cultivating servant

A guide to growing servant leaders

cultivate |ˈkəltəˌvāt|verb [ with obj. ]

  1. prepare and use (land) for crops or gardening.
  2. try to acquire or develop (a quality, sentiment, or skill)

I don’t know about you, but I didn’t grow up on a farm. I grew up in the suburbs, and nothing grew in the front or back of our house that I should have been eating. So when I learned the concept of cultivation, I related it to the second definition above. As I’ve grown in cultivating leaders, I have found the first and original use of the word very instructive.

The Industrial Age can fool us into the idea of assembling a leader like we would a car. We feel we only need the plans and some parts. But leaders aren't cars; they’re not manufactured. Leaders are something more organic. They grow.

The path to leadership is not a linear one. Though lists are undoubtedly helpful, you don't become a leader just by checking all the boxes. Growing as a leader takes more circuitous routes. It's amidst the challenges and possibilities of this journey where leaders are cultivated and grow.

I've held a leadership title for almost 20 years, but my journey began before that and continues today. This cultivating leaders project has had its own journey as I've written parts of it over the years. I hope it provides you with perspectives that give hope and practicals that offer help.


What is Servant Leadership?

To some, the term servant leadership may seem like an oxymoron, with two conflicting concepts. I don’t see it this way. When a leader takes the servant approach, it brings about a more effective and purer form of leadership. To be a servant leader is to decentralize oneself and lead from influence and vision rather than power.

To be a servant leader is to decentralize oneself.

I’ve heard servant leadership described in several settings, and it is certainly a broad topic. This section will introduce four postures and four practices that I believe are characteristic of a servant leader.

Postures of a servant leader

Your posture determines your approach and attitude as a leader, and it has to do with how you view yourself as the leader and the people around you. There are skills needed to lead, but competency can’t replace character, and posture reflects one’s character.

These are three postures I see in servant leadership:

  1. Placing others before yourself
  2. Character and growth over output
  3. Be replaceable

You are the leader to serve your team, not the other way around. A servant leader defines success in terms of their team members. If the team isn’t thriving, it won’t succeed. As a servant leader, sometimes your role will be one of protecting your team. Other times it will be providing what they need or removing what’s unnecessary.

Lead from influence and vision rather than power.

Reflect on these three evaluative questions to ask as a leader:

  1. Who gets the credit when we reach a goal? Do I redirect praise to my team?
  2. Do I take the time to identify areas of growth opportunities for my team?
  3. Do I get out of the way when someone on my team is better at something than I am?

Both this posture and the next will require patience as a servant leader as you may need to yield your expectations and timeline. 


Projects, deadlines, deliverables, outcomes, goals, and metrics are all critical to a leader. Often your leadership may be evaluated by the output of your team. Similar to placing others before yourself, servant leaders value the growth of their team over what they produce. You can’t rush or manufacturer growth; it takes time.

Feedback is first about their growth and secondarily about their output.

You will still hold your team accountable, as you’ll see in the practice of consistent and candid feedback. But the feedback is first about their growth and secondarily about their output. This posture moves your interactions with your team from being transactional to relational.

Consider these four questions to reflect on:

  1. How do I respond when I’m interrupted by a team member who needs help?
  2. Am I willing to allow someone to do something I could do faster in order for them to learn?
  3. Do I respect people’s boundaries when it comes to workload and time off?
  4. Do I model this by respecting my own boundaries?

That last one gets a lot of leaders. If you don’t value yourself over the project, your team will likely not feel that freedom either. Given time, you will multiply what you are. If I’m a workaholic, my team will intuitively understand that’s also what is expected of them, and they will either follow me down that path or go somewhere else. I’ll cover this more in sustainable leadership, but valuing growth over output starts with you as the leader.


I have built many teams over the years, and it’s a great joy to be able to step away and see them thrive without me. Affirm your team members that they could do your job. Some feel threatened by being replaceable, but it can also be a path to widening the scope of your own leadership through delegation. Invite them to give presentations to your leadership. Allow them to take ownership of critical projects. 

Given time, you will multiply what you are.

Consider these four questions to reflect on your posture of being replaceable:

  1. When was the last time I invited a team member to do something that would traditionally be my role as the leader?
  2. Am I leading in such a way that team members would want my job?
  3. As the leader, do I feel the freedom to take time off?
  4. Does my team feel the freedom to hold meetings without me?

In Why You Can't Skip Resting As A Leader, I explore further how resting makes space for new leaders. 

Practices of a servant leader

A leader’s posture describes how they approach others, and their practices demonstrate what they do to live in alignment with that posture. Because of this, you’ll see a lot of continuity with the postures of a leader. I tried to keep these four practices both practical and actionable:

  1. Making time for relationships
  2. Candid and consistent feedback 
  3. Sweep the floor
  4. Learn from those you lead

How you prioritize your time will significantly influence your leadership impact. It will take intentionality to prioritize people in your schedule. Expectations can play a significant role here, and clarity is your friend regarding team norms around communication and meeting.

