6 reasons why your business strategy might not be working

Over the past five years, I’ve spent lots of time and lots of money on business strategy – somewhere in the ballpark of at least $30K on business coaches alone, all who showed up with the promise to one-up the last business coach and help me build a system that would attract more clients and drive more revenue. 

If you’re a business owner, you get this type of investment. If we want to grow, we know we can’t do it all on our own, and we’re taught that the sure-footed way forward is to dig deep into our pockets and shell out big for business coaches who promise to guide us every step of the way. 

But as I look back over those precious $30,000, I sometimes wonder about the ROI of my investments. 

Many of those coaches sold me on 1:1 personalization but delivered a one-size-fits-all formula instead. 

Some of them promised to get into the muck and mire with me but never really plunged in. 

Others thought they knew what I needed, but their strategy always seemed to be a few millimeters off from my heart. 

In what feels like a too-late epiphany (according to my bank account), I now understand that with many of those business coaches, they didn’t work for me because I simply didn’t know what I didn’t know. I thought I needed strategy. But what I really needed was someone to tune into the calling of my heart and help me draw an unshakeable throughline back to my business. 

As I wonder about what really made me so eagerly say YES to all of those investments, I think it comes back to the fact that business strategy is often couched as the sexy first stop in our business growth journey. 

But if you’ve been burned by a business or two, then inherently, you can probably agree with me when I say that strategy isn’t the magical panacea it’s advertised to be. 

In fact, when it’s positioned as a “do this if you want to be successful” investment, strategy becomes a poison apple because it (un)intentionally hides one very important truth of sustainable business ownership: The most brilliant strategy is unusable if it’s built on a misaligned foundation. 

(Just Google South Padre Island’s Ocean Tower or the Transcona Grain Elevator for visual proof.) 

This feels like it should be a simple and oh-so-obvious truth, but as I think about my own experience and recount the stories of other business owners, it’s clear that many of us have hedged all our bets on the promise of strategy – only to walk away feeling bruised, battered, and beaten. 

This is probably a good time to insert a quick disclaimer. 

I love business coaches. 

When you get a good one, you see the entire world differently. A few years ago, I invested in a mastermind with Rob Marsh and Kira Hug, and those two still stand out in my mind as coaches who understand the unique marriage of strategy and alignment. I’ve also worked alongside Stephen Woessner and Erik Jensen at Predictive ROI – and those two helped me authentically dig myself out of a dark tunnel after working alongside the wrong business coach. 

But I’ve also worked alongside some business coaches who just didn’t get me and just never delivered on their promises. They never really learned about ME, never wrapped their heads around my message, never invested in truly learning where I was actually trying to take my business. And those experiences sucked. 

You can feel like a failure when you connect with the wrong business coach. I’ve felt the weight of this heavy millstone around my neck, and I know I’m not alone. Fellow business colleagues in the trenches and many of my clients have voiced the same feelings of defeat: We lifted up our mattresses for our precious dollars, and months later, we realized nothing in our businesses actually changed (besides more overwhelm, more stress, and a few thousand dollars less to our name).

It’s really easy at this juncture to blame the business coach – but as I’ve thought and thought and talked and talked about this, I think the bulk of the blame might belong somewhere else. 

It’s not about bad business coaching (at least, not entirely). 

It’s not even about bad strategy. 

It’s really about misalignment – because the truth is, if you haven’t done the work to align the calling of your heart to the business you’re building, then all the strategy in the world isn’t going to save you. 

[Now at this point, maybe you’re saying, “That feels good, Lindsay. But how in the heck do I know if my real issue is alignment?”]

My answer: You know if your issue is alignment by getting super honest about what’s really driving your need for help. This next list isn’t exhaustive, but it should help you start to know if you’ve maybe put the strategy cart before the alignment horse. 

6 ways to tune in and identify if you need alignment over strategy: 

1. You can’t shake the feeling that you’ve been created for something MORE. 

2. You know the work you’re doing is bigger than the title you’ve given yourself, but you can’t see a way beyond your current reality.

3. Your proverbial cup runs over every time you get a chance to lead with your passion and impact someone else’s life – but too often, that cup isn’t getting filled.

4. You’re frustrated with your work because it’s not allowing you to show up with your values. 

5. You feel like you’re spending all your energy on the wrong things and often wonder, “Is this really worth it?” 

6. You’ve done all the right things, checked off all the boxes, followed all the right experts, but it all feels like it’s leading you on the road to nowhere. 

I talk to so many business owners who feel like this – and so many of them say, “If I just had the clarity to really know what I should do, I wouldn’t hesitate to make a big move.” 

That clarity they’re asking for? They want to be seen, to be heard, to be validated, to be supported, and more than anything, they want permission to align their business to the calling that’s been placed on their hearts. 

Strategy can’t deliver that clarity because in the game of business (and life) strategy always comes AFTER alignment. 

Alignment first.

Strategy second. 

Action last. 

It’s a bold pushback and a straightforward truth, but it needs to be said: Without clarity and alignment, strategy will always fall short (at best) and lead you in the wrong direction (at worst).  

Is your heart calling you into something bigger? 

Have you tried to put a plan into motion but feel like it’s taking you backwards? 

Have you sought out wisdom and expertise but still feel unseen and unknown?  

It might be time to do the deep work of alignment.

As founder and owner at Storyhouse Fifteen, I help founder-led brands and small business owners align their business to the calling on their hearts – in smart, strategic, and impact-driven ways. I offer 1:1 alignment coachingmessage strategy, and listening tours. Learn more at storyhousefifteen.com