Steve Jackson: Lead with Passion

guest post[Note from Daniel: This guest post, from my friend Steve Tolman, is part of an occasional series about important career role models. I also worked with Steve Jackson, and I agree with Tolman that his energy and dedication instilled many great skills in those who worked on his teams.]

While I worked at PowerQuest, and Symantec after its acquisition of PowerQuest, I worked with a man named Steve Jackson.  He started somewhere around 1999 or 2000.  In our organization we had about seven or 8 Steves so we all went by our last names.  I was simply, “Tolman” and he was “Jackson.”

Jackson was the director and VP of all software engineering.  He was my manager and quickly became my friend.  He took his job very seriously and I learned a great deal from him.

By the time I left the team in 2008, I had learned how to run a team, how to build and release software, and how to work well with people.  One of my peers, Lane Johnson (one of the best managers I have ever known, who left the team at the same time) asked me what it was that made Jackson so dang good.  We thought about it for a while and concluded that there was not that proverbial one-thing-you-need-to-know that made him great, but more along the lines of about a bazillion qualities.  A little time brainstorming gave us a list of 45 different skills, techniques, or approaches.  Here are just a few of the highlights.

Believe in the individual

Jackson’s default mode was to trust people.  Trust them to fit into the team and trust them to do their job, but expect them to do a stand-up job for you.  Get the right people on the bus (read the book Good to Great for more info), give them an assignment, then get the heck out of their way and let them shine.  To find these people, interview for the right skills including the soft skills (like humility) that help people fit into a team environment.  After all, a job is way more than just using technical skills to accomplish a task.  Once they have done the job (task, assignment, favor, etc.) always (always!) pay credit where credit is due.  If you steal credit even one time, you destroy trust which may be irreparable.  While these great people are doing a stand-up job for you, be sure to be as generous as possible in rewarding them – bonuses, comp time, promotions, etc.  Oh, and also bring a life balance to the team.  Understand that people work to live and do not live to work.  That is, allow team members to pay attention to life outside of work and let them go to whatever family or personal activities they need to.  Of course, they still have to get their job done, but this flexibility allows people to still have a good home life and fit in well at work.

Sometimes a team member does not fit well on the team.  When you discover this, put in place a plan to help that employee improve.  Sometimes the team member will improve in which case they are praised and given more tasks to complete.  Sometimes they will choose not to improve and will leave.  While this is always unpleasant, it maintains a very high level of accountability and performance on the team.  Frankly, teams like this.  They like it a lot.

Strengthen the team

Don’t be afraid to manage by walking around; the better you know people personally, the better manager you are.  Use online resources to measure team morale: send out an annual (and anonymous) survey to the team polling how the department is doing, hold luncheons with team members at random.  Always be on the watch for morale concerns and make sure people know they can vent, ask questions, etc. without any fear of backlash or retaliation.  (I often took Jackson up on this and he heard many ears-full of my gripes.)  Once you have heard the issues and concerns, be sure to address them.  Quite possibly, half of your time will be addressing team morale and effectiveness issues but doing so properly will always pay off with big dividends.  Be a part of the team.  Jackson considered himself just another team member.  That’s not to say he wouldn’t make the hard decisions – he certainly did that, but he never lorded over anyone and he always brought a well grounded approach with him to work each day.

Expect intense accountability

If there was one thing that made Jackson boil it was a lack of accountability.  His teams were always expected to deliver on time, on scope, and on budget.  Everyone knew this too.  Advocate pushing down responsibility where appropriate, empower people to do their job, and hold them accountable.  With Jackson, we worked long and hard (massive understatement just now).

In 2003 I was assigned to build and release a product that had some serious legal requirements for the company.  Missing the date was absolutely not an option.  This project quickly turned into a death march for the team.  As we progressed through the work, we discovered that much more code was required to get the product to work than we originally scoped – many times more.  There is probably a whole book that could be written about this project, the obstacles we overcame, and the lessons we learned from it.  Suffice it to say that this project became known as the black hole project because it sucked in all available resources.  It seemed that no one could escape its ever-increasing gravitational pull.  This led to about a year of 8 a.m. to midnight or 2 a.m. days.  I was wiped out by the end of the project (which we released 9 days early, by the way, but we won’t talk about being on budget for this project!)

Jackson kept us accountable for the work even though it grew and grew (and grew!)  He and I spent many long hours dealing with crisis after crisis, discussing how we could complete the work on time.  He was very instrumental in suggesting solutions and approaches that kept the project on track.  The lesson I learned was that even though he held me directly accountable for the work, he was very willing to be involved in keeping the project going by helping me with some of the absolutely overwhelming obstacles that seemed to love jumping in our path.  Bottom line: we all worked our back sides off but we did it together as a team and we grew because of it.  Some of the most powerful lessons I have learned in my career came in the year of the black hole project.

In spite of the often brutal hours, Jackson was always our champion.  He bought team munchies when the going was tough.  He bought untold thousands of dollars of dinners for our late nights.  We had celebration lunches and parties whenever we shipped a product.  While he held us accountable for the work, he always celebrated our successes and rewarded the team accordingly.

It is fair to call out that while you can expect the very best from your team, you should also expect them to have fun.  It turns out that teams who work hard together tend to play hard together too.  This does marvelous things to a team’s morale.

Train and mentor

Working for Jackson meant that we were always reading a training book, attending a class, or otherwise learning how to be better.  Train your teams on your process, your culture, your toolset, your technology, and anything else you think is appropriate.  Once you complete a training topic, talk about how to implement it into your team and then actually make changes that implement those ideas and approaches.  Then, the management team should hold their teams and each other accountable to actually perform the new behavior until it becomes a part of your team’s DNA.

Not everything will work, but you will never find ways to improve until you just start trying stuff.  Be sure that you plan in some fun.  We would often attend “training” films.  These were usually newly released movies that everyone wanted to see.  True to his generosity, Jackson would often buy out the movie showing and, for a very nominal charge, invite our family members to attend with us.  How cool is that?

Whether it was go karts or pop-bottle rockets, Jackson always found a way to combine mentoring with fun.

Whether it was go karts or pop-bottle rockets, Jackson always found a way to combine mentoring with fun. Photo credit: Thedovardhana Kote (Flickr)

Spend a lot of time mentoring your managers.  I was one of Jackson’s managers that needed a lot of mentoring.  Fortunately, Jackson is a very patient person and could show me a better way to solving many of the issues we faced.  He taught me to deal with issues as they came up.  Usually the issue worked out favorably but sometimes the resolution was painful.  I learned how to handle both.

My time working with Jackson lasted about eight years and was the single greatest experience of my career up to that point.  Since then, I have used the skills I learned while working with him to make my subsequent teams into high (or higher) performing teams.  While I am not as good at it as he is, I have enjoyed good success and continue to refine those skills as I work with my current team.  Jackson is still my friend – with Lane, we often get together for breakfast or lunch and catch up on life.

Hey Jackson, thanks for the lessons!


steve-tolmanSteve has been a software pro for over 29 years.  In that time he’s worked as a tester, technical editor, programmer, and manager.  He’s done all of this with both onshore and offshore teams.  Currently Steve works at Perfect Search as the Director of Engineering.

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