Simple Ain’t Easy

Let’s start with some definitions for the purpose of this post. “Simple” refers to how hard it is to understand a thing, while “Easy” refers to how hard it is to accomplish a thing. Frequently, after walking a founder through a product framework or sales process, they’ll say, “Shit, that sounds so simple when you describe it like that.” And it is. But that doesn’t mean it’s easy. You can grasp these concepts in seconds, but it can take years for you to master them.

I often have this conversation when explaining to a founder that they are responsible for communicating the why and the what, and they need to let the team determine the how. “You need to communicate to your team why this is important and what success looks like,” I say. “Oh, ok! Got it!,” they say. “Mhmm, sure,” I think in my head (or, often, out loud). When we talk the following week, I ask them how well they communicated the “why” and the “what” and I rarely get a positive response.

That’s when I tell them that this simple task (communication with their team) could be their full-time job for the next year. Then the founder calls me crazy. 

Like. Fucking. Clockwork.

I had this very conversation with a CEO last week. He had identified a potentially huge opportunity, and was ready to hand the idea to a recent hire. But giving an employee an idea without significant context is setting you both up for frustration, failure and disappointment. I explained that the CEO likely needed to spend several hours over a few days coming up with a list of reasons why this opportunity was important, and, after that was done, whittle it down to just the one or two primary reasons why the idea is REALLY important. 

And at this point, he would only be half done. 

Next, he would need to define what success looks like and how his direct report would know the task had been completed properly. The CEO would need to set the constraints (i.e., spend no more than X, finish no later than Y, don’t impact the existing projects) or he’d practically guarantee it would end in failure. All together, I estimated this process would take about eight hours. 

“For each idea I have, I have to spend eight hours figuring out how to communicate it?” he asked. Yup. It’s not easy. With consistent practice, you’ll get better at it and the process will take less time. Initially, though, thinking through all the angles will be time consuming. You’ll even want people to test you on your thought process. Did you think about sales? Yes. IT? Yes. Product? Yes. Legal? Fuck. 

I can count on two hands the number of founders who have been willing to do this “simple” task without hours of coaching and coaxing. Founders and executives don’t do things that are simple for the plain fact that they’re not easy. 

That’s because simple things are better known as HABITS. It’s rare to find simple, one-off projects. Putting a man on the moon was not simple, which is why we’ve only done it a handful of times. But what about checking in to a restaurant or coffee shop every time you stop by in to score sweet deals and bragging rights? Remember Foursquare? 

Early on, I predicted that Foursquare’s check-in feature wouldn’t survive longer than a few years. After a few weeks or months of use, the novelty would wear off and a person would forget to check in, losing their hard-earned mayorships even though they didn’t stop visiting their favorite places. Simply launching an app and hitting a single button in the moment was too hard for most people to remember. And to be fair, you may have forgotten about Foursquare, but they haven’t forgotten about you (Dennis Crowley, I see you).

Think about the last time you tried to get into an exercise routine. Or consistently wake up earlier. Or quit smoking. None of those things are complicated, but all of them are hard to accomplish. We don’t fail at them because they’re complicated, we fail at them because we don’t prioritize them and think about them (let alone do them) on a daily basis.

This website is called Obvious Startup Advice for a reason. I hope that every post makes you think, “Oh shit! Why didn’t I think of this, it’s so simple.” Every one of these aphorisms, these little snippets of advice, should be part of your founder toolkit. And they’ll only make it in there if you’re prepared to spend dozens of hours (or more) mindfully practicing them. 

So how do you ensure practice? Well, this too is simple (natch). Schedule time in your calendar. Make a list. Write it on a post-it note and slap it on the edge of your monitor. Ask your team to remind you. Get a coach (hi!). If you’re going to do something that’s simple but not easy, you’ll want to set up forcing functions that keep you from slipping.

Like most things in life, it’s just about showing up and doing the work, day after day. It’s just not that complicated.

— Eric Marcoullier

I’ve lived this article pretty much every day of my life. Pretty much everything on this blog is sourced from the hard-earned wisdom that comes from fucking things up over and over, but this lesson has left some particularly bright marks.

I try not to sell my coaching to hard around here, but this time I want to speak plainly. The reason to get sa coach is 10% education and 90% accountability. The coaching relationship is wholly unique in that a peer (not an employee, manager or investor) will regularly hold your feet to the fire. Just as we’d all benefit from a therapist and a mentor, we would all benefit from a coach.

If you’re interested in where to start, I’m always up for meeting new people. My focus in on first- and second-time founders who haven’t yet established product/market fit. If I’m not the right guy, I have plenty of coaching friends and can help you find the right person for your situation. Hit me up at or my coaching site.

(Photo by Thanh Nguyen on Unsplash)

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