the work in your business. It’s about balancing what needs to happen today with what you’d like to happen tomorrow.

If there’s a note to end with, it’s probably the idea that strategic thinking isn’t really optional anymore. Actually, it’s completely vital in a world where employees and managers alike have greater access than ever to data concerning customer demand and market insights, domestic and international competitors, productivity, production capacity and all the rest of it. Suffice it to say, in a digitally connected world, refusing to think strategically means leaving a lot of high-quality information on the table.

Whatever else a changing world economy means, it’s clear the functional skills we learn at college and trade schools are only part of the portrait of an effective leader and team member. The rest is made up of skills that are a little harder to teach — analysis and strategy chief among them — but which seem to grow more important by the day.


there’s one strategy that I’ve hoping to implement in 2020. I know someone who has a Monday morning staff meeting where they define ‘what we’re doing this week’, then evaluate the following Monday.

i feel like that would help strategize and define timeframes. Sometimes I feel like projects are just ongoing, without any defined timeframe, and that weeks sometimes go buy without anything getting done.

I agree. I currently have a Friday morning staff meeting to discuss big topics that the team needs to be aware of but I feel like it hasn’t been as useful as it once was following some internal changes. Plus, things discussed Friday morning are frequently forgotten by Monday. I am thinking about moving it to Monday mornings and using the strategy focus to discuss what we accomplished/missed the prior week and what we need to focus on for the current week.

11 minutes of a Ted Talk discussing strategy.

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That…was an interesting article. particularly if one was to actually write down the 5 points and review/implement them specifically and individually.

Research shows that nine out of 10 organizations fail to deliver all of their strategic goals. Why? It seems that we forget to ask the right questions when it comes to strategy implementation.

Last one on my list

Since the LinkedIn post isn’t working, it leads to this article.