Now’s the time to work backwards so you can go further faster
This feels like a very personal letter since, at the end of every quarter, I take time to reflect on where I’m going and which levers will get me there the fastest and easiest way possible. I’m actually off to Costa da Caparica in Portugal for a weekend of surfing, journaling, reflecting, and planning with some of my favorite people – stay tuned for updates. So know that you’re getting this update raw and in real time.
Some say those who wander are not necessarily lost, but I’d argue they’re probably not sure where they’re going either. And while reflection is personal, it’s also practical because it helps me course-correct. Surfing is where this lesson hits hardest. It’s one of the deepest sports I’ve had the pleasure to practice — it teaches me more than any other. The first core lesson in surfing is that you go where you’re looking. Look down and you’re on your way to meet the bottom of the ocean, look forward and you move toward the beach, look to the sides and you carve your own path.
To know what to do next, we need direction. On a less poetic, less surf-related note, all my clients are in some sort of planning season or period right now (and I’m sure you are too), so I want to make sure you have the right tools to succeed and ensure that everything you are building is towards the future you want to create.
The most important question I ask
As a coach, much of my work is helping clients look past their blind spots (which we all have) and gain perspective. I can usually see things they can’t because they’re “in” the situation. One of my favorite sayings is: You can’t see the island if you’re on it. Maybe that’s why one of my favorite things to do in New York is take the ferry to see Manhattan for the greatness it truly holds, which, in my opinion, you can only appreciate from the water.
The question I ask that consistently gives my clients perspective is some version of: What are you trying to achieve? Other variations include:
Why does this matter?
What does success look like here?
What’s the outcome we care about?
If we’re wildly successful, what happens?
Why?
Why now?
This question removes the person from the immediate problem and all the limitations they’ve already created around it. It pushes them to focus on the future and imagine a different reality. That shift brings clarity and gets them thinking about what actually matters: the results. I say it all the time — it’s not about the activities we do or the features we build, it’s about the impact we achieve. This question frames the impact.
Now I didn’t give you five different versions of that question “just because.” I did it because most people (you included) are vague the first time they answer it. The best way to get to specificity is to ask the same question again in different ways until the result becomes clear and ideally measurable.
What to do once you know where you want to go
Once you’ve rubber ducked your way into a clear answer about what success looks like, it’s time to use one of my favorite techniques (borrowed from Amazon): working backwards. Working backwards means starting from the outcome you want to achieve and then figuring out the steps you need to take to get there.
The beauty of this approach is that it keeps the focus on the outcome — not the output or the task at hand. It frames everything through the lens of what you’re trying to accomplish.
It sounds simple, and it is, but I constantly see people make the same mistakes while thinking they’re applying it. Or worse, they list it as a guiding principle but fail to use it for high-leverage activities that could significantly impact their leadership development or product practice. If it were up to me, that changes now. I’m going to break down 3 high-leverage practices that transform once you apply this technique.
Product Ideas: The shift from "what if we built..." to "what problem are we solving?"
I’ve never heard anyone pitch an idea by saying, “I have a terrible idea, everyone, listen up!” When teams pitch ideas, they often sound smart. Slick, even. A shiny integration, a clever AI-powered feature, something a competitor just launched. But when you ask, “What are we trying to achieve?” or “Why are we doing this?” — the room goes quiet. That’s because we’re trained to fall in love with solutions, not outcomes.
Before any idea is brought to the table (and I know a lot are being pitched right now because of planning season), we need to align on the single most important business outcome we’re solving for. Anything that doesn’t contribute to that isn’t a “good” idea right now because it doesn’t move us closer to the objective. Brilliant ideas without clear business goals and serious product discovery are just expensive experiments.
As fun as idea generation can be, the real work isn’t coming up with ideas — it’s choosing the ones that move the needle in the right direction. And to do that, you need to know what the needle is. Bonus lesson: When someone brings a half-baked pitch, use that as a coaching moment. Ask: “How does this help us solve [INSERT OUTCOME]?”
When my clients get enamored with another “great idea,” I make them pause and work through 3 questions:
Great product leaders are not collectors or sorters of ideas. They master focus and clarify what success looks like by setting one clear objective, so the best ideas and experiments become obvious.
