On the Transition from Management to Leadership

Dave Bour
12 min readSep 15, 2021

A while back, I wrote about what help me in making the transition from independent contributor to manager. I will always have more to learn in managing people, but the next stage of learning to lead does not have to wait.

As we move along the path, the concepts become more amorphous, less concrete. For example, as an IC you’ll configure the server and as a manager you’ll hire and coach team members to build the server. In a leadership position, you’ll align the use of servers with organizational and business goals.

The first section focuses on understanding and defining leadership, the second on skills and responsibilities, and in the third, we’ll look at some of the key practices to help them strongly develop.

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 way to visualize this role is through an analogy of boy scouts /girl scouts. An IC is the young new scout, a manager is the teenage ‘leader-in-training’ responsible for herding a group of 4 scouts, and the leader is the adult (hopefully!) navigating the landscape. If you think about the wants, needs, and mindset of a scout, a herder, and the leader - they’re so different!

Scout (immediate): How much longer until we’re there? This pack is heavy. I have to go to the bathroom.

Herder (next step): Are all four of them here? — 1, 2, 3, 4, check. Are we still with the group? We can stop ahead at that tree for the one who needs to go to the bathroom.

Leader (long term): The next series of hills will require a rest afterwards. Are we still on the right bearing? Is the weather holding?

The scout’s needs and concerns are immediate as their responsibility is for only themself, the herder’s concern is group dynamics and next step as their responsibility is to get the group to the next stop, while the leader is concerned about the setting the destination, the velocity of the mission, and identifying potential threats or opportunities.

This also means that the realization of needs will vary by role as a scout will most quickly realize their needs and a herder will realize their needs a little slower, perhaps at the end of the day when they setup camp and achieved another day of progress. A leader, however, may rarely realize their needs as their ability to navigate the landscape is evaluated at the end of a 10 year career.

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.

Being on the front lines carries significant risk — bullets are flying over her head and she has to deal with them while directing resources. As a Senior Director, if you dive in and start configuring a server, that work will directly come at the expense of time spent strategizing, but even worse, it loads a program into your memory that shifts your mental thinking to the immediate (What commands do I need to run to install that role?) and your actions will follow suit, becoming more focused on the present task.

To summarize:

  • 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.

First, leaders are fantastic empathizers and this is a key difference between good and great. An empathetic leader will naturally garner support through their daily interactions because their foremost concern is the employee’s wellbeing. Which makes sense — think back to when you felt heard by a senior leader. Even if they chose to go in another direction, being heard feels fair.

Second, leaders are consistent in their messaging. They’re almost a broken record as you’ll generally receive the same guidance each time. Every leader will have a foundation from which they return to as a starting point for solving problems. Some leaders focus on establishing processes while others take a successful future-state and work backwards. No matter the foundation, they’ll demonstrate that all of the complicated matters in our day to day can be distilled down into simple, actionable steps.

Third, leaders interalize, and operate from, a core value system. A building block for consistency, this is the framework for making the most important decisions at the intersection of business objectives, the ego and reputation, group dynamics. It requires knowing oneself, which is an investment in itself and, a somewhat separate process from business. Do you think taking time to get to know yourself would be a recommendation from a “boss” or a leader?

To be a good leader, you must be willing and able to actualize these aspects of leadership in combination with your personal flair. What are some of the unique characteristics you’ll bring to the table? Categorically speaking, there are a few leadership types you may identify with and the traits they espouse.

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.

Either consciously or unconsciously, leaders set the example of how to behave in groups. Employees will mimic their behavior, adopt their methods, and generally attempt to rise to the level of their leader. As a new leader, you must take time to reflect and develop your value system and moral compass. This, in turn, will be consistently applied to every interaction.

Given the importance, let’s examine some of these traits in detail and consider how they can be a part of your value system.


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

Acts of Compassion includes sharing with the needy and listening without judgement. At it’s core, compassion is about improving the circumstances of others. It is developed as an ability to prioritize context over expectations. It’s putting the individual ahead of the outcome, expectation, or want and in a way, it’s taking the long view over the short view.


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:

If your goal is to retain employees, your ability to remember what it feels like in their position and read between the lines to capture the nuances of their situation will improve the liklihood of this outcome. If someone is caring for a sick family member and falling behind on a project, compassion will call for reducing stress, perhaps by extending the project timeline but empathy will call for adding paid time off to allow them space and time to care for their family. Empathy takes the solution a step further.

