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How To Get The Most Value From Your Bookkeeper

There you both are.

You’ve both put yourself out there, taken a chance on one another and here you sit, giddy with excitement and nervousness about what could potentially lie ahead. After all, the goal is to plan a future together so to say that there’s a lot on the line is a massive understatement.

You fidget mindlessly with a straw wrapper and hope that the conversation proves effortless and engaging. Intimate, even.

‘Could this be it?’ you both ask yourselves. ‘The One? Could this be forever?’

And it just might. It certainly has the potential – but only if you know exactly how to get the most out of your … bookkeeper.

Sure, it sounds like the trappings of every first date. But, if we’re really honest with ourselves, it’s not so dissimilar, either.

Because as the landscape of employees changes – that is the seismic shift from in-office employees to those who work remotely – leaders must be adept at modifying how they hire and delegate to their teams. Or, in this case, their bookkeepers.

But know this: Finding and ultimately hiring a bookkeeper that is The One – successful, capable and extraordinary – is possible.

And it starts with the Three E’s – establish, explain and execute – to lay the right foundation for the right results.


You can’t hire for a role you don’t know and understand yourself. Take the time to get prepared before ever scheduling the first interview with a prospective bookkeeper. It will save you both wasted time and energy as you’d otherwise muddle your way through the hiring process without a clear understanding of, well, anything.

So if your intention, for example, is to hire a virtual bookkeeper, be sure to include that detail in your dating profile, err, job description. Seems obvious, but it’s an oft-overlooked detail that is pretty critical. Include detailed language about your expectations and any opportunities related to the virtual nature of the position. Be sure it emphasizes the need for timely digital communication and specifies equipment requirements, like a laptop and high-speed internet.


Now is the time to clearly share your expectations, availability, and scheduling.

First, outline your more general, overarching expectations – of them and their role, as well as any measurable objectives.

Next, it’s time to get a little – read: a lot – more granular. Define your expectations regarding availability by phone, text, email, chat or otherwise. Share your goals, objectives and deadlines, being sure to explain exactly how those items will be tracked and measured. Schedule meetings – whether onsite, weekly, monthly or quarterly – and explain your expectations regarding attendance in advance.


This one is where the rubber meets the road – and can often prove most challenging. Everything that has come before this is all for naught if you aren’t ready to hand over the reins to the person to whom you’ve entrusted your bookkeeping.

But – and this is big but – this is also when you stand to get the most value from your bookkeeper.

This is when you must trust your bookkeeper to do that for which they were hired. But this isn’t a blind handoff; you can still stay connected and engaged without micromanaging.

And the trick is to listen. Listening is at the core of emotional intelligence, and great listeners also ask questions. Actively asking questions not only helps you better understand your bookkeeper, but makes them feel more valued, too. After all, they are the experts here, so this would be the time to defer to their experience and expertise.

Now, your bookkeeper feels – and hopefully is – valued and you get value from your bookkeeper. Win-win.

Sounds like a match made in heaven, right? Maybe – just maybe – even a forever kind of match.

Good thing you took a chance on that first date, huh?

Get Back To Your Vision. Leave The Bookkeeping To The Experts.

This is cause for celebration: You’ve decided to delegate a few piles off your desk – and this is a huge step for any leader. To help you take the next step – choosing the right bookkeeper – here are some of our favorite interview questions we use when looking at potential bookkeepers. And, because we’re just cool like that, we’ve also given tips on what to look for within answers.

Happy hiring!