Leaps of Strategic Faith

“Strategy” is one word that seems to have lost meaning. I see it thrown around and used for anything, including “so what’s our snacking strategy tonight?” I’ve written before that you don’t need a “tech strategy.” Instead, you should aim to leverage tech as part of the company’s overall strategy. One such tool I’ve been using when advising founders is to consider your “leaps portfolio.”

Doing It Wrong

Let’s start with a short and real horror story. I once saw a company with a product ready in an up-and-coming market right before the hype train. It’s one of those opportunities where things align, and you get lucky to be at the right place and time. However, even though they had a solid tech team, they failed to think strategically. Their innovation was stunted, never getting enough attention.

Fast forward a year or so, and the executives realized they had completely dropped the ball. Right when their market was exploding, they stayed still. They refactored their website, improved some processes, but failed to introduce any innovative value to their potential users. Funny enough, they had a few people in-house who spotted opportunities early enough but did not get any time to research them further. The company’s biggest successes came from guerrilla hacking sessions, not due to what they had in the roadmap.

That’s an unsustainable position to be in and one that too many companies are prone to. We get so myopic when it comes to our strategy—if we even have one—that we sometimes don’t even see what’s right under our noses.

No Risk, No Reward

As bad as the small-minded roadmap is, it seems to be getting even worse right now. Having spoken to hundreds of executives recently, I will wager upwards of 90% are wholly entrenched in “belt-tightening” thoughts. Those living on venture capital have no will to… venture.

The bad news is that sitting still in our industry is impossible. If you are not actively pulling yourself forward and trying new things, you are deteriorating. The goalpost keeps being moved by those who have not stopped innovating and experimenting. The only path forward is to understand that you—as a tech executive—ought to manage your risks intentionally. So, what are your leaps?

Planning Possible Leaps

Next quarter, my next book, Capitalizing Your Technology, will be published. It’s all about helping founders and executives use technology as an offensive weapon instead of merely a tool. One of the core concepts I’ve been using quite a lot in coaching CEOs during the rapid changes in our industry is being proactive with your strategic leaps.

A strategic leap has the potential to propel a company forward considerably. We’re not talking about another nice feature but something remarkably unique. While Fortune 100 companies probably have these happen successfully every few years, for young startups, you usually need one successful leap a year. After all, if you plan to 10-100x your sales/DAU/etc., you have to make a leap. Merely doing what you’ve been doing all along harder won’t cut it.

No specific leap is guaranteed to work. Otherwise, it would simply be part of the regular roadmap as a feature, and all your competitors would likely already be working on it as well. Therefore, if you need to succeed in one, you probably allocate time to experiment on 2-3. How do you even come up with those? By making the time to think strategically about the market and the direction the industry is heading, considering technological advances, staying playful, etc.

Thus, the steps ahead need to address innovation on several levels. At the executive level, the leadership team has to make time to think big and place bets regularly. That’s why you should refresh the strategy at least once a year (e.g., I facilitate Sentient Strategy® sessions that take 1-2 days). You should also talk about this regularly as part of leadership meetings.

The tech innovation level is different. You want to avoid cases as I described earlier, where your team has the right ideas and no time to experiment. That’s why making room for innovation is crucial, for example, by introducing intermissions to your process as opposed to hackathons (AKA “creativity cages”). You can get a complete guide by downloading the free sample chapter from my last book.

Lastly, there’s the matter of addressing failure. No leap will be big enough if you don’t have faith that you’ll be alright if you fall. Your team has to know that not every idea has to be a home run. Embrace the possible failure and speak about the concept of placing sensical bets—like Nassim Taleb’s barbell strategy for risk management.

If this sounds hard, especially to those of you who haven’t practiced the “executive” part of your “tech executive” role, consider getting help. I help executives lead exceptional teams and have a free global community for executives to help each other.