Empathy has a second benefit of putting yourself in the shoes of the customer. You may be able to develop more useful products and processes by applying it to your deliverable.


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.

The ability to be rational will depend on your personality. While I wouldn’t call him irrational, Elon Musk has not garnered a reputation for serenity. Or, his bar is set so high that what seems rational to another is seen as underwhelming to Mr. Musk. In any case, he has been the first to say that, above all his roles, he sees himself as an Engineer. And you, as a leader, will need to be rational.

This value will often be used to re-focus employees closer to the ground. They will be pulled in a lot of directions and without the benefit of your decade+ experience, will embody a more reactionary policy.

In your 1:1’s, you can reiterate that everything will take time, that they’re still on track, everything is going well, and you believe in them. They’ll walk away with a renewed confidence in the objective and that emotion will be infectious.


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.

Putting the group or the company before one’s own needs is necessary as a leader. While it can be a learned behavior, it is best working to make this automatic by practicing humility and gratitude.

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.

As a business, there’s no crow’s nest. Instead, we’re going to use Operational Key Reults (OKRs) to align our departmental goals with the overall business and use Key Performance Indicators (KPIs) to measure progress against our objectives. Our industry experience and connections will allow us to monitor the landscape for opportunities requiring course correction.

An OKR consists of annual, bi-annual, or quarterly departmental objectives that support organizational priorities. If you’ve worked at a company where the feeling was of dispersement, where everyone who pressing in a different, or worse oppositional, directions; then OKRs will be the tool that create alignment between departments to create a concerted push. An example of an OKR follows.

Organizational Goal: To Provide the Best Customer Experience in our Industry

IT OKR: Reduce customer support wait time by 25% through adoption of an Omnichannel Customer Support Platform in Q4

IT KPIs: Evaluate Three Omnichannel Platforms, Trial One Omnichannel Platform, Direct 10% of customer inquiries through new platform to measure for reduction in wait time in Q4.

Metrics: Customer wait time (minutes)

In the example above, the Organizational goal is generic. The departmental OKR specifically support it with a deliverable and the KPIs are designed to signal progress against the deliverable.

Both OKR and KPIs are specific and contain three characteristics— a time constraint (in Q4), a measureable success outcome (reduce wait time by 25%), and how the outcome will be achieved (implementation of omnichannel support platform).

The role of an IC in this project is to evaluate and configure the platform. The manager will resource the evaluations and maintain oversight of the configuration to track the KPIs. She will report on the KPIs to leadership, who will help re-prioritize attention to certain OKRs that become more important over the course of the time constraint.

In sum, these items will provide the boundaries for the team to develop a roadmap, which includes the departmental objectives aligned with the organizational goals, the departmental structure/org chart, and plans to resource the objectives which may include changes in headcount or budget.

Photo by Nick Seagrave on Unsplash

Once you’ve articulated a vision for the direction of the team, you’ll be responsible for keeping a pulse on the morale of the group and on new opportunities that require acknowledgement.

If you’ve moved up the ladder within an organization, it can be difficult to adjust your pulse on morale. While you may be tempted to keep tabs on your team or department, that’s really a responsibility of the department manager. As a leader, you’ll need to tap into the general sentiment of the organization — is there a lot of momentum behind projects? Do you have high churn? Compare the sentiment after a funding round announcement to a Tuesday in the middle of summer and you’ll see how the sentiment can shift.

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.

To summarize:

  • 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.

Research at least least three leaders whom you feel may best further your leadership skills. Choosing leaders from different categories and from within your own will be more beneficial. Follow them on social media, read their books and biographies, watch their videos. Once you understand their framework, take what works for you and apply it to your own.

Do your personal own work. You won’t be successful as a leader with demons in your own life. This is a strict requirement to leadership, you will not be successful as a leader until you thoroughly know yourself.

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.

Interact with people. The feedback from interactions will allow you to find what works and what doesn’t and refine your methods. Organize a group hike, offer to take on additional responsibility at work or through volunteership.

Learn to espouse your core values in your personal life. Good leaders are consistent in their thoughts, words, and actions. Identify how you can apply your core values to all daily interactions and get started! Give money to the needy, volunteer your time, pick up trash on the sidewalk — whatever they are, make them automatic.



Dave Bour

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