I preschedule time for meetings in my weekly schedule so they don’t feel like interruptions when they come up. I also really leverage 1on1s with my team to make time for people. We’ll also cover 1on1s in the practicing leadership section.


Depending on your personality, providing feedback one could seem easier or harder. But the truth is most leaders struggle with consistent quality feedback. 

I define consistency here as both regular and timely. If you establish a cadence of feedback, your team grows more accustomed to it. The frequency needs to be often enough that a team member can actually do something with the input.

A servant leader’s relationship with their team is one of mutuality. The team will learn from you and you from them.

Candid includes both being honest as well as being specific. If feedback is vague, then people won’t know how to grow from it.

A counterexample might be helpful here. I once received feedback that an anonymous team member thought I didn’t make the right decisions a year before the feedback was given. I’m not trying to be vague; that’s all the info I got. I had no idea what they were talking about or what to do with it. This kind of feedback isn’t worth anyone’s time to give or receive. 


This was actually an expressed value on a few teams I led. We took it from Patrick Lencioni’s book, The Advantage. It applied to the whole team, but I had to go first in setting the example as the leader. Be willing to do the grunt work. Don’t see work as beneath you just because you are the leader. 

As a leader, I can prioritize my unique contribution and still be willing to sweep the floors.

Sweeping the floors doesn’t mean you must do any and everything asked of you. A leader often needs to ask, “What are the responsibilities and actions that only I can really do as the leader?” As a leader, I can prioritize my unique contribution and still be willing to sweep the floors.


A servant leader’s relationship with their team is one of mutuality. The team will learn from you and you from them. Recognize when you learn from your team. Be curious about what they do and why. Platform your team members to train others both inside and outside your team. Create the expectation that you are better together.

These postures and practices are just the beginning as we discover how to help servant leaders grow. Next, we’ll explore the core concepts of cultivation and growth.

How Do Leaders Grow?

About ten years ago, we lived in an apartment on the 5th floor in a city of over 7 million people. But out of our back windows, I could see a thriving urban garden. Only a few years before, it was merely a dump from the nearby construction site. I remember one morning seeing an older man standing out there picking up one brick at a time. He slowly cleared out a small space about the size of a dorm room and planted a garden. Over the next year, the whole area transformed, overflowing with growth.

Urban Garden

My son and I were inspired and decided we should grow something too. The following spring, we planted cucumber, basil, and jalapeños on our balcony. What did we learn? It is not as easy as it looks. We didn’t know what we were doing. We would try it one way, watch the results, try something different. In this process, I struggled with the following:

  1. Feeling the lack of control.
  2. Having to wait and see.
  3. Not picking the fruit too soon. (waiting for that first jalapeño was tough!)

In the following two years, I learned many lessons through that little garden. These lessons were timely and applicable to the challenges I faced outside my balcony. When I am cultivating growth in myself or in those I lead, I face similar struggles. I’m still learning in this area, and I hope you also benefit from this learning journey together.

The roles in cultivating

Cultivation is a process, not an event. Though it certainly involves science, cultivation often seems to be more of an art. It requires skillfully playing a variety of roles at critical moments to see growth. It is hard, long-term work, and you may feel unequipped for it. I know I do. But I think every leader can grow as a cultivator by learning the roles involved.

I've identified six critical roles in cultivating and each has a link to a post to explain it further.

  1. Provide what is needed. Discover the 5 Essential Provisions to Help Leaders Grow.
  2. Protect against danger. What is The Leader's Role in Protecting when it comes to cultivating leaders?
  3. Prune that which hinders. See how Less Can Be More When Cultivating Leaders.
  4. Watch/wait to allow time for the process. Find out Why Leaders Need Patience.
  5. Rest to heal and restore. Resting as a Leader is essential for you to stay in it long-term.
  6. Repeat/Restart through the seasons. Being an Agile Leader allows you to grow from your experiences.

Six roles may feel like a lot. And well, it is. But don’t worry, you don't play every role simultaneously. Just like in a garden, leadership has seasons, and by knowing the season, you'll know which role is needed. Discerning the Current Season is a critical skill to learn as you cultivate leaders.

Remember, it's the long game we're playing. If you're trying to become a leader overnight, this post isn't for you. In each of these roles, you will learn and grow. As a seasoned leader, you will feel more natural and intuitive.

Cultivation often seems to be more of an art.

It's tempting to look for shortcuts. These are dangerously disguised as being more effective methods of growth. Shortcuts promise growth without all the time and work. But you can't manufacture growth.

