Faces of the Executives’ Club: Jason Orloske

Written by: Brady Drake

Founded in 2015, The Executives’ Club of Fargo-Moorhead is a club designated exclusively for CEOs, Presidents, Founders, and serial entrepreneurs to have extraordinary conversations.

We were lucky enough to interview a number of those visionary leaders and are even luckier to get the chance to share them with you over our next few issues.

Want to join the club? Head to the100.online

About Jason Orloske, Founder, Bridge the Gap Consulting

Jason has over 20 years of experience in delivering strategic value and operational efficiencies across a variety of industries, including technology, healthcare, biotech, retail, and legal and regulatory. He is experienced working with executives and their teams to uncover opportunities, right-size solutions and drive execution through implementation.

Jason founded Bridge the Gap (BTG) Consulting in 2018 to help executives and their teams turn vision into reality. After working alongside consultants from “Big 5” firms who followed their playbooks to the letter, even if it was a burden to the client, Jason felt there had to be a better way to deliver projects. Since then, he has led several strategic projects, including a $2.5M digital business transformation, M&A integration, and leading the Project Management Office (PMO) for a $3B publicly traded company.

Besides BTG, Jason is an avid cyclist and runner who loves camping with his family around North Dakota and Minnesota and JASON volunteering time to local non-profit events.

What is an important lesson you learned about business in 2022?

The Great Resignation helped identify good managers who can keep their people and bad ones that cannot. People are not a commodity. They are a competitive advantage.

What are you most looking forward to in 2023?

Growth and Connection. I plan to grow my network in the FargoMoorhead area as most of my clients have been outside of this area over the last two years. I look forward to connecting with local companies and professionals.

Take us through a typical day in your life.

My day usually starts before 5. I get up and head to Family Wellness to get a workout. I’m starting my training for some early spring races, so I need to get some good gym time in!

At the start of the workday, I normally have four to five update meetings with the various teams I interact with or lead. This aligns us with the work to be done that day and identifies any issues we can help each other overcome. These meetings are:

Project Meetings: what tasks are in progress, any issues foreseen and are we on track to deliver quality output on time

Operational Readiness: help operational teams be ready for what the project will deliver or with a major milestone they have coming up (i.e. yearend readiness).

Leadership Updates: give a short, crisp status to the leadership team on projects and operational readiness, as well as any larger issues or decisions needed.

After that, the only thing typical is to be ready for anything! As a trusted advisor, I’m brought into any number of conversations or issues that need immediate attention or long-range planning. “Hey, can you help with…” or “So, we’re thinking about…” are typical at the start of these discussions. I love the variety and challenges these bring, as well as seeing the client and teams be successful.

What’s the worst piece of advice you’ve ever received?

“Sometimes you just have to scare them a little.” This was told to me in 2011 by a director who said if someone couldn’t deliver, I should tell them their job was on the line. This transactional thinking may work in the short term, but it’s not an ongoing strategy to retain talent.

What keeps you at night?

Two things:

1. Does my team have what they need to be successful? I get work done through others, so I want to make sure they have the tools.

2. Are we doing the right thing? The pace of business and consumer changes are only getting faster. We have to continually look at our projects and ask if they’re delivering strategic value, or if something else is a higher priority.

What would you give a Ted talk on?

“Never Underestimate the Gift of Adversity” From leading tough projects, to dealing with tougher people, to grinding through an ultra-distance race, never bet against yourself because you just might win! Every adversity we face is a gift, an opportunity to learn and grow. Chances are, you already have the tools to be successful, you just don’t know it yet.

How does the reality of your job differ from people’s perception of it?

Where to begin? When most people hear “Project Management”, they think of someone who creates a schedule and then continually updates it. They also associate it with endless amounts of paperwork and status reports. Are schedules and statuses part of a project manager’s job? Yes, but, it’s a small amount.

Here’s how I operate.

Engagement. I spend a lot of time focused on the people I’ll regularly interact with. By getting to know them, understanding how they work and the best way to communicate, I establish trusting relationships.

Begin with the end in mind. By understanding a company’s strategy, we can prioritize the work needed to make it a reality. I like to talk governance (a 10-letter 4-letter word to some) so only the right work gets prioritized at the right time. So often I hear people talk about having ten #1 priorities. Governance is key to reducing this. We also try to clearly define “done”.

Pragmatic approach to planning and issue resolution. I once created a 300- line project plan. It was only valid the day I created it. Never again! Now, I start with the delivery date and work backwards, focusing on the key milestones. Every project I’ve led has had issues, so I ask the team to bring them forward as soon as they even think they have one. Let’s solve it as a team!

Focus on outcomes, not the process. Sure, processes are important, but where I focus on a lot of energy is on the outcomes.

What are we delivering to the company? I can make just about any process work, but if I’m using a great process on a nonvalue add project, I’m doing the company a disservice.

What’s one thing the local business community could do to help you/your organization?

When you or someone you know has too many priorities and doesn’t know where to start, BTG consulting can be your trusted partner to get you off the ground!

What’s your “Why”?

Though I’m a consultant, I like being thought of as a “Helper” more. I get my greatest sense of achievement seeing a team do something great.

What part of your job would you use an “Easy Button” on, If you could?

Meetings. I don’t like meetings, but I have a lot of them!

What’s one characteristic you believe every great leader should possess?

The ability to create a psychologically safe environment for their people to work in.

What’s one way you foster creativity within your organization?

I ask “What if…” questions. The more you ask this, the more creative the solutions will be.


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Brady is the Editorial Director at Spotlight Media in Fargo, ND.