People

Did you promote your early, lead developer to CTO, regardless of whether or not they should be your CTO?

There is a lot of confusion on what a CTO actually does, and much of this has come from the business practice of using the title as a reward for a long-standing key contributor.  It could be that they have the skills and tools to be a great CTO, but unless you are holding them accountable to do the job of the CTO, you are likely not getting what you need.

Do you worry about losing key personnel and how you would replace them?

It’s natural as a company grows that key people rise to the top and make themselves indispensable. However, it is the job of management to make sure that there is redundancy where possible, and assets to help in the event of a disaster.  You can do this in a way that includes and values these key people, and it will probably relieve some stress for them too. People leave, people retire and people get sick. Don’t get caught not planning for these foreseeable events.


Process

Does it take weeks for a new developer to become productive on your team?

A professional software group focuses maniacally on eliminating wasted time. If a new team member isn’t productive and working on real issues within a few days of onboarding, you can’t effectively scale the team to meet customer demands.  

It’s after 5 o’clock, do you know where your code is?

If technology is a key asset of the business, then the code that it is built from and the way it is built are also key assets. If the code is not in a secure, backed up, modern version control system, then you are at risk. If the build process relies on one or more developers, then you are at risk. These are examples of smaller tactical issues that unnecessarily add risk and overhead to your business, and are a leading indicator of trouble to come.

Product

Do you lose sales because you’re too busy or the opportunity is too large?

If your product takes a lot of resource to deliver/support/train, performs badly in larger installations, or requires customized versions of the code, it can limit your ability to land larger deals.