Trellis & Branch | About a 5 minute read
In Alice’s Adventures in Wonderland, Alice comes to a fork in the road and meets the Cheshire Cat.
“Would you tell me, please, which way I ought to go from here?”
“That depends a good deal on where you want to get to,” said the Cat.
“I don’t much care where,” said Alice.
“Then it doesn’t matter which way you walk,” said the Cat.
“So long as I get somewhere,” Alice added as an explanation.
“Oh, you’re sure to do that,” said the Cat, “if you only walk long enough.”
I love this exchange because it describes so many businesses I meet. They are working hard and moving fast. They are certainly getting somewhere. The question is whether it is the somewhere they would have picked.
Why a plan matters
When a team is busy, it is easy to confuse motion with progress. Every new request feels urgent, every opportunity looks worth a try, and the calendar fills up. Without a clear destination, there is no way to tell which of those things deserve a yes.
Jordan Peterson writes in 12 Rules for Life: “We cannot navigate, without something to aim at and, while we are in this world, we must always navigate.”
I read that as good news for a business owner. You are going to make decisions every day whether you plan to or not. A clear aim just makes those decisions easier and more consistent.
Start in the future, then work backward
One exercise I use with leadership teams is to start with a date well ahead, say ten years out, and describe what you want to be true then. Who are you serving? What problems are you solving for them? What is your revenue?
Then work backward. What needs to be true in five years to make that picture possible? In three? In one year? Who will be in charge of each initiative needed? Each step gets more specific, and by the end you have a short list of actions with names and dates attached.
Get the whole team on the same page
A plan only works if people can see it. Write it down. Put it where the team will run into it: on a wall, in onboarding, at the top of the weekly meeting. Pick two or three numbers that tell you whether you are on track, and look at them on a regular rhythm. Give every priority a named owner.
Then say it again. Leaders usually get tired of repeating their vision long before their teams have really heard it. A good check is to ask a few people, separately, to describe where the company is headed. If the answers match, you are aligned. If they don’t, that is useful to know, and it is fixable.
Strong opinions, weakly held
There is a counterweight to all of this. You will learn things as you go. Customers will surprise you, a test will fail, a market will shift. A plan that cannot bend will eventually break.
Forecaster Paul Saffo is known for a phrase that captures the balance: strong opinions, weakly held. Commit to your best current thinking and act on it with conviction, and then go looking for evidence that you might be wrong. When you find it, change your mind quickly and without embarrassment.
Both halves matter. The strong part gives your team something to rally around, because people cannot row toward a maybe. The weak part keeps you honest and lets you improve. Here is how I like to put it into practice:
Keep the destination steady and the route flexible. Your vision and who you serve should change rarely. How you get there can change.
Test and learn. When a big assumption is holding up your plan, run a small test before you bet the business on it. Give it one owner, one number and a date, usually 30 to 90 days.
Decide in advance what would change your mind. Write it down before the test begins, so you are reading results honestly instead of defending a favorite idea.
Review on a set rhythm and share what changed. When the team hears “here is what we learned and here is what we are adjusting,” a change reads as progress and not as chaos.
Believe fanatically. Flexible does not mean lukewarm. David Senra, who has studied hundreds of history’s great founders on his Founders podcast, puts it simply: “I think the best founders are missionary.” They hold their vision with an almost crazy level of commitment, and that belief is what carries a team through the hard stretches, even as the route changes.
A few questions to sit with
If you wrote the headline about your company for ten years from now, what would it say?
Who, specifically, are you serving today? Who do you want to serve then?
Do you win on price, quality, speed or service? Does your team know which?
If you could accomplish only one thing this year, what would it be?
What would you need to see to change your mind about your current plan?
You do not need perfect answers. A rough plan you can act on, and keep improving, beats a perfect plan you never finish.
If it would help to think this through with someone, I run short working sessions with leadership teams that end with a written vision and a sequenced plan for the first twelve months. I would be happy to talk about what that could look like for you.
Nicole Ciavola, Principal Consultant, Trellis & Branch
Sources: Lewis Carroll, Alice’s Adventures in Wonderland (1865), chapter 6; Jordan B. Peterson, 12 Rules for Life: An Antidote to Chaos (2018); David Senra interview with Tim Ferriss, September 2025; Paul Saffo, as discussed in “Betting on Strong Opinions Weakly Held,” Educause (1998).