In Chapter 6 of the classic children’s novel, Alice in Wonderland, Alice is meandering down a road and encounters the Cheshire cat in a tree.

"Would you tell me, please, which way I ought to go from here?" [asks Alice.]

"That depends a good deal on where you want to get to," said the Cat.

"I don't much care where—" said Alice.

"Then it doesn't matter which way you go," said the Cat.

"—so long as I get SOMEWHERE," Alice added as an explanation.

"Oh, you're sure to do that," said the Cat, "if you only walk long enough."

That’s a fine approach if you’ve fallen down a rabbit hole, but not very strategic if you’re a CFO looking to provide strategic leadership to your company.

Opportunities to automate the finance department and your broader organization are literally everywhere! But this transformation will only take place when the tech-savvy CFO is willing to:

  • Adopt the right mindset
  • Ask the proper questions
  • Assess the impact of the status quo, and
  • Act (get it done)!

Adopt the Right Mindset

If you’re going to be a proper catalyst for automation, your primary goal / focus must be to equip every individual in your organization to make the highest and best use of their time. If your people are your most important assets (and they are), it’s critical to view them (and treat them) as such.

I met with a CFO recently of a highly successful family-owned business. In spite of many decades of profitability and company growth, he shared his frustration that his financial team was content completing the same, labor-intensive tasks, creating the same backward-looking reports, and enduring agonizingly long close times. In spite of their resistance to change, he was determined to “change the mindset” of the team and provide the tools they need to make a more strategic contribution to the organization.

I invite you to start thinking like my CFO friend and endeavor to automate time-wasting, soul-sucking, low value-added processes and empowering your people to be more efficient, more creative, and more strategic.

Ask the Proper Questions

Once you’ve got the ultimate goal in mind, it’s critical to ask questions that properly uncover your most pressing automation needs and opportunities. Below are a few sample questions that can apply to any organization in any industry:

1. What are we doing in spreadsheets that should be done more quickly, more accurately, more collaboratively and/or more securely? Common culprits include:

  • Financial reports
  • Operational analysis
  • Dashboards, KPIs, metrics
  • Deferred revenue management
  • Budgeting and forecasting modeling
  • Allocations
  • Expense reports
  • Timesheets

2. What data do we enter more than once for the sole purpose of keeping multiple, non-integrated systems current?

3. For what processes do we primarily rely upon email and / or physically moving paper around one or more offices? (e.g. approvals – purchase requisitions, AP bills, timesheets, expense reports, etc.)

4. Where do we need greater security or auditability of our people’s access to or activity with data and applications?

5. In what scenarios do we lack a “single source of the truth” that is causing inefficiency, confusion, and poor internal or external customer service?

You probably have other questions that apply to your organization. Write them down while you’re thinking about it, and then ask key team members for their feedback. (They’ll be happy to share!)


This is a good place to stop reading and get busy on the above action items! Tune in next time for the conclusion of the article and ideas on what to do with all the candid, uncomfortable, and shocking, but vitally important truths you’ve just learned from your team!