My laptop felt unusually warm while it hummed. Was it humming too loudly? Everyone stared silently at each other through the Zoom window on their computers, waiting for someone to give the right answer.

Finally, our CEO Massimo alleviated the awkward tension and answered his own question. “Let me be clear, we shouldn’t build this just because I think it’s a good idea. If none of us know why we’re doing this, let’s not do it.” His smile reassured me of his sincerity.

And he seemed to reassure everyone else, too. The lead iOS engineer started sharing his concerns, and a constructive conversation ensued around the feature we were planning to build.

It was the first time I felt like I was genuinely encouraged to speak up in a work environment. Even though I was one of the only non-technical team members, Massimo genuinely wanted me to contribute my thoughts. All eight members of our scrappy startup team did the same. Against the backdrop of my work experience to that point– corporate speak, company politics, and unnecessarily confusing business meetings– Massimo was a breath of fresh air. He led our team in a way that cut through all the fluff and got to the crux of every issue.

Massimo, an Italian with a shaven head living in London, was the gift bestowed upon me after years of yearning for a mentor. Although we only worked together for 18 months, the year and a half I spent asking him questions and observing him in action permanently changed my brain. 

Despite having years of management experience, my stint working with Massimo turned me into a leader. I went from agreeable in the workplace to someone who thought and spoke independently. I became a team member who challenged others’ thinking for the sake of our joint mission, rather than giving way to the most senior person’s idea in a meeting.

Massimo’s mentorship trained me to prioritize relentlessly, and manage up in doing so. Gone were the days when my manager would put a new, urgent priority on my plate, without me opening a conversation on how we should reprioritize my open work streams.

In my Post-Massimo Era, the change I’m most proud of is the clarity I have in decision-making where I used to need to ask a peer or superior. 

Within an organization, everything Massimo touched was left better than he found it. I’ve realized that anyone could wield his power to make a workplace or product better if they adopted just a few of his core mental models.

Wield Massimo’s Power

When a problem would inevitably arise, Massimo often brought one of four frameworks to solve it. Since crystallizing these lessons, I’ve leveled up professionally, negotiated a promotion, and unexpectedly, became a much more effective parent.

Massimo’s Four Frameworks:

1. Start with why. And always return to why. It will crystallize what’s important and solve every debate.
2. Use Kanban. It helps us produce a minimum unit of value with every task as opposed to doing busy work, and ensures we’re always shipping new value to users.
3. Consider the best and the worst possible outcome. Even in an information silo, we can use these hypothetical scenarios to answer “what should be done?” in all possible situations.
4. Define the successful outcome first, and work backwards from it. This works in every quarter, month, week, day, meeting, and every conversation.

Start with Why

As Simon Sinek wrote, “The best companies in the world don’t just know what they do and how they do it, but they know why they do it.” When Steve Jobs ran Apple, their advertising didn’t tell you what they sold or how it worked. Computers are boring— no one resonates with a description of how they run. When the iPod came out, he didn’t tell you what it was. No, it was “1,000 songs in your pocket.”

That’s what we, the consumers with a wild variety of music taste, that’s what we want! That’s why we bought iPods.

When you’re a small team with a limited budget, starting with why is critical to survival. Otherwise, we’ll spend our time doing too many things that don’t matter, and we won’t build the stuff that does matter. A really helpful way to start with why in practice is to start with the job to be done.

Are you building something for a consumer? When you inevitably come up with all these great ideas for new features to create for them, start with this template:

When… 

I want to… 

So that…

For example, “When I (a new user) receives an email from the company, I want it to include my first name and preferences, so that it’s more relevant, personal, and engaging for me.”

Massimo ensured that every ticket we opened— from product to engineering to marketing— started with the user job to be done. You couldn’t begin working on the scope until the job to be done was defined. And it was remarkable how much that constraint aligned our team when we got together to work on the ticket.

Most importantly, the job to be done (JBTD) was always written from the customer’s point of view. Not from our perspective as the company. We could just as easily write this JTBD as “When a new user visits our website, I want them to be forced to enter their name, email, and preferences, so that when we send them an email, it is personalized to them.” The scope of the ticket could be exactly the same— we’re going to set up an email capture form on our website to send personalized marketing emails.

“But why do I care, as a user?” Massimo would ask. “What value do I get by entering my details on your website?”

That’s the “why” we’d always start with. So everyone is always clear on why— the customer’s why— we’re doing anything.

