How Leaders Can Support Team Success: An Interview With Nikole Dickman

“I think a large part of the small business owners’ journey is that they find themselves where they didn’t think they were going to be, and then they have to find a way to make the best of it.”

Still on the fence about whether or not to start a business? If you are, then you need to meet Envoy Managed Services CEO Nikole Dickman. Nikole’s IT company is the title sponsor for the Badass Business Summit this September, and the story of how Envoy was created might inspire you to take the leap from employee to business owner.

So Nikole’s journey from finance expert to CEO started when the company that she used to work for decided to relocate her and her team. But instead of moving, she started a business, brought the team back together, and became the outsource partner for her previous company. It was a bold move for someone who had never really been a CEO of a company before.

“I didn’t think that this was something that I was going to do. And in the end, it was a big shift to go from managing an organization to trying to figure out how to lead an organization,” Nikole said. “I think a large part of the small business owners’ journey is that they find themselves where they didn’t think they were going to be, and then they have to find a way to make the best of it.”

Nikole admitted that none of it was planned out in advance. But she knew the business idea was viable, so she followed her heart and her gut. “Why not take the chance? What’s the worst thing that can happen?” she noted. “The worst thing you can do is fail, and as long as you make something out of that failure, you learn a lesson.”

Of course, going from startup to scaleup is not without its challenges. Nikole quickly found out that building relationships was crucial to business success. While a lot of companies would send their sales teams to attend conferences and networking events, Nikole wanted to attend them herself so she could talk with the people they want to work with. In fact, she said they never had a sales team because she didn’t feel comfortable having one.

“That’s sort of what made me decide to get involved and push outside of my comfort zone,” Nikole explained. “I was in a sales meeting a while back, presenting, and one of the people in the room asked me, ‘You’re the CEO, why are you here?’ So I thought for a moment and said, ‘I’m here to figure out if we’re going to work well together.’”

To be clear, Nikole is not an IT expert. She doesn’t know all the intricate ins and outs of IT even though she runs an IT company. But what she did was she took what some would consider a weakness and turned it into an absolute strength.

“I felt like, how can I possibly go out there and talk to people? I’m the wrong person. I can’t answer those technology questions. But I understand it on a basic level enough to communicate the message,” Nikole explained. “There’s a lot of people sitting on the other side of the table that really need what we have, but don’t want to talk in acronyms and all these high technology terms. So what I thought was something that was going to hurt the sales process, I think helped it instead.”

“We have technical people that are there to talk about all the details. But it’s a relationship; and it’s still trying to fill the needs of the clients. I think maybe not knowing all the technical terms helps that in many cases,” she added.

But things didn’t always run smoothly for Nikole and her company. A couple of years ago, a major client decided to downsize and Envoy’s services were no longer needed. Throughout it all, Nikole emphasized the importance of the team. She believed that everyone has an important role to play and they either succeed together or fail together.

“Do I really want to let part of the team that we started the company with go just because that’s the easy answer? No,” Nikole stated. Instead, she got the team together and asked them to help her figure out a way to move forward. At that point, it was either go big or go home, so they formed what became known as Growth Task Force to ensure that she could keep her team together.

Nikole’s passion to protect her team is truly inspiring. So I asked her how somebody could rally their team like she’d done? How could they get their team to up their game and jump on board?

According to Nikole, having a foundational relationship with the team members was important. So as a leader, you need to take the time to get to know the people that are around you. You need to invest in them, understand what drives them, and what motivates them.

She also pointed out that business leaders shouldn’t be afraid to be vulnerable, that they shouldn’t be afraid to go to their team and say they don’t know the answer. “You’ve got a team around you for a reason, use them. They’re going to have ideas and they see your business from a different perspective. So there’s absolutely no shame saying, ‘I don’t know what to do.’”

“Anyone should surround themselves with people that are smarter than them, and have their own talent set. To not tap into that and use that would be a shame. Everyone around us is what makes our company successful. We all play a part and everyone has a perspective.”

So how important is it for a CEO of a company or somebody who’s running their own business to be authentic with their team, with the world, with what they’re doing? Well, Nikole believes that there has to be a balance between being authentic and being too open.

“There’s a balance and it’s not perfect, but you kind of have to feel your way,” she explained. “You have to be authentic, but that also comes from knowing that you can deliver on what you said, that you’re going to keep your promises, and that you are trustworthy. All those things build into it. So if that’s really who you are, then that should come through authentically.”

You can see that Nikole has learned a lot about herself in the past five years, and despite all the struggles she faced, she has come to appreciate the journey to get to where she is now.

“I didn’t ever think this is what I would be doing, but now it feels like this is exactly where I was supposed to be,” Nikole said. “I love feeling uncomfortable, and not because that part’s fun. I don’t love the fact that we go through challenges or crises or places where I’m forced into a decision. But I’ve learned to appreciate that this is where I am right now.”

That was one of the most powerful statements she made during the interview. Nobody goes through life and says, ‘Let’s see how uncomfortable I can get.’ But Nikole has evolved in the past five years, and she has transformed into something more.

“It has been an evolution to go from trying to please everyone. I think for a while, maybe that insecurity and just trying to keep everybody happy was actually stopping me and the people around me from doing what we needed to do. You can’t please everyone. But I certainly felt like that was my job. They’d taken a chance on this. Somehow I had to make sure every day and every decision I made everyone happy and that’s exhausting. It can’t happen that way. So it’s been an evolution.”

“How do I give everyone a voice, but not a vote? How do we make sure everyone feels heard and that they’re living their best life while being a part of this team without trying to cater to every single person’s needs and wants? It’s a balance for sure.”

As we neared the end of the interview, I had to ask Nikole if she had any advice for anyone who’s contemplating starting a business or transition into another business during the current situation, and she said that you have to make sure you have a sound financial model first.

“How are you going to do it? How are you going to pay for it? How is that going to work? How are you going to get your voice out there? How are you going to sell? It takes a long time to fill the funnel, unfortunately. So there has to be some sort of a plan,” Nikole explained. “You have to know that it’s going to work, then listen to yourself. If your gut and your heart tell you that you can actually do this, and you’re all in, then I would say jump in.”

So what’s next for Nikole Dickman? Where is this journey going to take her?

“I don’t want to necessarily know what the future holds. I want to be able to figure out what works right now, what we’re going to do to be elastic and continue to remain relevant and do things that are going to help our team move forward. I don’t want to write my script yet. And I know that you need, from a business perspective, 10-year, 5-year, short term plans. All of those things are necessary. But if you plan it all out and you’re not open to seeing what else is in store, then you’ve just limited yourself, and I don’t want to do that anymore,” she noted.

And that, ladies and gentlemen, is Nikole being authentic.