There are a lot of companies being run by technical founders (myself included). We've learned on the fly, grown our bag of tricks, and have seen enough problems solved that we can smell a solution a mile away (or so we’d like to think).

Transitioning from intense concentration and long hours flying by in the zone to working through process improvements and culture improvements, all while trying to earn your paycheck…. Well, that’s a big adjustment. It doesn’t always work, but I’m living proof it can.

I’ve since found my new flow, and better ways to achieve it, but it took quite a while to understand what had to change for that to happen.


The good ‘ole days: staring at a terminal and creating all day long!

Who I Used To Be

When I used to work and think about work, it was about programming. It was laser focused, headphones on, leave me alone - I’m achieving progress.

That type of time and focus was achievable in a very specific, low interruption environment, where I had the work laid out in front of me and knew what needed doing next.

Most of that time, I was learning faster than I ever had. And it was all because I had massive amount of pressure for results (perhaps an unhealthy amount from myself) and large, solid blocks of time to concentrate without interruption.

Now, my job feels more like I’m spinning multiple plates every day… Credit

Who I Am Now

Today, I run a multifaceted agency. On any given day, I have to think about at least a dozen startups or products. As well, I ensure the grease is between the gears on each active production schedule. Finally, I have internal meetings to coordinate, external meetings to discuss new projects, current projects, and repeat projects. Toss in a bit of e-mail, and I've got a nice day filled with about 8 seconds to really focus on my company.


Flow is much different for the non-maker. Credit

What Flow Looks Like For Me Today

To say the least, I’ve had to re-think what it means for me to work my way into flow. I find that what I remember most about flow is that feeling of effortless creation.

Creation for a CEO or leader works differently. What you create more often than not are models for how you understand your business world to work, both external opportunities and pressures as well as internal ones. From there, you create experiments or directives and wait for the results.

How you create that model, I’ve found, is often a matter of understanding enough to ask the right questions. Part of flow for me is being able to ask experts (both from my own staff and partner as well as external experts) the right questions to get the best answers. As well, asking myself the right questions leads me down better paths and potentially better ways to create more value at my company.

Part of the creation process is also understanding the problems that are creeping into your company before they've had a chance to root themselves. This requires a strategic view of your company’s core business drivers (a few examples from my company: capacity, efficiency, customer satisfaction, estimates vs. actuals, etc), and holding a mental model of that business stack in your head is remarkably like programming.

Once I’ve done the legwork for myself and started stretching my thinking into new areas, flow occurs and I’ve found more nimble and elegant solutions far more successfully for my business.

Zipping around the mental model of my business, identifying key areas of improvement, creating more value in places I couldn’t before, and solving real pain points my customers are facing gives me that old feeling back again.

You can do the same yourself if you haven’t tried. Think about your company from the moment it was introduced to your current customers’ minds.

There was a process they went through to decide to pay you. This is what happens no matter if you run a services company or a product company, if real money is used or you are charging some other form of capital (time, social, etc). You should be able to identify the key buying factors customers used to decide to work with you. If you can’t, well, you’ve got some work to do!

After all is said and done, though, flow demands progress be made. So to tie it all off, I try and make sure after a session of brainstorming and discovering solutions, we shape our findings and turn them into experiments, with falsifiable hypotheses and goals and with actionable cut off dates for failure.

This gives you a benchmark to measure against and a failure scenario to avoid. Those failure scenarios can help you drive directives and decisions to help lower the risk of those scenarios. They also help to create the motivation to not allow that failure, and to implement the objectives now and not later.

I find it particularly effective when I’m needing a little more motivation than normal. “Don’t want X, Y, or Z to happen? Time to get to work, Keith.”

A good failure scenario is specific. There should be zero questions as to what happens if conditions are or are not met. This gives us optimistic visionary types no out when it’s time to make the decision down the road, unless the situation goes off in a wildly unexpected direction of success. Anything else, and your decision is already made for you. In general, I like to operate in two week chunks, with weekly updates. Depending on the size of your company, you may want more or less time for each iteration.

Equally as important as your failure scenarios are your success scenarios. You should try and figure out ways in which along the path to success, you fortify yourself from falling backwards, and determine the next steps to take should you hit your goals. That’s the fun part, of course!

After sessions like that,where all aspects are considered and I feel confident about the new directions we’re taking, I can’t wait to get back to work the following morning and start implementing the vision, sharing it with the team and getting their feedback.

And, of course, inevitably modifying it all over again when the real world shows up and I have to update my mental models of how that new world works. But when you look at the world with a new perspective on flow, you’ll end up falling in love with that process.


Pretty much what it feels like all the time (see what I did there? :P) Credit

My Biggest Barrier: Time

This is the toughest part. As leadership, your decisions are often needed multiple times throughout the day as communication occurs. And as much as I love that time with my company, customers, and staff, flow only comes from real focus.

My solution currently is to pick a day of the week where my business partner and I head to one or the others’ house after work. We set aside roughly 6 hours (it’s a long day of work, but worth it to us) and leave it open ended as to what needs to be discussed.

Occasionally, we’ll let conversation drift and wander off topic or onto another topic we might want to discuss next. The important thing is that we give ourselves the time to do it, though.

Which is, of course, the hardest part for any entrepreneur steering a running company. Diverting your attention from operating and executing long enough to pause and take an assessment, generate solutions, and potentially pivot requires fortitude, dedication, and time, our most precious asset.


Staying Optimistic

I consider most entrepreneurs to be masochists, stubborn, naive, or all three. They have to enjoy taking a beating every day as reality proves them wrong in some areas, right in others, and often for baffling amounts of reasons. All while the clock is ticking in the dollars and cents sort of way.

Giving myself the time to get back into the flow and the opportunity to be more successful is critical to how I inject growth faster into my business.

Doing so, though, can be tough. It can grind you down, especially when you know what the finish line looks like and can see it clearly, but have obstacles in your path. Or have to deal with particularly difficult decisions and follow through on them. And to be completely honest, looking back to see your mistakes or near misses is never fun or exciting.

But the more often you do it, the easier it becomes, and the more frequently you can pivot or improve your product and market fit.

And when you’re competing with people who are better funded than you, have been around longer than you, and have better relationships or better distribution channels than you do in your vertical, it’s key that you continue pushing the limits of your and your team’s capabilities in sustainable ways.

So I stay optimistic by viewing each challenge as a new way to apply my skills and try new ways of looking at a situation. Failure scenarios can be bleak, but I stay motivated by knowing that the only real way I can avoid them is by actually getting out there, forging ahead and better shaping my company.

Remember, even the big companies don’t stand up to market forces without significant time investments and difficult decisions from their leadership.

Getting back in the flow, staring down consequences, pushing the company forward, and watching the team execute alongside me are all rewards no matter the result.