Personal Exploration

by Rocky DeStefano

Some of you may already know that I’m in the midst of a new stage of my career.  My previous employer was acquired by a larger entity and I felt it necessary to re-evaluate where I was headed professionally and personally so I stepped away for a bit and have been quietly interviewing with a few really cool organizations.  I’m honored that these organizations/people consider me worthy of their time and I’m really flattered to think that they’d make room in their organizations for me.  It got me thinking about what I’m decent at, what I love to do and where I need to grow, this post is a view into the journey I’m on and to be honest it’s more self-reflective than enlightening but was important for me to articulate at least once as I figure out the next step in my career. 



I’ve been extraordinarily blessed over my years to work alongside some of the greatest minds and most accomplished practitioners and leaders in our industry.  I owe so much to these people for believing in me, mentoring me, pushing me to be better and I can’t possibly stand by and just “take a job” or “further my career” I need to create, build and help others reach new levels.  I’m not at their level and perhaps never will be but I can strive to mentor the next generation of leaders to do better that they otherwise might have.   I’ve been part of both disastrous business decisions and some of the most amazing results companies have achieved in our lifetime.  I’m learning each and every day from everyone around me how to more fully understand and therefore deal with situations.   I don’t for a moment think that I’ve got the answers and it has to go this way, but I do know when it’s the wrong way and I’m unafraid to say so.  That endears me to some and creates chasms with others.   I’m ok with that.

If you want more about the roles/companies I’ve participated in – check out my LinkedIn page.  I’m completely open about my professional life. 


Next Steps:

I’ve been blessed with a number of opportunities to consider.  Most of these had natural conclusions based on organizational culture / location, timing or other reasonable considerations.   I appreciate every second people have taken (and are taking) to talk with me.  I learn from every one of these interactions about how I can help, how I might not be the right fit in certain circumstances or how I might need to be more patient.  To that end I’ve come to a point where several branches lie ahead of me (and probably more that I haven’t yet considered – but these will do for illustration purposes).

Option A:  I can go it alone.  Visible Risk is a viable company and I can fairly easily find projects to keep myself busy and engaged for the foreseeable future.   The downside is that it doesn’t
quite “feel right” because I feel like I should be doing more (what impact am I having?)  It’s not a bad option to have but at times feels more like a crutch than a mission.  How odd is that? 

Option B: I can start something anew.  Having the self-confidence to succeed in any situation is a freeing thought.  It doesn’t remove fear, it simply provides an opportunity to adapt and overcome it.  I have some ideas here (I’m never at a loss for ideas) but this is a path that requires commitment to your “best idea” and not just another idea.  I need to refine the best ideas a bit further before I jump back into this route.  This is possible if I’m patient but the timing seems to be inconsistent with my need to help.

Option C:  Joining a team.  I am most successful in very small companies.  There is no such thing as too-early for me.   I’m not necessarily suited to be employee 50001.  That’s not so say I’d avoid all large companies there are some with very progressive business units that focus in a manner that would excite me, but overall those opportunities seem very hard to find from the outside.  If I could find the right team, right focus, similar values and keen timing – the world would be even more fantastic.

Currently I’m leaning towards option C but doing so in a way that doesn’t preclude me from exploring Option A and B until I find the right Option C.  That said – it is probably the wrong approach.  I need to explore these organizations without the “net” of A and B and let them stand on their own merit.  I get too entrenched in battles of this trade-off for that one. 


Recent Influences:

                To many to list but I’ve interacted with no less that 2 dozen companies over the past 30 days that all have interesting attributes whether that be technology, leadership, vision or passion (or some combination therein).  Some things that have become apparent to me are simple but evasive principals that I’ve noticed to some degree over the years at companies I’ve lived at.  Most importantly is the feedback from the field (customer and field teams) into development.  In most software worlds this is a gate controlled by Product Management and in some cases it is done very well, but in all cases can get better.  Recent trips to Silicon Valley only served to crystalize that point for me.  Companies like Google, Facebook, Twitter, LinkedIn and so many others made a crucial change in the landscape and not because of the service they offer but through the means they deliver.  Software was fundamentally altered when companies started designing to the user instead of for the user.  Live feedback is supreme.  I used to think that the only way to get this level of feedback was through Services, field teams or customers/partners feeding requirements back to development and was constantly frustrated by how slow that process would work or how many misinterpretations were possible in it.  Certainly that is still a viable feedback loop as are User Conferences and other observable interactions but I’ve come to learn that the software needs to be designed around the user and constantly evaluate its usage by (and value to) the user.   Some amazing thoughts going on there and it has changed my perspective completely.   Whomever I work for next will “get” it.  This is an area I intend on exploring much more fully in the coming years.



Location:  Depends on the position.  As a family we’re heavily tied to Austin/Round Rock as far as “home” is concerned.  I’ve traveled for the better part of my career, much of it 100% for extended periods.  In all honesty I’m connected enough at my home office(s) that I’d argue I’m better prepared to do battle from here than just about anywhere on Earth.  In other cases my connectivity and resources are not nearly as important as the day-to-day interaction with the team(s) I’ll support so I’ll endure the TSA massages to be at the location(s) that make the most sense for everyone involved.  Really this question is more suited to your company’s organization culture than it is to my preferences.  I’ll be wherever I need to be to ensure the success of the mission.

Compensation:  I value long term commitment to a mutually beneficial relationship.  Remuneration is important but it is not the first thing I’m seeking in this relationship.   I’m looking to be mentored by your Exec team, Board, and customers.  I have a need to better myself every day.  On the financial side of the equation equity is a strong motivator.   I’m willing to find the right balance to make sure the benefits of the relationship are strongly valued by all involved.

