The First Sally

The Knight’s First Ride

Don Quixote’s first adventure—his “first sally”—is a disaster.

He rides out alone, with no plan, no partner, no supplies. He picks a fight with merchants, gets beaten senseless, and has to be carried home by a neighbor. He names his horse, polishes his armor, picks a lady to dedicate his quest to—all the preparation that doesn’t matter—but skips everything that does.

His second sally is different. He brings Sancho. He carries food. He still tilts at windmills, but he survives. He learns.

The difference isn’t that Quixote suddenly got smarter. It’s that the first failure taught him what actually matters.

The PM Version

The first 90 days as a PM in a new role are remarkably similar. Here’s how it usually goes wrong:

Week 1: You arrive with energy and a head full of ideas. You’ve seen what worked at your last company, and the gaps here look obvious. Before you’ve finished onboarding you’re sketching solutions on whiteboards, proposing changes to the sprint process, suggesting a new prioritization framework. The team smiles politely. They’ve seen this before—the new PM who starts fixing before understanding why things are the way they are. They nod, and they wait for you to burn out.

Week 2: The ideas keep coming, but now they have a specific flavor. “At my last company, we did it this way.” You start importing the rituals and tools that made you successful somewhere else—the exact standup format, the particular roadmap template, the review cadence that worked with a different team in a different market with different constraints. Nobody cares about your last company. They haven’t told you that yet, but the eye rolls in retro are getting harder to hide.

Week 3: You need a win. Something visible, something fast, something that proves you belong here. So you grab the most obvious low-hanging fruit—maybe a UI cleanup, maybe a process tweak, maybe a quick feature that’s been sitting in the backlog. You ship it. It feels good. But the easy visible thing wasn’t the important thing. The real problems—the ones the team has been grinding against for months—are harder, messier, and nowhere near your radar yet. You’ve shipped motion, not impact. And the team knows the difference.

Week 4: By now you’re in every meeting, reading every doc, trying to own every decision. You haven’t asked anyone for help because you want to show you can handle it. But you’re drowning—context is overwhelming, relationships are thin, and the team doesn’t trust you because you haven’t trusted them. You rode out alone, with no partner and no supplies, and the merchants are closing in.

First sally. No partner. No supplies. Beaten up by merchants.

What Actually Works

Here’s the second sally version—what works when you start somewhere new:

1. Listen Before You Fix (Weeks 1-4)

Quixote rode out ready to change the world. He should have spent a week understanding it first.

In practice: Your first month is for listening. Talk to every team member, key stakeholder, and a few customers. Ask: “What’s working? What’s broken? What have you tried?” Take notes. Don’t propose solutions yet.

2. Find Your Sancho (Week 2)

Quixote’s second sally worked because he had a partner who understood the terrain, knew the people, and could tell him when he was charging at a windmill.

For PMs: Find the person who knows where the bodies are buried. The engineer who’s been there three years. The designer who understands the users. The support lead who knows every pain point. Buy them coffee. Listen hard.

3. Map Before You Move (Weeks 3-6)

Sancho always knew the road to the next town. He didn’t just wander.

The rule: Before proposing anything, map the current reality: What are the actual metrics? What does the roadmap look like? Where are the commitments? What’s been tried and failed? You need this map before you can navigate.

4. One Meaningful Win, Not Three Quick Ones (Weeks 6-12)

Quixote tried to fight every battle. Sancho focused on getting to the next inn. One clear destination.

The approach: Pick the one problem that: (a) the team cares about, (b) you can actually influence, and (c) will be visibly better in 90 days. Put all your energy there. One real win earns more trust than three performative ones.

The 90-Day Traps

Watch for these first-sally mistakes:

• Talking more than listening in the first month—you don’t know enough yet
• Changing processes before earning trust—the team doesn’t know you, and change from a stranger feels threatening
• Optimizing for visibility over impact—choosing what makes you look good over what matters
• Going solo—not building relationships before you need them

Each is a knight riding alone into a fight he doesn’t understand.

This Week’s Challenge

If you’re in your first 90 days (or about to start), do these three things before Friday:

1. Find the person who’s been at your company longest and ask them what the last three failed initiatives had in common.
2. Write down your top assumption about the product—then find one piece of data that either confirms or kills it.
3. Block 30 minutes with your most skeptical engineer and ask: “What should I know that nobody’s told me yet?”

If you can’t do all three, start with the first one. The second sally is always better than the first.

The Second Ride

Quixote’s first sally taught him one crucial thing: you can’t do this alone, and you can’t do it unprepared.

Your first 90 days in a new PM role are your first sally. You might get some bruises. That’s okay. The question is whether you learn from them.

Bring a Sancho. Pack supplies. Listen to the locals. And when you ride out, ride toward something that actually matters.

Put this into practice

Start your new role with structure, not assumptions. The Opportunity Assessment helps you map the landscape before charging in.

Get the Template →