Victoria and I were 24 hours away from signing the worst deal of our lives.
The acquisition offer sat on the table. Life-changing money. The buyers kept calling, increasingly exasperated. Our lawyers had the paperwork ready. All we had to do was sign.
But something felt off.
We couldn’t articulate what it was. The numbers looked good on paper. The timeline was aggressive but manageable. The buyers seemed legitimate. And yet, neither of us could pull the trigger.
So we hit pause. Made some calls. Asked ourselves the hard questions we’d been avoiding.
By the time we walked back to the negotiating table, we knew exactly what needed to change. The result? We held out for 35% more than the original offer.
Here’s the thing about big business pivots—whether you’re walking away from a deal, changing your business model, or completely rewriting your strategy: The decision always feels urgent. The pressure is real. But urgency is exactly when you need to slow down and ask the right questions.
These are the ten questions that have saved us from bad pivots and guided us toward the ones that transformed our businesses.
1. What problem am I actually trying to solve?
This sounds obvious, but most pivots start with a symptom, not the actual disease. “We’re not making enough money” isn’t a problem. It’s a symptom. The problem might be your pricing, your target market, your service delivery model, or your sales process.
Before you pivot, get brutally specific about what’s actually broken. Otherwise, you’re just rearranging deck chairs.
2. What does the data actually say?
Feelings are valid. Data is essential.
When we were deciding whether to walk away from that first acquisition offer, our feelings said “this doesn’t feel right.” But the data, from our financial and legal advisors, told us exactly WHY it didn’t feel right. The payment structure put too much risk on the back end.
Look at your numbers. Your client feedback. Your market research. Don’t pivot based on panic or gut instinct alone.
3. Who am I asking for input, and why?
Your Kitchen Cabinet matters here more than anywhere else.
We’re not talking about your mastermind group or your business bestie who always tells you what you want to hear. We’re talking about the people who will tell you the truth even when it’s uncomfortable.
Before our pivot, I called my private equity contact who had zero emotional investment in our decision. Victoria sat down with her attorney who had seen hundreds of deals go sideways. Both independently flagged the same issues.
Who in your circle has the expertise AND the objectivity to help you see clearly?
4. What am I willing to lose?
Every pivot has a cost. Time. Money. Relationships. Market position. Momentum.
When we pivoted from our original business model to focus exclusively on enterprise clients, we walked away from some revenue. We turned down projects that didn’t fit the new direction. We risked alienating some of our existing client base.
But we were willing to lose those things to gain what mattered more: scalability and enterprise-level pricing.
What are you willing to sacrifice? If the answer is “nothing,” you’re not ready to pivot yet.
5. What happens if I do nothing?
This is the question people skip because it’s terrifying.
Sometimes doing nothing IS the right move. Sometimes the current path just needs more time, better execution, or minor adjustments. But sometimes doing nothing means slowly drowning while you convince yourself the water isn’t rising.
Play out both scenarios. Where are you in six months if you pivot? Where are you in six months if you don’t?
6. Is this a micro-move or a wrecking ball moment?
Not every pivot requires burning everything down.
We’ve made both kinds. Sometimes you need to take a wrecking ball to your entire business model. Sometimes you need to make small, strategic adjustments and give them time to work.
The mistake is treating every problem like it needs a wrecking ball OR treating every systemic failure like it just needs tweaking.
Know which one you’re facing.
7. What’s my financial runway for this pivot?
Hope is not a business strategy. Neither is “we’ll figure it out.”
Before you pivot, know your numbers. How long can you sustain the business during the transition? What’s your break-even point in the new model? When do you need to see results to keep the lights on?
Victoria and I have walked away from “golden opportunities” because the financial runway didn’t support the risk. That discipline has saved us more than once.
8. Am I pivoting toward something or running away from something?
Running away from a problem is different than running toward a solution.
If you’re pivoting because you’re burned out, frustrated, or scared, pause. Those feelings are valid, but they’re not strategy. Fix the emotional stuff first, then decide if you still need to pivot.
The best pivots come from a place of clarity and vision, not desperation.
9. What does success actually look like on the other side?
Define it. Write it down. Get specific.
Success isn’t “making more money” or “being happier.” Success is: hitting $X in revenue by Q3, landing three enterprise clients in six months, reducing my working hours to 30/week while maintaining current income.
If you can’t articulate what success looks like, you’re pivoting blind.
10. Can I live with myself if this doesn’t work?
This is the question that cuts through everything else.
Because here’s the truth: Some pivots fail. Some bets don’t pay off. Some risks don’t pan out the way you hoped.
But the real question isn’t whether you might fail. It’s whether you can live with yourself if you don’t try.
Victoria and I have made a lot of pivots over 30+ years in business. Some worked brilliantly. Some face-planted. But the ones we’ve never regretted, even the failures, were the ones we made with clear eyes and honest answers.
The worst pivots were the oneswe made under pressure, without asking the hard questions first.
So before you sign that deal, walk away from that client, or burn down your business model to start fresh—pause. Pour a cup of coffee. And work through these ten questions.
Your future self will thank you.
