• Wendy Castleman

10 Surprising Lessons About Being A Strategic Leader

Updated: May 23, 2019



I was reflecting the other day about some of the more disconcerting lessons I’ve learned in my career. Many of them fell into the bucket of thinking that a leader was one thing, but finding that it was really something else. I thought I’d take a moment and share some with you.

1. You don’t have to come up with the answer to be seen as the strategic leader. You have to be effective at listening and reflecting and gaining agreements. This was surprising because people seem to look to you as the leader to have all of the answers. The reality is that in this age of massive change and diverse information, nobody can actually have all of the answers. What is important is that you can engage people in gaining their perspectives, and that you can synthesize this information effectively. The key to being seen as a leader, though, is in reflecting what you have heard and gaining agreements with others on decisions and actions.

2. Being vulnerable makes you more approachable, likeable and trustworthy. Okay, Brene Brown has been telling us this one for a while. I learned it in the weirdest place. I was in a leadership training class and had just received 360-feedback that shocked me and shattered my ego. I then had to share what I’d learned from reviewing the feedback with a big room of impressive peers. I was honest about my surprise, my confusion and my fear. I stepped away feeling pretty much like a loser. But, suddenly, people began to come to me and offer guidance, help and encouragement. I was given new opportunities and was able to address the feedback and gain new respect from others. By being vulnerable, I became real. People relate to real. People rally around real.

3. It is more important to acknowledge than to advocate. This goes hand in hand with #1. People on your team need acknowledgement to feel like they have been heard, they make a difference and that they are important in the effort to execute the strategy you are all working towards. When people don’t feel acknowledged, they can withdraw and become challenges to your ability to pull off the strategy. It is important to advocate for people too, but if they don’t feel acknowledged, no amount of advocating will change their behaviors.

4. Enforcing Agreements is easy when you have made and written agreements. Most of the time we aren’t working on something alone, there are others involved. When others are involved, there should be agreements about what roles and responsibilities you have, how decisions will be made, and what process you will use. I have made the mistake of assuming we’ve agreed on things, when we might not have actually agreed. This is really one of those “duh” things, but when you have a verbal agreement and act in good faith, sometimes things change and people forget the commitments they’ve made. When things are written, it’s easy to point back to the agreement and ask if they are still on board or if you need to revisit the agreement.

5. Empathy is important for groups as well as individuals. Groups of people have culture, history, expectations and emotion, just as individual people do. When leading a group, taking time to gain empathy for that group can take you a long way in determining strategies that may work for them.

6. Regular updates and checking in on progress related to strategic priorities ensures that they stay in the forefront. Ever make a plan with a team, perhaps for how to change things, and then find yourself creating the plan again the next year because no one was able to actually carry out the plan the prior year? It’s like a New Year’s Resolution - it’s likely only to hold until the next thing comes along that captures focus. To keep something in the forefront, tracking it regularly is necessary. Consistent action creates change. Therefore, providing (and requesting) regular updates and progress against strategic priorities ensures that progress will, in fact, be made. This is not about micromanaging.. It’s about tracking. No judgement should be given about the updates, just adjustments to improve over time.

7. What is more important to hold onto. How can flex depending on circumstances. There are usually many ways to accomplish things. As a leader, it is your role to define a strategy (What), and then to empower your team to attempt tactics in service to that strategy (How). The WHAT shouldn’t change, as it is what you are aiming to achieve. If you change it too often, or have too many WHATs to achieve, it becomes nearly impossible to make progress. If you are a leader, try to empower your team to figure out HOW to attain WHAT you are trying to achieve. If they have difficulty with the HOW, you could suggest a few to illustrate the concept that you might accomplish something in multiple ways.

8. DNA evolves and devolves. Because people on a team change over time (either with new people, or just from the growth and development of the members), what the team is and can do will also change over time. As you bring new people into a team, they have an impact. When people leave a team, they take something away. If you have created a high performing team that executes strategy effectively, you need to make sure to monitor and respond quickly to change the environment. Otherwise, you may wake up one day and find yourself with a completely different situation than you’d anticipated. I saw this at my old job, where over time the DNA shifted and one day we realized that some of the foundational skills and concepts that we relied upon had faded away. If we’d kept addressing the changes that were occuring, we could have avoided having to start climbing all over again after having reached our pinnacle (and fallen from it)..

9. Passion over Puppets. As a leader, try to ignite the team’s passion for what they are doing and the strategy that you are working towards. People who are passionate are more self-motivated and engaged. People who are told what to do and given no leeway to do things their own way become de-motivated and can derail your progress. It’s true that passionate people sometimes stir up trouble and may fail spectacularly by taking bigger risks, but that is always better than having a team of puppets that rely on your direction for everything they do. That is because puppets don’t innovate. Puppets don’t inspire each other. Puppets, ultimately, aren’t passionate enough about the strategy to make sure they execute it.

10. You get what you measure. If you want to attain a goal and execute on a strategy, you need to measure your progress. If you don’t, you won't know when you are moving in the right direction. I always had an allergic reaction to tracking metrics, setting goals and doing performance reviews. It seemed like such BUSYWORK. How could taking time to measure progress be a better use of time than working on producing? As counterintuitive as it may seem, I have noticed that everytime I figure out how to measure something and track it, I can make significant progress towards my goals. This has played out in my personal life (including losing 50 pounds, spending more time with family, running, etc) and in my business life. If you have a clear vision, a concrete goal, a realistic strategy and track metrics relating to that strategy, you WILL get significant progress towards achieving the goal and realizing the vision. You might actually achieve it.

#leadership #strategy

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