The opportunity and risk of changing something in your startup is a daily matter on the head of every manager. It's hard to decide what to do and what not to do. Especially when you've already invested a bit in the status quo. Product, system, processes, team, brand. These past decisions created company elements that provide some flexibility, but maybe not all you need.
Any decision can be the best thing or a catastrophe. But you should look at pivots, big and small, in a positive light. Opportunity and risk should indeed scare the shit out of you - but it was your decision to join the startup world in the first place. The biggest risk was joining and that's already past! So be happy about the flexibility.
My general rule of thumb is to implement all ideas that improve whatever the customer is already a happy buyer of. Everything which you are currently NOT providing him and that you think that the customer wishes is dangerous. More often than not, you should not do it.
I consider worthwhile exceptions the cases when you're currently not doing something but there is significant overlap between this new thing and your current thing in all categories:
- Who. Same Decider, Payer, User, Consumer?
- What. Same product category, brand, price points?
- When. Same Time of sale, Repurchase pattern and Sales funnel?
- Where. Same Target location?
- How. Same operations for sourcing, production, marketing, sale, delivery and customer service?
- Why. Same pain solved?
If all or many of these 18 items are the same, then it's probably just an extension, not a true pivot. If you're changing most of them significantly, then you may as well close the company and setup a new one.
Another aspect to consider is wether the current offering is performing well or not. If it is, you're considering adding features or a new business line which may improve business; risk is small if you are responsive and scale the changes smartly. If the current offering is not good and your cohorts are miserable, your pivot can be a life boat; or pivoting can be just running away from one problem and looking for another one.
In any case, you should consider the complexities of the iteration. Will you end up with 2 teams or one. Is investment big or small. How much cash do you have and how the team will take it.
One clear example is the move from B2C to B2B or the reverse. Its tough because you change many things in Who (Decider, Payer at least), Why, a bit of When (Sales Cycle) and How (Marketing, Sale, Customer Service) and possibly What, Where.
The important thing is to have an objective discussion around what it takes to pivot. It will still be harder as there are many unknowns, but at least you can chart the effort. And in the end, follow your will.