Questioning a purchase

Today I was chatting with someone looking for opinions about project management software. It would have been easy to weigh in with a list of reasons why that person should try Basecamp.

But what if that isn’t the right way to help them?

Instead, I offered the following list of questions that I use when trying out something new. The answers to those questions might lead her to Basecamp, they might not.

What problem am I trying to solve? How does this help me get there?

This question is an old friend. A constant companion as I muddle my way through life. What am I trying to do? Do I know? Child questions spawn, dragging me closer to an imperfect answer that works for now. There is something powerful about the way asking a question reveals flaws in my understanding, or illuminates new avenues to explore. The beautiful thing is, behind each answer I find more questions.

Am I looking for something to help me do my work, or am I looking for something to change how I work?

How often do you really challenge the underlying assumptions about why you work the way you do? Picking up a new piece of software, or looking at a new process is a great time to pause and reflect. Are we doing this because it’s the right thing to do, or has it “always been that way”?

Does using this result in better work? How do I measure that?

This is one of the child questions that comes from asking what problem I want to solve. How am I going to know if making this choice is worthwhile?

If there is complexity, is there a payoff?

Not all complexity is anathema. Taking something complicated and turning it into something simple is a noble endeavour. Deciding not to do something is incredibly freeing. And yet, there is a place for complex processes, if they make life better at the end.

Does using this save me time?


This doesn’t do X. Does that matter? Could we do without?

When considering a move to something new, I often catch myself discounting a product because it doesn’t do something I’m used to. I’m trying to get better at ignoring that impulse, and being more open to changing how I work.

Are there any questions I’ve missed? Do you have a personal favourite you ask when looking at a new piece of software, or a new way of working? Let me know!

At Basecamp, we’ve got so many questions, and we’re having a blast trying to find the answers. We love questions so much, we built automated questions into the latest version of Basecamp. If you are looking for a calmer way to work, why not grab the questions above, and see if Basecamp 3 is the answer?