The Two Kinds of Colleagues

Several years ago, a CEO I worked for told me that he saw basically two kinds of people: those who are excited by the possibilities of a new idea, and those whose response begins with, “The problem with that is…” As someone who was constantly on the lookout for the next new thing, perhaps to a fault, it’s no surprise that he prized the former type of person. I sympathize with his preference for the former type of colleague. I’m all for realistically assessing costs and benefits, but you can't approach brainstorming that way.

When it’s your job to bring new ideas to life, you need enthusiastic people there who are willing to consider the possible. As a first-time founder myself now, I've gained even more appreciation for this. When I wanted to build a platform for bringing business software users and makers together (which eventually became UserMuse), I was grateful to have people who could suspend their skepticism and evaluate the idea a little generously at first. New ideas are fragile; if put under too much pressure immediately, they dissolve before they can crystalize into something stable.

When I think about my favorite people with whom I’ve worked in my career, the common thread across all of them (aside from not being jerks) has been their eagerness to think about why some new idea might be awesome before they think about why it won’t work or what will be hard about it. Those are the people with whom I can spend all day in a conference room and leave energized rather than depleted. As a product manager, (the best part of) my job is to identify problems whose solutions will be valuable and then arrange the pieces to build those solutions. I need to work both with people who enjoy new ideas and can realistically assess whether they’ll work in practice. The best colleagues can do both, but I’ve found that so many smart people have their optimism coached out of them during their careers.

It’s easy to get jaded in business once you’ve been on a project that went off the rails and gained the experience that comes with that. After you’ve seen a few corporate initiatives kick off with fanfare only to fizzle later, you can start to lose faith in things getting done at all. And even when things do get done, you can still be scarred by the experience if the costs or effort required are dramatically underestimated and you’re on the hook to make it all work. Then there’s Shiny Object Syndrome, which keeps certain types of leaders from staying the course strategically. It can be maddening to work for these types and it understandably dampens their lieutenants’ enthusiasm for big, daring ideas. As we learn the pitfalls to avoid and hone our ability to reject bad investments, we naturally help others to avoid them as well. And as valuable as sharing that experience is to an organization, there is such a thing as overdoing it – or more specifically, doing it at the wrong time.

The Downside of Seeing the Downside

The reason why you’ll find a hundred different versions of Steve Job’s admonition that “focus is about saying no” is because it’s good business advice. But by the time most people reach middle management they’ve already picked up plenty of scars from misadventures along the way; they often don’t have a problem saying “no.” The desire to avoid repeating past mistakes causes many people to adopt a defensive posture by default. Their minds reflexively produce thoughts like, “We’re already stretched thin as it is,” or, “that’s a notoriously competitive market,” when they hear new ideas. Make no mistake – those instincts keep companies from making rash decisions and throwing good money after bad.

And yet…

As much as businesses need experienced hands to spot potential problems, they need boldness too. It’s hard to innovate without taking risks. And for many leaders, that’s what makes their jobs fun in the first place. The opportunity to do something new is what gets many of them out of bed in the morning, and it is a bummer to always be met with pessimism from the troops. Experience is great, but if it becomes an impediment to original thinking, then that experience is shackling the business.

This often creates a dilemma for young professionals, because having to implement the ideas of others is perhaps the defining characteristic of the early career stage. In this stage, you get intimately familiar with operational constraints of a business without having much big picture responsibility at first. That means you experience the painful aspects of change without sharing as much in the upside. In a company that is operationally mediocre it can make this layer of the organization cynical about any new idea coming from the top. They come by their mindset honestly when they greet new ideas with a laundry list of reasons why they won’t work. That said, it’s bad for their careers because it discourages people from bringing cool ideas to them down the road that they’ll actually want to be a part of. Even worse, it can earn them the label of being a “small thinker,” which is something that can become self-fulfilling over time as opportunities stop coming their way. Since being a magnet for new information and ideas is basically the whole point of networking, a pessimistic mindset really works against these people.

So how do you reconcile the need to give ideas a fighting chance with the self-preservation instincts that come with experience? To me, it’s all about presentation and timing.

Curb Your Skepticism

Here’s a thought exercise I like to give people to illustrate the importance of considering opportunities before problems:

Think about the company you work for today: who its biggest competitors are, what challenges face the business, and especially all the things that have had to break the right way for your company have gotten this far. Now ask yourself, if someone pitched you on that exact same business before it ever existed, would you have invested in it? If the question doesn’t apply to your situation, then ask if you think you would have invested in a search engine called Google in ~1997 when Yahoo! and AltaVista were on top of the search market with a slew of also-rans.

In other words, would you have thought the present was possible before it happened?

If you consider that the vast majority of new businesses fail, the fact that your company is even around to employ you already defies the odds. I consider myself an optimist, but I doubt I would have bet on the startup I currently work for making it as far as it has. The competitiveness of our industry is and the audacity of the product vision would have probably scared me off -- and I’d be willing to bet that the same is true of many employees of both startups and mature companies alike.

The point is, if your company’s present seemed unlikely to you, maybe you should relax your skepticism a little bit. You stand much to gain and nothing to lose by overriding that initial instinct to fixate right away on the weak points of a new idea. Instead, try suspending your initial disbelief and letting yourself ask, “what if?” What if this could really work the way the other person thinks? What would it mean if this came true? Instead of shutting down that line of inquiry right away, let yourself at least consider the possibility that it might be awesome. There will be plenty of time to think through the operational challenges of making it happen; try being optimistic at first.

Even a small change in how you present objections can make you seem more receptive to new ideas. Replacing “the problem with that is…” with, “one thing we’ll want to look into is…” not only makes you seem more open to new ideas, it makes you seem friendlier. If and when you do raise real objections subsequently, it will come across as well-reasoned rather than knee-jerk skepticism. That’s the best way and only way I know of to balance pragmatism with optimism. Some of the ideas that come your way will be good; you don’t want to steer those to someone else or nip them in the bud prematurely.

Remember, new ideas are fragile.