Roles because we're in relationships

Relationships are inherent to leadership. If there aren't other people, then who are you leading? Cultivating leadership also requires an inward focus. In a sense, I also have a relationship with myself. How I view and understand myself has a profound impact on my leadership.

These roles we already looked at and the habits we will explore can be applied both to leading others and leading yourself. Like a weekly 1on1 is critical to leading others, a weekly review is essential to leading yourself.

Your relationships will shape your leadership. Who you are journeying with will shape your leadership as much as who you are leading and who you are following. I encourage you to consider your companions as you embark on this journey of leadership.

The beauty of cultivation

This past summer we moved, and I'm working on a new garden. It reminds me of the beauty in the balance and tension found in cultivation. I have responsibility but not control. I both provide and protect yet also prune. These same principles are instructive when I manage projects and programs at work.

When I think of cultivating leaders, it involves my engagement today but with my vision set in the future.

Cultivation requires action today, but It's also playing the long game. Sometimes the first fruit of your labor is years away. But in time, that fruit matures and multiplies. When I think of cultivating leaders, it involves my engagement today but with my vision set in the future. This need for long-term vision is present, whether with my kids or my co-workers, with myself or those I lead.

Growing as a leader isn’t a quick process. I haven’t arrived and won’t arrive tomorrow either. At first, this slowness bothered me, but now I find the patience and kindness of it life-giving. In this next section, we’ll continue by exploring the journey of a leader.

How Does Mentorship Work?

I cover some of this in Who You're Following Influences Your Leadership, but here I wanted to lean specifically into mentorship. Mentorship is a topic that gets a lot of attention but can be lacking in the practicals needed to get started. Here are four tips for beginning mentoring and being mentored:

  1. Timebox the commitment
  2. Clear expectations go a long way
  3. Mentee sets agenda
  4. Finding a mentor

Timebox the commitment

Mentorship often becomes a longer-term relationship, but it doesn’t start off that way. Just like you would want to date someone before getting married, it can be helpful to start with a shorter-term, lower-commitment mentoring relationship.

Work together to set a timeframe you’ll each commit to and then evaluate how it’s going. Are there adjustments to make? Do you want to continue? How long this timeframe is will depend on how frequently you’re connecting.

New mentors will often be hesitant because they are not sure it will be a good fit or if they have time. Ask if they would be willing to meet once a month for a year and then evaluate. Setting clear expectations about the commitment should address these concerns. Speaking of expectations...

Clear expectations go a long way

Most miscommunication or misunderstanding comes from unclear expectations. As you’re establishing expectations, you’ll want to identify what will be the right cadence to connect with your mentor. It could be weekly, monthly, or quarterly. It can also change in certain seasons of life where more guidance is needed.

You might need to adjust your expectations. You’re not looking for Yoda, who will make you the best Jedi to save the whole galaxy.

Your mentorship may be focused on a particular aspect of your life (family, career, spiritual, economic), or it may be more broad, flowing through all these areas. Both the mentor and mentee should be clear on the scope of topics to be covered.

You might need to adjust your expectations. You’re not looking for Yoda, who will make you the best Jedi to save the whole galaxy. You’re looking for someone who has walked before some of the roads you are now walking on.

Mentee sets agenda

One change that catches people off guard is that the mentee actually does more to guide the process. While the relationship is mutual, the mentee is likely to drive the process to establish a regular cadence when connecting, as well as what content they’ll connect on. It’s essential to have good communication early on to set expectations for both the mentor and mentee.

This characteristic is also common to facilitating 1on1s with your team members. They set the agenda. Because of how we perceive power dynamics, it usually takes some repetition before this feels normal.

Finding a mentor

You may be thinking, “This all sounds great, but where do I find a mentor?"

Look for formal programs. Your employer may have a mentoring program already set up. Look up professional associations or even churches in your area. They often have mentoring programs established. As a PMI member in Austin, I quickly took advantage of their mentorship program to connect with someone who had been in project management longer and in different contexts than myself.

While the relationship is mutual, the mentee is likely to drive the process to establish a regular cadence when connecting, as well as what content they’ll connect on.

Start searching. Depending on the kind of mentorship, start looking around and ask someone to be your mentor. Even if you don’t know them well, you can still ask. People will feel honored. If you (or they) aren’t sure if you’ll be a good match, try it out for a while. Think through ahead of time what your expectations are and communicate them when you ask. Someone who might make a great mentor may say “no” because they aren’t clear about what you’re asking of them.

A 5-day journey to living from your priorities

It’s easy to spend our day reacting to what comes at us. What if you could be proactive, intentionally making decisions based on your priorities? It is possible!
Our five-day short course guides you through the process of identifying your life priorities and scaling them day to everyday decisions. You’ll learn how to establish a rhythm to build good habits and grow a team that will be with you in the journey.

Sustainable Leadership

Being a Healthy Leader

You hear a lot of talk about having a balanced life or a balanced diet, or a balanced whatever. But what does balanced mean? Is it a 50/50 split?

