Banner image for Scaling New Heights 2025, the premier accounting technology conference in the United States. The image features the conference theme and dates.
 

Working With My Spouse: Different Styles, Shared Success

Debra Kilsheimer
Posted by Debra Kilsheimer on Oct 21, 2026, 10:08:28 AM

The first time I went to my now-husband Hal's house, I asked if I could check my email. "Sure," he said. I sat down at his computer, fired up AOL, and heard the dial-up modem connecting to the internet.

"You don't have high-speed internet?"

"That costs money. What do I need that for? This works just as well."

Except it didn't.

Every time I used his computer, I waited for a page to load while Hal saw no reason to change anything. I kept telling him to try high-speed internet. Months later, he called me, all excited. "Guess what I did? I got them to give me three whole months for free." Not long after that, we were having dinner with friends when Hal started telling them how wonderful high-speed internet was. "You really need to get this," he told them. I sat there thinking, “I've been telling you this for months.”

I kept my mouth shut. That was probably good practice for the next 25 years.

Know what belongs to whom

About a month after Hal and I met, I was let go from my job at a law firm. After a temporary job with a CPA firm ended, Hal said, "Why don't you come work with me until you figure out where you want to work permanently?" I had already worked in CPA firms and knew there were things I didn't want to repeat. I hated tracking time in six-minute increments, and I hated hearing, "Because that's how we've always done it." I told Hal I'd work with him, but only if I could run the accounting side the way I thought it should be run.

"All right. Give it a try."

Hal loved tax and didn't particularly like bookkeeping, so tax became his and accounting became mine.

Apparently, there's something to that. A study of 184 copreneurs, couples who jointly owned and managed businesses, looked at how they divided responsibilities and made decisions. The researchers described those partnerships as being based on a clear division of responsibilities and mutual trust and confidence.

His tax calendar is still a piece of paper. I would never do that. When I hear him complain about a client who keeps creating problems, I immediately start thinking about how to fix it. "What if you did this?" I'll ask. "What if you changed that?" He listens and then changes nothing. Apparently, he would rather complain. They're his clients.

When I hear about new software, I get as excited as I did when I was a kid and heard the Good Humor truck coming down the street. Hal wants to know what's wrong with whatever we're already using. If you picture the technology adoption curve, I'm on one end, and he's on the other. Together, we make average.

I once got excited about a new piece of practice management software. Hal didn't think we needed it. I did, so I signed up. We never got it implemented, and I couldn't get out of the contract. I paid $1,794.75 for software we never used. Hal never said, "I told you so." He could have.

Figure out what is worth the fight

Hal creates his invoices in Microsoft Publisher. Support for Microsoft Publisher ends in October 2026. When Hal heard that, he came into my office and asked, "What am I going to use instead?" I suggested QuickBooks Online. "I'm too old for that. Maybe I'll learn Word." I've been hearing that he's too old to learn new technology for about 25 years. They're his invoices. Microsoft Publisher can slide. Pricing can't.

This summer, a longtime client opened a restaurant, and we started doing the accounting before we'd settled the additional fee. I should have settled the price first. I didn't.

By July, I told him we had to talk. My normal starting price for a restaurant is $2,500 a month. Because he had been a client for 20 years, I offered to add the restaurant for $975. Hal thought we should add only about $400 to $500. About $100 a week.

Hal didn't want to risk losing a client who already paid us $18,000 a year. I saw it differently. We had built the accounting so the client could see what was happening in the restaurant: daily sales, credit card deposits, cash, payroll, and the transactions moving between the restaurant and the retail business. He could see whether the restaurant was actually making money. It wasn't about how long the work took. It was about what the work was worth.

Hal would have made a different decision. He told me what he thought, I listened, and he trusted me to make the decision. I would make the same decision today.

I couldn't have built it with another me

When I went to work with Hal, he already had a successful practice. Hal was happy. I wasn't. I wanted to try new technology, build the accounting side differently, and see how big we could make it. At one point, our little home-based practice reached $1 million in annual revenue. We did that while disagreeing about an awful lot of things.

I couldn't have built that business with another me. I didn't always listen to Hal, which is how I ended up paying $1,794.75 for software we never used. I could probably make a very good case for getting rid of his paper calendar. I don't. It works for him.

If you're going into business with your spouse, don't expect to agree on everything. You won't. There will be times when working together is harder because you're married, not easier. But after 25 years, I wouldn't have wanted to build this business with anyone else.

Hal and I met online. Think about that for a minute. I met a man on the internet who was still using dial-up. During our first phone call, I asked what he did for a living. "I'm an accountant," he said. I rolled my eyes and thought, “Oh my gosh. He's probably really dull.”

He wasn't.

Not long after that, I walked into his business with plenty of opinions about how I thought accounting should be done. He listened. "Give it a try."

Some of our ideas worked. Some of them cost $1,794.75. I am the luckiest girl in the world.

And if Hal ever tells me he's ready to learn QuickBooks Online, I'll think Christmas came early.

Topics: Operational Advisory


 

Sign up and stay plugged into the education, news pieces and information relevant to you.

Subscribe to The Woodard Report today! 


Do you have questions about this article? Email us and let us know > info@woodard.com

Comments: