It’s two weeks after launch.
The new Q3 feature is live.
The team’s exhausted, but proud.
Sales understood the value, the messaging was solid, and we hit the launch date.
Everyone’s calling it a win.
But revenue hasn’t moved.
Customer success says accounts are “interested,” but adoption is spotty.
Everyone did their part. And yet, the goal of upsell revenue didn’t happen.
From Failures to Success
Last week, I asked us to Imagine Failure to Succeed. We took a goal: launch a new feature in Q3 to drive upsell revenue, and forced ourselves to picture it falling apart.
Not just listing risks, but by stepping into the failure.
And in doing so, we uncovered real gaps: unclear ownership, weak rollout, no adoption plan.
This week, I want to flip the script.
Same goal. But this time, imagine it succeeds.
The feature launches cleanly. Customers adopt it. Upsell revenue flows in just like we hoped.
Now ask:
What needs to be true for that to happen?
Start with Defining Success
What does success actually look like?
Too often, teams launch initiatives with vague goals (“release the feature”) or incomplete direction (“do your job”).
It feels obvious…until it isn’t. I’ve seen smart teams fail simply because they never aligned on what success looked like.
If we remember anything from this post, let it be this:
Clarity matters.
So, let’s define success for our Q3 launch:
- 30 existing customers adopt the new feature
- Those customers generate 10 new G2 reviews (4 or 5 stars)
- We generate $100K in upsell revenue
All before September 30th.
Notice: success isn’t just the release or generate upsell revenue.
It’s what the launch is specifically meant to achieve.
Imagine Success
With clear goals in hand, we can now imagine what success actually looks and feels like.
Picture this. It’s October 1st.
We’re celebrating. The feature hit its marks.
Revenue moved. Customers love it.
The team is fired up.
Now ask: What must have gone right to get here?
Was it luck? Timing? Or did we ensure the right things happened?
That’s where this question comes in:
What needs to be true?
Failure vs. Success: A Useful Contrast
Last week, I encouraged us to imagine failure to uncover blind spots. That exercise works because it forces you to think beyond the obvious. But it’s not complete on its own.
Here’s why:
Psychology and behavioral research show that imagining success, and defining what must be true, builds clarity, alignment, and belief. For example:
- The Pygmalion effect shows when expectations are clearly communicated, people often rise to meet them; so specifying success conditions can actively shape outcomes;
- Self-efficacy theory explains that believing in your ability to succeed increases persistence and effort, but this belief is strongest when grounded in realistic understanding of what’s needed; and
- Recent evidence shows that merely focusing on failures doesn’t always drive learning. We still need a positive vision to guide constructive action.
Here’s how the two compare:
Purpose
Imagining Failure: Surfaces what can go wrong.
Imagining Success: Defines what must be true.
Benefit
Imagining Failure: Reveals blind spots and risks.
Imagining Success: Builds clarity, focus, and energy.
Outcome
Imagining Failure: What to avoid.
Imagining Success: What to ensure.
Both are important and work well when paired together.
Q3 Success Imagined
Back to our example: what needs to be true for the Q3 feature to meet our goals?
Here’s a possible list of “what needed to be true”:
- A webinar announcing the feature had 500+ customer attendees
- Customer Success spoke with 400 targeted accounts by August 15
- Sales had 100 qualified opportunities in the pipeline by August 30
- G2 review prompts were built into onboarding and surfaced at key milestones
Each of these “truths” is concrete and testable. They don’t just identify risks; they define what must happen to reach our clearly defined goal.
That’s the power of imagining success:
We move from hoping it’ll work… to engineering a specific plan that makes it work.
Key Takeaways (TL;DR)
It’s not enough to avoid failure. We must also need to define success clearly, specifically, and in advance.
Imagining failure exposures the challenges we face.
Imagining success forces us to be specific about what has to go right.
We need both. One protects us. The other aligns us.
So, as we charge forth on an initiative, let’s be sure we know what success looks like and we know what needs to be true.
Try This
Take one active initiative this week, big or small.
Step into the future and imagine it worked. Fully.
Now ask: What needs to be true for this to happen?
What would you see? Who would be involved? What milestones would you hit?
Would this match what others on the project could imagine?
Go talk with them. Find out.
Alignment takes this clarity.
