/ Mediocre Management

The Visionary

Humans love stories about visionaries. More than one global spiritual movement has been built on the foundation of a story about a Visionary. In the corporate world, especially in technology and innovation, Steve Jobs is an almost religious icon.

Why are we obsessed with Visionaries?

We love visionaries because we can project superhuman powers on to them.

For those who are anxious about change, there's a comfort in knowing that someone is looking into the future and preparing for the changes to come. In an uncertain world, it's reassuring to believe in magical, benevolent forces shaping the future.

For those who embrace change, there's a natural tendency to project oneself into the role of visionary. It is exhilarating to think that a mere human can be elevated to visionary status by predicting the future and building for it. "What if I'm the next Steve Jobs!?" is an intoxicating thought that occurs to many a budding entrepreneur. And because most "overnight success" comes after a decade of toil, the "next Steve Jobs" and the next entrepreneurial failure are pretty much indistinguishable (until they're not).

The Good Tendencies

Effective visionaries tend to be excellent orators, and (at least publicly) very charismatic. They are surrounded by a Reality Distortion Field, a sort of bubble that follows them everywhere they go and casts a haze over the cold hard facts. They are magical thinkers, compelling speakers, and they are given the benefit of the doubt both in the moment, and in the revisionist history that follows their success. In retrospect, their luck, their mistakes, and their flaws are erased and only the vision and execution are remembered.

Visionaries are, by definition, not entirely rational. And we need them. A rational thinker would never build an innovative startup, because the math doesn't add up. A rational thinker would stick to their cushy job at Google making six figures. It requires a significant leap of faith, magical visionary thinking, to quit your job, take out a second mortgage, and start building in your garage.

In other words, the risks and sacrifices required to build something unprecedented require irrational thinking.

If irrational thinking isn't dumb, then it's visionary and magical. To quote Spinal Tap, "there's such a fine line between stupid and clever". Often the distinction between dumb and visionary is blurry until the market either validates the model, or the business fails!

The Mediocre Tendencies

While a bit of irrational thinking may be required to get a novel business model off the ground, there are ways in which the Visionary tends towards mediocrity.


Visionaries often treat their Sales Pipeline like it's Accounts Receivable. In other words, they take for granted that deals on the horizon will close, and they build their budgets with optimistic assumptions. They socialize these assumptions with their team, their investors, and their advisors. If you give them the benefit of the doubt, that's just inspirational leadership. In reality, it's probably more accurate to call it fraud (or at least reckless negligence).

The irony is that if the deals do close, history rewrites that fraud as a bold vision of the future. But deals often hinge on factors that are not within the team's control. So the difference between closing and not closing, vision and fraud, often boils down to little more than luck.


The "Vision" in Visionary usually refers to a product vision. It's rare that Visionaries pride themselves on their ability to build an innovative go-to-market strategy or financial model. They tend to believe that their vision for the product has intrinsic value.

It doesn't. In fact, it's probably a liability.

For starters, a product vision is arbitrary by definition. It is based on a data point of one: the Visionary's perception of a market's demand. If it was truly based on data, it wouldn't be called a vision.

When building a novel product, it is paramount to have an agile, experiment-driven mindset. Every assumption must be scrutinized. Every investment of time and capital must be warranted by data. Every challenge must be approached scientifically: What is our hypothesis? What are our assumptions? How can we test those hypotheses and assumptions efficiently and come to a statistically rigorous conclusion? Visionary thinking is antithetical to the scientific method.

So Visionaries tend to make arbitrary product decisions and they struggle to adopt a scientific mindset. But that problem is actually compounded by another mediocre tendency of Visionaries: they are often product perfectionists.

Reid Hoffman says "if you're not embarrassed by the first version of your product, you've launched too late." Many Visionaries have an emotional relationship to their product. The alignment of their product and their product vision is tied deeply to their sense of self. Any product short of the beautiful vision they hold is a personal embarrassment. This leads them to build arbitrary assumptions on the foundation of other arbitrary assumptions.

In other words, an arbitrary assumption isn't so bad if you get it into the hands of customers and validate it quickly. But if you are unwilling to put anything short of a finished product in front of a customer, you will inevitably layer arbitrary assumptions on top of other arbitrary assumptions, compounding the problem.

Lastly, the sheer volume of creative output from a Visionary can overwhelm a small team. When resources are limited, success requires focus. A Visionary may have 15 great ideas, but if they can't pick 1 to focus on, their vision gets lost in the chaos.

