On the Transition from Management to Leadership

The Leader Role

While we generally know a leader when we see or hear one, I believe the best way to convey ideas is through analogies.

Photo by Mael BALLAND on Unsplash

A certain level of confidence is required to delay need-realization because it is through this validation that we are confirmed to be on the right path.

While it may be necessary for a leader to “get in the trenches” sometimes, this is ideally reserved only for scenarios where it is truly necessary. In a battle, a lieutenant directs troops far from the front lines. It’s not a matter of honor, it’s a matter of being effective.

  • A leader’s role is to identify the future-state or horizon, and respond to opportunities as they arise.
  • A manager’s role is to shepard the group to close the gap between current state and future state.
  • An IC’s role is to execute on the tasks necessary to close the gap.

Aspects of Leadership

When I think about some of the great leaders I’ve followed, there are several key points that overlap between all of them.

The General

Tony Robbins, Simon Sinek — A defining characteristic of this type is conviction. These leaders provide clear directions and answers. There is no question in their mind that this is the way. In some ways a coach, the associated characteristics include charisma, extroversion, confidence, and firm compassion. This type is more process oriented than goal oriented and likely believe that getting the process right will ensure progress towards the worthy goals. They have to straddle the line of being authoritative and too prescriptive.

The Equal

Gandhi, Martin Luther King Jr. — A defining characteristic of this type is an ability to advance a movement. A modern example is Russian Opposition Leader, Alexei Navalny. They appeal to an innate or natural conviction, shared amongst many, to right a wrong or effect transformative change. Somewhat closer to the spiritural side of the spectrum, their message and mission is just and moral and their work is to sound the call to others that any sacrifice towards it’s end is worthy. Associated characteristics are natural-introversion, reflection, firm loving-kindness, and outrageous compassion. A bit more difficult to describe with words, this type of leader is better conveyed through non-verbal communication and emotion.

The Stalwart

Captain Picard from Star Trek, Examples of this type will largely be personal to you, they’re often not public. A defining characteristic is reliability. They articulate a vision and create shared responsibility towards achieving it. Most often found in business or community organizations, they understand a problem, envision a solution, orient a group towards it, and maintain the course. It may take years to achieve, but at every turn, they’re there — dispelling fear, reiterating the goals, answering questions with questions to empower and invoke thought, soft compassion, and navigating the obstacles. Their associated characteristics are similar to that of parental figures — they care, show disappointment when appropriate, point the way, and enable you to succeed.


Shared amongst all leadership types and a basic component of good human beings is compassion.


Empathy is a multiplier. You can be compassionate in an individual circumstance, but if you can put yourself in someone’s shoes, your accuracy will improve. For example:


This may also be described as ‘keeping a level-head’, ‘keep calm and carry on’, providing clarity, or dispelling fear. Rationality is instilling confidence in others that we will overcome the challenge ahead.


Time, energy, attention, money — all leaders will put the needs of others ahead of themselves. Simon Sinek puts this best in his book, Leaders Eat Last, where you can find many wonderful examples of leadership. He draws heavily upon studying military processes, which, also, espouse selflessness.

Take some time to reflect on your recent interactions and, where appropriate, ask yourself how you applied compassion, empathy, rationality, and selflessness.

To summarize:

  • Leaders develop a core value system which is consistently applied to all their interactions.
  • Compassion, Empathy, Rationality, and Selflessness are common leadership values.
  • There are different types of leaders, each embodying a unique framework to lead.

Define Future-State & Track Progress

The terminology you’ll find commonplace in a leadership role — roadmap, alignment, trajectory — point to identifying the prize and keeping your eye on it. If we were on a ship, IC’s would be rowing, the manager would be steering, and the leader is in the crow’s nest, watching the horizon.

Photo by Nick Seagrave on Unsplash

No matter the general sentiment, yours is always upbeat. Many people are looking at your nonverbal and verbal communication for clues in how they should feel about the organization. This is best recognized early in this new position.

New developments in the industry or environment can be positive (opportunity) or negative (risk). The degree to which either will occur is likelihood. There may be a potential risk that the project timeline slips due to staff out sick. Or, there is potential opportunity for the project to complete early due to increased availability by staff. At a leadership level, your scale is generally greater and may include merger and acquisitions or significant developments affecting your industry, like a new regulation (think GDPR or COPPA). These are the items that should pop onto your radar for control.

  • A leader will be responsible for alignment of departmental objectives with organizational objectives.
  • A leader will be responsible for creation of departmental roadmap which includes plans to accomodate departmental initiatives.
  • A leader maintains a positive attitude, on display for all to adopt.

Key Exercises

In this section, let’s review some of the concrete ways to improve your leadership capabilities.

Understanding yourself is the result of journaling, meditating, therapy, and feedback. There’s no goal or finish line and the process never really ends.

However, you’re making progress when you understand your default reactions, modulate your emotions, and create a buffer between stimuli and response.



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Dave Bour

Dave Bour


Building IT infrastructure and teams where there was none before. Fitness, wellness, and adventure enthusiast. Engagements at theitplan.com