Bomb

7 Failures I Needed to Succeed

Here is a list of seven failures from my professional career, how I met those challenges, and in some cases, turned them into opportunities

Underestimate

Eager to please throughout my career, I was burned many times, and in some cases continue to be burned by underestimating the effort required for an activity, or task, which roll up to the delivery of features, or meeting a milestone. In my earlier years, I “shot from the hip” to senior management, and they held me to those commitments. Over the years, I’ve been fortunate enough to document and mitigate risks. In addition I learned additional tools, both process and communication / people skills:

* “Interesting point, let me consider, and get back to you.” You don’t have to provide an answer right away. Consider the scope and impact of the questions you are presented. Unless you are almost certain of the answer, try to defer.

* Planning Poker (Agile) collaborative (blind) estimates make better estimations. Through collaboration, you reach joint commitment. You eliminate the “boss knows best” factor.

Hearing but not Listening

Throughout my personal and professional life, I’ve struggled with this aspect of communication, more so earlier on in my life. Two people have a meeting, and discuss their point of views regarding the same topic. They both leave the room, and have two polar opposite prospectives of what was communicated.

Even in the same language, things get “lost in the translation.“. There are many process tools to better your communications style. You hear what you want to hear. You don’t probe deep enough into another person’s perspective.

Overestimate

Adding too much margin into an estimate, being conservative in your effort estimate at times may not be the best course of action. “Right Sizing” the estimate is typically the desired approach unless otherwise guided by the appropriate stakeholders. There are lots of tools for Effort estimation, poker planning, and fist of five are just two examples.

Army of One – Embrace Opportunity

I was brought into a development team as a Software Quality Assurance manager for a well known Financial Services organization. I was to build a team of QA staff as well as mature their process workflow, e.g. implement software change management.

The department’s QA resources per team dwindled, letting go these resources, and not growing the teams as first advertised during the interviews. I found myself constantly working with the team putting out fires. Best case scenario, I worked “after” hours just to work on the strategic stuff like process improvements, and automation. I stuck to the opportunity to learn as much as possible. Sticking with the job, I built my knowledge and relationships that would wind up propelling my career to later on build and manage a 50 person, global team.

Build it and they will Come…Bull!

I chose to try my own startup at some point in my professional career. I had worked for a startup firm out of college, but that was not the same as my own self startup. There were lots of balls to juggle, decisions to make and prioritize. After a year and a half, I shutdown the company, more money going out than in, and I was also “relatively” self funded.

One of the several ill choices I made was “Build it and They will Come.” At the time it was 2009, and the mobile frenzy was just starting to heat up. Feb 2009, Apple was at 30 USD per share! 30! I built a client/server mobile application for expertise transactions, way ahead of my time. I was almost entirely focused on the development of the solution, I clearly lost sight of the focused requirement of building market share. I did post Press Releases, but I didn’t embrace digital marketing as a core spend and activity for my business.

Needless to say I was “The Best Kept Secret”.

Chasing the Sun

As a software product, startup firm, you need to segment your product to align to a target audience. However, honing in on the target market maybe problematic if the “fish aren’t biting”.

You find yourself reassessing the strategic and tactical goals of your product, pivoting often to eventually find your “pay dirt”. There may be fundamental influences to your ecosystem, such as a shift in a 3rd party product previously seen as complementary now seen as “overlapping”. Sales pitch and marketing approach may need to change along with your product.

Although pivoting often may be the name of the game, you still should recognize the cost in adapting to change. Process flows like being “agile” and Scrum help to smooth the pivot, as these processes revolve around constant development iterations and reflections every few weeks.

Time to Pull the Parachute Cord

I still have trouble with knowing when it’s time to say when. I enjoy troubleshooting problems, business, people, process, and technical. So, how long do you work on problem before you pull the ripcord?

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