Strategy sounds like momentum.
Progress.
Growth.
It’s the word companies use when they’re feeling bold.
But in practice? Strategy work is messy. It forces decisions you’ve been avoiding, exposes habits you didn’t realize were habits, and reveals whether your team is actually aligned—or just politely nodding.
Because deciding to change is easy. Following through is where most teams fall apart.
In my work, I’ve seen the same pattern play out: founders get clear on a new direction, but nothing actually changes in how the business runs. The old workflows stay. The same metrics get tracked. The same incentives get rewarded.
If you’re evolving your model—great. But be honest: are you evolving your behavior too?
The Myth of the Clean Slate
There’s a common misconception that you can just… start over. New strategy. New deck. New org chart.
But strategy isn’t a reset button. Most of the time, you’re building on top of existing culture, legacy operations, and emotional attachments—whether you admit it or not.
If your company has grown quickly or shifted lanes, chances are you’re still carrying old assumptions: how you make money, who your customer is, how your team works together, how you define success. You don’t need a whiteboard. You need to know what to leave behind.
This is the part I work on most: helping teams unstick themselves from their old model. It’s part operational therapy, part clarity sprint. And no, it doesn’t always come with a brand refresh.
5 Hard Questions to Answer Before You Change Strategy
You don’t just flip a switch on strategy. You earn it—by asking uncomfortable questions early, before things break. These are the ones I return to most when working with teams in transition:
1. Do you know what not to do anymore?
In music, sunsetting isn’t failure—it’s strategy. That old rollout playbook, that extra imprint, that side hustle that’s not scaling? Letting go creates space to focus, and focus builds growth.
2. Can your team actually execute this?
You can’t shift to brand partnerships, catalog value, or direct-to-fan unless your team structure, tools, and incentives support it. Changing your vision without changing how you operate is a setup—not a strategy.
3. What will break when this starts working?
You land the sync, the placement, the viral moment. Great. But what next? Do you have the infrastructure to fulfill merch, monetize fans, onboard partners, or even just keep up with demand? Indie wins fall apart without support systems.
4. Are you still rewarding old behaviors?
If your KPIs are stuck on monthly streams but you’re building long-term IP value… there’s a mismatch. Changing strategy means rethinking how success is measured—from artist deals to internal bonuses.
5. Can you explain what you do in one line?
If your pitch to an investor, brand, or fan takes three paragraphs, it’s not ready. Clarity is leverage. A clean narrative builds confidence, attracts partners, and keeps the team aligned.
What Strategy Work Actually Looks Like
Strategy isn’t a deck. It’s not your new mission statement or a brand refresh.
In my work, strategy is what happens after you say you’re going to do things differently—and then realize how many parts of your business have to catch up.
This work is messy.
It means tearing down decisions that once made sense but don’t anymore. It means identifying the real blockers—sometimes people, sometimes process. And it means doing the uncomfortable thing: making a choice. Because growth doesn’t come from doing more. It comes from doing fewer things better.
Here’s what people don’t always see:
- Brand ≠ Ops
A clear brand story is great. But if your operations don’t back it up—if your artist strategy, label deals, or release cadence still say “old model”—then the market will feel the dissonance. Strategy is when those two things match. - Positioning Needs a Process
Saying “we’re focused on catalog” or “we’re going global” means nothing if there’s no system behind it. You need tech, partnerships, team alignment—and a roadmap for how it actually rolls out. - Change Takes Repetition
Shifting direction isn’t just about announcing a new path—it’s about reinforcing it constantly. You’ll need to repeat it in meetings, 1:1s, Slack threads, decks. People internalize change at different speeds. And just when you think they’ve got it? Say it again.
This is the kind of work I do with founders and leadership teams in music and media—when it’s time to rethink the model and actually implement something better.
Not in theory. In practice.
For Your Stack: 4 Books on Changing Strategy That Actually Stick
If you’re thinking about changing your strategy, here are a few titles I keep coming back to—because they go beyond frameworks and dig into the actual work of making change happen:
- Reset: How to Change What’s Not Working by Dan Heath (2025)
A new release on recognizing when your strategy’s off—and how to course-correct before it’s too late. - The Hard Thing About Hard Things by Ben Horowitz
Still the sharpest look at what it really means to lead through chaos, reinvention, and internal resistance. - Good Strategy Bad Strategy by Richard Rumelt
Essential reading for anyone confusing vision with action. Especially useful when you’re writing the fifth version of your “why.” - Working Backwards by Colin Bryar and Bill Carr
A great breakdown of how Amazon operationalized strategy—clear example of turning positioning into process.
No fluff, no manifestos. Just clarity, trade-offs, and staying the course.
Strategy Is Just a Story, Until You Act On It
It’s easy to build the story. It’s simple to then back that story up with a long range plan model that works
But a story without structure is just marketing. A story without stamina is just noise.
If you’re thinking about changing your strategy—really changing it—ask yourself this:
Are you ready to change the business?Because that’s what it takes. And if any of this is resonating—let’s talk.
