Optimism For Geek Leaders

Sometimes when I talk with tech people turned into executives, even CEOs, they lament how they seem to lack capabilities other successful executives have. It sometimes feels more like a humble brag: “I could never BS people like that guy.” Those who sell effectively are “sure the sun circles them.” However, being influential as an executive doesn’t mean that you should be spreading lies and selling snake oil like a lousy guest on Shark Tank. You’re letting yourself off the hook too easily if you think you can just shrug and move on.

Even the executives who belittle those who can persuade and sell (to others and themselves) would usually admit their companies or departments would probably be better off were they better at that, too. Therefore, instead of coming to terms with your current capabilities, accept that there is something worthwhile to pursue here and get better at it. At its core, what you are probably lacking isn’t the ability to lie effectively but to be more optimistic.

It’s Not Lying If You Believe It

I’m going to put aside blatant lies such as claiming your product is already being used by companies when you don’t have anything ready or claiming certain capabilities exist just because it will help close the sale, regardless of what is really possible. Those rarely last long and lead to unpleasant headlines (see Theranos). It is only a tiny minority of leaders who act like this anyway. The majority of persuasion and selling effectively is more about painting a picture of the future that could be in a way that entices and motivates the other person.

When one describes where the company is headed, what it will achieve, the grand vision, and how awesome it will be for employees, it is not lying if the founder genuinely believes this is possible. The key trait of these “classic CEO” types is that they honestly think things will be alright and possible. This is a necessity for most types of effective leadership. Do you want to raise money? You’re selling a story. Close clients? Selling a story. Hire talent? Again, stories. Furthermore, when you want people to connect to your vision, work hard to achieve it, become autonomous, and take the initiative, they have to understand the company’s vision and believe in it. Compelling storytelling and persuasion make all the difference in the world when we want to motivate others.

Thus, your first step forward is to realize there is nothing wrong with deciding to look on the bright side and focus on that. Yes, you currently have a crappy MVP but stop looking down at your keyboard. Look up! Do you really believe things will remain like this in a year? Probably not, right? Believe and focus on that. Talk about that future, and you’ll slowly solidify how strongly you believe, and so will those around you. The famed “Steve Jobs force field” wasn’t a web of lies. He just believed in the possibility of things so intensely that others were sold, too.

Shedding Your Tech Pessimism

Another aspect here is that people who come from a tech background have usually made their career on being incredibly good at spotting issues and juggling all ways something might go wrong in their heads. A senior engineer often spends entire planning sessions busy warding off potential scope traps by pointing out problematic areas and requests that require more details. While this is useful for someone doing code reviews, it is not what makes great leaders.

Leadership requires that you be optimistic most of the time rather than assume everything is flawed and about to explode. This mindset shift can be aggressive for techies but is nevertheless required. On whose team would you like to be? The CEO that’s selling a dream or the one that pokes holes in every item on the roadmap and points out precisely what might go wrong? You need to radiate an executive mindset.

As I described in The Tech Executive Operating System, an executive mindset is about radiating an atmosphere of “it’s possible” and positivity. It is what makes people follow leaders. It is critical for tech executives to let go of this part of their engineering background (at least mostly) to be able to act as effective executives. One last note, life is simply nicer when you stop fretting about everything that could possibly go wrong and obsessing over it. Risk management, sure. Risk OCD? Not so much.

I’ll be talking and taking questions live in a session about my upcoming book, Capitalizing Your Technology. Join us for free.