📬 Transformation Urgency: Creating action without turnaround adrenaline

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I’m always looking for a new challenge. Send me your trickiest CFO dilemmas (anonymously if you wish), and I’ll answer them here.

👉 Send me your questions by filling out this form.

Now, on to today’s Mailbag.

We’ve got some great topics. Here’s what’s on tap:

Now, let’s get into it.

(Im)Patience from Charlotte, NC asked:

I previously worked in a turnaround situation where decisions were made based on combating what was going to kill us quickest. It was tough work, but on the whole, the core team was aligned on what the issues were, and did everything we could to fight them.

I'm now in a company that's more of a transformation play. Things are slowing, but nothing is imminently on fire. Outside of my boss (the CFO) and our new Chief Revenue Officer, there is no sense of urgency to fix the issues we are facing. You've written a lot on what to do in a turnaround situation. Any advice on how to drive alignment, results, and urgency in a transformation situation?

I feel your pain, (Im)Patience.

When everything is on fire, alignment comes for free. Everyone knows what’s going to kill you first, and the business naturally moves at a breakneck pace.

Transformations are harder. If nothing is imminently on fire, everything starts to feel optional.

One important thing I’ve learned during my career: the best results always come from being impatient with action but patient with results. Turnarounds don’t allow patience with results. Transformations do. But that does not mean you can be relaxed about pace.

The mistake many teams make is confusing “no crisis” with “no urgency.”

Transformation work lives squarely in the “important but not urgent” box. That is the most dangerous quadrant; where good work goes to die. If you don’t force urgency into it, it will always lose to today’s inbox.

Change needs a platform. A reason why this matters now.

In a turnaround, the platform is real and obvious. In a transformation, you have to create one. Not by lying, but by making the future consequences visible and unavoidable.

A few practical ways you can do that:

First, create a compelling vision of the future with transformation. Make it realistic but still inspiring. People need to see what good actually looks like. I shared how to do this in a recent piece here.

Second, create a painful alternative future without transformation. Paint an exaggerated but not sensationalized picture of where the business could end up if nothing changes. Be explicit that it’s not the most likely outcome, but ask the uncomfortable question: even if it’s a five percent chance, is that a risk you’re willing to run with this business?

Finally, narrow the agenda aggressively. One reason transformations feel slow is that they try to fix everything at once. They’re too big. Pick one thing. Do it properly. Get the boulder rolling.

The hardest part of any transformation is getting started. Once you get a few visible wins on the board, momentum starts to build on its own.

TLDR: In transformations, urgency doesn’t appear by default. You have to create it by making future pain visible, narrowing focus, and demanding speed on actions even while results lag.

Big Lebowski from the US asked:

I landed a job as the head of finance at my first venture-backed company (early stage, product market fit, AI company). I’ve only ever been in boot-strapped companies before, so “the board” was always the owners I saw every day.

At my new company, the board consists of a top-tier VC firm with other high-profile people. This is the first time I’m going to be working with a proper board of directors. Thankfully, I have a good team and CEO with me who have a long history with them.

For me, how should I operate the board room knowing these are VC investors, and is it any different than the advice you have given before?

Thanks for the question, Big Lebowski.

You’re right that I’ve written a fair bit on boards already, so that’s a good starting point.

That said, what you’re stepping into now is materially different from what you’ve experienced before, and it’s worth being explicit about why.

1. Fiduciary responsibility actually matters now: In an owner-managed or bootstrapped business, “the board” is usually just the owners. Your duty is basically to deliver what they want, within reason. If you’re unsure what that is, you can just ask them.

With institutional capital and a broader cap table, your fiduciary responsibility shifts to the shareholders at large. That’s a more abstract concept, and it requires a much firmer internal compass about what is genuinely in the best interest of the business and its owners over time.

2. These are true non-executive directors: You’re now dealing with people who are not in the business day-to-day. That’s a double-edged sword.

At their best, they provide perspective, pattern recognition, and a great network. At their worst, they’re far enough away to miss nuance but close enough to be dangerous. Either way, you are their primary source of truth. That is very different from working with owners who see everything themselves.

3. J-curve cashflows feel weird if you’ve only bootstrapped: In bootstrapped businesses, you learn to spend what you’ve earned. In a VC-backed business, by definition, you are spending money that the balance sheet hasn’t earned yet. You’re pulling forward growth based on belief in product, team, and market.

That can feel profligate the first time you live inside it. Get comfortable with that discomfort, but don’t let it turn into sloppiness.

4. Growth dominates everything: A VC board ultimately cares about one thing: growth that unlocks the next step up the valuation curve. Everything else is subordinate to that.

They will talk about culture, hiring, burn discipline, and governance, but those are all in service of hitting the metrics required for the next round and, eventually, a liquidity event.

5. Caliber is high, operational depth varies: This is a generalization, but many VC board members are extremely smart, very pattern-oriented, and more academic than operational. Some have outstanding operating experience. Many don’t.

That means they can be brilliant at asking questions and spotting inconsistencies, but sometimes wildly underestimate what it takes to actually execute inside a business. Knowing which type you’re dealing with matters.

In other words, what you had before wasn’t really a board in anything other than name. This is night and day.

First, be crystal clear on what you’re being measured on: What are the non-negotiables? It’s usually something like: grow ARR from X to Y in 12 months, keep CAC below Z, churn below A, and runway above B.

Once you know that, you need to know those metrics cold. By component. By cohort. By driver. You should never be surprised by a board question on them. And make your monthly reporting outstanding across those metrics.

