Close-up photo of a Clarkia (one of my favorite native wildflowers) from my garden.

Leadership lessons from my garden

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Since leaving my most recent position, I’ve found myself with plenty of time to spend in my garden. The timing could hardly be better – October-December is planting season for most native plants here in California as the winter rains spur growth and renewal. For Californians who are in tune with our natural cycles this is a time of abundance and wonder as new life emerges everywhere. It is my absolute favorite time of year.

Some of my earliest positive memories revolve around gardens. As a child, food from our garden was an important part of how my family survived right at the bleeding edge of the poverty line. As I grew up I spent many weekends helping my parents and grandparents dig, plant, and weed. I’ve planted gardens everywhere I’ve gone in the years since.

So what does any of that have to do with leadership and startups? As it turns out, gardening has a lot to teach for those who can slow down and listen, and many of those lessons are directly applicable to the business world.

Every Garden starts with an idea – and a plan

To plant a successful garden you have to take the time to understand your space. While different gardeners may disagree about what the ideal is, they each start with a vision. You don’t need to know the details of where every plant will go, but you do need to understand your unique opportunities.  Things like how the light moves and where it’s blocked by trees or buildings, where and when the rain comes, what the soil is like and how water will be absorbed, and – crucially – what you can change.

A product has a similar beginning. You must understand the landscape and the opportunity before you write the first line of code. Identifying the places where you can add unique value, how your company will be differentiated, what kind of user experience you want to create, and where the opportunities for feedback, revenue, and growth – soil, water, and light – will come from. It’s possible to grow a garden in almost any conditions. But you have to be willing to adapt to those conditions and pivot as they change. How will your company adapt to a drought if you don’t get the valuation you were hoping for at your next round of funding? What can you plant that will allow you to weather tough times? Your plan will change, but you have to have a plan.

If you want flowers, you have to plant flowers

In an uncertain world I know that my future will always contain beauty because I am planting flowers today.  My garden is more than 80% native plants – the space between my fruit trees is sown with wild california poppies, woodland strawberries, clarkia, and other wildflowers. The fence line is bordered by wild lilacs, roses, sage, giant matilija poppies, rhododendron, and more. While spring is of course the headline event, every season of the year has its breakout stars and the distribution of flowers changes from one season to the next depending on the beautiful chaos of wind and rain scattering pollen and seeds.

An organization is similar. If I want the people on the teams I manage to create beauty and find fulfillment, I need to do the work of planting flowers – helping them set goals, develop skills, celebrate wins, and learn from failures. Not every plant will thrive in every position, they each have their own requirements for sunlight, water, and soil. People are no different. Take the time to invest in your people, help them plant flowers, and celebrate their blooms while making sure they learn from their failures.

Your garden will tell you what it needs – but you have to listen

Planting flowers is just the first step. Every plant has its own language and it’s easy to get it wrong if you don’t know what to watch for. For example, earlier this year I transplanted a lilac from one part of the yard to another as I was filling in a new garden bed. The native hazelnuts I planted nearby were thirsty and needed regular water to get established, so I frequently watered the lilac at the same time. It wilted and started dying back so I watered it more but it just got worse. It wasn’t until I went and did a bit more reading that I realized I was killing it by over-watering – California lilacs want their roots dry during the hot months of summer!

It’s easy as a manager to make a similar mistake and assume that the people who report to you need the same things you would need. If my lilac could speak it would have said something like “I love the new position! Getting more sun is fantastic and the soil is ideal! But please stop watering me so much – I’m drowning and need to get my roots re-established before I can grow here!” Taking the time to stop and ask your employees and customers what they need to thrive – and building trust so they can answer honestly – is absolutely critical to your garden’s success.

Take time to understand your users

More than just a place to find peace at the end of a long day, my garden is habitat for bugs, birds, rabbits, foxes, and more. As I was writing this a hummingbird flew in the open door from my garden into my office before turning around and heading back to its current favorite flower – a native red salvia that is in full bloom. The adjacent woods are home to racoons, deer, mountain lions, bears, and so on. All of them are users of this space in various ways and my garden is designed to accommodate and shape that usage. 

The deer would love to get in and eat everything, but strong fences keep them out and I’ve planted food plants for them along the edge of the woods so they aren’t as intent on knocking down my fences. The rabbits will get through or dig under any fence I could build, so I accommodate them by planting things that I don’t mind them nibbling – and by making the space friendly for the foxes and owls that eat the rabbits. The bear and the mountain lions know to stay clear of the garden, but are welcome to come and drink from my pond placed outside the fence so they can access it without doing damage.

