Working with executives that used to be very good at their hands-on jobs, I often see they are very skilled in similar things. One such skill, which is priceless when working closer to the implementation, is that they become world-class experts at poking holes in ideas and approaches.

Good technical people are excellent at debugging, and that boils down to trust nothing, having a massive almanac of different issues in their heads, and being able to run through it very fast to eliminate. If this sounds familiar, it’s because it’s a lot like every episode of House, just that we’re debugging ideas and approaches instead of people.

This specific skill, though, means that we grow skeptical and pessimistic for the vast majority of ideas, even more so when it comes to novel approaches where there’s no clear path to reach the destination. Real innovation often means that you will have to start working on something to realize what’s possible. If you always wait until you’re 100% sure about an objective’s possibility, you surely will not be taking enough risks.

Especially when you have a leadership position, it is essential that you treat new approaches often with the default mindset of seeing how things might work out, and being optimistic, instead of ruling things out immediately. In my work with clients, I often see this clash between non-technical founders and their hired CTOs/VPs. The founders do their job, which is to come up with innovation, new business opportunities, and setting a vision that getting to will require real effort. The technical leadership, which in many situations holds all the cards as the gateway to scheduling the work to happen, smother all these ideas when they feel they are too risky.

I know it’s a cliché, but do you think Apple would have been the same Apple had it not been that Steve Jobs pushed for things that no one thought are doable? This mindset, to an extent, is the one you should default to in order to enable to forward movement of your organization. You can keep the criticism where it is appropriate, which usually means behind closed doors with the executive team. However, when you are in the brainstorming phases, you should be spreading the motivation and optimism across your organization, instead of squashing every dream for reaching a more significant opportunity.