As a solo PMM, I was drowning in possible priorities: competitive intel, launch plans, sales enablement, content calendars. Then my manager gave me advice that changed how I approached everything:
“Dharitri, you should ‘Always Be Curious!’ To be honest, I didn’t fully grasp what he meant until curiosity became my primary lever for influencing revenue.
As someone without a big team or massive budget, strategic curiosity became my primary lever for influence. The challenge? Knowing where to focus that curiosity.
Let me break down the five areas where strategic curiosity has the highest impact on revenue and how to prioritize them when you can’t do everything.
1. Be curious about what actually closes deals (not just what generates leads)
B2B deals don’t close because a buyer liked your demo. They close when a buyer trusts that choosing you is the safest and smartest decision they can defend internally.
When deals stall late-stage, it’s rarely about missing features or pricing. It’s because the buyer cannot confidently align internal stakeholders or defend the decision upward.
The curiosity shift
Instead of asking, “How do we generate more demand?” I started asking, “What makes a buyer feel confident enough to say yes?”
That shift took me out of top-of-funnel dashboards and into deal reality. I got curious about:
- Where trust breaks down in late-stage conversations
- Which objections signal risk, not disinterest
- What champions struggle to articulate internally, even when they want to buy
I spent more time reviewing our CRM (Pipedrive) data, analyzing closed-won, stalled, and closed-lost deals, than reviewing GA4 marketing metrics.
What PMM can do
Move from feature messaging to problem ownership. Reframe your product as the solution to their critical business problem, using their language, metrics, and constraints.
Enable internal alignment, not just external persuasion. Build persona-specific narratives that help sales speak to:
- CFOs about ROI and risk
- IT teams about security and integration
- End users about workflows and adoption
Not as separate pitches, but as one cohesive story, buyers can carry internally.
Reduce buyer effort at every stage. Late-stage deals often stall not because of objections, but because buyers don’t know the next step. PMM can remove this friction by creating:
- Business case templates
- Executive-ready summaries
- Clear approval paths and timelines
The impact
When buyers feel guided (not pressured), confidence accelerates, and it becomes the closing mechanism, not feature volume or discount pressure.
2. Be curious about where revenue is leaking (the expensive gaps)
Revenue doesn’t just leak from lost deals. It leaks quietly after the deal is signed, through churn and missed expansion.
Revenue usually leaks in three places:
- Deals that should close but never do
- Customers who leave because they never saw real value
- Customers who stay but never expand
If you only focus on new business, you miss these gaps.
The churn moment that changed my focus
I once reviewed two lost customers who had something important in common.
They didn’t switch to a competitor. They didn’t complain loudly. They simply stopped using and paying for the product after 5-6 months.
Both customers were using only 2 out of 6 core modules of our solution – the ones with the lowest business impact. The modules that delivered the highest ROI were never activated.
Even more concerning, the admins at these companies didn’t know we had features that directly solved the problems they originally bought us for.
This wasn’t a product issue. It wasn’t a sales issue. It was a value clarity gap and a post-sale communication gap.
And this is one of the most common ways customers churn.
Not because they’re unhappy. But because they’re unsure.
- Unsure if they’re using the product the right way.
- Unsure if they’re missing something important.
- Unsure if the value they were promised will ever show up.
Over time, uncertainty turns into silence. Silence turns into churn.
What can PMM do
Design post-sale onboarding for outcomes, not education. Reframe onboarding around value milestones, what customers need to do to see ROI early, not feature walkthroughs.
Build CS enablement for expansion conversations. Redesign QBR frameworks to surface unrealized value, creating natural moments for upsell without forcing the conversation.
Launch proactive value discovery campaigns. Highlight underutilized capabilities tied directly to customer pain points. Make value unavoidable.
The impact
When customers understand what they bought and how it maps to their success:
- Churn becomes predictable and preventable
- Expansion becomes a byproduct of usage, not pressure
- Revenue durability improves without increasing acquisition spend
This is one of the highest-ROI areas for PMM, yet one of the most underinvested.
3. Be curious about the real buying committee (not just your icp persona)
Your ICP document might say “Head of HR,” but the deal often dies because the VP of IT said no.
In enterprise B2B, deals are decided by a committee:
- CFO cares about ROI and payback period
- End users care about ease of use
- IT/Security cares about risk and integrations
- Director/VP cares about strategic fit
If your messaging only speaks to the person who filled out the form, the deal will slow down or quietly die once others get involved.
