When your strategy isn't landing, the instinct is to defend it harder. Two product leaders share what they did instead, and what it revealed.
You've done the work. Customer interviews. Data analysis. Roadmap planning. You walk into the room ready. And the room isn't with you.
It's not a blowup. No one flips a table. It's quieter than that. A womp womp where you expected applause. A sales team that can't close on something you spent six months building. A CEO who's nodding but not really nodding.
That moment (that specific, deflating moment) is what Episode 4 of Product Leaders Lab is about. Betsy Shaak, VP of Product at Voxpopme, and Michelle Green, Director of Product at Cohley, both lived it. Both found a way through it. And their paths couldn't be more different, because the misalignment they were facing came from completely different places.
Most product leaders treat strategy misalignment as one problem. It's not.
There's misalignment with the business, where your strategy makes sense in isolation, the product is solid, the market wants it, but it's pointing in the wrong direction relative to where the company is actually going. You might not even know it until you've been pushing for months.
And there's misalignment within the team, where your strategy is right, but the people around you aren't seeing what you're seeing. A key stakeholder catches something you missed. The vision isn't landing. And you find out the hard way, often in a room full of people.
The reason this distinction matters: how you diagnose the disconnect determines everything about how you fix it. Defending your strategy harder is almost never the answer. But what you do instead depends entirely on which type of misalignment you're dealing with.
Betsy was running a major API program at Voxpopme. Three hundred partners. Great technology. She believed in it completely.
"You can have the best product on the market. You can hit all of the numbers. You can hit every single thing that's really impressive and fantastic and full of value. But if you can't take it to market, you might as well not build it."
She was pushing hard for investment. Leadership kept pumping the brakes. And she couldn't figure out why. Not until she found out what was actually happening on the business side.
The company was quietly developing solutions to compete with the very partners her API program was serving. Leadership was making acquisitions. They were about to go to war with the ecosystem she'd been building for. Of course they weren't investing in it.
"If I would have had a better business sense, I would have known: this is why you're not investing in this."
The strategy wasn't wrong. The technology was great. The market wanted it. But it was completely disconnected from where the business was actually going, and she'd had no visibility into that until it was too late.
Her answer, developed over the years since, is to build a genuine partnership with sales. Not a transactional relationship. Not a quarterly sync. A real one. Because sales is the function with the most visibility into where the business is actually heading.
"Once you start connecting what you're doing on a daily basis to the larger business goals, all of a sudden making the decisions becomes so much easier. It's like putting butter on the pan."
Betsy is honest that this didn't come naturally. She struggled early in her career to empathize with salespeople: their pace, their incentives, the sheer volume of their days. Her CEO gave her a deceptively simple piece of advice: go look at their calendar.
Not a framework. Not a new meeting cadence. Just open their calendar and see what their day actually looks like. How many calls they're on. How much time they spend in procurement conversations. How much they're juggling.
"You're gonna see, God, that AE, do you know how many calls they're on a day with people? Do you know how much time they're spending prospecting?"
That shift in perspective changed how she approached the relationship. From there, she started sitting on sales calls. Acting as a sales engineer for a day. Listening to how the team pitched, what clients said in response, what language they used when they heard something new.
That last piece (the call recordings) became her early warning system. Every pitch. Every client reaction. Every word a customer uses when they hear about a new release. It's continuous signal on whether the strategy is pointing in the right direction.
"Early signal from a new release: that can be the difference between steering you in the right direction and you going down the tangerine route for like five months, right? And then they're like, actually we wanted oranges."
The partnership she's built now runs both directions: product helping sales close deals, sales bringing product into discovery conversations. But it started with something much simpler. Empathy before strategy. Showing up in their world before asking them to understand yours.
Michelle's situation was different. She wasn't disconnected from the business. Her team at Cohley had a clear goal: reduce the content review cycle using AI. Get brands their assets faster. The strategy was right.
But the moment she showed the designs, the customer success team wasn't with her.
"It was that first moment of me showing the designs. I was all excited, look at what we're gonna do. And it was kind of met with a womp womp. Like that's not exactly what they were excited about."
Michelle's original vision was to deliver AI-generated feedback directly to the creator: flag what was wrong, let them fix it, move on. Clean. Fast. Logical from a product perspective.
