Sr. Director of Technology

Jonathan Goldstein is a member of the ProjectDirectors.Org community. He shares his story on why he became a Senior Director of Technology in the following interview:

Why did you become a Project Director?

I became a Project Director because I found myself gravitating towards situations where I was called upon to solve big problems.  I also really liked the notion of being the person that was responsible for bringing teams of people together and collaborating to get things done.  To me, this is what Project Management is all about.

What work were you doing previously?

Prior to my career in Project Management, I was a Business Analyst and also a Pre-Sales Consultant.

What are you doing now?

Now, I am a Sr. Director of Technology.  My main responsibility is to run my company’s PMO.  Lately, I have shifted away from traditional project management and am focusing on helping my company move to Agile Development.  This doesn’t mean that the role of PM is going away, but our responsibilities are certainly changing as we engender more self-organized, self-managed teams.

When was the moment you decided to make the change?

For me, it was two fold:

  1. I saw that PMs had a stronger career track into executive management. So that somewhat forced my hand.
  2. I was given an opportunity to try out one project in a PD capacity and I was hooked.

Are you happy with the change?

Absolutely.  I love what I do!  I sometimes wish I had the skillset to be a developer, but I also know that my personality profile, and overall skillset, skews me in this direction.

What do you miss and what don’t you miss?

Certainly in those moments where I feel the pressure of the entirety of my company’s project portfolio on my shoulders, I long for the days of being an individual contributor. But, I really can’t say I miss anything.  Everything happens for a reason, and I have been blessed with a pretty awesome career, thus far.

How did you go about making this career move?

I met with a lot of PMs, PMO directors, technical mangers, etc.  And I also was blessed with meeting an EVP who became a strong mentor to me.  I am where I am today because of him.

What didn’t go well? What ‘wrong turns’ did you take?

In the beginning of my career, I think I attempted to take too much on too quickly.  I also got a little impetuous and wanted the fruits of success that I had not yet earned.  So, I had a little too much hubris and not enough work experience to know how to handle the challenges that come with over-reaching.  Eventually, it caught up with me and I paid the price.  Those were not fun times.  I ended up not only failing on the project, but losing that job.

With that kind of failure, comes a lot of humility if you allow it.  I often encourage my team to take a moment to acknowledge failures.  A cold hard fact of our human condition is that we learn from failure sometime more than we learn from success.

I’m a different person today because of that experience, but also my choice to learn from it.

How did you handle your finances to make your change possible?

I have been lucky to be in organizations that funded my development.  With the exception of graduate school (I received an MBA in 2012), the companies I have worked for always funded my training and development.

Like I said, my MBA was the exception. I paid for that myself with help from my parents.

What was the most difficult thing about changing?

As a pre-sales consultant, or even a BSA, it’s really easy to take stock of what you have accomplished.  Either the demo works or it doesn’t.  The sale came or it didn’t.  Or the analysis deliverable was complete and accepted or not.

As a PD, it’s harder to define your value because often projects fail for reasons that have nothing to do with your personal contribution.   This can be demoralizing.  So I had to establish other measures of my business value.  Tangible measures like increased velocity under my leadership vs. before (if I am inheriting a project) or just velocity over time.  And intangible measures like: do people enjoy working for me? When I get assigned to a project, do they breathe a sense of relief or is it a sigh of despair.  At this point in my career, results + likeability are super important.  You can be the world’s greatest mind, but if no one enjoys working with you, it really doesn’t matter how much you know.

What were other difficulties and how did you overcome them?

Nothing is coming to mind.

What help did you get?

1) I am an avid reader.  So pick up a book.  Not just on Project Management, but on Leadership and General Management.  Learn how other people lead and you can plow those “learnings” into your own leadership style.

2) Mentors, mentors, mentors.  Find people who are smarter than you, more successful than you and learn from them.

3) Don’t be afraid to hire people who are smarter than you or better than you.  You’re in a leadership role for a reason.  Don’t be afraid to hire someone who might be better at you in a certain skill area and learn from each other.  Empower them to contribute to your organization’s culture.

What have you learnt in the process?

Be confident, but be humble.  Submit yourself to the vagaries and lack of control that this field exhibits.  You can’t always know everything you need to know.  So accept that today you are going to accomplish what today enables you to accomplish.

If something is in your way, don’t let it fester.  Escalate.  Assemble a team to find a resolution.  Or get to a place where you can acknowledge that you have done as much as you can about that particular risk or challenge.

Don’t be a dictator.  Your company has blessed with a management role.  It’s not a micro-management role and very few people like being micro-managed.  Be a coach.  Be a guide.  Be a mentor.  And your project teams will rally around beyond your dreams.

What do you wish you’d done differently?

Well, you learn by failing.  So there are very few things I would do differently, because every experience bad or good has shaped who I am today.  I certainly have some events in my career that I wish I could undo or redo, but the reality is that if I had never done those things, I wouldn’t have incorporated those lessons into who I am today.

Don’t be afraid to fail.  We don’t always learn by succeeding.  Sometimes constant success gives you a dangerous hubris which can become un-inviting.

What would you advise others to do in the same situation?

It sounds very Zen, but let the cards fall.  Just go!

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