Leadership is hard.
As leaders, we are called on to make decisions and set direction. These moments, whether explicit or implicit, heavily impact our leadership. When we do well, it goes well. When we don’t… things don’t go well.
In my years of leading, working with leaders, and observing leaders, I’ve noticed a quality that seems to capture doing this well: compassionate strategic decisiveness. All three elements need to be present. Often leaders tend to exercise only two of these elements (or one!) and it’s to the detriment of their leadership.
Here’s each one broken down:
Compassionate
If we exercise strategic decisiveness without compassion, people get hurt.
Humans aren’t simply a resource, they’re people. Though we lead companies, organizations, initiatives, and projects, fundamentally, leaders lead people. People have hopes, dreams, desires. People pursue the good life - they want to flourish; they want to live well: as good people, providing for their lives, connecting with others, doing meaningful work.
When people don’t have those things, or struggle to get those things because they get in their own way, others prevent them, they lack vision or competence or character… the leader’s response is compassion. Compassion has an awareness complement: we are aware of people’s suffering, an affective component (we feel for them) as well as an effective component (we seek to alleviate or prevent it).
In this and out of this we lead. Compassion provides the frame and end (telos) for our leadership. Are we aware of how well are people are flourishing? Do we see the gaps? Do we feel it? Does it move us?
Out of that awareness and affective experience, we seek to lead people in a way that contributes to their flourishing: helping them grow and develop, guiding and empowering them to contribute to the team and its shared goals, fostering a sense of unity and camaraderie, and creating a sense that they are seen, protected, and cared for.
Our strategic decisiveness must be rooted in and aimed at compassion otherwise people suffer.
Strategic
Our compassionate decisiveness must also be strategic. A well-intentioned bad decision is still a bad decision, and bad decisions, in addition to costing time, money, and progress, also cause suffering for people.
While all leadership is benefited by wisdom, the strategic is the most so.
There are probably millions of pages written on strategy, so here are just a few thoughts:
Strategy takes into account as many factors as necessary. Not too many (every seasoning doesn’t make a meal better), and not too few. How do you know how many factors are necessary? This is where wisdom comes in and this is an example that well illustrates the nature of wisdom. Wisdom involves the whole person, not just rational analysis (though it does use that). I’ve seen bad decisions made with way too much information as well as too little. The latter seems fairly self explanatory, if you have too little information, there are relevant factors you missed. But shouldn’t too much information be better? Then one can be sure the relevant information is captured. However, information gathering and manipulation can be a stalling tactic. Making a decision is daunting, it can be scary. Gathering and manipulating information is far less so. Too much information can also obscure what is truly relevant. Too much information can also create a false sense of security: we have a lot of information so we will definitely make a good decision.
Relevance is determined first by goals, then weighing constraints, advantages, and trade-offs. Timing and sequence are also important: what, if done first, benefits all of the other stages? Will I miss something if I start too late? Too early?
Listening to those you lead, weighing their insights and desires is important and relevant. Seeking advice from peers and mentors also serves to shape the strategic.
Like any other trait, if you want to grow in the strategic, ask people you know who are good at this for advice, and try to put yourself around them. Books help, but wisdom is well caught in addition to being taught.
Decisiveness
If we are compassionately strategic, but not decisive, people will be confused.
Decisiveness includes four fundamental parts:
1. Finality - if one is decisive it’s because they’ve decided; they’ve staked their claim, made their bet, etc etc. An open-ended decision is not a direction. It’s a choose-your-own-adventure story. As leaders, people are helped by finality. They are served by an answer to the question “what are we doing”?
2. Time - some decisions are definitely made too quickly, but, in my experience, leaders tend to drag their feet. Decisiveness is daunting. Considering is safe. Waiting can be strategic, but can often be anxiety and fear taking control. Many opportunities have been missed from failing to respond or for responding too slowly. Being decisive means being timely. Adjust your speed accordingly.
3. Clarity - decisiveness is clear. If you’re unsure about being clear, ask for feedback. Nods don’t count. Ask someone to repeat back to you what you’ve said. Work on it until it’s clear. And, once it is…
4. Communication - decisiveness is communicated well. Clarity and finality can be lost in the communication. Finality can be scary; it’s easy to dial back the level of finality in order to make it seem like your decision is one of many options. If it’s not, say it’s not. Communicate clearly. Communicate on time. Communicate to everyone who will be affected.
Make a timely decision, commit to it, and communicate it with clarity and certainty.
Compassionate strategic decisiveness is risky, but people are worth the risk. Focusing on this will help the goals and purposes of your organization as well. A well-aligned team with a sense of camaraderie who are bringing and becoming their best selves at work will do things that matter.
