That Entrepreneur Hasn’t Got a Prayer

Note: A version of this post appeared in my semi-regular column on AlleyWatch.

It’s a little surprising that entrepreneurs don’t pray more.

The best entrepreneurs are missionaries, not mercenaries. Even if they are not explicitly pursuing a social impact startup, they are driven by the sense that they can, at least in some small way, make the world a better place.

What’s more, so much of the startup journey hinges on fate. Being at the right event, at the right time, to meet the right investor or chancing to catch the attention of an influential journalist or hitting the market at just the moment when it is receptive to your disruptive service… and just before your competitors get there. Even if you do everything right, so much hinges on fate.

Lastly, karma pays a major role. Founders routinely do favors for people they have just met, paying it forward, knowing that sometime, somehow, some of these favors will pay dividends.

Hmm…. Sounds a lot like religion to me, albeit one oddly devoid of prayer.

A few years ago, I resolved to pray daily. I can’t say I’ve quite hit that mark but I succeed more often than not. And while I try to set aside a few minutes for free-form meditation on whatever issues most stress me, I’ve come to see the value of a structured liturgy.

One prayer, known as “The 18”, consists of 19 (Yes, 19. Long story.) short paragraphs, each an acknowledgement of God’s provision of a specific benefit (e.g., wisdom, health, financial success) and an implicit request for the same. It’s far from the most poetic or inspiring prayer. In fact, it’s pretty much a checklist. And therein lies the brilliance.

You achieve what you focus on. If you are looking for biz dev opportunities, you’ll see them everywhere, from sporting events to thanksgiving dinner (e.g., “oh, your cousin works at…”). If you are looking for a tech hire, you’ll find a way to mention it every chance you get (e.g., “So what’s new?” “Actually….”). So if you take a few minutes each morning to run through a structured checklist, you are basically attuning yourself to those opportunities.

It’s not that God is specifically answering those prayers (although who knows?) so much as that the act of praying opens your eyes to what’s already there. It’s as if $20 bills are strewn across the sidewalk and all you need to do is look (up from your smartphone) to see them.

What’s more, focus changes how you perceive events. When your train suddenly goes express and skips your stop, you could get annoyed at the delay. But if your focus is on getting in shape, you’ll enjoy the extra exercise. If an API you rely on is discontinued, you can either rue the setback or welcome the opportunity to see what additional functionality you can access with the newer APIs. It’s all a matter of mindset.

Scott Adams, creator of Dilbert, used to write “I, Scott Adams, am a successful syndicated cartoonist” 15 times each day. Ultimately, (and with the help of George Shultz and Gary Larson’s retirement) he became the #1 cartoonist holding a pen. He credits this affirmation with focusing his mind on the potential opportunities that were out there for the taking.

So what are you going to pray for today?

I Know What Your Biggest Weakness Is. Do you?

Note: A version of this post appeared in my semi-regular column on AlleyWatch.

I interview a lot people – applicants to Dreamit’s accelerator program, prospective employees, interns, etc. – and one of the questions I never ask is, “What is your biggest weakness?”

I’ve learned that you never get an honest answer. At best, it’s a test of the candidate’s negotiating skills as they try to figure out what the lowest ‘offer’ they can put on the table is that is just credible enough to keep the bidding going. At worst, it’s just an invitation to lie. But the real reason I never ask this question is, I already know the answer. In fact, your biggest weakness is the same as mine:

Our biggest weakness is the weakness we are not aware of.

We all have parts of our skill sets that are not as strong as others and we all have character traits which, while positive in some situations can be counter-productive in others. But since we know what these are, we generally have ways to compensate for them or even to neutralize them entirely.

If it is a set of skills that were lacking, we choose people with those skills to help round out our team. If it is a critical skill that we think we need to internalize, we take the time to find the resources we need to study up and get up to speed.

If we have a tendency to make quick decisions but are currently facing a complex problem that requires analysis to tease out all the possible repercussions, we put processes in place to make sure that we have examined the problem from every angle. Conversely, if we find that we tend to analyze problems extensively, we learn to recognize when we are in a fast-moving situation and create decision rules that ensure that we know when our analysis is good enough to make a decision so we don’t miss out on opportunities.

But if we are not even aware of the weakness…?

Recently, I screwed up. I was concerned about one of our recent tweets and I posted my feedback to our Slack channel. Read a certain way, it could have been perceived as critical of a colleague’s performance. I frequently discuss with entrepreneurs the importance of proofing emails by putting yourself in the shoes of the recipient to make sure there are no ambiguities or potential tone issues before hitting Send. I also caution all the Dreamit startups I work with that the speed and informality of social media can lead you to share info that you should really think twice about making public (or at the very least, phrase differently for public consumption). But the relative newness of Slack tripped me up. It feels fast and frictionlessness like texting or Twitter but is neither fully private nor fully public. Unlike email, you don’t initiate a post by entering the recipient’s email address or by selecting between Reply & Reply All; the path of least resistance is posting to the entire channel – effectively default Reply All – and you have to actively switch from the original channel to a different channel to direct message someone. In short, it felt familiar but functioned differently. I had a blind spot I didn’t know about… until the crash.