As much air time as balance gets, I think to be a healthy leader, we need intentionality in what we leverage.

Whether it's the visuals of a scale or remembering playing on a seesaw as a kid, I think most people default to this idea of balanced meaning 50/50. This assumption makes finding balance elusive. So what do we do? Let's look back at the seesaw. What happens when you move the pivot point away from the middle. Now, something small can lift something heavy. This is called leverage.

As much air time as balance gets, I think to be a healthy leader, we need intentionality in what we leverage. Leverage is at the core of the 80/20 rule. There is a shift from "How do I make these things even?" to “How do I leverage what's essential for the most significant impact?”

Living by priorities

If you’re going to focus on what’s essential, how do you identify what that is? You can find your priorities by starting at the end and then working back to your daily life. Clarity on your priorities is a must for healthy, sustainable leadership. These priorities will inform your goals, strategies and ongoing reviews.

As the adage goes, “If you aim at nothing, you’ll hit it every time.” Without clarity to measure progress and growth, you will always struggle, strive and hustle to get ahead.

The practice of rest and celebration

There will always be more work to be done. This unrelenting demand creates stress motivating us to keep grinding it out. When we’re driven, it’s easier to critique and grind rather than rest and celebrate

We keep going in this same direction because when we keep delivering, others will commend us. So we stay grinding until we burn out.

So how do I rest and celebrate instead? These are areas I still struggle with but have seen growth over time. I’m going to share some early action points because if you’re starting where I did, I think they’ll be the most helpful.

I was terrible at celebrating. Without thinking, I would focus on the places where I fell short or where we could improve as a team. I knew this wasn’t helpful, but honestly, I didn’t know how to do better. However, I had a team member who was pretty good at celebrating, so I delegated it. I hoped she would serve our team well in this area, and I could learn from her example. If this is an area you also struggle with, is there someone on your team you could invite to lead?

When it comes to rest, I started by putting it in the schedule. I keep a detailed PTO doc not because my employer requires it but because I know I won’t take time off if I don’t. After doing this for about three years now, I’ve noticed a shift in “normal.” Working at a healthy pace is beginning to feel normal versus feeling uncomfortable before.

Taking a growth mindset

I’m a big fan of the CliftonStrengths tool. My top 5 strengths are:

  1. Achiever
  2. Strategic
  3. Learner
  4. Competition
  5. Belief

In an exercise, I wrote out how these strengths work together. Here’s what I wrote, “ “ As you can see, these strengths can easily lead me to be a driven person. And while this can help reach goals and outcomes, it doesn’t invite health as a leader. 

Growth happens over time and not usually in a linear way. Intellectually I know this. I also believe God is in control, that He has an intentional path laid out before me. But I struggle to allow what I know and believe to guide what I do. I forget and need to be reminded. 

My tattoo

I now have a tattoo that reminds me that my life is like a path with unevenly spaced steps. There are seasons of intensity and seasons with a slower pace. Some of these seasons are long, and some are brief. I don’t know what’s ahead, but I don’t have to be anxious because I believe God does know. My tattoo is a visual reminder of this. 

Getting tattooed might seem like an extreme step, but learning to live at a healthy pace has been a central theme to my journey for decades.

Over this time, some of the questions I ask have changed.

  • From “Am I there yet?” to “Am I headed in the right direction?”
  • From “What should I do today?” to “What do you have for me today?”

These questions represent a mindset shift from seeing growth as a destination to seeing it as a journey.

Leadership Over The Long Haul

Cultivating leaders is playing the long game. It’s not taking a shortcut or trying to find the leadership equivalent of a get-rich-quick scheme. You may have heard it said, “You can do less than you think in the next year but more than you think in the next five.” I’ve seen this play out true time after time. But it can be so easy to lose perspective and return to a short-sided view. 

Find key relationships

I remember in my early 30s constantly feeling anxious about the progress I was or wasn’t making. I felt like I was behind. Then, over the course of one month, I met two people who radically changed their vocation in their early 40s. One of them was in their late 40s the other was in his 60s. A light went on as I realized that I could wait ten years, make a substantial change and still have over 20 more years of significant contribution. With that reality staring me in the face, how could I be behind?

A lack of perspective is one of the critical reasons I encourage young leaders to find other leaders ahead of them in their journey. They can provide a perspective that often de-catastrophizes the immediate issues you’re facing. 

Relationships, in general, are essential for sustaining leadership over the long haul. If you want to go fast and flame out, you could go it alone. But if you’re going to go far, go together. You will find encouragement and empathy from those alongside you, and then you will find wisdom and perspective from those ahead of you.

 Write tomorrow’s headlines

Another way to adjust your perspective is an exercise I call writing tomorrow’s headline. Imagine you’ve just picked up a newspaper from 10 or 20 years in the future (yes, I know that’s a lot further than tomorrow). 

Write the headlines if you were successful in living out your priorities. What was the result? How did you get there? What happened along the way? 

Now try the inverse. What if your worst fears came to fruition? How did things turn out? What we’re the pitfalls you encountered?

Now with these future perspectives, how would you coach yourself in your current situation? This exercise isn’t a replacement for relationships with other leaders, but it can serve as a tool when needed. It is also an excellent exercise to facilitate with your team to adjust the horizon of your shared perspective.

Avoiding Burnout

You are not behind. For years as a leader, I struggled with feeling behind.  One day a friend asked, "Behind what?" I started to answer with a list of everything I needed to do but then paused as the question sunk in. What was I behind? What standard was I using to judge myself? To what pace was I comparing my progress? I was speechless and eventually just said, "I don't know." That day I took a long walk to process the question. In many ways, I feel like I've been taking that same walk ever since.

These roles, habits and tools provide a framework to recognize and celebrate growth. They provide a path to follow but give grace when we feel off schedule.

As much air time as balance gets, I think to be a healthy leader, we need intentionality in what we leverage.

While you could read through this in one sitting, the practice and mastery will come over time. Receive this as an opportunity to enjoy the process, not just the destination, because let's be honest... as leaders, we're always in process; we never arrive.  When we embrace that reality, there is so much freedom.

It’s not uncommon for a leader to not see when they’re approaching burnout. Whether it’s a blind spot or something you’re actively trying to ignore, this evaluative question can be profitable. 

Would others want your job?

So often, we see leaders bragging about how many hours they work or emails they get. Our culture gives out badges of honor for overworking. If you don’t actively work to move against this current, you will be swept away by it.

Your flawed hero story.

When there is a challenge or crisis, it’s tempting to go into hero mode and save the team. It feels good, everyone cheers, but it isn’t sustainable. There are moments where we need to go above and beyond, moving for a while at an unsustainable pace. But those moments are far fewer than they appear.

Consider a real hero’s story, a hero with flaws. When you start looking at hero stories, often the same influences that make them also drive their weaknesses. This exercise is another time I like using CliftonStrengths. Take your top five strengths and create a superhero who embodies those strengths to the greatest extent possible. Now, what is their kryptonite? What are their flaws? 

My drive for achievement helps me endure great difficulties, but it also prevents me from truly resting. My strength of strategy empowers me to navigate complexity, but it also generates anxiety when I can’t puzzle out a solution. When I over-depend on my strengths, it almost always leads me to behaviors that lead to burnout.

When you start looking at hero stories, often the same influences that make them also drive their weaknesses.

Take time to process your version of a flawed hero with a close friend. How can you recognize when you’re walking down that path? What can you do in those moments to exit the path to burnout and restart?

Practicing Leadership

What Does a Leader Do?

The responsibilities of a leader feel endless much of the time. When faced with more than you can possibly do, how do you decide? When I read my first job description as a leader, it was overwhelming. I eventually recognized that my responsibilities were spread over different seasons. As a leader, less is more, and you need to identify the critical tasks on which to focus

As a leader, your job is to facilitate clarity and direction

When it comes to the questions, “What can only I as the leader do?” I think the answer most often has to do with cultivating an environment for growth. As the leader, you play an irreplaceable role in creating a culture within your team or organization.

As a leader, your job is to facilitate clarity and direction. When the team faces uncertainty, you can lead them to identify what is happening, what it means, and what we will do about it. In times of intense change and uncertainty, the answers to those questions may change daily, but you can continue to daily push for the same level of clarity and direction at that moment.

Leaders innovate, solving problems in a new way. And at the same time, a leader is often called to repeat the same task of cultivation over time. They protect, provide and prune. They iterate, evaluating and adjusting their leadership. This faithful work isn’t as flashy, it may not draw broad praise, but in the end, you will have stewarded well what you were entrusted with.

Habits of a Leader

Cultivation requires a lot, but the fruit is worth it. Habits can help make the work easier. Don't think of habits only as the things you do over and over. Consider what behaviors you wish were easy or automatic. What are daily actions characteristic of the leader you want to become? By establishing habits that match your vision, you establish a foundation for that vision to be realized. The book Atomic Habits has been an excellent resource for me to continue growing in this area.

I’m not giving a list of habits to implement but mindset shifts that will help you identify the practices you need to cultivate.

1. Focus on the Environment

2. Form and Function

3. 5 Whys

4. Don't Ignore the Season

5. Make Time for People

Like the roles, don't try to tackle all of these at once. They are not sequential, so read through each and decide which habit you will establish first. Some of these include multiple habits so take your time. Enjoy the process as you cultivate growth in yourself and others.

As the leader, you play an irreplaceable role in creating a culture within your team or organization.

