Why October Is the Time to Start Planning Your Tax Season Hiring

October can feel early to start thinking about tax season hiring.

You still have several months before January. Year-end work has not hit yet, and there are plenty of other things that need your attention right now.

But if you already know you will need another bookkeeper during tax season, this is exactly when I would want to start planning for that hire.

I have seen what happens when firms wait until the workload is already there. Once January arrives and everyone is busy, hiring becomes one more urgent task on top of everything else. You are reviewing resumes between deadlines, trying to schedule interviews around client work, and hoping you can get someone hired and trained quickly enough to actually help.

That is a hard way to make a good hiring decision.

October gives you something that will be much harder to find a few months from now: time.

You Don't Want to Start Hiring When You Already Need the Help

There is a difference between knowing you will need someone and reaching the point where you needed them three weeks ago.

When you start early, you can think about what the position actually requires. Do you need a junior bookkeeper who can handle routine bookkeeping work with some oversight? Or do you need someone more senior who can work independently, troubleshoot problems, and take more responsibility off your plate?

Those are very different hires.

It is much easier to make that distinction now than when your team is overloaded and you are simply looking for someone who can start as soon as possible.

I wrote about this in my blog Why the “We Need Someone Now” Hire Can Cost Your Firm More Later. Urgency has a way of changing what we're willing to overlook.

A candidate has several years of experience. They know QuickBooks. They interview well. When you desperately need help, those things can start to feel like enough information to make an offer.

Sometimes they are. Sometimes they aren't.

Starting earlier gives you room to find out.

Hiring Is Only the First Part of the Timeline

One thing that can get overlooked in tax season hiring is that your timeline doesn't end when the candidate accepts the offer.

They still have to start.

They need to learn your firm's processes, understand their responsibilities, get familiar with the clients or accounts they will be working on, and figure out how your team communicates and handles questions.

If you wait until January to hire someone, you may be training them during one of the busiest times of the year. The people responsible for getting that new employee up to speed are often the same people who are already managing a heavier workload.

Even an experienced bookkeeper is going to have questions when they first start. Someone needs to review their work, explain how your firm handles certain situations, and help them get familiar with the clients and accounts they’ll be working on. When your team is already stretched thin, finding time for that can be challenging. 

That can put everyone in a difficult position.

The new employee needs help, but the manager does not have much time to give it. The manager needs the new employee to take work off the team's plate, but the employee is not ready to do that independently yet. The manager hired someone because the team needs help, but for the first few weeks, that new employee may actually require more of the manager’s time. 

There are questions to answer, work to review, processes to explain, and corrections to work through. Eventually, that person should be able to take work off the team’s plate. But there is a period before you get there, and January is a tough time to absorb that extra workload.

Starting the hiring process in October gives you more options. You may not need someone to begin immediately, but you can work backward from when you want that person ready to contribute and build your hiring timeline from there.

Use the Extra Time to Ask Better Questions

Having more time does not mean your hiring process needs to become longer or more complicated.

It means you can be more deliberate about the information you collect.

A resume can tell you where someone has worked and how they describe their experience. An interview can tell you how they communicate and give you a much better understanding of what they have actually been responsible for.

But you have to ask questions that get beyond the surface.

Instead of only asking, "How many years of bookkeeping experience do you have?" ask them to walk you through the work they handled themselves.

What did a typical month look like? What did they do when an account did not reconcile? What kinds of mistakes have they found in a set of books? When did they know they needed to ask someone else for help?

You are not trying to catch the candidate with a difficult question. You are giving them a chance to show you how they think about the work.

That is why we created this month's resource, The Better Bookkeeper Interview: 10 Questions to Ask Before You Make an Offer. It includes questions you can use to get a clearer picture of a candidate's actual experience, along with tips for asking questions in a way that gives candidates room to explain how they work.

Know What You Still Need to Verify

Starting the hiring process earlier also gives you something that becomes harder to find as tax season gets closer: time to make a careful decision.

When you are not trying to fill a position as quickly as possible, you have more room to verify a candidate’s bookkeeping skills, look closely at the results, and decide whether they are actually ready for the role you need them to fill.

If you uncover a gap in October, you still have options. 

Interview skills and bookkeeping skills are two different things, and you need time in your hiring process to evaluate both. 

If someone gives a strong answer about reconciliations, that is useful information. But if reconciliations are going to be an important part of the job, you may also want objective evidence that the candidate can actually complete that work correctly.

The same applies when you are hiring a senior bookkeeper. Someone may be able to talk through how they would approach a messy set of books. Before putting them in charge of client work, you may want to see how they perform when they actually have to identify and correct problems.

October gives you time to decide what needs to be verified before you make an offer.

You can determine what the interview will cover, what references can help you confirm, and where you still need evidence of practical bookkeeping ability.

For me, the missing piece was having a practical way to verify the bookkeeping side before the hiring decision was made. That’s why I created BookkeepingIQ’s live-proctored bookkeeping assessments, designed to help employers see what a candidate can actually do before making the hiring decision. 

Give Yourself Time Before Tax Season Gives You a Deadline

You may not need another bookkeeper today.

But if you know you are likely to need one for tax season, October gives you the chance to make decisions before the pressure is there. You can define the role, start looking at candidates, conduct better interviews, verify practical skills, and leave enough time for onboarding before your team is at its busiest.

I would much rather answer those questions now than try to answer them in January while also wondering how quickly someone can start.

If tax season hiring is on your list this year, now is a good time to start figuring out what you need and what you want to know before you make an offer.

If you're starting to think about tax season hiring and want to keep the conversation going, connect with me on LinkedIn. I regularly share what I've learned about hiring bookkeepers, evaluating candidates, and making better hiring decisions before the busy season hits.