Business Tech: Planning

"No plan survives contact with the enemy" - Authorship disputed

"In preparing for a battle, I have always found that plans are useless but planning is indispensable." - Dwight D. Eisenhower

In fiction writing, we use the terms planners and pantsers. In programming we usually call that second kind of person a cowboy. In my experience, nearly everyone in IT has a bit of both in them. We tend to push one view of ourselves over the other. It is time to value both.

Anticipate, Then Do

When I train programmers and analysts, I start with "Anticipate, then do" to break the habit of believing dangerous things like:

  • It compiled so I did something right!
  • There's an output so it worked!
  • The total field is displaying a number, no need to check further.

Those are all easy traps to fall into in our field. Teaching people to have specific expectations before seeing the outcome is a great way to bring planning into their natural process. When my students anticipate and get a different result, they get to see if the result is wrong or if the anticipation is. That's a big step in critical thinking.

So, on the face of it, planning is awesome and cowboy-ing is a sloppy idea. Until, of course, something goes wrong.


The worst part of any plan is the attempt to mindlessly adhere to it. We've all been in that situation, where we commit to a plan and now people are walking around with it in their figurative back-pockets, waiting to whack us with it whenever we deviate.

However bad that is, when we do it to ourselves, that's worse. Plans fail. It happens. The route to success in most cases is knowing when to deviate from the plan and why.

Regardless of how you approach a project. Some things will go badly. Often, that will land you in a what-the-hell-happened meeting.


When things go awry, you need to be agile in your thinking. You need flexibility in your approach. You need the inner-cowboy. When plans fail, the ability to pivot and come at it from a new angle is incredibly useful.

I recall one project where I realized the better solution four hours before it had to go live. My co-worker and I rewrote nearly everything, tested it, and deployed the new version. The planned version was okay but the new version was spectacular.

Sometimes it's enough to generate a win. And a win is better that a postmortem meeting. Inspiration isn't planning. It's the cowboy way.

6 People You Meet in Postmortems

The doom-criers are a special breed who exalt in being right that things are going wrong. Please understand, as a practicing pessimist, I applaud the ability to see the pot holes in the road. It idea, however, is to use that vision to steer around them.

The panic-prone don't have that future vision. Every bad thing is a surprise to them. Their burning need is for someone to comfort them. It is often more important to them than solving the actual problem.

The not-my-table people don't make things worse. They also don't believe it is their job to make things better. These are some of my favorite people. They have reasonable boundaries and expect you to fix the things in your area while they attend to their area.

The how-can-I-helps are even better. They have the wonderful, and often unreasonable, belief that the company is holistic. They want all the parts working and see themselves as responsible for acting accordingly. These are my absolute favorites.

The see-there people are a special sort. I've had any number of bosses who find a solution based on doing something I have no authority to do. Instead of doing this as a how-can-I-help, they point at the solution as if it is a failure of your vision that you didn't do the same thing. Fortunately, I've had bosses who are how-can-I-help types as well.

The rest are, well, the rest. Not everyone fits in the five neat boxes I've outlined above.

Problem Solving

When a plan fails, that's a problem… which is no problem for us. IT people are good at problem solving. It's part of the job whether you are strictly software, all hardware, enmeshed in the networking, a polymath sort, or fulfill any other roles. Our industry attracts people who want to work out the kinks and beat the limitations.

We need to treat every project as a thing in search of a solution. Not just the technical part, the people part as well. Manage expectations up front. Keep people apprised of the right turns and wrong turns. Minimizing the surprises is a critical path to the least worst outcomes.

Personally, I'm far from perfect at this. Still, it pays to work at it. Just remember: failure is always an option. Plan accordingly.


Charles Barouch is the CTO of HDWP, Inc. He is also a regular contributor to International Spectrum Magazine, a former Associate Editor for both Database Trends and for Gateways Magazine, a former distance learning Instructor for CALC. He is presently the Past President of the U2UG. Mr. Barouch has presented technology and business topics in front of hundreds of companies, in a wide range of product and service categories. He is available for on-site speaking and consulting engagements in and out of the United States.

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Nov/Dec 2018