 Focus on the Environment

Cultivation is often indirect. We are working to create an environment that allows, invites, and stimulates growth. It is our responsibility as leaders to focus on the environment and the culture of our team.

Let’s look at four characteristics:

  1. Space
  2. Allowing 
  3. Inviting Stimulating

Space is needed for leaders to grow. Leaders tend to wait until a potential leader is fully ready before they begin letting them lead. However, we need to get out of the way, allowing the leader to grow into the space created. 

As a leader, it's critical to evaluate if you are giving space for new leaders to rise. Does the culture of your team revolve around you and your decisions? Or does the team feel empowered to make decisions and even mistakes?


What commonly stands in the way of someone stepping into leadership? Usually, it’s the current leader. Is there enough space to allow others to lead?

If that’s the case, then I must ask, “Am I willing to get out of the way? Am I willing to let someone fail? Even fail with something important?” Answering this leads to a secondary question, “Which is more important, the project or the developing leader?” A leader will complete successful projects many times over, but a successfully completed project doesn't necessarily multiply leadership.


Would others want your job? Are you leading in a way that others would have the desire or courage to do it? I’m not saying falsely make it look easy or glorious, but how often do you see a leader exhausted, stressed, and spent? Are you inspired to be like them? What about someone who can be joyful in uncertainty or failure? Does your leadership inspire others?

Inspiration is just the first step; you also have to invite people. Your invitation needs to be clear and compelling. Are they being called to something clear and specific? Do both you and they know what you’re challenging them to do? If asked about their responsibilities, would your answer and their answer be the same?

What commonly stands in the way of someone stepping into leadership? Usually, it’s the current leader. Is there enough space to allow others to lead?

When you initially plant or transplant a plant, you want to fertilize it well. If you want growth, the necessary resources need to be readily available. Do you know which resources your new leaders need?

Stimulation can come from many sources. It could be a tool to use or a guide to follow. It could be a person with experience whom someone could watch or seek counsel. I’ve even found biographies helpful in this way. Maybe it’s training to help prepare this new leader.

Creating the right environment is both an art and a science. We don’t grow in a vacuum. Our environment has a significant impact on our growth as leaders. We need to be intentional to allow enough space, invite others into that space, and provide what is necessary to grow.

Form and Function

Function relates to purpose. It answers the question, “why?” and defines the reasons you have to do something. Understanding function leads you to consider the necessary preconditions or assumptions for an activity and the desired outcomes. The 5 Whys is an excellent exercise for surfacing the function.

Form is the visible shape or configuration of something. It encompasses the methods and strategies. Form answers the questions of “what?” and “how?” After clarifying the function, form fills in the details and plan for how to realize the purpose.

Function must come first. It directs the purpose of your strategies and actions so they can take proper form rather than merely having activity for activity’s sake. Focusing on form without function leads you to emulate an activity without knowing whether it will help you reach your goal.

Function, or principles, enables you to adapt methods or forms to your circumstances and adjust to the continually changing environments around you. Function can act as a filter by which to evaluate new ideas. Understanding how both function and form are necessary will be essential to growing as a leader. 

5 Whys

This simple habit delivers a significant impact by uncovering assumptions, root causes and new ideas.

Here's how it works. You ask "Why?" 5 times. It's that simple

Five isn't a magical number, but it's enough to get to underlying causes but not so many that you start to frustrate people. The key is to move past symptoms to causal factors.

I don't feel like every question has to be, "Why?" Asking "How? When? What? or Where?" can also be helpful. "Why?" seems to be the most effective at getting to the cause of things.

I will use the 5 Whys in one of two ways:

  1. I tell everyone I'm using it to facilitate a discussion challenging the team to keep digging deeper.
  2. I can also use it subtly by keeping a curious posture and continuing to ask questions.

This habit is a great one to teach your team. It will empower each one to do the discovery work that's necessary to leadership.

Don't Ignore the Season

The critical habit is recognition of the current season and allowing that to inform what you do. This recognition requires both knowing The Kinds of Seasons and How to Discern the Season.

But don't stop at just awareness; you need to know how to respond. I would love to give you a script for responding in a given season, but the reality is my seasons are probably different from yours. So instead, I'll provide you with guidance for Creating Rhythm in Your Seasons. By creating a regular rhythm of rest, reflection and change, you will learn discernment and gain insight. These rhythms can be short with a daily cadence or longer with an annual one. The key is consistency over the long haul.

Make Time for People

A pitfall I fell into early in leadership was seeing people as interrupting the work I was trying to get done. This perspective mainly resulted from unmet expectations. I had an expectation about how I would spend a specific time, like Tuesday afternoon, and then someone would call or come by at that time with a question or wanting to work on something else.

Stewardship of your time as a leader is a critical skill. If your schedule doesn’t align with your priorities, you will continually feel the friction of this misalignment.

