I used to loathe having anyone tell me I needed “more years of experience” to succeed at something. Now that I have more grey hair and joints that don’t work as well, I have to admit that some things do simply take time. Though I still think this phrase is overused when people don’t have a more useful response.
One seemingly unrelated pursuit that has made this obvious is learning to grow bonsai trees. Luckily, for the impatient like me, some lessons from bonsai can be applied to condense the learning process and pack more learning into each chronologic year.
For a skilled practitioner, a high class bonsai tree can take a decade or more of planning and execution to craft. Some trees are centuries old. For an unskilled practitioner, creating a tree of this caliber is impossible without learning more. So what makes this so complicated? There are two main drivers:
- There are a huge number of variables that can influence the tree’s growth. Some of these are: the tree species or cultivar, growing location, pests, inputs (water, sun, fertilizer, oxygen), root structure, pot choice, and each individual tree’s history.
- The feedback loops are slow. It takes a full year to see how a tree responds to the different seasons of the year. Repotting a tree may speed or slow growth patterns for years. Pruning one year may impact growth habits the following year.
Lots of individual variability and long feedback loops? This sounds a lot like building products with teams. In a team, each individual has unique preferences, people take time to adopt new habits, and each company and market has its own fluctuating dynamics.
Because of the combination of variables and slow feedback loops, one needs “years of experience” to become skilled. Yet, for those that don’t like waiting around, there is some good news. There are three ways I’ve observed to accelerate learning for Bonsai:
- Harvest the wisdom of others
- Buy a lot of trees
- Extract maximally from your experiences

Harvest the Wisdom of Others
There’s an adage along the lines of, “A fool learns only from his own mistakes. A wise man learns from the mistakes of others.” This mentality is core to minimizing the time required to master a subject. In bonsai, this often takes the form of going to club meetings, watching a lot of Youtube, going to in-person seminars, or, for the serious, doing an apprenticeship. Learning these lessons from others also distills the other’s years of time spent into a lesson that can be learned in a small fraction of the time.
In other domains, learning from others takes various forms. As some examples: talking with peers/mentors, reading books or articles, listening to podcasts, observing what works and doesn’t for other teams in your company.
Keep an eye out for creative ways to learn from others. One of my favorite experiences in the past was forming a small managers group across various functions at Slack. We met weekly and rotated who was presenting a problem. The group then asked questions to help coach the person to a better understanding of their situation and plan how to proceed. One fun benefit of this was that it exposed me to non-engineering management situations. Having this group meet over a long period of time also provided a better longitudinal view of others’ problems. What sounds like it could work and what actually works are not always the same. This is part of what makes learning in both bonsai and management such a lengthy process.
Recommendation: Find sources of leadership guidance that you can learn from and keep a steady feed of consumption to ensure you are always learning. Consider: what are 3 resources you can make a regular habit of learning from – be it people, books, blogs, podcasts, or otherwise. Take one action now to build a habit around one of these resources. This could be: setting up a coffee meeting, downloading a new podcast, or setting aside a regular time in your day to read a section from a book.
Buy A Lot of Trees
If you have one bonsai tree, you get to see how one tree responds to one set of changes. There’s nothing wrong with that, but it’s not fast. For example, if I try partially defoliating a trident maple in the spring and notice that it responds with minimal growth in new branchesmaybe I misapplied the technique or this tree was weak to start with. I won’t know if the issue was caused by: 1) this unique tree, 2) my timing, 3) the weather in my yard 4) some other factor. I will have to wait to try again next season to see if results differ.
Many practitioners who want to accelerate their learning will buy more trees. Having 5 trident maples to defoliate would mean I get to see 5 experimental years in 1 year. It also provides for more controlled experimentation, as the trees in the same location are likely getting the same watering, sun, fertilizer, etc.. Then, if they are behaving differently, it is more likely that other differences are driving that difference.
The management equivalent here is to expose yourself to as much as you can. If you have an opportunity to manage more people or teams, that is a good way to see more variation. However, that is often not in your control. You can still impact this by finding ways to interact with many people and projects so you can see more problem-solving scenarios end-to-end.
Often this takes the form of raising your hand when opportunities arise: Does a summer intern need a manager? Does a new initiative need someone to part-time manage while they hire a full time manager? Does another team need help hiring? Is there a new manager who needs onboarding guidance? Keep an eye out for situations that will give you more opportunities to see teams and projects in action.
Recommendation: Find ways to make sure you are being challenged in new ways on a regular basis and also to observe and learn from others doing the same. Consider setting up coffee meetings with other leaders, including those more senior than yourself. Ask them what challenges they are facing currently and consider offering to help.
Extract Maximally from Your Experiences
It’s possible to work for 10 years in a role and learn very little if you’re not extracting the lessons from your experiences. One can learn passively, but it’s hard to argue that the passive approach is the fastest. Surgeon Atul Gawande has an aphorism to “count something“. When you apply this kind of objective observation to situations you help reduce the noise in the signal and improve your rate of learning.
In the bonsai world, serious practitioners will run experiments. For example, trying different fertilizing regiments or different soils to see which create the best fine branching. One could simply try different ways and use intuition to decide which works best. But this approach is prone to a lot of potential bias. It’s hard to remember what really happened, and it’s easy to fall victim to something like confirmation bias and take away the wrong lessons. [Good word of the day here: apophenia: the tendency to perceive a connection or meaningful pattern between unrelated or random things such as objects or ideas.]
In management, it can be very hard to determine if a given course of action was the right one. It’s not always as easy as running an A/B experiment, but that doesn’t mean it’s not worth measuring something. I personally use journaling as a way to capture my observations and thinking on different issues. Sometimes, I will start a blog post at the beginning of a project and then review later on to see which of my early assumptions turned out to be valid. Retrospecively processing why my original intuition was wrong helps me refine my predictions next time.
Sometimes extracting learning can be as simple as writing down lessons before one forgets them. I’m sure I’ve forgotten 99% of what I’ve experienced managing, but if I marginally improve my retention, it compounds my progress. Using these lessons to teach or mentor others is also a good way to both pressure test and validate your ideas and learn from others.
If you need a place to get started, consider one of these prompts:
- What projects are you and your team currently working on? What measures do you have in place to indicate it is progressing as expected? What measures might you be missing?
- What project recently ran into surprises or challenges that needed your attention? What could have been done to avoid that challenge from arising? Is there anything from that lesson you can apply to current or future projects?
Recommendation: Set aside time to capture and synthesize your observations, challenges, and lessons you are learning. Build a habit of doing this on a regular basis. Use your calendar to set a recurring reminder to make sure you have adequate time set aside.

Final thoughts:
One check I like to ask myself is: am I on track to have one year of experience 10 times or 10 years of experience? This helps me examine my rate of progress and ask whether I need more exposure to learning from others. Are my personal velocity and experience accumulation high enough? And, lastly, am I being intentional in structuring my thoughts and lessons so I can retain and apply them in the future?
Some things can’t be rushed, and I begrudgingly admit that I have needed years to learn some lessons. I hope these ideas help give you a framework for how to operate within the constraints of this reality to minimize your time to mastery.
If you like management-related analogies, you might check out a couple of my other posts: