Karen McDonald has been a small business owner for over 25 years. For the last 12, she’s been juggling two businesses: Cascade Accounting and Tax, which helps SMEs navigate their finances, and Wise Owl Legal, which offers legal service management software.
As the founder and leader of both, Karen ensures everything stays on track.
“I keep everybody going,” she explains. “I determine the priorities, the outreach, talk to the law firms, understand their needs, and make sure that’s in our product.”
So, how does she juggle two thriving businesses at once?
Lists and metrics
“We’ve got lists of lists upon lists, and everything’s on a list,” Karen says.
This year, she’s working to consolidate everything into one comprehensive list. For each staff member, she keeps a single page detailing her priorities for them.
Karen also closely monitors business metrics. For example, she tracks how long it takes her team to complete tasks and uses that data to streamline operations.
“By knowing those metrics, I can make sure I’ve got people in place to do all the right things,” she says.
Making the most of technology
Karen describes herself as a “power user” of tech, embracing both well-known tools like Word and Excel and newer innovations. She credits her deep dive into technology as a key to her success.
“I’m the nerd that in the 90s, I was doing a job in town… on the bus on the way in and out, I had an Excel book, which I read cover to cover.”
She also makes it a priority to train her staff on the latest tech.
“When we have a huddle with the whole team, I always try and bring them something new that they can do with technology,” Karen says.
To ease the process of introducing new tech, Karen and her “offsider,” Gemma, test new products first. They document how to use them, then “drip feed” the information to the rest of the team.
“We will introduce [a new technology] to people as it’s relevant, but we also don’t want to overwhelm anyone. Gemma and I have the overall picture of the systems, and we just get other team members involved as it relates to their work.”
Systems and processes
Karen uses project management software called Start Infinity, a tool she and Gemma chose after trying several options. Along with this, she relies on Word, Excel, and QuickBooks to manage her operations.
Crucially, she uses her own software, Wise Owl Legal, in her accounting business for billing and document management.
“We run our accounting practice through Wise Owl Legal. That’s our document management and billing system. It then talks to QuickBooks in the back end.”
This integration allows Karen to effectively manage both businesses at once.
“If there’s something wrong [with Wise Owl], we find it first,” she says. “And, you know, people ring up the support, and they’re getting people who really know the product, which helps because it’s rare that we get a support call we can’t answer off the top of our heads.”
Both of Karen’s businesses are also entirely paperless, thanks to her introduction of PDF-XChange over a decade ago.
“We were already using Wise Owl and saving all our documents, but being able to effectively do all our editing on screen, do all our accounting work papers on screen has just been wonderful.”
When asked if she could have managed both businesses so effectively without her deep embrace of technology, Karen’s answer is simple.
“No.”
For Karen, new technologies aren’t just a “shiny new tool”, but essential to keeping her businesses thriving.
