Thinking about Thinking

Thinking about Thinking

Everyone should reasonably expect their leader to think. And most everyone would likely claim that thinking is a hallmark of sentient beings and like breathing or heartbeats, happens automatically, or to use the medical term autonomics. We will leave the discussion of sentience in some leaders for another day. Today I want to talk about ways to think. Intentional thinking.

In defining the many elements of a sustained leader, a leader who can assume the position and maintain their leadership without fatal flaws or faux pas, thinking is broken into three subsets – critical, systems, and strategic.

The first of these, critical thinking (, forces you to understand whether the information you’ve been given makes sense. Too often people blindly accept what they are told and never ask the very important “why?” Certainly the credibility of the source of your information bears consideration, but it is important to think critically about what you have been told. Sadly, this skill is rarely found at any level of our current educational system. A brief review of many social media posts will provide you many examples of people who posted information without simply asking “why” first. You bring to your leadership role a wealth of experience and knowledge. Hopefully it is mostly relevant and accurate, but as a leader you will often be thrust into arenas that exceed your experience and knowledge. You must rely on other team members – on their knowledge and experience in addition to their credibility. You will rarely be given every piece of desirable information on which to base your decisions, but it is always a mistake to fail to ask the “why” question and assure yourself that what you are being told makes sense – either directly to you or to the brains you have borrowed from other team members.

The second type of thinking is systems thinking ( and considers how the many moving parts of your organization play well together – or don’t. All organizations have their unique systems – whether they are software, chain of command, procedures, policies, or organizational alignment. The sustained leaders studies the systems within their span of control. They understand that all systems require inputs, perform a function, and produce outputs. Bad or erroneous inputs, or a deficient, broken or simply wrong function will create bad outputs. IF you are only relying on the system to perform without seriously thinking about it, you will find yourself relying on outputs that are wrong, or worse – dangerous. In many contexts, these failures can seriously impact or end your leadership journey.

The third area in which the sustained leader must think is strategic ( Strategic thinking asks five questions – where are we, where do we want to be, what do we have to do to get there, who will lead those actions, and how will we measure our progress? Each of those five questions are important to consider in creating a strategy and converting that strategy into a specific action plan. Most of us have seen a strategy with no action plan, or a series of disjointed actions that do not seem to support any specific strategy. A leader must have a vision for the team. Whether it is expressed as a dream or an ambitious goal, a vision attempts to frame the answer to the second strategic question. Coupled with the first – an honest assessment of where the team currently exists (and this is not the time to be lying to yourself or the team) you can now conduct what is popularly called a “gap analysis.” This points you in the direction of what must be done. The action plan must be both practical and executable even if it may require new or different resources. One or more of those resources might even be a new employee, consultant, or contractor. The point is that progress is the result of people – not systems or processes. Having the right people with hands-on the progress is essential. Then finally you have to be able to consider the way in which you will measure successful accomplishment. Too often, choosing the wrong metrics will lead you to the wrong result – with all the consequent wasted effort and resources as well as recriminations. Each step in the strategic thinking process drives the successful results that are sought.

When you consider thinking in the context of the sustained leader, it become easy to see that thinking is not always well done when left to your autonomic nervous system. The sustained leader must engage in all three types of thinking on a constant basis – intentional thinking with intentional results. A failure to think about decisions, projects, systems, strategies, and even resource deployment will yield less than optimal results. The sustained leader always seeks the best outcome for the team, its vision, and its mission. You owe it to your team to engage in thinking across all of these dimensions. Ask the critical questions, dig for the facts (Element – A sustained leader is fact-based), understand the systems, and lay out an effective and achievable strategy. It would be terribly unfortunate if your answer of “I just didn’t think….” led to the derailment of your leadership journey.

With an extensive career in government contracting, Tom has found many examples, both good and bad, of leadership. These posts are based on his latest book, Sustained Leadership WBS, published by Morgan James. Tom is available to speak to your team on the importance of developing sustained leaders.


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