Use Kanban to Ship Value

The Kanban method revolutionized manufacturing at Toyota through a beautifully simple principle: visualize work, limit work in progress, and keep things flowing. Picture an assembly line. On the factory floor, physical cards signal when new parts are needed, ensuring nothing gets produced before it’s necessary and nothing sits idle. This “just-in-time” system eliminated waste and dramatically improved efficiency.

“Stop starting, start finishing” was plastered across the top of our Kanban board in Notion. As Peter Drucker wrote in The Effective Executive, the most productive people do just one thing at a time. Though it seems counterintuitive, focusing on one thing at a time actually helps you get more done. 

Massimo had an endearing way of making me feel like an idiot for overcomplicating things. When he pulled up my Kanban board and saw four different tickets in progress, he called me out. “How are you working on all four of these pieces of work at once?”

This logical fallacy is a trap that all productive people can easily fall into, but we become truly effective when we complete a valuable piece of work every day. That means finish what you started before starting something new. Otherwise, you’ll have 10 works in progress that no one sees, and thus, no new value is created. Publish the article that just needs the finishing touches. Send the newsletter that’s 80% complete. Submit the app build. Create something now, perfect it later.

Best Case, Worst Case

“Should we do this, or that?” We can always answer this question by imagining the absolute best possible outcome of doing each, and the worst outcome of doing each. You should also envision the best and worst outcome from not doing each option.

This framework was particularly valuable when we were working with incomplete information – which, in a startup, was all the time.

I put it to the test on Christmas Day while sprinting to coordinate what I hoped would be a massive virtual event with our cofounder for the new year. My teammates were off enjoying time with their families, and I was holding down the fort. But I faced a dilemma: our Zoom license had a 100-seat limit, while we had over 1,000 registrants. Should I accept only 100 of them, or should I accept them all? If I accepted everyone and more people showed up than could get a spot, they might get upset. But if I accepted just 100, we surely wouldn’t get a 100% attendance rate, meaning we’d have empty seats when more people wanted to get in. And I couldn’t upgrade the account limits without presenting my case to leaders who were out of office.

Using the “Best Case, Worst Case” framework, it instantly became clear what I should do: the best-case scenario for accepting all 1,000 registrants significantly outweighed the worst case. So I did it. This decision kicked off a series of massive events, which forced us to progressively upgrade to 300, 500, and then 1,000 seats on our Zoom license so we could host hundreds of people per event.

Define Success First

This framework transformed our meetings. Instead of diving straight into discussion, we’d start by defining what a successful outcome for that specific meeting would look like. Having a clear objective enabled us to be respectful of each other’s time and avoid meandering conversations that didn’t achieve our intended outcome.

But where this framework really shined was in quarterly planning. Most people approach goal-setting by asking, “What do we think we can achieve?” – a question that inevitably leads to setting the bar too low. Massimo encouraged us to flip this approach on its head. “What would have us jumping for joy in three months if we achieved it?” he’d ask. This simple reframe helped us land on ambitious – yet still achievable – targets.

Once we had our moonshot defined, we’d work backwards. How could we achieve this? What resources would we need? Which team members needed to be in place? How much budget would it require? What were we willing to sacrifice in the name of this goal? By starting with an inspiring vision of success, we not only stayed focused on what mattered, but we discovered we were capable of so much more than we initially thought.

Defining success at the outset works on every time horizon. Use it to set your quarterly OKRs, your monthly initiatives, weekly planning, and daily to-do’s, all the way down to one-hour or 30-minute chunks. 

The Mentor You Never Had

If you’re like me, you’ve spent years envying anyone with a mentor. You’ve imagined having that wise voice in your ear, that steady hand guiding you through uncertainty, that secret weapon giving you an edge when you need it most.

But now I know that mentors aren’t magical beings with all the answers. They’re people just like you and me, navigating the same uncertain world we all inhabit. What sets them apart isn’t some innate wisdom—it’s their tried-and-true frameworks for cutting through complexity. Beyond their years of experience, what they really possess is a set of mental models they return to, again and again, when standing at life’s crossroads.

If you read this far, you now have 80% of what you need to lead yourself (and maybe even others). The next time uncertainty looms, remember: Start with why—it will illuminate your path forward. Define your most ambitious vision of success, then work backwards to make it real. Set up a Kanban system that keeps you shipping value, week after week. And when you’re stuck, let the clarity of best and worst cases guide your way.

These aren’t just business frameworks—they’re tools for thinking clearly in a complex world. They worked for Toyota on the factory floor and for us in our scrappy startup. They worked for Massimo, and they still work for me every day, in business and in family life.

Want to leave your mark on this world? You don’t need to wait for the perfect mentor to appear. Take mine– the mentor you never had.