Smartphones didn't help this. Now I was always accessible to my team and others. I needed to add some structure. I began by theming my days and block scheduling my time. I still do this by having chunks of time for focused work where I turn off all notifications and my calendar is not free. And then I have other spaces of time that I've pre-allocated for meeting with people. This way, when someone wants to meet, I offer my preset times, and it doesn't feel like I'm giving anything up because the decision was already made in the past.

I also use 1on1s to prioritize time with my team members. As I’m learning to live from my priorities, I continue to add new habits to help me prioritize time with people.

Tools for a Leader

I don’t know what your job is, but if it’s anything like mine, you’d often find yourself learning to do something new. You’d also often be overwhelmed by the abundance of available and recommended tools. Does that sound familiar?

Finding the Right Tools

There are many tools out there. You don’t need to be proficient with all of them, but there are likely a few key ones. The Pareto principle, named after the Italian economist Vilfredo Pareto, observes that about 80% of the effects usually come from 20% of the causes. Considering this, we can assume that a handful of tools cover 80% of what you do.

How do you choose these few tools? The how-to-choose question is the crux and the most challenging part of applying the Pareto principle in everyday life. This selection process is what we will need to coach others and ourselves to cultivate leaders.

So here are three steps to walk through in trying to discern which tools are the vital few.

1. Inventory your regular activities

2. Consider your context

3. Observe others

Inventory Your Regular Activities

Think about what you do most often. What activities are most core to the work you do? Which pursuits usually have the most significant impact? Identifying these can be hard just off the top of your head, so grab your calendar and look at the past month. What did you do? What about the past six months or year? If you have a task management tool, review the things you’ve done and look for patterns. 

If you want to know where you’re going, then you must know where you are and where you’ve been.

We’re looking for 2-4 categories of activities. Your list doesn't need to encompass everything you do; remember, 80%. If the categories are too general, they won’t be much help to you. Try brainstorming a list of categories and then get the most specific, narrow down to 2-4, which still encompass 80% of what you do.

Consider Your Context

Not every tool is suitable for every environment, like a standard drill bit for a concrete wall. Where do you work? With whom do you work? These realities will significantly influence what tools you need. What are the unique needs and strengths of your audience?

Go back to that list of activities you created in the last step, now consider what barriers you often encountered. Use these barriers to identify what functions your tools will need to perform. I talked about function and form when we looked at principles and habits. Now that we understand the function, we can move on to form.

Observe Others

Everybody has tools. Take time to observe others who do similar work in similar contexts and see what they use. Don’t just take it at face value but ask why they do things the way they do. Have they always done it that way? If they have made changes, how did they decide, and what were the results?

Here are a handful of the tools I use:

  1. Productivity: Asana, Miro, Google Workspace
  2. Communication: Slack, Zoom, ConvertKit
  3. Creativity: Adobe CC, Sketchup, Byword
  4. Learning: Skillshare, LinkedIn Learning, Master Class, Coursera

Tools for Stewarding Your Time

Stewardship of your time as a leader is a critical skill as a leader. If your schedule doesn’t align with your priorities, you will continually feel the friction of this misalignment. I've highlighted four time-related tools to help you best prioritize and allocate your time.

  1. 1on1s
  2. Scheduling
  3. Gap Months
  4. Reviews

Another essential habit that I began was having weekly 1on1s with people on my team. If you haven't heard of 1on1s before, check out how I do it or look through the many resources on manager tools. Here's a quick overview

  • Always weekly. Schedule your 1on1s each week, and don't cancel it.
  • 30 min. The meeting doesn't need to be extended. 30 minutes will help it stay focused.
  • They set the agenda. This one surprises people. The direct report, not the leader, determines the topics.
  • Running notes. I keep a shared google doc for my direct reports to collect questions or topics, and I can preview it before our meeting.

Some questions need to be asked right now, but many fall in the category, "I'll ask when I see them..." Having a weekly 1on1 ensures that they'll see you this week. This regular rhythm allows people to write down questions or ideas they have rather than shooting them to you in an email or slack message.


Scheduling is specific to each person’s context, so this will require discernment as you apply it for yourself. Here are some schedule hacks I’ve used to help me grow as a leader.

  • Manage energy rather than time. I place my focus work during my best hours in the morning. Meetings (other than standups) stay in the afternoons.
  • Focus on the chucks of your day. A tight minute-by-minute schedule feels good but isn’t resilient enough for the realities of today’s schedule.
  • Keep meetings short. Moving meetings to 30 minutes has freed up so many hours to my schedule. You could probably cut your current meeting lengths in half.
  • Stay out of your inbox. Email can eat up your whole day if you let it. My email stays closed except for batch triage. I have three times that I triage my inbox. This habit allows me to respond promptly while still focusing on priority work.