Product Strategy: the shift from “build X, Y, Z” to “we’re focusing on X business problem”
Strategy work often gets mistaken for storytelling: vision decks, high-level priorities, maybe a three-horizon framework if we’re feeling fancy. But none of that matters if we’re not anchored in a real problem worth solving — something specific, painful, and tied to business health. Real strategy starts with brutal honesty about what's actually broken or missing in your business.
Are you losing customers because of a specific gap in your offering?
Is there a revenue ceiling you keep hitting?
Are operational inefficiencies eating your margins?
The business problem has to be concrete enough that you'd know within 90 days whether you're making real progress.
Once you have that anchor, everything flows differently. Your roadmap stops being a wishlist of features and becomes a series of calculated moves toward solving that problem. Your team stops debating what to build next and starts focusing on what gets you closer to the outcome that matters.
When leaders are building strategy they start from what they think they should have: a presentation, a doc, a story, but not from what they actually need which is focus and clarity. Working backwards in strategy means doing the really hard work to define this first.
One of my past clients, The Palace Company, faced this exact challenge. Initially, the team was focused on “building these 15 restaurant reservation features.” But once we anchored the strategy in a real business problem—“guests can't get reservations at their preferred restaurants”—we reframed the goal: how might we increase the percentage of guests who can dine at specialty restaurants by 30%? As a result, they hit the 30% increase and built none of the original 15 features. The business problem became the North Star that led to the right solution.
The takeaway? When the strategy is anchored in a clear, high-priority business problem, teams don’t waste time building what’s not needed — they solve what actually matters. A great product strategy focuses the team on the most important business problem to solve right now and gives them the clarity to know when they've solved it.
Meetings: Design for the result, not the agenda
Talk about a controversial topic. People have all sorts of opinions about meetings, and definitely one of the reasons why they’re talked about so much is that they are extremely expensive. Run the $/hour on a meeting with 5 senior people, and you’ll very quickly see how much we should care about well-run meetings.
Despite how costly and disruptive meetings are, most of them are bad and some could have been an email. To ensure that meetings, workshops, and offsites are actually productive, there’s a small shift you can start implementing immediately: before you send that calendar invite, complete this sentence: "By the end of this meeting, we will accomplish _____." If you can't finish it with something specific and measurable, you don't need a meeting — you need clarity about what you're actually trying to achieve.
Here's where it gets interesting and where working backwards comes in: once you have that outcome, let it reshape how you design the meeting. If the goal is "decide whether to run additional experiments to validate X," your agenda shouldn't be a general discussion. It should be a sequence that gets you there: present the key options, review the decision criteria, hear from each stakeholder, then decide.
The outcome should dictate everything: who's in the room, what materials you prepare, how much time you need, and what conversations you have.
Need a decision? Invite the decision-maker and the people with critical information, not everyone who's "interested."
Need creative problem-solving? Design for divergent thinking first, then convergent.
Need alignment? Prepare the specific points where alignment is required.
I've seen leaders completely transform their effectiveness by asking "What does this outcome require?" instead of "What should we talk about?" The outcome you are looking for determines your agenda.
When meetings become outcome-driven, people show up differently, contribute more meaningfully, and leave with actual clarity about what happens next. Meetings finally deliver the return on investment it takes to have them in the first place.
This scoop is a little different. This one comes in the form of an invitation…
During my last visit to the Bay Area earlier this month, I got to hang out with one of my favorite product people of all time, Shreyas Doshi. Shreyas is one of the most insightful and introspective people I’ve ever met, and I feel lucky to get to call a friend and a mentor. Shreyas has this deep belief (which I share) that a lot of the answers are already inside us, but we just don’t always listen to them.
So next time you’re about to make an important decision, set a key meeting, or join a high-stakes call, I want you to ask yourself: What am I trying to achieve? What does success look like here? Then, actually listen and course correct based on your answer.
This is how I’ve shaped my intuition as a coach, and it’s also how I’ve sharpened my product sense. I know this might feel like a bit of a cliffhanger… which means you’ll just have to stay tuned for the next edition 😉