Fortunately, it was only a fender bender. My colleague pointed out what I’d done and I deleted the post. No lasting harm done.

But with the tools we use changing so rapidly, with the competitive landscape we operate in evolving so quickly, you have to wonder what other accidents are just waiting to happen.

So yeah, I already know your biggest weakness. Except that I don’t. And neither do you.

Startup CEOs: You Must Change

Note: A version of this post appeared in Fortune magazine’s Entrepreneur Insider network under the headline “How to Get Your Employees to Stop Wasting Time”

Congratulations. You’ve got some customers, you’ve raised some money, and now you’re ready to expand your business.

Now you’re in trouble.

The problem is that the very skills that got you to this point are largely unsuitable to take you to the next milestone. You need to change. You need to dodge hand grenades rather than jump on them.

The startups at Dreamit are all “A teams.” If there’s a problem, everyone raises their hand. Or as one of my partners likes to say, they see a hand grenade and everyone jumps on it. Sometimes they even wind up fighting over who gets the grenade. And even after they have assigned the problem to one team member, the rest of them will probably still end up walking over to that team member with more suggestions.

This is great when you’re an early-stage startup, but once you’re at 10 people or more, it’s just not workable. That team member will end up wasting more time interfacing with the other team members than actually solving the problem. You, the CEO, need to be able to assign the task to one person and have everyone else get out of his way and do their own work. Divide and conquer.

The change, though, has to begin at the top. Of all the un-scalable resources and all the un-scalable inputs in the world, the least scalable commodity of all is the CEO’s time. That’s why large corporations pay armies of people to guard their bosses’ time as if it were gold in Fort Knox. You’re not there yet, but you have to start thinking that way. Yes, you still need to be accessible. And yes, you still need to have your pulse on everything going on in the organization. But if you try to do everything, or even just the most important things, you won’t get anything done. You need to start dodging those grenades.

Start by drawing up a list of all of the important things that you need to accomplish over the next couple of months. Then, item by item, figure out who within your organization can tackle each task. The key here is not to find the person best suited to solving the problem, but rather to identify everyone capable of addressing it. This gives you the most options when it comes to divvying up your resources. If you find that you systematically are out of resources overall or lack resources to attack certain types of problems, then you know who your next critical hire is. Most importantly, your goal is to get as many of those things off of that list as possible so as to free up your time to focus on what’s going to move your business forward as a whole.

At this point, several of you are probably objecting. You’re probably thinking, “But these are mission critical items. I need to nail them perfectly, not just do them well enough.” Truth be told, the number of situations where that’s true is far fewer than you’d think. It’s more important that you focus your attention on growing your business than on resolving tactical issues, no matter how important that specific client is nor what the impact of a particular technical decision might be.

There’s a story I heard in business school about a professor who shows up to class with a bucket. He starts off by putting some rocks in the bucket, filling it to the top. He then asks his class, “Is this bucket full?” The class answers that it’s full. He then takes a bag of gravel and pours it over the rocks in the bucket. The gravel fills in the spaces between the rocks, and the professor turns to ask the class again, “Is this bucket full?” The class, again, seems pretty certain that the bucket is full. He then pulls out a bag of sand and starts pouring that on top of the rocks and the gravel. The sand filters into the spaces between the gravel and the rocks until it reaches the top of the bucket. The professor asks the class again, “Is this bucket full?” The class isn’t quite sure at this point, but ultimately most of them agree that it’s finally full. Then the professor takes a jug of water and pours it on top of everything in the bucket, and it seeps into the sand and the gravel and the rocks until it reaches the top of the bucket. The professor turns to the class and asks once more, “Now is the bucket full?” The class is, at this point, too uncertain to even answer, so the professor smiles and says, “Don’t worry, it really is full now. What does it teach you?”

The students decide it means that no matter how busy you think you are, if you’re smart about your time, you can always fit in a few more things. The professor looks at them sadly and says, “You missed the point entirely. If I’d started with the sand and the water, would I have been able to get the rocks into the bucket?”

The rocks are the big strategic initiatives that move your business to the next level. When your startup is very early stage, the rocks are obvious. In fact, pretty much everything is a rock at that point. But as you grow your business to the next stage, more and more of what you deal with are actually just pebbles and sand. That’s why you build your team up—to take small things off of your plate so you can focus on getting the rocks into your bucket.

No matter how hard you try, though, you will still be so busy that you won’t know what to do with yourself. The difference is that now you’ll be focusing on the things that actually matter.