Interviewing:  I’m happy to interview with anyone on your team!  I view this as an opportunity to learn about you equally as much as you wish to learn about me.  I will talk to your competitors, customers, ex-employee’s, current employee’s, investors, industry analysts and anyone else that a few hours on Facebook, Twitter and Linked-in make readily apparent.  I encourage you to do the same about me J 

Title:  I’m not a slave to a title.  I’d prefer “Rocky” @ yourcompany than XXX of YYY any day.   That said the contribution I make is not usually at the individual contributor level.  I’m closer to senior executive than I am to manager with the benefit of still being “hands on” and very passionate about doing things in a manner consistent with the needs of our customer/market.  I get “it” from a technology, business and market perspective and understand the relationships between them.    

Role:  What is your biggest need?  Seriously I’m not one for a single role.  I’d rather solve a problem and as part of that teach someone to grow into that role and manage that team/capability moving forward.   Lately my value seems to be creating Services teams within Product companies in a non-traditional manner.  I’m not a guru at it, but building offerings that adds value to the customer, partners and the overall market is relatively intuitive for me.   Understanding the nature of that role is interesting as well but that’s a book in itself.  I’d like to be part of the senior management team and help move a company beyond the current limitations they face.   

Vision:  Long-term success is much more important than short term gains.  I can build a company to several million or even tens of millions in revenue.  I’ve even been a part of one start-up that wound up being worth significantly more ($B) than that.  At this point I’m more interested in building a company that has a reasonable shot at doing things right.  Customer Focus is the key for me.  We must adapt on a daily basis to our customer’s actual needs not to an abstracted understanding of how we as the vendor can provide a solution that might hit some of their requirements.  The company I work for will inherently understand the difference. 


Personal Opportunities:

Biggest Weakness:  Patience.   I abhor anything that takes forever to accomplish.  Counter that with the fact that I’m a perfectionist at times and there you will find an interesting study in itself.   If there is a problem to be dealt with I prefer to deal with it head on, immediately.  If no one else acts on it you can be sure I will address the issue.  Clarity as early in the process as possible is a key. 

What am I doing to work on my weakness?  Well in addition to raising my four kids I’ve recently taken on Coaching 3-4 year old T-Ball.  Seriously, Try it.  It is an amazing thing to see how your actions are mirrored by those around you, good and bad.  It always amazes me how much people can do when prepared properly and trusted to do the right things.   In one day we went from a team of dog-piling ball hogs to a cohesive unit trusting each other to get the ball.   Making the right priorities known and consistently evolving that vision together works a lot better than assuming everyone gets it and hoping it’ll work out.

2nd biggest weakness – Introvert by nature.  I’d much rather gather Intelligence than express my ignorance.  Blogging/Tweeting helps me reach out and stay connected and refine thoughts a bit better prior to inserting my foot too deeply in my mouth.  I also do a fair amount of public speaking to help move past this but in the end I’ll always by default seek a corner table rather than a space in the spotlight or on a stage.

Oh yeah… One last “gotcha”:  I don’t do excel or PowerPoint.  Honestly I’ve found both lead to antiquated thinking or unnecessary and restrictive boxes.  If you process is managed by either I believe that it is destined to failure.  I’ll help you fix that, but I’m giving you fair warning….  I’m going to blow up your process and create a much better one that is managed with the right tools and by the right people. 


Some things I’m decent at:

I’ve heard I’m not horrible to work with/for.  I’m not one to call on everyone that works for my on a daily basis, but I understand where everyone is mentally and work very hard to ensure it is positive for the company and for the individual at the same time.   I love my team(s) there is no other way to put it.  I’ll never put anything ahead of the team which admittedly can limit my usefulness in certain circumstances but I believe in my team(s).  I’ve managed teams of between 2-150 over the years.  If anything I’ve learned that mentorship skills outweigh my people management skills.  In most cases I feel strongly that people deserve much more attention than I am able to provide on a daily basis.  I can manage but I always Mentor.

Technical Comprehension:  I can break/build just about anything.  Whether it’s a lab or an enterprise solution I’ll take it apart and understand it to its core and then figure out how to best solve problems using that technology within the environment that exists.  I never do this by myself.  I surround myself with people much more versed in the technology to absorb and learn from and apply it in real-world situations.  I don’t claim competency until I’ve mastered it a few hundred times.

Business Acumen:  The most fun projects I’ve done recently were the ones where I evaluated companies for M&A or Investment for Exec/Boards or VC’s.  Digging into a company’s technology, people, culture and extracting there essence combined with my understanding of the current market and my perception of where the market is headed is something that hits on my primal traits.  I’m by nature an Intelligence analyst.  I can ask the right questions, understand the Bias involved and get to the truth very quickly.  I’m not always 100% but I’m never wrong J  (Kidding I’m always learning).




I’m just another 30-something year old gentlemen full of first world problems seeking to make a difference that is meaningful in our Industry.  I come with my experiences, my lessons learned and a hunger to learn.  I’m insanely passionate about people and doing things right and will push you and the company I work for upwards with all of my energy.   I enjoy obstacles (once) and fiercely look to squash them moving forward.


My Apologies:

This blog post has turned out to be much more self-explorative than I originally intended it to be; maybe it’ll help someone else figure out their path?  Maybe it’ll just scare potential employers away in any case I sincerely appreciate you taking the time to consider my thoughts!


-          Rocky