Why Your Strategy Is Already Dead Before You Present The First Slide
The team that designed it expected applause and immediate support. No one told them they needed to give people a reason to care.
Microsoft’s Kin phones underwent 2 years of development, got a major marketing push, and had a clear teen target audience.
But problems started early, as the product team’s strategy was never fully shared or co-owned, even within Microsoft org itself. Long-delayed and a victim of internal politics and friction between software and hardware teams, Kin phones were doomed before a single one landed in a teen’s hands.
Worse, carrier partner Verizon controlled pricing and insisted on charging teens $30/month for business customer data plans on top of other base Verizon charges for voice and text.
Microsoft senior product manager for mobile communications, Greg Sullivan, somehow believed that it was all a “positioning” problem:
“Once [customers] realize the value of this, they’ll realize it’s a great deal.“
Not sure how anyone could spin a phone that lacked basic features like apps, maps, or even a calendar as a “great deal” for customers.
Worse, Microsoft’s rollout never gave Verizon a reason to support or protect a strategy they never helped design, just to risk their own recurring revenue.
The result was a clear Where to Play and How to Win that was killed by the way that strategy was brought to life. The Kin lasted just 48 days before Microsoft pulled the plug on one of its higher-priced failures, at a net cost of around $1 billion.
Think about your company. What do you think is the cost of spending one or more quarters of multiple teams’ fully loaded salaries on a strategy that dies? All because the other people, teams, and partners who needed to support it were never part of its design or given a reason to care?
The best strategies are social
You’ve done the hard strategic work. You designed matched choices. You tested them. You drafted a Money Story. Now you walk into a room full of stakeholders and present it.
And somehow you think when they hear the brilliant strategy that you’ll get enthusiastic approval and expect everyone to spring into action and know exactly what to do to make it happen?
Fat chance. That has never worked, and will never work. But it’s not your strategy’s fault.
Strategy is social. People across your organization at every level need to understand the strategy, feel invested in it, be able to contribute to it, and see their own contributions as valued and represented as part of it.
But most product teams treat stakeholder engagement as either an annoyance or a single activity with two expected outcomes: present the finished work to unanimous praise, or have everyone necessary to the strategy’s success just fall in line and start “executing.” In reality, there are three fundamentally different types of stakeholders we engage with across three very distinct meeting dynamics, and each requires a different approach you need to design intentionally.
If you’re still treating every stakeholder the same, and every meeting interaction the same, you’re just scheduling meetings and hoping for the best.
And hope, as we all know, is never a strategy.
How to Throw Away Five Zeros
Years ago, I was coaching a leader on their function’s strategy.
At the most basic level, we were trying to be clear about who their group served and how they’d “win.” I had reservations about their choice of “end user.” Worse, they never discussed their approach with any other function leads. They simply decided and pressed forward.
Six months later, a cascade of issues emerged. Teams across the organization were pulled into fixing deep structural problems that required countless hours of additional manual work, dragging an entire division backward. The approximate cost: hundreds of wasted hours, on the order of high tens of thousands of dollars of wasted effort and delay.
Fortunately, the leader chose a different approach in our strategy work together the following quarter.
They stopped treating their function’s strategy as their choice alone.
They brought other function leads into the conversation. They found out what those leads were actually dealing with, what mattered to them, and how they could make choices together that reinforced the entire group’s efforts. They listened, adjusted, shifted, and formed a coalition ready to move forward with a different end-user customer focus and matched “How to Win.”
The following quarter started with training the right end-user, killing festering regulatory problems before they had a chance to start.
While the basic strategy remained fairly similar, because they invested in designing it collaboratively, everyone around it changed. The result was like a siloed kitchen staff finally meeting, agreeing on a menu, tasting, and talking for the first time before dinner service.
Same ingredients. Fundamentally different cooking and dining experiences for everyone.
More than you think
There aren’t two kinds of people: those you’re trying to get a “yes” out of to move forward, and the rest you expect to just “get with the program.”
There are no fewer than three, each with very different needs.
And every meeting isn’t about either “pitching” or “influencing.”
There are no fewer than three specific types of meetings you’ll need to have to build and bring your strategy to life, and they aren’t interchangeable.
The Hidden Cost of Not Building Your Strategy Collaboratively
Trying to shortcut strategy’s collaborative nature isn’t just personally and professionally damaging, it has a real financial impact.
A product team of five people (PM, Designer, three Engineers) at a blended fully-loaded cost of $200K per person carries a minimum quarterly cost of roughly $250K.
If your strategy requires support from 3-5 stakeholders to proceed (and that’s for a small org), and you haven’t understood them or designed the right way to connect with each, your strategy will die for at least one to two quarters. The cost of not intentionally designing your collaborative strategic moments is that anywhere from $250K to $500K in team salary is wasted working towards something that will never move forward and deliver its intended business and customer outcomes.
Add in the opportunity cost of what the team could have been building, and that number easily doubles or triples.
What can you do to stay ahead of this kind of product team strategy malpractice?
You can start by running a quick check on your current work.
The Closing Audit
Take just 15-20 minutes and run these two questions against your work in flight:
How easy is it for you to name 3-5 people whose support is crucial for your strategy to move forward?
How quickly can you estimate your team’s fully-loaded cost? How aware are you of the potential cost of a single stalled month?
What’s Still Ahead
Knowing you need people is the easy part.
But learning the hard part, the part that can save your company $250k/quarter, means knowing:
Exactly which of the 3 meeting types to use for each person.
How to avoid the “Deference Trap” with senior VPs.
The exact AI prompts you can use to map these interactions in minutes.
Paid Subscribers Learn How to Get the Right People On Board the Right Way
The free section showed how great strategies die when product teams treat stakeholder engagements as either a burden or a checkbox.
The paid section teaches you how to design the right moments for the right people. You’ll learn how to understand your stakeholders’ needs, design the right meeting interactions for each, and apply Roger L. Martin’s revolutionary “Jobs to Be Assigned” framework.
Three artifacts, each building on the last, ready before your next leadership meeting, so that your strategy’s chance of success isn’t left to chance.
Your Turn to ENGAGE
I’m looking for a few product teams and Product Trio leads (PM, UX, and Tech) on active product teams who want to give their strategy a better chance of succeeding, and learn what it takes to design stakeholder engagements before walking into their next strategy meeting.
Reply ENGAGE and let me know a bit about your team and your upcoming strategy conversations.