There are obvious analogies from each of these creatures for the different types of users we encounter in our products. Taking time to understand the full set of users and their use cases has allowed me to design, build, and grow a garden where they can all gain something of value in balance with each other. Left unchecked the rabbits, deer, mountain lions, and bears could each destroy my garden. But none of them do because I’ve done my user research and incorporated their use cases in a balanced way.

Make room for Caterpillars

Everyone wants butterflies in their garden. Far fewer understand that to get butterflies, you need caterpillars. This is critical.

It is far too easy for inexperienced founders and product people to get fixated on the next shiny object – the butterflies that they imagine will descend on their garden by the thousands. And so to prepare for that they plant showy non-natives like butterfly bush that provide lots of nectar. But butterflies don’t appear from nothing, they have to be caterpillars before they get their wings. And if you rip out all the native “weeds” that the caterpillars eat, you’ll never get your butterflies.

In the product world, your caterpillars are things like technical debt and bugs which, if neglected, can have major negative impacts on your performance down the road and slow down your development. They can also be things like doing customer research during your scoping process and taking the time to polish a new feature through user testing instead of just throwing it over the fence and hoping. Caterpillars are often ugly and poisonous and they eat your plants since time taken to address tech debt is time you’re not spending releasing the latest shiny thing. Many gardeners spray them with insecticides and kill them off only to wonder why butterflies never appear. Don’t make that mistake.

Identify your weeds, and learn from them

One of the interesting things about gardening with native plants is that the definition of a weed is a bit different. Where other people see wildflowers encroaching on their perfect manicured lawns, I see the english and spanish grasses that invade my wildflowers as the weeds. The line between a bug and a feature can be just as thin. A plant in the wrong place is a weed, even if someplace else that exact same plant would be part of the plan.

Take the time to identify the weeds in your organization – the bad habits that bleed money, energy, and joy. Maybe it’s the sales team not being disciplined with their expense accounts as they woo clients or managers who make a habit of taking the credit for their team’s wins instead of spreading the sunshine around. Is your organization’s culture really a good expression of your values? How much are you asking people to sacrifice to meet your goals and is it a fair exchange? Dedication and a willingness to work hard are good things, but at many startups expecting people to work longer and harder as a substitute for hiring and scaling becomes normalized. This in turn creates burnout, cynicism, toxicity, and failure. Conversely, hiring too aggressively and leaving people without meaningful work is a one-way ticket to layoffs and bankruptcy. Take the time to think about your organization and identify your weeds then make a plan to get them under control.

No root, no fruit.

Gardens and organizations take time. It can take years for a tree to grow into its potential and start producing fruit. And while it’s possible to pay a lot more money to buy a bigger more mature tree, there’s no guarantee that the tree that thrived somewhere else will also thrive under the unique conditions of your garden. Conversely, you may not recognize success at first if it looks different than the way you would have done it. Especially at the early stages of your scaling process you’re going to be hiring people who know more about their areas of expertise than you do. Get them involved in crafting metrics and then hold them accountable. Misaligned expectations and watching the wrong kpis can have you digging up the tree you should be watering and fertilizing the tree that is already at its potential. Understanding what will drive success or failure for employees and products is the hardest part of being a leader. 

It takes time and work to identify the right trees for your space, envision how they will impact the plants around them, and understand the costs and benefits. A grand live oak is a keystone species that supports hundreds of other species of birds and insects. It also shades out and smothers everything that grows around its roots. Is that the right species for the space you have? Only you can decide – but understanding the acorn, the sapling, and the old oak and how they will change and impact others over time is something you have to learn.

To conclude

Gardening is a labor of love for me. Aside from producing fresh flavorful and nutritious food for my family, it is my refuge. A place where I can see the impacts of my work and feel that I have reshaped the world around me to add beauty. An oasis overflowing with life. 

I’ve been in the startup world for more than 12 years now and I’ve seen some beautiful gardens, some truly barren patches, and far more that straddle the line between the two, never quite reaching their potential. Everyone focuses on being the next unicorn, and that’s fine. But any storyteller will tell you that the best place to find a unicorn is in a lush garden.

You don’t have to plant your garden in a day. In fact, it’s impossible. But you can start by taking the time to sit down someplace beautiful for a few minutes every day and think about your garden – whatever that is to you – and what you can do to help it thrive.

To learn more about California’s native plants and how your garden can be habitat, visit