Three questions for better project kickoffs

Getting better collaboration with a single simple email

It’s no secret or special insight that the way in which we begin a project has a tremendous influence on the overall outcome. Just like the way in which you begin a journey — your preparation, skills, maps, and gear— can make or break the endeavor.


At Crema, we begin every project with what we call Strategy & Alignment Sessions, large blocks of collaborative work & exercises to make sure that we’re beginning our journey with the right gear, the same maps, and at the same trailhead. We walk the team through a series of exercises including the Lean Canvas, Elevator Pitch, Story Spine & perhaps a few others, depending on the client and project.

We often hear that these 1–2 days are massively helpful for clients, not just from a project standpoint, but in how they think about the rest of their organization. And so in the spirit of constant improvement, I wanted to explore how we could get even more out of these sessions & considered a few angles:

  • How might we hear the quiet ones? Whether we’re working with asymmetrical power dynamics, introverts, or people who prefer time to process before responding, we want the best input from everyone. And yes, this helps extroverts as well.
  • What do we do in these sessions that can be done beforehand?
  • How might we prime everyone’s minds for the kinds of questions & topics we’ll discuss?
  • How might we get our many assumptions out into the open as early as possible?

The biggest opportunity for me was to draw out the beliefs & assumptions within the group, to map out the collective headspace, if you will. As Dave Gray notes in Liminal Thinking, “Sometimes people come into conflict not because they disagree, but because they fundamentally misunderstand each other.” Let’s get those misunderstandings out into the sunlight, right?

After gathering & looking through a lot of historical pre-meeting participant prep work, my exploration has now become a few questions around what we believe to be true about the product in the market, what we believe to be true about the project as it sits within the organization, and the things we’re aware of but not sure about.

Get practical:

We’ll send an email a day or two ahead of the session that includes something like the following:

From your perspective:

  1. What will make this product successful in the market?
    Specifically, how is this product uniquely qualified to address customers’ needs?
  2. What will make this project successful inside the organization?
    Communication, alignment with larger business objectives, and systems integration are common themes here.
  3. What factors will help or hinder these successes? 
    Risks, ambiguity, potential changes, and fixed dates are common themes.

It’s all about everyone understanding the context in which we’re building a product. If we don’t get the context right, then the words we use (and the meaning we each put behind them) will create more dysfunction than we know what to do with.

These questions are all neatly intertwined & interdependent; ideally, the responses build on each other. We have come to expect misalignment, deep insights, and curious levels of participation. This is not about getting the right answers, but understanding how the team has approached the project thus far and working with them to set a meaningful trajectory from here on out.

Finally, these questions set the tone & expectations for the discussion we’re about to have: this ain’t no walk in the park. We’re going full-on 14er.

👉 Upcoming experiment: In lieu of the email, one could also put those questions into a Google Form (and even collect them anonymously).

📈 Product in the Market

What will make this product successful in the market?

This one’s first because it’s easy: it’s where a lot of folks spend their thinking, planning, & product time. This is why we add features, what we rush to deliver, and where we pin our hopes. It’s also where much of the misalignment lies, usually in one of a couple ways.

What matters from the outside? // Photo by Kate Ilina on Unsplash

For one, this question will indicate how well the team knows their customers & their customers’ needs, not to mention how these customers are understood within the company. Are the answers framed around the company or the customers? Who’s the beneficiary?

We’ll also see responses that are more like indicators of success than enablers of it: KPIs & metrics. This sets up the meaningful metrics conversation nicely, but it’s critical to not substitute metrics for actual customer value. But there’s a silver lining: the metric-oriented responses provide a helpful window into the various who-values-what questions we get into during the alignment sessions. It’s the difference between, “We reached the top!” and “We hiked four miles today, but have no idea where we are.”

Regardless: there’s almost always a really good vision for what the product could be, even if it’s nestled in the day-to-day product concerns.

🏢 Project in the Organization

What will make this project successful inside the organization?

Now that we’ve considered some things, we turn our focus to the organization that we’re a part of. And this is hard because we often see ourselves as somewhat isolated producers when in reality don’t realize how tightly coupled we are. But think of all the hitches you’ve had in projects. At least a handful have probably been related to some misunderstandings, miscommunication, or lack of awareness within the organization.

Just another train in the yard or cargo on the move? // Photo by Max Vertsanov on Unsplash

Furthermore, projects that have received significant traction, praise, and visibility might have followed—intentionally or not—certain unwritten rules or cultural norms. How might the team take advantage of those? Or even write new ones? Good framing & positioning of the team’s work can generate greater advocacy & momentum than you ever expected.

A project’s success or failure hinges on how it lives & moves among internal folks:

  • Do people know why the project exists?
  • Do they believe it’s going to work? According to what values?
  • Do they understand what’s true & not true about it?
  • Do they know its status & trajectory?
  • Do they feel in the loop about it?
Friggin’ Lumbergh

Even if you’re a two-person startup, this matters: how do you communicate with your funding team? Your board? Someone cares. And how you communicate with that Someone will affect the outcome of your work.

This is also tricky because folks assume that the answers to the first question are the same as answers as the second: “If I get a conversion rate of X%, then all questions are answered.” But what if you don’t get that? What if there are more productive & realistic things we can do in the meantime to set ourselves up for later success? What if we just did a good job of telling people what’s going on? There are business metrics and there are organizational outcomes; don’t conflate the two.

Many of the weakly performing projects I’ve seen, studied, and been a part of were weak because the team underestimated their connectedness to the broader organization(s). We may not like these dependencies, and we can work around or minimize our exposure to them, but we can’t pretend they aren’t real.

Have you ever been on an adventure with someone who clearly wasn’t up to the task? Maybe they’re out of shape or foolishly ill-prepared. They’re going to hold up the group and you’re gonna have a bad time.

🤔 Factors of Our Success

What factors will help or hinder these successes?

In any project, there’s a list of external factors & variables that will affect our outcomes. Fixed timelines like an industry tradeshow, sales conference, supposedly unpredictable authority figures, or vacations or…the weather above timberline in the summer. It could be anything, and what it is doesn’t really matter. What matters is that we all know what these factors are, our dependencies on them, and the probability of them materializing.

How might we prepare for the storms we don’t expect? // Photo by Nathan Anderson on Unsplash

There are often ambiguities that leave room for varying interpretations. It can be helpful to probe those a little bit when discussing these responses, but once we’re aware of the parameters, we usually save the deeper digging for the Strategy & Alignment sessions.


In addition to getting all this on the table, this exercise has the added benefit of enabling richer relationships between everyone present: “I had no idea that you put so much value on that metric; that was really helpful” or “We’ve never seen all these things put together like this. I think we need to reconsider some processes & policies.”

Just like some thoughtful preparation & mapping makes for a great hike, these three questions can help you better understand the territory that lies in front of you. Of course, the map is not the territory, but without a map, you’re up a creek.


Tell us what you think in the comments. And really. Try this out & let us know how it goes. If your team is struggling with alignment, healthy project kickoffs, or you just want a hiking partner, we can help!

Huge thanks to Courtney von Nieda, Landon, & Alison for the feedback!