Second, invest in relationships outside the boardroom: Don’t limit your interaction to the formal board cycle. Spend time one-on-one where you can. Show that you’re thoughtful, prepared, and a straight talker. That reduces the risk of surprises for everyone.

Boards work best when there are no first-time conversations in the meeting.

Third, earn the right to influence: Do not assume they’ll automatically trust your judgment, even if they’re friendly. That trust is built by being a consistently reliable source of high-quality information.

Once they see that you understand the business, the numbers, and the trade-offs, (and that you deliver on their requests and your promises) they’ll start listening when you have a point of view. When that happens, use it sparingly. Save your influence for the moments that matter.

Do those things well, and working with a top-tier VC board can be one of the most intellectually rewarding parts of the job.

TLDR:

VC boards are fundamentally different. Get clear on the few metrics they truly care about, master them end-to-end, build trust outside the boardroom, and earn influence by being a consistently reliable source of insight before you try to shape decisions.

Jon K from New York City asked:

Hi, I’m head of finance at a $10M ARR growth equity-backed startup that I joined nearly 5 years ago.

I came up through math and computer science, and eventually took over the role here through circumstance. I fear it’s an issue because - though I love it - perhaps I lack the background credentials for future growth: I have zero accounting or finance degrees, nor work experience besides this. Will it limit me in the future?

I’m 27 years old and considering what to do to best position myself to be a CFO long term. Stay put? MBA? Specific type of role? Thanks!

(PS - I’d say we’re past MVFF but not quite stage 3. I’m the generalist you described in stage 2 — I use an outsourced accounting firm for accounting and do all FP&A, board reporting, etc. I really love your blogs, which I just discovered last week: it feels like finding gold for me!)

Thanks for the question, Jon K.

First off, congratulations. What you’ve done by 27 is seriously impressive.

It’s also a great sign that you’re self-aware enough to be thinking about blind spots early. The core challenge you’re naming is real: You need to grow at least as fast as the business so you remain the generalist it needs. That gets harder, not easier, from here.

The right answer depends on the details of what you’ve actually learned over the last five years, but I’ll give you my honest view.

While not everyone agrees with me, I do believe accounting fundamentals matter for a CFO. You are the accountant-in-chief, whether you like it or not. You can hire great people around you, and you should, but you can’t outsource accountability.

I am not suggesting you go and get an accounting designation. You’re past that stage. The reps you’re getting as Head of Finance in a real business are far more valuable. But I would strongly recommend some focused executive education in accounting fundamentals. A few intensive days that really lock in how the statements fit together, how judgment shows up, and where risk hides.

I did three years in Big 4 audit at the very start of my career, and I’ve leaned on what I learned there ever since.

You’ll hear plenty of people say you don’t need to be a CPA to be a CFO. That’s true. But it helps more than people admit. My inbox is full of first-time startup CFOs who came from banking or consulting and say some version of the same thing: “I feel completely out of my depth.” So yes, upskill here. Take a genuine interest. And hire a great, experienced controller you can learn from.

In your specific case, there’s another dimension. You’ve only ever worked in this one business, and you don’t have a formal business education. For that reason, an Executive MBA could actually make sense. Not for the credential alone, but for exposure to other operators, industries, and problems. And for broadening how you think about business as a system. It’s a big commitment ($ and time), but I think, in your case, it’s worth seriously exploring.

That said, don’t lose sight of this: you’ve already done the hardest part. You’re in the seat. You’re operating at $10m ARR. The best experience you can get is still at your desk every morning.

Just don’t leave anything to chance. Lean in hard. Ask stupid questions. At $10m ARR, there shouldn’t be a single part of the finance operation you don’t understand end-to-end.

TLDR:

You don’t need formal finance credentials to be a CFO, but you do need accounting fundamentals. Upskill deliberately, hire a strong controller, consider an Exec MBA for breadth, and keep growing at least as fast as the business.

A few of the biggest stories that every CFO is paying close attention to. This is the section you might not want to see your name in.

Arthur Andersen and Enron (or at least its IP) are back? Is it 2001? If so, can we have another Strokes album too please?

What’s the saying? Ninth times the charm?

Per SecDef Pete Hegseth, "The Department cannot resolve decades of war, neglect of America's defense industrial base, and soaring national debt through unchecked spending."

Someone’s got to step up and lead the ultimate finance turnaround… I DO NOT volunteer as tribute.

According to the study, “Only 14% of 200 U.S. finance chiefs surveyed by professional services firm RGP said they’ve seen a clear, measurable impact from their AI investments to date.” But… “two-thirds (66%) of those polled said they expect to see an impact within just two years.”

Honestly, short term ROI is totally the wrong way to be thinking about AI spending.

“Thanks, we’ll take it from here.”

ICYMI, here are some of my favorite finance/business social media posts from this week. In the words of Kendall Roy, “all bangers, all the time.”:

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Let me know what you thought of today’s Mailbag. Just hit reply… I read every message.

In Saturday’s Playbook, we talked about leading major system change as a CFO. It’s one of the toughest and least glamorous responsibilities we have, but when it’s done right, teams emerge stronger, more capable, and more energized. Check out the newsletter here.

Disclaimer: I am not your accountant, tax advisor, lawyer, CFO, director, or friend. Well, maybe I’m your friend, but I am not any of those other things. Everything I publish represents my opinions only, not advice. Running the finances for a company is serious business, and you should take the proper advice you need.