It’s no secret that many individuals, and indeed, businesses, often wonder when they should rope in a professional to help manage their finances. “Is it time to hire a bookkeeper?” you might ask. “How do I know who would be the best fit for my business?” I encounter such business and bookkeeping questions frequently, and, though it may not be the satisfying answer you crave, the truth is, it depends on a myriad of factors, just as I’ve explained in my previous posts on S Corps and C Corps.

If you are a business owner who takes your venture seriously, treating it like a bona fide business – including having separate dedicated bank accounts for business expenses and personal spending, similar to a paycheck from an employer – it might be time to seriously consider bringing a bookkeeper into your fold.

“Just because you can, doesn’t mean you should,” is something my team—and clients—hears me saying all the time. This applies particularly to bootstrap bookkeeping. 

Can you juggle it all by yourself? Probably. 

But should you? Probably not.

However, it also applies to hiring a finance pro without a detailed get-to-know-you process.

Here’s why. 

A good bookkeeper does more than ensure your books are clean, compliant, and ready for your CPA. They also understand the best strategies to allocate your costs — or at least they should. Doing so can help you optimize your spending and finances efficiently, understand your cash flow, and thereby, maximize your profitability. 

Any accounting pros worth their salt ask lots of questions that probe into the nuances of your operations. In addition to asking what you’re doing, they should also focus on why it matters. When they understand that, they can better advise you on opportunities for greater efficiency in spending and processes. 

The number one question your bookkeeper should ask is “Why?”

I’m a big fan of Simon Sinek and his book, “Start With Why.” 

One word, three tiny letters. It’s the most important question in any business. And it’s your finance pro’s sharpest tool because it helps them dive deep into your business to find out

  • Why you do things a certain way
  • Why you consider specific opportunities 
  • Why you have specific goals  or make specific changes

You’ll get this question a lot during onboarding, as your finance team maps out the unique aspects of your business. But it’s not just for their (my) understanding. It’s also for yours. So much of the time, the why and the what of your business lives in your head, and when you’re asked for details and have to explain it to someone else, you get a great deal of clarity.

However, “Why” isn’t limited to onboarding. It may happen every time you bring on new team members, set a new goal, or have a new type of expense. And, you’ll likely find that you start asking your bookkeeper for their advice because of their unique perspective on your business.

What if they don’t ask “Why?”

A finance pro failing to ask “Why?” is like a ship’s navigator having a faulty map or hazy compass. Your business could go completely off track without someone keeping a close eye on operations or spending, and asking about specific expenses or strategies.

The last thing you want is misclassified financial data, extra expenses, or books that fall outside of compliance. In addition to cash flow problems, it limits your capacity to grow or meet your business goals. 

Ultimately, not asking “why?” can create a ripple effect of missed opportunities, mis managed resources, and less-than-optimal finances. 

“Why?” goes beyond bookkeeping

Why doesn’t only matter for your bookkeeper. Any professional you hire should be asking “Why?” because they’ll get great insights into how you do things and—more importantly, how you think.

Asking “Why?” goes beyond identifying areas of improvement. It often inspires new, innovative ideas that have the potential to propel your business lightyears forward, simply because you’re getting an outside perspective that sees your business in a new light.

That means if your finance team isn’t digging deeper, you should flip the script and ask them “Why?” 

If you’re ready to work with a bookkeeper, controller or fractional CFO who is committed to your success and ready to ask you “why?” or if you don’t think your current professional is digging deep enough, we’d love to chat. Schedule a call with us!