What lost deals taught me
I reviewed every lost opportunity over 12 months. Clear patterns emerged:
- 33% ended in “no decision” – Not a lack of interest, but a lack of internal alignment
- 35% stalled due to lack of leadership buy-in – Momentum at the team level, but never reached senior leadership
- 25% had no clear timeline – Perceived need, but not enough urgency
- Remaining went to competitors – Often because they engaged leadership earlier
These deals didn’t fail because of pricing or features. They failed because we enabled only one buyer in a decision made by many.
What PMM can do
Enable multi-threading early. Partner with sales to move beyond single-threaded deals:
- Create messaging decks for multiple roles, not just the champion
- Equip champions to bring others into conversations confidently
Refine the funnel to reach decision-makers sooner. Prioritize demos with:
- Decision-makers or strong influencers
- Buyers who understand business impact
- Accounts with clear paths to leadership
Anchor conversations in business outcomes. Shift from curiosity-driven demos to conversations focused on business impact, risk reduction, and clear success metrics.
The impact
Demo volume stayed steady. Deal quality improved.
Enterprise deals don’t stall because buyers aren’t interested; they stall because the right people were never engaged at the right time.
4. Be curious about why buyers choose competitors (not just what competitors do)
When a deal moves to a competitor, teams often assume: “They discounted” or “They were cheaper.”
But in enterprise B2B, price is rarely the real reason. Most deals are lost because the competitor made the decision feel clearer, safer, and easier to approve.
That’s why competitive intelligence shouldn’t be about finding competitor weaknesses. It should help you understand what buyers believed when they chose someone else.
Why deals really move to competitors
Across competitive losses, the reasons usually fall into four buckets:
- They framed the problem better – Made it feel specific, urgent, and expensive to ignore
- They sold to the full committee, not just the champion – Had clean stories for Finance (ROI), IT (safety), Leadership (why now), and End Users (adoption)
- They made proof easy – Short ROI summaries, one-page comparison guides, vertical-specific examples buyers could reuse internally
- They made the process easier – Gave champions a clear path: what to do next, how to get approvals, what to send leadership
What this means for PMM
Competitive intelligence shouldn’t be about finding competitor weaknesses. It should help you understand what buyers believed when they chose someone else.
Win-loss analysis uncovers real decision drivers and helps you adjust positioning, messaging, enablement, and packaging based on what actually happened in deals.
5. Be curious about why deals stall (the silent revenue killer)
Closed-lost deals are visible. Stalled deals are far more expensive.
They consume sales effort, inflate forecasts, and create the illusion of pipeline health while quietly killing momentum.
The most important question isn’t “Why did we lose?” It’s: “Why did this deal stop moving?”
Because most stalled deals aren’t lost, they’re underenabled.
What a $400K stalled deal taught me
We had a $400K opportunity that looked solid: strong champion, multiple stakeholders, clear problem alignment.
Then it went quiet for more than 120 days.
When I joined a check-in call, the blockers surfaced quickly:
- They didn’t know the budget approval process
- They weren’t sure how to present ROI internally
- They hesitated to approach the CFO without concrete proof
We hadn’t lost the deal. We had assumed the buyer knew how to buy.
Why deals stall instead of closing or losing
Stalled deals signal:
- Agreement without urgency
- Interest without executive confidence
- Fit without a clear decision path
Because no one says “no,” these deals linger. They represent recoverable revenue if friction is identified early.
What PMM can do
Help buyers understand how decisions get made. Surface and clarify:
- What approval steps typically look like
- Who needs to be involved, and when
- What questions leadership will ask
Strengthen the ROI narrative early. Ensure value is tied to business outcomes from the first serious conversation, framed in measurable terms with risks addressed upfront.
Support internal alignment, not just external selling. Help buyers align stakeholders, anticipate objections, and move from interest to commitment.
The impact
Deals don’t stall because buyers lose interest. They stall because the path forward feels unclear or risky.
When you help buyers understand how to move forward, you don’t just close more deals, you improve deal velocity and forecast reliability.
Getting started: Where to focus first
If you can only prioritize one area this quarter, start with #5 (Why Deals Stall).
Why? Because stalled deals represent the most immediate, recoverable revenue. You already have buyer interest; you just need to remove friction.
Quick win action plan:
- This week: Review your top 3 stalled deals with sales. Ask: “What’s blocking the buyer from moving forward?”
- This month: Create one enablement asset that helps buyers navigate internal approvals (business case template, executive summary, approval timeline guide)
- This quarter: Implement a regular stalled deal review process. Make “buyer enablement” a standard part of your deal progression framework.
Once you’ve reduced stalled pipeline, expand to #2 (Revenue Leakage) and #3 (Buying Committee). These three areas create a compounding effect: better deal quality, faster velocity, and stronger retention.
Strategic curiosity isn’t about doing everything. It’s about focusing your energy where it creates the most revenue impact, even when you’re a team of one.
