Executive Decisions
Two brief examples of tough decisions I’ve made and how to prepare for them.
Executive decisions come in a few flavors that I’ve had the fortune to taste in my journey from corporate programmer, to a bootstrapped startup programmer, to freelancer, and now to a small bootstrapped agency with multiple departments and big projects.
All of them are the types of decisions every entrepreneur makes day in and day out while operating their business. Some of them taste good, some I’ll never want to taste twice, but you can rest assured that if you’re starting up a business, you’ll make all of these types of decisions during your tenure multiple times over.
I’ve found this type of decision making to be a lot like riding motorcycles: there are those who have gone down, and there are those who will. At some point or another, all of us deal with the tough decisions (as I just did), and we won’t always “win”. I’m writing this today in the spirit of others sharing their honesty during their hardest times. Here’s to hoping the article helps prepare you if you’re contemplating the leap, or at the very least, you can commiserate.
The Gut Decisions
These decisions, at least from my perspective, typically involve complex scenarios that require too much data to collect (or no data is available) to actually help inform a choice. Instead, what we are left with is just enough information to identify a problem or opportunity, but know we won’t have enough information to know the outcome definitively prior to making a decision.
How I prepare for these types of decisions:
Reading as much as I possibly can generally helps me. Being able to connect the dots between two seemingly disparate ideas is a great strategic skill to have, and I’ve found the more I’m able to read, the easier those connections come (@medium has been awesome for this). Much of what happens in my gut decisions relies on intuition. For me, I feel that there’s nothing magical about that. It’s simply my brain piecing together connections in the background, and that requires lots of current information to feed it.
How it can damage your business:
Gut decisions are great because they are “easy”, they are fast, and they allow you to move on with your day and feel like you’ve made a dent in the progress you’d like to achieve with your company. But I have certainly made decisions in my career that were based on gut when they could have warranted a closer look at the forecast, or perhaps I hadn’t explored the various scenarios and outcomes as much as I’d like, or I thought I wouldn’t have time, etc…
So, don’t fall into the trap of always just relying on your gut like I’ve done in the past. You’ll end up “shooting from the hip” instead of responsibly slowing down, analyzing your options, weighing things carefully, and implementing your decisions confidently.
But when it’s time to make that gut decision, and you’re convinced there’s no alternative, go for it, and stick to your guns. There’s generally no going back, at least very easily.
In Practice:
The best example from my business: opening up the transparency in our company to show everyone our numbers as opposed to only business development focused roles.
The Theory
We could get a few unexpected ideas from various departments if we let them see the full picture.
Potential Failures
We also might open a huge can of worms if people start doing “funny math”, as my business partner says; or that information leaks; or…
Results
We made the gut decision to test out the theory. We’re still measuring the experiment, but so far, so good. There have been several new experiments born because of this. Because there’s really no hard evidence to support the potential upsides or downsides that I can find via my own research and peers, I’d consider this largely gut.
The “Only Decision” Decision
This is my least favorite type of decision. It’s a decision that’s pretty much made for you already, you just have to go out there and implement the action surrounding it, drink a cup of concrete to harden up, and strap on your armor for what’s to come. This can be something like an obvious choice in your next marketing strategy, or even something as painful as when to re-allocate budgets and all the experiments and initiatives that are either proven invalid or go on hold.
How I prepare for these types of decisions:
In general, I’ve found that while these types of decisions are often time sensitive, you’ll generally see them coming a ways out and can gracefully react to them. Operating a startup is a lot like dancing in a really crowded room (a terrible analogy for me because I’m a horrendous dancer, but I digress) — you’re trying to impress your dancing partner and any audience members watching you (market,company,staff,region,etc), while avoiding all the clumsy hangups that other events or people on the dancefloor could cause (competitors, cash flow, production cycle, etc). If you can look around often enough (Learn How To Forecast! Do It Often!) and artfully move through the dance floor, you’ll get noticed in a good way.
On the other hand, if you have to trip on something before you change course, you’ll get noticed in a bad way. So keep your head up and look around as often as you can without detracting from your dance. Your future self will thank you.
How it can damage your business:
Too many of these decisions will begin to force you into corners you weren’t prepared for, or shape your culture and company in ways that you can’t anticipate and slow down all the pace you’ve worked hard for. Making this type of decision too often means that you’re not forecasting often or far enough, and are in reaction mode.
If you find yourself in this situation, the best you can do is remain professional, align your company for recovery as quickly as possible, and regain control as soon as you can. Sometimes this means a hurry up and wait scenario. Sometimes your feet are to the fire and you have to hustle. But whenever you can, try to avoid losing the agility you need to make tough calls in advance.
In Practice:
Early on my company ran into a lot of attention after launching a worldwide, award winning story book app in the first year of the iPad’s launch. As most first-time entrepreneurs think, I felt like bigger was better. We began to grow our company, adding in layers of management and non-production roles to support our growing team.
The Theory:
Our customers were beginning to ask for more time with us, and were referring more products to us than ever. We were already at the brink of management with as many production members of the team as we had along with the many customers in our shop. Our goal was to hire management to help us poise ourselves for further growth and be prepared for the workload and team growth ahead.
The Results:
Due to a perfect storm of events (which, by the way, happens way more often than you’d expect), we were unable to sustain middle management. Growth didn’t happen as fast as we would have liked, and our runway was far shorter than we had time for repairs. On top of that, our customer base felt disconnected from the product design & development, and satisfaction suffered. We had to cut back our staff, and eat those costs in one of the most stressful crunches we’d ever been in. This decision still haunts my thoughts today.
I was backed into a corner and my hand forced, all because my past self failed to ensure he was forecasting often and properly, and I wasn’t asking my customers often enough what their feedback was.
Today, my business partner and I have an all-hands meeting with our company at the beginning of each week, and a private meeting between the two of us to discuss progress and the next weeks plans and forecast.
A Clear Conscience
Most executive decisions affect many more people than just myself. They pretty much always affect every employee in my company, either directly or indirectly. And sometimes those decisions won’t be flattering (why didn’t you see this coming, Keith?!).
As long as I’m able to do as much forecasting as possible, and have as much foresight as possible with the resources and time I have, I’m able to stay a few steps ahead of most decisions and continue to operate in the transparent fashion I love. Because of this environment, generally when the tough decisions come around, they’re already being expected.
For me, the most difficult part about leading my team is that I have to live with myself and the decisions forever after, and the people that I effect will remember how I handled it. This is why it’s not “just business” for me, ever (a double edged sword on occasion).
Ultimately, treating the team with respect, being generous when I’m able (compensation, forewarning, etc), including the team to obtain insight, and trying to make difficult decisions easier to live with after the fact helps me make sure I feel good about the tough decisions I’m required to make every day.
Remembering that I’m not alone and that the sun will still come up tomorrow are powerful tools I’ve used in the past to deal with everything a startup can throw at me. I’d love to hear your own battle stories and help however I can, even if it’s just commiserating!
