Jason Orloske, founder of Bridge the Gap Consulting and Senior Consultant at Digineer, credits his success and confidence in project management to his late mentor Pete Blissinbach. Orloske, who first began his career in project management in 1999 while working for a legal publishing company, never intended to go down that route. It wasn’t until meeting Blissinbach that he realized project management was the right fit for him. Reflecting on the beginning of his career as a project manager, Orloske shares the invaluable lessons learned from Blissinbach.
How did you get started in project management?
I was working for the Thompson Corporation, called West Group back then, in the Minneapolis area. I was doing data acquisition and transitions. An author would write a book, a pamphlet, or whatever it would be and send this information to us. We would then take the information and go in two directions: one, to print the legal textbooks, and two, print to the CD ROMS. So there was a whole new book series that was coming out and this person, who was a project manager, was someone I hated, everybody hated him. We would be sitting in a conference room and he would walk through the door saying the same thing every week, “You’re not doing your job, you’re all terrible, you’re falling behind schedule, you should all be fired.” One day he came in and said “You guys suck, you’re not doing your jobs right.” I said back to him, “I have an idea. What if we, instead of running one at a time, run these two tracks parallel?
I think we would get done quicker.” He turned bright red and he goes, “OK slick, if you think you can do better, do it,” and threw his project binder at me and walked out of the room. He never came back. I talked to my boss and she said, “Well if you want to do this project, go ahead, but you’re going to need some help.” I said back to her, “Yeah, I do.” Then I was exposed to the world of project management, through Pete.
What are you doing now?
Right now I have my own LLC, Bridge the Gap Consulting. I’m also a senior consultant for a company called Digineer. I consult on project portfolio management. If companies have an idea of what they want to do from a project management standpoint or if they have a strategy but don’t know what to do, that’s when I get a phone call. I can help flush things out a bit more, understand where things are with them, where they want to go, and start to prioritize the tasks of the project. I like to say I turn vision into reality by helping their teams out. I run their projects from start to finish and then I’m out.
My family and I moved from Minneapolis to Fargo in 2013 to get away from the traffic and the hectic lifestyle down there in the cities. My commute time to work in Minneapolis was an hour and ten minutes, one way. It just got to be too much. We just wanted a smaller community. We thought about either coming here, or I had a good friend of mine that worked down in Kansas City, MO and he said, “Well if you’re on this side of the city there are all the major companies and you wouldn’t be driving more than 15-20 minutes.” I thought, whoever offers a job first, is where I will go. It was Fargo.
We love it here, we love our neighborhood. I’ve kind of got myself into some of the entrepreneurial ecosystem, the executives club with people like Patrick Metzger. I feel that I made a good establishment here and I will continue to grow that presence.
How did you meet your mentor, Pete Blissinbach?
My mentor came in 1999. My boss said, “If you’re interested in project management, I will help you out in that field but I can’t mentor you directly, you need to bring in somebody else.” She had heard of one project manager and put us in contact with each other. There was this guy who had just started, his name was Pete Blissenbach. Pete was from California and had been doing project management for 15-20 years. He was a California kid, had long, blonde hair, and was a surfer. He only moved to Minnesota because his wife had family there and wanted to move closer. I got to meet him and said, “Hey can you help me, because I really need some and I don’t know what I’m doing.” He said, ‘“Yeah absolutely.”
He was in his late 40s at the time, and I was in my mid-twenties… He was my first mentor and was the most impactful person. I attribute my 20-plus-year career in project management to him because he guided me onto that path.
What were some of the key lessons you learned from Blissinbach?
He taught me three big lessons.
The first one was probably the most important: relationships. The art of project management really are the relationships and trust you develop. He was once leading an effort where it was two project teams who didn’t like each other and were constantly arguing. So he goes, “I’m going to bring you to this meeting and you’re going to hear yelling and screaming. People are going to be pointing fingers at each other and it’s going to be very uncomfortable. But you’re going to learn a lot.” We sat down, and he was right. These four people start yelling at each other, cursing and calling each other names and I’m kind of leaning forward like, “I think we should say something.” He just puts up his hand and goes, “Let the animals kill each other, and when they’re done, make friends with who’s left.” He just sat there and waited. Eventually, it was just two people that were arguing. He goes, “OK, everybody stop. You’re basically saying the same thing so let me kind of tell you what I’m hearing.” So he really taught me the value of taking a step back and that sometimes you have to let the conversations just happen, and then you come in. Only then was he able to build trust, not only from him to the person he was talking to, but even amongst the others. It was just really interesting to watch his thought process of, you know, conflict is going to happen, but sometimes you need to let it go. Once you get down to just a couple of people, build a relationship with those couple people—especially since they’re the leaders of those groups. And then get aligned after that. That was probably my most fond memory of him because he was just so laid back about it and didn’t get upset at all.
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The second thing he really mentored me on was project schedules. Clients want to have a schedule of when we are going to be done. Earlier in my career, I would make these humongous schedules, 400 lines long for each individual task. The thing he taught me was that the schedule will be correct on day one, but it will be wrong on day two and until the very end. If I showed you a 400-page project plan, you’d be like, “No way.” If I showed you ten, just the key dates, those are the things people understand. Know that simpler is better and less is more when planning out how long your project is going to take. Don’t get into too much detail because if one thing goes wrong, everything else is going to be wrong underneath it and you’re going to spend more time correcting your project plan than the project itself
The last one is status reporting, which is a huge part of project management. Everybody wants to know how we’re doing on time, cost, and whatever else those metrics are. You don’t need a book, you just need one page, simple things. If you can’t read it in ten seconds or less and understand the current state, you’re doing something wrong. So again, less is more, keep it simple.
Were there any other valuable lessons you learned?
Those three are the big ones, but I always think back to his value of relationships more than anything. He would stress that with me over and over again. There’s the formal aspect of relationships: I owe you a status report and I want to make sure that you understand it. Where you really can get worked up is informal relationships. So take people out for coffee, take them out for a beer after work. Whatever it would be, just have an informal conversation, get to know them on a personal level because that just builds that relationship capital. Once you have that relationship capital built up, later on, you can negotiate something or ask for a favor. Relationships above everything else will help you get your work complete. I was very nervous early on in this profession, because you deal with the senior management level all the way down to the front line workers, so you’re dealing with the whole range of workers, personality types, and different seniority levels. He helped me to remain calm especially when I was talking to those senior-level people. He would say, “They have no idea what you’re talking about so you have to dumb it down. Remember, they’re probably the dumbest person in the room, not you.” He helped me with all that, just gaining that self-confidence.
He also got me to take on harder and harder projects. Originally I was just taking on some of the print acquisition ones. So writing a new book or whatever it would be, I would put the project plan together for it. Soon it became very mundane and routine because you’re doing them all the time, it’s just operational. An opportunity came up to take on a technology project, they asked me if I wanted to do it and right away I said, “I don’t know if I’m able to or have the knowledge.” Pete told me, “What you already know will help you be successful.” He really pushed me to try something that was a lot harder and outside of my comfort zone.
What was the dynamic of your mentor-mentee relationship?
Our mentor-mentee relationship was pretty informal. We did have a personal relationship, having coffee at least once or twice a week. I remember having so many meetings with him just to sit down and talk. I mean one day he said “I’m not here for a cry session but if you need to do that, I’ll be here.” I would bounce things off of him all the time, and I had questions every time we got together, or scenarios for him. He just had this real laid-back style of he would listen, ask a few questions and kind of sit there and say, “Dude have you thought of this?” … He would never tell me what to do but he would ask questions and kind of guide me to try something else.
We had this mentor-mentee relationship for about 18 months before he left the company.
Where do you think you would be without his mentorship?
If I had not had this relationship, I think I would’ve stayed in the more operational hole of data acquisitions. I thought it was OK, it wasn’t hard, it wasn’t easy. I think I would’ve stayed in something like that role as opposed to projects. As soon as he exposed me to that world, I was hooked pretty fast.
Do you still keep in touch with Pete?
We stayed in contact for a while after he left, but eventually lost touch…On one of his last days—which was the first time I ever hugged a coworker—I said, “Hey you really helped me out, you know.” … We stayed in touch for a while and then about 6 years ago or so somebody told me that he had passed away unexpectedly. Otherwise, I would’ve loved to have gotten him on the phone again. He was very influential.
Have you repaid the favor of mentorship to others?
I’m on the MSUM board for their project management group so every chance I get to either talk to the students or be a panelist or whatever. I want to pay it forward for everything he did for me.
Trusted Project Management Expert
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