The Weight of Owning OKRs
Executive leadership gathers the team, shares a vision (maybe), and announces ambitious growth targets. Revenue goals that excite investors. Market share objectives that inspire confidence. Customer satisfaction metrics that sound great.
The meeting ends, and everyone looks to you.
The OKRs just landed squarely on your shoulders. You're the one expected to translate aspirational metrics into actual outcomes. To chart the course from here to there. To build the roadmap that gets the business where it needs to be. Fine, this is what you do.
But you know… the vision is less-than the clear flag it needs to be and the strategy you're building upon is dated & dusty, heavily biased, or straight-up non-existent.
A Sinking Feeling
You can only work with what you have, and when you're doing all the things you've always done and you're not seeing the same results, you can only expect it to continue. Your efforts haven't been hitting the mark. Turning the dials (that used to work) is simply falling flat.
It creates an uneasiness, creeping uncertainty that your efforts are ineffective and falling apart, and it's contagious. Your teams are feeling it, too. Everyone wonders: Is it the market? The technology? Our customers? WTF is going on?
You and the team have been working harder than ever. Velocity is high, shipping regularly. But the numbers just aren't cooperating. The OKRs that once felt achievable, weren't met and have compounded over time. Now, they feel impossibly out of reach.
Your Unique Perspective
You're the bridge between executive vision and ground-level execution. Between what stakeholders want and what customers actually need, leading the teams that bring vision to life. You have both a broad and deep perspective - a perspective few others in your org can relate to, if anyone.
You're seeing symptoms that signal a bigger challenge:
Decisions based on institutional knowledge. The last formal research initiative happened long ago (if ever) and the findings are buried in a deck somewhere. Instead, customer insight comes through support tickets and sales team feedback.
Teams struggle with alignment. Product prioritizes velocity. Design prioritizes style & flow. Engineering prioritizes technical debt. Everyone's working hard. But, every negotiation on WHAT to do is challenging and contentious. Even when folks do agree, the results are still just okay.
Endlessly putting out fires. The backlog is full of requested features and bug fixes. Everyone is executing with discipline, slowly chipping away - but to what end?
Your roadmap "is what it is." You have priorities, timelines, resource allocations. But you feel more hopeful than confident that your teams' effort will bring the performance you need.
All of this is very common - at businesses big and small, across industries - and should not be casually described as failures of effort or intelligence. Individually, we strive to address each problem as they come. The intensity compounds over time, and suddenly, here we are. Even from your unique perspective, it can be very hard to see these scenarios as symptoms of a larger, more foundational strategic problem.
What's Actually Missing
When your teams are working overtime to put out fires in a desperate attempt to deliver solutions they can only hope will make an impact, there are several critical elements missing:
Current & meaningful insights into customer behavior and needs.
Team alignment on what success actually looks like, not just lofty metrics.
Ways of working that includes timely experimentation and user feedback.
Validated solutions tied to specific business outcomes.
This is where strategic design partnership makes the difference. Don’t fall for the bloated agency model that functions as another silo. Pass on tactical contractors who perform a single function, deliver a deck and disappear. You need embedded experience strategy & design leadership that cultivates your internal teams while ensuring we ship measurable results - the executive peer alternative to expensive agencies and inexperienced independents.
As Principal, Experience Strategy & Design, I partner with leaders like you at strategic inflection points. We collaborate to gain a sharper perspective on how we can deliver against the OKRs: we better understand your customers, your business, the marketplace, your products & services, your ways of working, your team structure and capability, your tools and technology, your brand and tone of voice.
This focused perspective makes obvious the blind spots in your strategic foundation. The places where institutional assumptions no longer match market reality. The gaps between what you think is working and what's actually driving (or blocking) business outcomes.
When you can see clearly, confidence comes naturally.
When To Start
The timing reality: We are just three months from next quarter’s start.
Strategic foundation work takes time. Comprehensive customer research takes 4-6 weeks. Synthesizing insights into actionable frameworks and product enhancements takes another 4-6 weeks. You want all this done and teams aligned ahead of your quarter or PI planning sessions.
Of course, you can expect some immediate impact from embedded strategic design leadership. Quick wins exist in every organization - immediate coordination improvements, clearer decision frameworks, rapid validation of key assumptions. But building the durable strategic foundation that sets you up for confident execution? The research, analysis, insights, executive buy-in, prioritization, requirements gathering, and backlog refinements needs to start now.
You're Not Alone
Your unique role is inherently lonely - navigating levels of the org, balancing complex dynamics and competing priorities. Making tough calls with incomplete information, and few peers to lean on.
I partner with 3-5 product leaders maximum - those at strategic inflection points who recognize this moment demands embedded experience strategy & design expertise that cultivates teams and ships measurable business results. Together, we shine a light on your current strategic foundation, identify blind spots, and build the frameworks that empower your teams to execute with confidence.
This isn't about adding another vendor relationship. It's about the principal-level strategic design leadership you wish you'd brought in earlier - before the OKRs landed and the pressure mounted. If you're seeing these symptoms and feeling the weight without strategic foundation, let's talk about whether this partnership makes sense for you and your business.