How to Get More Out of Your CFO (and How I Think About It Differently)

Bob Wang

Aug 27

4 min read

If you're a founder reading this, there's a good chance you've had at least one frustrating experience with a finance person. Maybe it was a CFO, a controller, or a consultant. They were smart. They knew the numbers cold. But somehow, every conversation left you feeling like you'd just sat through a lecture you didn't sign up for.

I've seen this from both sides. I've been the entrepreneur — I built and sold my own firm;
I've been the CFO who walked into a company mid-crisis and had to earn trust fast; and
I've been the outside advisor called in when a CEO and CFO just weren't clicking.

Nine times out of ten, the problem isn't talent. It's translation.

The Detail Trap

Most CFOs come up through finance. They spent years in accounting, FP&A, audit, or corporate finance. They were trained to be thorough, precise, and methodical. That training is incredibly valuable — until it becomes the way they communicate everything.

I once stepped into an engagement where the outgoing CFO had built a 47-slide board deck every month. Forty-seven slides. Every variance explained, every ratio trended, every footnote footnoted. It was genuinely impressive work. The CEO told me he usually skimmed the first three slides in the car on the way to the meeting.

That's not a lazy CEO. That's a founder who thinks in decisions, not data. And the CFO was giving him data and waiting for him to find the decisions inside it.

Founders Think Differently — And That's the Point

When you've built something from nothing, you develop a specific way of processing information. You want the headline first. You want to know what's working, what's broken, and what you need to decide right now. The supporting detail matters, but it matters after you know where to focus.

This is how I think about it: start with the punchline.

"We're going to miss Q3 revenue by 12%, and here's what I think we should do about it."

Now you have the founder's full attention. Now they're leaning in, asking questions, engaging with the details — because the details have context. They have a reason to care about them.

Compare that to: "Let me walk you through the Q3 revenue analysis. If you turn to page seven..."

Same information. Completely different impact.

What I've Learned Running Businesses (Not Just the Numbers)

Here's where my path diverges from most CFOs, and I think it's why founders tend to connect with how I work.

I didn't come up through a finance function and stay there. I built my own accounting firm from the ground up and sold it to Deloitte. I was the CFO who helped navigate a company through a $100 million private equity exit — not as an advisor watching from the side, but as a member of the team in the room when the hard calls got made. I went on to work as a principal at a private equity firm, evaluating businesses from the investor's side of the table.

That arc changes how you show up. When I sit down with a founder, I'm not starting with the chart of accounts. I'm starting with: where is this business going, what's in the way, and what levers do we actually have? The numbers are how we pressure-test the answers — they're not the starting point.

I've been the person lying awake at 2 a.m. wondering if a bet was going to pay off. That doesn't make me a better accountant. But it makes me a different kind of CFO.

Practical Ways to Make Any CFO Relationship Work Better

Whether you work with me or someone else, here are a few things I've seen make the CEO-CFO relationship dramatically more productive:

Tell your CFO how you want information delivered. Some founders want a 15-minute weekly standup. Others want three bullets in Slack on Monday morning. Others want a monthly deep-dive with a whiteboard. Your CFO will match your rhythm — but you have to tell them what it is. Most won't ask because they don't want to seem like they're not doing enough.

Ask for recommendations, not just reports. Push your CFO to come with a point of view. Not "here's what happened last month" but "here's what happened, here's what I think it means, and here's what I'd recommend." If they're not used to this, it might take a few rounds. But it transforms the relationship from reporting to partnership.
Give them the context they're missing. Your CFO can't read your mind. If you're thinking about launching a new product line, exploring an acquisition, or considering a big hire — tell them early. The earlier they have context, the more strategic their input becomes. Too many founders treat the CFO like a rearview mirror when they should be using them as a windshield.
Don't confuse thoroughness with value. A CFO who sends you a short, clear email with the three things you need to know is not doing less work than one who sends a 30-page report. They might be doing more — because distilling complexity into clarity is harder than just showing all the work.

The Difference Is the Starting Point

I've worked with brilliant CFOs who struggled to connect with their CEO, and it almost always came down to the same thing: they started in the weeds and tried to build up to the big picture. Founders need it the other way around. Big picture first, then earn the right to go deep by making the details relevant.

That's how I work with every client. I start with where your business is headed, what decisions are on the table, and what you're trying to build. The financial detail supports that conversation — it doesn't replace it.

If you're a founder looking for a CFO who's actually sat in your seat, I'd love to talk. Not a pitch meeting — just a conversation about where your business is and whether I can help.

Let me know how we can help! Reach out to Tee Up Advisors at info@teeupnextgen.com