The one thing most Q1 kick-offs skip (and why it matters)

👋 Hey friends,

Earlier in the year, an engineer on one of my teams sent me a message.

They wanted to take on more ambiguous projects in 2026. Not the stuff we’d already scoped out or had clear solutions for. They wanted to tackle problems that required real discovery. Bigger swings. Things we hadn’t figured out yet.

I had to read it twice because this doesn’t happen often.

Most engineers want the opposite:

But here was someone actively seeking out the messy, undefined work.

This was music to my ears. Because it told me something important: this engineer wasn’t just interested in executing a roadmap. They were genuinely curious about our users’ problems. They wanted to solve hard things, not just build features.

That kind of ownership doesn’t happen by accident.

It happens when you’ve spent months getting your team bought into why you’re building something, not just what you’re building.

And that’s the part most Q1 kick-offs completely skip.

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Here’s how most Q1 planning goes:

Leadership shares top-down strategy sometime in Q3. PMs take that strategy, turn it into a roadmap, (the strategy changes 2 or 3 times before Q4 🤣), and show up to a Q1 kick-off with a deck that says: “Here’s what we’re building this quarter. Here are the timelines. Any questions?”

The team nods. Maybe asks a few clarifying questions. Then everyone goes back to their desks and starts working.

By February, the energy’s gone.

People are treating the work like a to-do list. No one’s pushing back or suggesting better ideas. Nobody’s taking real ownership.

The problem isn’t the roadmap. The problem is you’ve left your team out of the thinking.

If you want engineers and designers who care about the problems you’re solving, who proactively seek out harder, more ambiguous work, you can’t just hand them a finished plan and expect them to be invested.

You have to bring them in earlier. Way earlier.

Here’s what we do, and it starts months before Q1:

Before I even start thinking about Q1 roadmaps, I run a brainstorming session with my tech leads and designers.

The goal isn’t to decide what we’re building. It’s to understand how they’re interpreting the top-down strategy we’re hearing from leadership.

I want to know:

This is the part most PMs skip. They hear strategy from leadership and immediately start translating it into features.

But when you involve your team in that interpretation phase, two things happen:

I’ll be honest, this brainstorming phase can feel like a time sink. You have to find the balance between getting good input and not letting it drag on forever.

But when I skip this step, I feel it later. The team’s less engaged. The work feels more like marching orders.

From that brainstorm, we narrow down to a handful of big bets or “boulders” we want to move over the next year.

Once we have our big bets, we don’t just assume we’re right.

We start talking to customers. Running research calls. Pulling in community threads, support tickets, competitor analysis. Looking for patterns that validate (or challenge) what we think matters.

We narrow down until we have a rough sense of what we’re going to work on and, more importantly, why it actually matters to users.

This is the second part most teams skip. They go from “leadership wants this” straight to “here’s the roadmap” without checking if customers actually care.

By the time we get to the actual Q1 kick-off, the team has already been part of the thinking for months.

But I still don’t start the kick-off with “here’s what we’re building.”

I start with the problem.

I manage multiple teams now, and I’ve learned to keep the kick-off structure consistent across all of them. It’s easier on me, and it keeps the focus clear.

The customer pain we’re solving is the same, but each team tackles it from different angles.

I also like to time these kick-offs close to a retro. Everyone’s already in a reflective mode, so it’s easier to have strategic conversations instead of just diving straight into execution.

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1. Start with the problem! Make it real!

I open with customer quotes and real examples that make the pain tangible.

Not “users want better reporting.” More like: “A customer told us it takes them 14 steps to build a dashboard, and by the time they’re done they’ve forgotten what they were trying to analyze in the first place.”

Make it specific. Make it hurt a little.

2. Talk about why now

Why are we solving this now? What’s changed? What happens if we don’t solve this?

This connects the customer pain to business context.

3. Walk through what we’re starting with in Q1

Now, and only now, do I talk about what we’re building.

But I frame it as “Here’s how we’re starting to tackle this problem” not “Here’s the feature list.”

4. Show how Q1 unlocks Q2-Q4

I always connect the dots forward.

These Q1 projects aren’t just tasks. They’re setting us up to solve bigger problems later in the year.

The team needs to see the arc, not just the next sprint.

When you skip the brainstorming and just show up in January with a roadmap, here’s what happens:

Your team treats the work like a checkbox exercise. They build what you tell them to build. They don’t push back. They don’t suggest better approaches. They don’t take ownership.

And by February, you’re wondering why everyone seems disengaged.

But when you bring people into the strategy early, when you let them help shape the thinking, when you validate it together with customers, when you connect the work to real user pain, something shifts.

They start thinking like product people, not just executors.

That’s when a designer suggests a completely different approach you hadn’t considered.

That’s when a tech lead says, “If we build it this way instead, we can unlock three other problems down the line.”

That’s when an engineer asks for more ambiguous work.

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If you’re running Q1 kick-offs in the next few weeks, here’s what you can try:

Before you finalize your roadmap:

Run a brainstorming session with your tech leads and designers.

Ask: “Based on what we’re hearing from leadership and what you’re seeing in the product, what problems should we be solving this year?”

Don’t decide anything yet. Just surface ideas. See where there’s alignment.

Before your kick-off:

Talk to at least 3-5 customers about the problems you think matter. Look for patterns.

If you can’t point to real customer evidence for why you’re building something, it’s probably not ready yet.

In your kick-off:

Start with customer pain. Real quotes. Specific examples. Make the problem feel urgent before you talk about solutions.

Then walk through your Q1 projects as “here’s how we’re starting to tackle this” not “here’s what we committed to.”

End by showing how Q1 sets up the rest of the year.

After your kick-off:

Create a doc or canvas that captures the “why” behind your Q1 work. Something you can reference throughout the quarter when decisions get hard or priorities get fuzzy.

Starting Q1 right isn’t about having the perfect roadmap on day one.

It’s about getting your team genuinely invested in the problems you’re solving.

When you do that, when you involve them early, validate with customers, and make the pain real, you end up with a team that doesn’t just execute. They take ownership.

And maybe, if you’re lucky, you get an engineer who asks for the hard, ambiguous work.

See you next Friday,

– Stef

💬 Want to talk product? I’m mentoring on ADPList! If you’re planning Q1 or figuring out how to get your team more bought in, you can book a free session with me right here.

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