How Leadership Differs in Structured and Unstructured Environments with Joseph Schmitt

In this episode of the B2B Leadership podcast, I spoke with Joseph Schmitt, Vice President of Customer Success at UpKeep Maintenance Management.
In this episode...

0:21 - Joe's background - Joe explains his role at UpKeep Maintenance Management.
2:08 - First leadership position - What led to Joe's promotion into a leadership position?
4:05 - A well-oiled leadership machine - What is a leadership environment like when everything is already dialed in?
7:26 - Key foundational principles - Joe looks to bring these key principles to an organization.
9:52 - Quantitative and qualitative measures - What qualitative measures are being looked at from a leadership perspective?
12:50 - Unified expectations - Do a team's expectations evolve over time or are they standard guardrails of how to operate?
17:06 - Mindset shift - How did going from an individual contributor to a leader change Joe's perspective?
20:44 - Autonomy versus neglect - How do you strike a balance in this area?
27:09 - Joe's advice to himself - What advice would Joe give his younger self?

Connect with Joe Schmitt: https://www.linkedin.com/in/josephschmitt/

Learn more about UpKeep Maintenance Management at https://www.upkeep.com/

Learn more about your own leadership style at:
https://www.30dayleadership.com/

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This episode was brought to you by B2B Leaders Academy

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Have you been part of both structured and unstructured environments?

In this episode, Joe Schmitt shares the differences between structured and unstructured environments from a leadership perspective.

Keep reading to learn more.

Joe's background

Joseph Schmitt is the Vice President of Customer Success at UpKeep, an Asset Operations Management solution company helping maintenance and reliability teams run their operations efficiently and effectively.

While a large majority of B2B SaaS businesses focus on the business, UpKeep focuses on the end-user, specifically, the blue-collar workers out there in the field who are doing all the critical things with their hands, to help them do their jobs a lot easier using technology.

First leadership position

What led to Joe's promotion into a leadership position?

Joe had an untraditional path to getting into technology and leadership. He didn't have any direction on what he wanted to do when he was going through college until he got involved in retail management.

He worked in retail management for a while and eventually made his way to Starbucks, where every aspect of the business has been figured out. And that's where he learned the fundamentals of what it's like to be a leader, which then led him to the opportunity of getting to work with startups, and then within technology.

The experience he had at Starbucks which had such great structure was super applicable to the startup world that did not have structure. From there, he started really understanding the style of leadership versus management.

A well-oiled leadership machine

What is a leadership environment like when everything is already dialed in?

Joe says, when he was in Starbucks, there wasn't too much to figure out. Everything was already dialed in. What they focused on was how to stay in line with the company's caliber.

A part of their focus was how to engage with their customers. Joe was able to showcase his previous physical customer service experience of providing value and bring it to the digital world that is still about providing value to the customers. There's a people element across the board as well. Understanding what the motivators are behind anybody's position is critical to the leadership role. That's a key piece that has to be done.

People often get a little bit hung up on the fact that if they don't get into this role, they can't get to where they want to be. But the reality is that you can learn at every single position, regardless of level, company, and industry. As long as you're growing and learning, you will be able to apply the tools you've learned along the way.

Remember that regardless of your background, each thing that you learn along the way paves the way for the next step.

Key foundational principles

What are some key foundational principles that Joe looks to bring to an organization?

Joe says the major key principle is the concept of autonomy and structure. The idea behind this is that you essentially are encouraging the roles to have autonomy and structure. It's balancing between the two.

For the structure piece, it's making sure that the team has a clear understanding of what's expected from them, both quantitative and qualitative as well. And they also understand what resources and guidelines are available for them. For the autonomy part, it's encouraging them to improvise and figure out how to actually achieve their quantitative measures in their role.

Nils calls it "guardrails and freedom". You have to have guardrails to provide the structure, but you have to have the freedom to operate within those guardrails, otherwise, everything gets really boring.

Quantitative and qualitative measures

What qualitative measures are being looked at in the autonomy and structure area from a leadership perspective?

Joe shared that in UpKeep, they have a CS expectations document that is structured in Meets Expectations, Below Expectations, and Exceed Expectations. And it's broken down into a few different categories that provide team members a structure, and an idea of what it looks like to be a good team member in the CS department.

With this, they learned that setting clear expectations gave the team guardrails that can be used in all situations. By having those clear expectations, everyone understands what's expected from them.

Unified expectations

Do teams' expectations evolve over time or are they standard guardrails of how to operate?

Joe says, for the most part, the core aspects of it have stayed the same year over year and have been adjusted over time depending on the situation.

They usually explain it to the team during onboarding so everyone has unified expectations. Having clear expectations from the beginning is very important. So, when someone does not do it, it's not that they're doing a bad job. It's just that they're not living up to the expectation that was set.

Mindset shift

How did going from an individual contributor to a leader change Joe's perspective?

Joe used to struggle with finding time to be strategic in his role until his mentor told him that he needs to delegate some of his tasks to his team members. He was told that you're withholding opportunities when you don't delegate out.

There may be something on your plate that another team member might be interested in or they could take ownership over. That's an opportunity for them to explore new parts of the business, or maybe even lead down to a new career path.

As a leader, that gives you the opportunity to focus on more strategic activities for your team to make a bigger impact. Give them the ability to make decisions that lead to the delegation as an opportunity.

That conversation he had with his mentor changed his view towards leadership. A fundamental mindset shift that you have to focus on different things and see the world from a different perspective.

Joe then started delegating things and viewed them as opportunities for his team members. Some of them quickly adapted that same concept of delegation as an opportunity which allowed them to excel in their respective roles.

Joe felt proud knowing that he has a team in place that can be totally trusted and who figures things out, but also understanding when they can approach Joe to brainstorm some ideas. Because there's a fine line between autonomy and neglect and not putting people on an island.

Autonomy versus neglect

How do you strike a balance in this area?

A lot of these potential guardrails and freedom situations can go off the rails because sometimes without the right balance there, you get total complete neglect.

So to balance this, make sure that the team is aware of when they need to get help, and that there are resources available. Try to connect with other leaders that are more experienced than you and have conversations with them around the outcomes of what you're trying to do.

While the team is building the process and structure, you also have to follow up on how the progress is going and help them find potential blind spots or make suggestions on what they can do better. That's how you create balance.

All of this leads to a self-sufficient team. A team that understands what you're striving to achieve both in your individual roles and how that impacts the actual company's success. A team that has the ability to make decisions on its own. A team that takes on new opportunities that will help improve processes in their current day-to-day activities.

Having a self-sufficient team helps as it allows leaders to have more time to be strategic and this will help you handle any situation.

Joe's advice to himself

What advice would Joe give his younger self?

The biggest piece of advice Joe would tell his younger self is to try not to control everything. Because even with being in places where there is an extreme structure on it, there are still opportunities to delegate out.

Another one is to take a leadership approach of motivating people to achieve their outcomes versus managing them to processes. It may come with different levels of team members' experience, but starting early on is important.

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