Stuck? Fix it now with two questions
A simple trick to find your way in the messy middle of product development.
“Trying to make some sense of it all
But I can see it makes no sense at all
Is it cool to go to sleep on the floor
'Cause I don't think that I can take anymore
Clowns to the left of me, jokers to the right
Here I am, stuck in the middle with you”
— Stealers Wheel, Stuck In The Middle
I was at home sitting at my desk, staring into my laptop screen. I was frustrated. I was a little annoyed. My typical positive outlook was already turning to pessimism — not a good sign for a Tuesday.
It was my fourth video call of the day, and I could feel the Zoom fatigue settling in earlier than I expected. My team was in a state of constant back-and-forth. We argued over small aspects of the design. We questioned decisions made weeks ago. We were all pitching ideas for what to fix or improve in the product, but it felt like our ideas were going in twenty different directions.
I find myself in a similar situation on almost every project. Some call it the “Messy Middle”; some call it the “Valley of Disappointment.” I like the “Trough of Disillusionment” (a concept from the Gartner Hype Cycle of Technology) because at this point, I frequently find myself disillusioned with everything about a project. I even start to question why the team is doing the project in the first place.
Feeling disillusioned is disorienting, and I was disoriented. I needed something to help me get back on track. My next call was with Emily Balbarin, a Senior Staff Product Designer at Spotify. Little did I know, this call would change the way I work forever.
Emily has a superpower.
She has a way of pushing every project forward. She moves past stalemates and blockers with ease. To me, it feels like magic. Like a power she was born with.
On my call with Emily that Tuesday, I asked her outright, “How do you do it? How do you push through and get past moments where it seems like everything is a mess?”
Without a moment of hesitation she said, “I just ask myself, ‘Where are we in the process?’ and ‘What’s the next decision we need to make?’”
What?! That’s it? Was her superpower just two questions?
I almost couldn’t believe what I just heard.
Suddenly, it felt like a fog had lifted. A clarity washed over me that I hadn’t felt in previous projects. It was liberating.
As soon as the call ended, I got to work.
I mapped out where we were in the project. I listed the most important decision I thought we needed to make to move the project to the next stage and shared my work with the team.
The change in momentum was immediate. Instead of arguing over minor aspects of the designs, debating new ideas we had, or questioning the project strategy, the team focused on the next decision we needed to make to move the project to the next stage.
It wasn’t only me. I sensed relief in the rest of the team, too. We had all been in our heads, overthinking our decisions instead of asking, “Where are we in the process, and what do we need to do to move things forward?”
Since that day, I have used this simple trick every week.
How I put this into practice
Today, when I feel frustrated, annoyed, and disillusioned and feel my pessimism rising, it’s a signal. A signal to use the power of these two questions to make forward progress.
Question 1: Where are we in the process?
Asking this question first is powerful because it immediately orients you.
In business, and especially in software development, we all like to believe we follow a disciplined step-by-step process with a distinct beginning and end, but the reality is: we don’t. Sometimes for good reasons. Sometimes you learn something that requires you to revisit earlier stages of the development process. Other times you start somewhere in the middle.
Asking where you are in the process requires you to step back to reflect.
Reflecting on where you are helps identify the next milestone you need to achieve. Often in projects, you get so much into the details you can easily lose sight of the bigger picture.
At Spotify, this is our bigger picture:
To help orient teams, we’ve created a diagram that shows the entire product development life cycle and gives us a common point of reference. Each stage in the cycle has a milestone, a deliverable intended to move the project forward. (We’ve also developed scorecards to rate our products at each stage.)
Our shared process helps orient the team in any stage of a project.
Once you’re oriented. You need to know what to do next.
Question 2: What’s the next decision we need to make?
The power in this question is twofold.
First, it focuses on forward momentum, getting into action. It doesn’t focus on asking more questions. It’s about decision-making.
Second, it centers on the goal, not the product. The team is pulled away from any specific solution and focuses on the next step. Agreeing on the next decision and the work needed makes the next milestone clearer. Suddenly, debates about minor factors of the project – like the styling of a button or the meaning of a word – become unimportant because they don’t contribute to the next decision.
Time and time again, I’ve seen this unlock a stalemate and create forward momentum.
Final thoughts
Getting stuck is a normal part of any project. There are endless ways to get unstuck. For me, these two questions will forever be my magic trick:
Where are we in the process?
What’s the next decision we need to make?
If you are in the middle of a project and you see it slowing down or going sideways, try these two questions. I am convinced you’ll find them as useful as I have.
Thanks Emily. ❤️
-Mat
P.S. How do you get unstuck? What worked and what didn’t? Hit reply – I would love to hear your experience.