Squishy conversations? Retain staff and challenge the status quo with Carla Caldwell


  • Carla Caldwell, founder of Caldwell Consulting and Training, helps accounting firm owners with tech implementations and training.

  • Sometimes the David vs. Goliath battle isn’t company vs. company. Rather, it’s a growth vs. non-growth mindset.

  • Carla encourages managers to have more “squishy conversations” with employees. This means acknowledging their lives outside of work.

Carla Caldwell didn’t follow the same path as the rest of her family. Medicine just didn’t appeal to her. But accounting and education did.

Working while putting herself through college was her first exposure to accounting and business administration. The company she worked for went through a software implementation that went unexpectedly poorly, but it led to an epiphany. 

“I realized all of my accounting knowledge and my nerdy techie knowledge could combine together as a big superpower,” she says. 

Her passion for tech education and accounting led her to education roles at Sage and Xero. But in 2015, she struck out on her own with Caldwell Consulting and Training. There, she helps accounting firms with tech implementations, process improvements, and education. 

Carla also operates Candella Accounting & Advisory Services, a group of nine women who do accounting and bookkeeping for nonprofits and small businesses. 

Carla joins her old friend and Karbon co-founder Stuart McLeod on episode 68 of the Accounting Leaders Podcast, where they reminisce on the pre-Karbon days and talk about tech innovation. Plus, Carla shares why accounting leaders should be asking “squishy questions”. 

Battling the status quo

At Xero, Carla worked on the leading edge of converting accounting to the cloud.

And in the early days of cloud accounting, it was more than just one company vs. another. It was a non-growth mindset and resistance to change that brought the biggest battles.

“It was exciting to explore something new and talk about different ways of doing things,” she says.

“I will never forget having a sign-on sheet on an iPad for people to use to check in for their CPE. It was a PDF on an iPad—it was the coolest thing. And it was so different and we said ‘Okay, we’re embracing this technology and we’re really going to do things differently and think differently’. It was exciting to be in the early stages of that.”

Not only was she at the forefront of the cloud accounting revolution, she was also a pioneer of remote work in the US. After she had her son, she petitioned Xero to let her work from home like her colleagues in New Zealand.

“I didn't want to be driving all the time,” she says simply. “Later on, when I started my own firm, we've been remote before remote was required and we’ve continued that way.”

The tech transformation

Stuart asks Carla what tech changes in the last 10 years have made the biggest impact. While she admits she’s no tech visionary for what’s next, she’s come to appreciate what technology enables accountants to do—especially when it comes to freeing up their time.

She likes that tech gives accountants time to do more valuable things, like getting more face time with clients or doing more advisory work. 

I think sometimes accountants and people in general can be afraid of technology. We have to learn to use it as a tool rather than feel like you're being completely replaced. Use that as a tool to enhance what you're already doing for your clients.
Carla Caldwell, Caldwell Consulting and Training

There are a couple of new changes she’s enjoyed. One is being able to meet virtually, easily. And the other is Karbon. 

“Karbon is the spine of our organization. It's the big deal of what we do inside of our practice, and has allowed us to really continue to grow and thrive as a remote team. We have a place to communicate and do all the things that we do,” Carla explains. 

Recommended reading: How to build an autonomous accounting firm culture

Having ‘squishy conversations’

In today’s market, it’s a challenge enough to find great talent. That’s especially true in accounting where the retirement rate is higher than the rate of new accountants entering the workforce. 

But once you get a great employee, the next challenge is to keep them.

“For our current talent, we have to value them and encourage them,” Carla says. “It amazes me that there are still people out there that think, ‘Well, you're salaried. So therefore, I can work you 80 hours a week, and you should just be happy to have a job.’ Those days—if they're not long gone—are on their way out.”

In addition to not overworking her staff, Carla has a unique approach to work-life balance. She prefers acknowledging that our lives outside of work are part of our work, too. She explains her concept of ‘squishy conversations’.

“We are seeing a definite need for us to address some mental health questions. In our society, we have a lot of people that are burnt out. And there's only so much motivation you can give people,” she explains.

“We do have to figure out how to continually engage with our team. And it's a lot more of what I call ‘squishy conversations’. We're chatting about families and asking ‘How are you feeling?’ Sometimes that feels a little odd for some of our leaders.”

Seeing your employees as whole humans and not just productive machines will create an environment where people want to stay. She finds this especially true with remote teams, where connection sometimes gets lost. Taking the time to check in mentally with the team can make a huge difference. 

But Carla also cautions that leaders need to be mindful when having these conversations: “They have to happen in a tactful way—right place, right time, and within boundaries.”

Living the dream

Stuart asks Carla on the podcast if she’s in her dream job. And she feels that she is. 

“It's a dream job. But I don't know that I would have ever dreamed it up,” she jokes. 

She enjoys speaking to groups at conferences and being able to pass on tips and tricks that firms can take back and put to use right away. And that’s also the future of accounting as a whole. Carla sees the potential to get more valuable time with clients. The growth opportunity lies in leveraging the tools that we have to grow alongside one another.

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