You’ll notice I have a basic framework that I inspect and adapt as I go. I’m trying to develop a harmony of flexibility and structure to get my best work done. Be intentional about how you schedule your time. Otherwise, you allow everyone else to dictate your schedule. 

If you want to go deeper, you can see my weekly schedules and schedule hacks from 2020 and 20201


It’s becoming more common for students to take a gap year before college to grow and learn about themselves and the world. A gap year is an opportunity for 18-year-olds to recalibrate or calibrate for the first time to the world around them.

Similarly, it’s not uncommon for us later in life to need to step back for a season of recalibration. We probably can’t take a year off, but a gap-month is often more possible than we might initially think. Rest is vital for any leader, and prioritizing it through a gap month can help you grow as a leader.

In 2019 I took four weeks off to step back, to evaluate and adjust things in my life. I felt uncertain about my future direction, but I knew that other adjustments were needed before I could begin to dive into that decision.

It’s not uncommon for us later in life to need to step back for a season of recalibration.

Sometimes, you're at a point where you need to step away, refocus, restore and restart. If that sounds like you, check out my guide for how to make your gap-month happen. I’ve broken it down into four steps:

  1. Designing your gap-month
  2. Prep for being out
  3. Taking your gap-month
  4. Re-entering

If you want to know where you’re going, then you must know where you are and where you’ve been. But the pace and chaos of life distract us and divert our attention away from this critical understanding. Regular reviews refocus our attention on what’s important. They help us grow as leaders.

Asking the right questions is critical to doing good reviews. Your question should come from your priorities.

Some questions fit better into different time frames. You need to ask yourself, “Can I make an observable difference in a day? A week?” If your goal is to read more, then a daily question of, “How many books did I read?” will likely not be helpful. A better daily review question would be, “How did I make time today to read?”

I know it can feel overwhelming to get started with regular reviews. Here are a few questions to get you started with a daily and weekly review:


  • What did I focus on yesterday?
  • What is the priority for today?
  • Is anything standing in my way?


  • What were my key priorities coming into the week?
  • Did I accomplish those priorities? Why or why not?
  • What was life-giving?
  • What was life-draining?
  • How did I manage my attention/focus this week?
  • What hindered me from managing my attention/focus this week?

For more context and examples, take a look at Personal Reviews Will Improve Your Leadership Starting Today.

Books for a Leader

Readers lead, and leaders read. Learning from the experience of others is an essential element of growing as leaders. While some of this can come from people you have proximity with, that will always be a limited group. Reading broadens your community, giving you proximity to many more people. 

Reading isn’t the only way to experience a book. I love audiobooks. They allow me to take in the content of a book at moments that otherwise wouldn’t be possible, like while driving. The main drawback I experience with audiobooks is it’s much harder to take notes. This is one of the reasons I still like to buy physical books, though ebooks also still allow for decent note-taking.

Taking Notes

These are in no way prescriptive. How you take notes should reflect how you personally mentally organize information. These are my go-to strategies for metabolizing the content of a book.


I underline relentlessly. It keeps me focused while reading, forces me to identify the key ideas, and makes it a lot easier to come back later and find a key passage. If I’m reading a book for a second time, I’ll use a different color pen for my underlining to see what new things stand out.


When I want to organize the concepts I’m learning; I will write a brief summary at the end of the chapter. In most books, there is usually a blank half-page at the end of one chapter or the beginning of the next. When I do this, I essentially have my personal cliff notes when I’m done with the book. This may seem like a lot of work, but it's not bad when you do it one chapter at a time. It also slows me down just enough to not rush through the content.


I love these little plastic tabs for tagging my favorite quote or passages from a book. It makes it easy to pick up the book and find a go-to section. Sometimes I add these as I go, and other times I’ll go back and add them when writing a chapter summary or after finishing the book.


I actually hated doing these in school. Maybe it was because I didn’t get to pick the books. I think it was also because I didn’t have a note-taking strategy. If I’ve been actively taking notes, writing a review is primarily a synthesis. The most significant impact of writing a review for me is thinking about how I will apply the book's core concepts. This is why I read the book in the first place. I wanted it to influence me and help me grow.

Something I’m beginning to do and will soon be posting online are 90-second book reviews. This takes it a step further and forces me to distill the content and takeaways down to what’s most essential

Books I like





You can find more books and other stuff I like at

Next Steps

Cultivation happens over time. Many trees don't bear fruit for years, but they may produce for a century once established. I'm excited about your journey. Enjoy the process, not just the destination, because we never arrive.

If you're still feeling a little unsure about where to begin, try these three steps.

  1. Find people.
  2. Establish initial rhythms
  3. Choose a habit to focus on

I'd love to hear what you're learning and applying for this project. Shoot me a message or connect on LinkedIn.

Want more cultivating leaders content?

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