Customer success pushed back immediately. Brands need to see the feedback first, they said. Legal reviews. Multiple rounds of edits. Subjective changes. Sending two separate rounds of feedback to a creator costs more money.
"What I was not expecting was for the customer success team, very knowledgeable, talking to the brands every single day, was that they thought the brand would want to see the feedback first."
They weren't being difficult. They were carrying information that product didn't have. And Michelle had to resist the instinct to defend her design and stay curious about what they were actually telling her.
The first thing she did: separate what was working from what wasn't.
"We had already validated that the brand wanted the asset analysis, that they appreciated the feedback and that they said, yes, this is a good list. Like, yes, it flagged it accurately. Now the question was: how do we display it in the UI?"
The feature was right. The flow was wrong. That distinction saved her from throwing out months of work.
Rather than arguing about whose instinct was correct, she proposed a test. Put the feature behind a permission toggle. Let some brands try it one way, others another. Watch what actually happened.
"We came to a compromise, right? We said: let's test it. Let's do an iteration. Let's see how brands respond. Let's see how creators respond."
The testing didn't just resolve the disagreement. It revealed something better than what she'd originally designed. Some brands needed to see the AI feedback first because of compliance requirements. Others were fine letting creators see it immediately. They were fundamentally different workflows, and neither her original design nor customer success's instinct had fully accounted for either.
The testing eventually pointed toward three distinct user flows — one of which involved fully automating the brief so the brand never has to log in at all. That possibility only emerged because Michelle stayed open to what the pushback was telling her.
The process change she made afterward matters just as much as the outcome. She now works to get designs in front of stakeholders much earlier — before anything is baked, before the big reveal.
"Always listen. I'm always looking to see — what brand is this going to impact the most? Do we have a list of brands that are willing to participate in the beta? And we have that list, I would say 60 days before it's even needed."
Sixty days before you need beta users, you already know who they are. That's not reactive. That's a system.
Betsy went outward. When her strategy wasn't landing, she didn't go back and refine the roadmap. She got into sales conversations. Looked at their calendars. Used their recordings as a continuous signal on whether she was pointing in the right direction.
Michelle went inward. She didn't defend her design. She investigated where exactly the disconnect was, validated what was working, and let the testing surface something better than what she'd built.
Both approaches were right — because they were solving different problems.
If the disconnect is coming from above — leadership isn't investing, the business seems to be moving in a different direction, sales can't close what you built — that's Betsy's signal. Go outward. Build the relationship with the people who have the most visibility into where the company is actually going. Get on their calls. Look at their calendars. Stop building in isolation.
If the disconnect is coming from right next to you — a key stakeholder isn't on board, a cross-functional partner is seeing something you're not — that's Michelle's signal. Go inward. Validate what's actually working before you change anything. Test instead of debate. Stay open to what the pushback is revealing. And build a process that gets feedback in the room earlier.
The trap most product leaders fall into: they treat both types the same. They defend harder. Or they panic. Neither works.
Both Betsy and Michelle had to resist the instinct to protect what they built. That's the thing most teams skip — not the tactics, but the willingness to face the reality before trying to fix it.
"Then there's one of two things that you do, right? You get defensive about it. No, it's working. You're just not using it the right way. Or you have like a mini panic attack of like, what's wrong? You face the reality." — Betsy
Most product orgs never build the relationships or the processes that would tell them earlier. They find out in the presentation, in the design review, after six months of execution. By then the cost of misalignment is real.
The leaders who navigate this well aren't smarter. They've just built better feedback loops before they need them.
The product leaders who navigate strategy misalignment well aren't the ones with the best strategies. They're the ones who've built the relationships and the systems that tell them the truth earlier — and who can hold their strategies loosely enough to let reality reshape them.
That's a different kind of product leadership than most orgs develop. It requires going outward when the instinct is to go inward. It requires curiosity when the instinct is to defend. It requires building trust before you need it.
As Betsy put it: "You gotta get over the pain of like — but it's my perfect little baby. I just gave it to you. You gotta get over it."
The strategy is a hypothesis. When the room isn't with you, that's not a threat. That's feedback. The leaders who figure this out fastest are the ones who can act on it.
Want to hear the full conversation? Listen to Episode 4 of the Product Leaders Lab wherever you get your podcasts:
