Does Your Team Agree on What Membership Should Be?
By Michael Gillespie on Aug 11, 2026
Different perspectives are healthy. Different definitions of winning are not.
In this issue:
- Perspective: Teams can work hard on the same membership while quietly optimizing for different definitions of success
- Insight: Productive disagreement starts by separating disagreements about purpose, priority, and evidence
- Outlook: Effective teams do not need to agree on every tactic. They just need to agree on what winning means for membership
QUOTE OF THE WEEK
“A team can disagree about how to win membership. It can’t indefinitely disagree about what winning means.”
PERSPECTIVE
Good Teams Can Still Pull in Different Directions.
I can honestly say that most membership disagreement doesn’t look like conflict among teams.
Most of the time, It looks like reasonable people advocating for reasonable things.
Teams across any business naturally want to optimize, design and aim for results that roll up to their specific functions. All while the founder wants to protect the original mission.
But eventually, someone has to answer a larger question:
What are we actually trying to optimize for?
Because every membership involves tradeoffs - Lowering the price may improve acquisition while changing member commitment. Adding benefits may improve perceived value while making the experience harder to navigate.
Increasing access may deepen relationships while making the model harder to scale.
Creating another tier may capture more revenue while adding operational complexity that can’t be effectively managed.
It’s not difficult to see that there’s rarely one objectively correct answer.
The right answer depends on what the membership is supposed to do for the member and for the business.
If that has never been made explicit, tactical debates become much harder than they need to be.
INSIGHT
Diagnose the Disagreement First.
I’ve worked with several teams on membership strategy. And believe it or not, after all the deep dives, data analysis and diagnostics, the entire conversation always comes back to successfully answering two key questions.
And I’m going to encourage you to run this same exercise.
Ask everyone meaningfully responsible for the membership to answer these two questions independently:
The primary job of our membership is ______.
We know it is working when ______.
Do not workshop the answers together. Write them separately, then compare them.
The differences are useful.
And when they appear, resist the urge to immediately merge everything into a sentence everyone can agree with.
Instead, figure out where the disagreement actually lives.
Most disagreements fall into one of three categories.
1. Purpose
You disagree about what the membership is fundamentally meant to accomplish.
One person sees it primarily as a recurring revenue engine. Another sees it as the deepest expression of the brand. Another sees it as the place where customers achieve a specific transformation.
That is a strategic disagreement.
It requires leadership to decide what the membership is ultimately there to do.
2. Priority
You agree on the larger purpose, but disagree about what deserves attention right now.
Your acquisition might be soft. Your engagement might not be what used to. Maybe retention is healthy but the experience has become too complicated for members.
This does not necessarily require a new strategy.
It requires sequencing - intentional pursuit of the single job to be done now.
Ask:
What constraint matters most in the next 90 days?
Then give the team permission to organize around it. Every current problem doesn’t have to become current priority.
3. Evidence
You agree on the goal but disagree about whether you are succeeding.
This is, without doubt, the one I see the most among teams.
Someone points to revenue and says the business is healthy. And then someone else points to retention and says the business is struggling.
That is usually a measurement problem.
Decide what evidence should tell you the membership is becoming healthier.
Often, it will be more than one metric.
But it should be explicit enough that the team can look at the same signals and have a productive conversation about what they mean.
That is the distinction:
Not every disagreement needs consensus. It needs diagnosis.
Once you know whether the disagreement is about purpose, priority, or evidence, the conversation becomes much easier to resolve.
OUTLOOK
Alignment is Good. The Definition of What Winning Means is Essential.
A healthy membership team should not think exactly alike.
Someone needs to own and surface each component of membership - from acquisition to engagement and customer support.
Different functions should bring different truths into the room. And alignment does not mean asking everyone to optimize the same metric.
It means ensuring those local decisions serve the same larger outcome.
As membership becomes more central to creator and founder-led businesses, this kind of organizational clarity matters more.
The membership is no longer simply a content program someone manages.
It touches pricing. Marketing. Customer experience. Product decisions. Revenue. Brand. Future growth.
More people will have legitimate opinions about where it should go - and that’s healthy.
But someone still has to protect the whole.
So this week, try the two-question exercise with your team:
What is the primary job of our membership?
How will we know it is working?
If the answers differ, don't rush to fix them.
First, ask why.
Remember, a mature team can disagree vigorously about how to win. It should never stay confused about what winning means.
Think about it.