Seeing the forest for the trees

For years now, I’ve ran my company in tactical mode - making small reactive decisions based on market changes, or customer feedback, or other direct influences particular to just our business. We’ve never been big on overall strategy, or long-term planning.

I’m not sure if this is something that’s particular to us, or if that’s the only viable way to run a small software company, but I’m curious if anyone here who has been running their business for more than a few years, is doing so with a larger, overall roadmap or strategy as to where to take the company?

I’m specifically asking those of you who have been running your companies for more than a few years. There’s a certain sense of ideology that exists in the early stages of starting a company that seldom materializes in the eventual path of the company, so I’m more interested in hearing from founders who have been doing this a while, but who have a larger plan that they are sticking to. How is it working out for you? Have you had to take tactical steps that you otherwise would not have just to abide by the longer-term vision?


Hi Andrey. I’ve run my company 14 years now. I can say we only looked at tactical stuff at first, because that’s all we had time for, and it’s what paid the bills. After a bunch of customers joined, we started to see some patterns and trends in their requests, which eventually started to guide our strategy. That said, we’ve had to take it all with a grain of salt, and we try not to think “strategy” further out than one year (quarterly goal posts).



At DNSimple we develop a yearly major initiatives document at the beginning of each year and then review it on a quarterly basis. Each initiative includes a strategic goal to give an overall sense of why we’re doing the things we’re doing. I consider it my responsibility as the founder and managing member of the company to spend some time just thinking about where the company should go in the next 3 to 5 years. I regularly discuss this with the entire team to get their feedback about the company direction.

As an example, in April we had a team meetup and we discussed the company growth strategy, new offerings we are considering, etc. Discussions like these help inform tactical decisions, which is why I think they are valuable and worth doing throughout the year.

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This is an interesting one because it’s something I’ve been thinking about recently.

When I started bliss the vision was fairly specific: fully automated music library management on home servers/NASes for technically inclined music lovers.

Now, from a bootstrapping POV I realised that I was more likely to raise immediate revenue via other channels. Thus, we ended up with a load of customers who use bliss to work on their computer’s iTunes collection, or whatever.

The trouble is satisfying these customers with the way the product develops and balancing that with work toward our ‘strategy’ of server based installs. We have made progress on the second, OEMing to server sellers etc plus some support in the NAS hobbyist community to package the app on specific NAS platforms. But it’s easy to be distracted (in the nicest possible way) by other customers and their requirements.

I do something similar to @aeden, 6-monthly assessments against goals, plans for the next six months, and review inbetween. The trouble is that when the 6 months comes around there’s always something else to be done, so while it does get done, I probably don’t take enough time to sit back and think.

It feels like I need some other higher level expression of my business goals and roadmap.

We’ve just done this recently (sort of under duress, because we looking at some debt financing options for growth that required a comprehensive marketing plan) and I have to say it has been very enlightening and well worth it. It coalesces all those things rolling around in your head about your business and forces you to think critically and strategically about them. Getting started on the exercise was the hardest part - sort of like that first mile when running - but once you get going, you get into a flow and channel your “inner Jack Welch”.

So now, we’ve got a thoroughly detailed view of the space we’re in, the competitive landscape, an honest strength/weakness/opportunities/threats (SWOT) analysis and well defined marketing and growth goals. The plan is to revisit this every six months or so and adjust as required.

Working normal customer support issues (i.e. tactical) will always trump whatever is in this document, but just about everything else from product development to marketing/sales will be guided by the strategy and goals outlined in the document.