21 Interview Questions to Hire a Great Controller

Before we get into the meat and potatoes of today’s post, I wanna give a shout out to friends of the newsletter (Tim Dillon voice) at Rillet for their latest fundraise. Based on this announcement it appears they will be funding AI native ERP innovation and the main stage at accounting Coachella.

I hope they send me tickets if Nickelback is playing this year.

That’s a big number!

Anywho! I wrote this post for Rillet’s accounting community, “Close Club”.

You can use this guide if you are interviewing a Controller for your own team (especially helpful for first heads of finance), or trying to get a job yourself (shameless plug: I can help you hire and get hired if you’re in market).

Cue the Semisonic and let’s get to it!

When I ascended to the position of Master of Coin, my first mission was crystal clear: find a badass Controller. I dedicated endless hours concocting interview questions that could separate the smooth talkers from the relentless go-getters.

The outcome? A comprehensive set of 21 thought-provoking questions; a case study of sorts for any Controller candidate to chew through.

And let me drop some knowledge on you about case studies…I firmly believe that every finance or accounting professional should take the time to complete a written case study.

Why? It reveals their written communication skills (a must for virtual teams), their wizardry in Excel modeling, their mastery of PowerPoint, and their overall attention to detail.

We can't have someone who can recite blog posts (like mine), yet can't deliver top-notch work. And if you lack the willpower or motivation to take on the challenge, well, I guess my screening tactic did its job. You've self-selected out.

Now, get ready to embark on a journey through my epic "take home questionnaire" for accountants.

You can feel free to add your own as they relate to your monetization model (SaaS, consumption, marketplace, B2B, B2C) as you see fit. Oh, and I’ve included some AI “build with Claude” tutorials below to see if they can FITFO (figure it the f out).

In honor of 50 cent, here are those 21 questions.

Walk me through your month end close process.
1. How many days would you aim to have the books closed by?
2. What would you accomplish on each of those days?
3. What’s a check you would perform or implement to ensure you are not moving too fast and sacrificing accuracy?
Tell me about a time you helped an employer save money. What was the result?
What will be your number one concern on a day-to-day basis, in a role like this?
Tell me about a system you implemented (other than NetSuite). What was the impact?
Tell me about a mistake you made while implementing a tool, and what did you learn from it?
Do you have any experience in setting up financial reporting controls? If so, please give an example of a control you were able to design and implement.
What governance would you put in place around cash?
Do you have any experience with audits? Please elaborate.
Where do you think hosting costs (AWS, GCP, Azure) belong within the P&L?
Tell me about your current order to cash reconciliation process.
Tell me about a time you deal with a difficult delinquent receivable situation and how you resolved it.
When do you propose to capitalize rather than expense a purchase?
What overhead expenses would you suggest we allocate between departments?
What was something you solved that used to keep your old CFO up at night?
Stack rank your level of comfort / expertise in the following areas: technical accounting, operational accounting, financial statement reporting, payroll, tax, treasury.
If you have a choice to pay for something using a wire, ACH or corporate credit card, what is your thought process?
Have you had any exposure to company equity plans? What impact would increasing an ESOP (Employee Stock Option Plan) have on the financial statements?
The CEO tells you we are launching a new product or expanding into a new country; what do you do?
How do you think about materiality and risk?
What spend management systems have you used in the past? What components were you able to automate by relying on a system?
Attached is a snapshot of our current P&L chart of accounts (using dummy data). What would you change? How could we improve it? Provide at least 5 recommendations [NOTE: attach your Quickbooks or Rillet or NetSuite export with dummy figures].

When it comes to the art and science of accounting, you need more than just an X's and O's kind of person. You need someone who grasps the underlying theory behind why the business demands certain actions. Sure, managing our financial position is part of the gig, but it's equally crucial to comprehend how it ties into our company's grand strategy. I'm not on the hunt for a mere number cruncher - that's a task we can outsource. I want a partner; someone who sees the bigger picture.

Getting someone who can successfully answer all of these questions, succinctly and accurately, will significantly de-risk your hiring decision.

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