Many senior leaders view themselves as “realists.” But this so-called realism is often just cynicism in a suit. Being optimistic doesn’t mean being naive. It’s a strategic advantage for those aiming above the obvious. It’s the hidden skill no one teaches executives.
The Comfort of Cynicism
Let’s admit the truth. For many, the cynical take that shoots down most new ideas within seconds is actually a protection mechanism. It protects your ego from realizing you were wrong, from taking any risks, and from feeling the pressure of stretch goals.
The invisible cost is that you stop aiming at anything that’s genuinely remarkable. To maintain the protective spell of cynicism, we must remain entrenched in our comfort zone, the killer of any innovation.
Optimism as a Leadership Lever
Precisely because it is such a rarity for many tech leaders, I’ve seen it transform organizations when executives were able to change their default stance. Thoughtful optimism—as opposed to blind optimism—opens possibilities and fuels exploration. It is how we do things that push us beyond mediocrity and the straightforward work.
Optimism is the main skill that allows you to lead people in the foggy territory of startups while maintaining your credibility. It’s how we build a strategy and plan without having certainty. When you eschew anything that’s not guaranteed to be a slam dunk based on your realism, you teach your entire organization to opt for safety over achieving anything unique. Optimism is so critical that I test for it as one of the eight crucial traits for senior tech leaders as part of Executive Mindset.
Cultivating Optimism
By this point in the article, I can envision a few options. One is that you’re nodding in agreement and are already one of those naturally more optimistic. Good on you! You can close this tab and move on, with my blessing. Others might acknowledge that they’re not optimistic, but even after the last few hundred words, don’t see the value in changing their ways. You can close the tab as well, because I have no idea how to get to you.
But, dear reader, if you’re one of those who want to work on their optimism muscle, I’ve got battle-tested tactics you can try that have worked for my clients over the years.
Suspend disbelief: I can relate to the fact that it’s easy to immediately poke holes in a new initiative and point out anything that might be problematic. For a nit-picker like myself, it can also be satisfying. But true innovation is only possible when we allow ourselves to stay with the ideas that sound impossible or weird at first, and see if anything comes to mind. Half the battle is just avoiding the knee-jerk reaction and letting your brain (and the rest of your team) tackle a certain problem for a bit longer before declaring it a lost cause.
Work backward from the goal: Assume there’s a solution. Assume the team will get it done. If that’s the case, what would have to be true for you to get there? You and the rest of the team can reverse-engineer from the result and see what happens. Like solving a maze on paper, it’s a lot easier to start from the exit and find the path that leads you to the beginning.
Live in the gray zone: When asked whether something is possible, don’t take the question as a binary one. Then, reaching for the “no” is much easier (are you a CT-No?). So, when asked about something, always consider the spectrum between getting it done perfectly as asked and not doing it at all. Often, somewhere on that range, we can spot at least one viable option that might be easier to pull off, but that will be good enough for your needs.
That’s something you rarely reach if you hurried to stop any consideration the second the first obstacle came to mind. Of course, this also requires you to be able to speak with your business counterparts effectively in order to articulate the different options and tradeoffs and to be able to spot opportunities as opposed to merely getting orders and executing on them (or rejecting them).
Play the odds: Similarly to the last point, you should also learn when it’s possible to embrace uncertainty and openly work with it. When asked to do something that you know is probably possible—so the feasibility itself isn’t an obstacle—but that might have other issues, like timing and cost, again, learn to play the spectrum. Rather than considering your options as committing to get something done or refusing it, speak about the options.
For example, you can say that the deadline is a stretch goal that you estimate the team has a 70% chance of hitting. It might require longer. Being clear about such an estimate (even when the number is more based on your hunches than any scientific theory) can allow you to move forward and find a path that the business didn’t consider at first.
In summary, playing it safe is the biggest gamble of all, because it all but guarantees mediocrity. The cynic might avoid looking foolish, but at the cost of looking forward to nothing in particular. Life’s too short to be remarkably unremarkable.