Most individuals can only effectively execute on one experiment at a time. There's a cognitive overhead in fully grasping a new project's scope. So if the Visionary can't filter their creative energy down and direct one tactical shift at a time, the team on the ground will find themselves playing an unproductive game of tactic whack-a-mole.

Are you a Visionary?

A little bit of a Visionary tendency can be healthy. Too much can kill your business.


A simple test: Can your CFO or CPA or COO recall a time when you implied to an investor, advisor, prospective hire, or colleague that a deal was closed, when in fact it wasn't? If so, was that recklessness? A one-off case of fraud? Or is there a systemic pattern of reckless bordering on fraudulent behavior?

If it's the latter, you probably shouldn't be the CEO.


A simple test: Can your VP of Engineering or CTO communicate your vision in one sentence? Can they point to what their team is doing on the ground this week to further that vision? Have they shipped a feature this week? When they shipped that feature, was there instrumentation in place to measure the adoption and usage? Did anyone talk to any customers who used it?

If the answer to most of the above is "No," something is very wrong.

If the answer to some of the above is "No," something might be wrong.

If the answer to all of the above is "Yes," congrats! You don't have a product focus problem.

But if you do have a product focus problem, it's either because you're an unchecked Visionary, or because you have ineffective technical leadership.

Both are crippling.

What to do if you're a Visionary

Stay calm! It's not the end of the world. Either you can mitigate the mediocrity, or you can move into a role where the mediocre tendencies are less of a liability.

Mitigating the Mediocrity

On the finance front, there are all sorts of ways to offset your tendency to treat the sales pipeline as accounts receivable.

You can simply delegate: "Check with our CFO on that."

You can lock down data: "The sales pipeline is shared on a need to know basis, and I don't need to know!"

Or you can hedge all your financial proclamations: "I am an eternal optimist, it's how I drive this business forward, so I am confident we'll close $100k this quarter!"

Irrationality is the underlying trait that drives a Visionary to mediocrity. So find ways to stay grounded in reality. You can run all your numbers by the team pessimist. You can set a coefficient on all your projections to adjust for optimism. At one point, I was such an irrational engineering leader that our Director of Product had a 12x multiple he'd use to adjust my estimates. There are two valuable lessons there: the first is that humans are predictably irrational. The second is that finding a counterpart who complements your strengths and offsets your weaknesses can lead to a team that is greater than the sum of its parts.

The rational thinker can't build anything innovative without the Visionary, but the Visionary needs the rational thinker to stay grounded, focused, and honest.

On the product front and beyond I recommend Kanban, a dead-simple methodology for organizing initiatives. If you suffer any of the mediocre tendencies of the Visionary, set aside at least an hour a week to prioritize your ideas, and bring along a more rational counterpart to help.

You don't need anything more than a bunch of Post-It notes and a wall with 3 columns on it. The three columns are Backlog, In Progress, and Ready for Validation.

Your Backlog consists of ideas that aren't ready for prime time. Keep these ideas to yourself. They are a distraction for everyone else. You should keep the ideas in the Backlog prioritized, with the most important ideas at the top, but only move a Post-It from Backlog to In Progress if your team is ready to take on a new project.

The In Progress column consists of initiatives underway. Each should have a clear owner, and ideally be broken down into tiny chunks. Constantly ask yourself - is there a simpler version of this that we could get to market faster? Every time you check in with individual members of your team, check in on each Post-It that they own, and ask if there are any blockers preventing progress. Keep the list small. As a general rule, no one should own more than one Post-It at a time.

Ready for Validation is (hopefully) the final step. It indicates that an idea has gone to market but its value hasn't been proven. In a dream world, you can validate all your initiatives with quantitative data. In reality, as one of my (non-mediocre) bosses once said: "We use the North Star for guidance, but we don't expect to get there". In other words, you may not always be able to validate initiatives with statistical rigor. But you should try, and you shouldn't consider a project finished until you've validated it in some form. If you can't validate it - send it back to In Progress with a new, measurable objective!

If all of the above methods of mitigation fail, then it's time to look in the mirror and decide if your team needs a new leader.

Visionaries make great CPOs (where P stands for Product or People). Product and Culture are two of the most critical domains of the CEO, but they don't have to be owned solely by the Chief Executive. If you bring in a leader to oversee the organization, set priorities and make executive decisions, you may find yourself much happier, focused on manifesting your vision!

Still reading? The opposite of the Visionary is the Analyst.