Rule #10 – If It’s Hard and Everyone’s Avoiding It, It’s Probably Worth Doing
Devon Coombs
CPA, MBA · Management Consulting & AI Strategy
How Running on Floating Ice and Leading Global Finance Teams - Reveals the Same Truth About Growth
TL;DR: What do polar bear guards, AI readiness, and culture-fit decisions have in common? Finance leader Melissa Kullander ran a marathon at the North Pole and built her career by running toward discomfort. In our conversation, she unpacks the mindset and methods behind long-haul leadership. Read on for 5 tactical lessons, or watch the full interview below.
There’s a scene I won’t forget from my interview with Melissa Kullander, a former finance leader at Oracle, Hitachi, and Workday. She’s running a marathon on a floating sheet of Arctic ice, flanked by polar bear guards while wearing a life vest.
That’s not a metaphor. That’s the geographic North Pole.
Melissa has completed 51 marathons, including one on every continent. But what fascinated me most was not her endurance; it was her mindset.
By day, Melissa has led billion-dollar finance transformations, cloud migrations, and global team turnarounds, often long before "cloud" and "AI" were headline trends. She’s not the type to seek titles or chase fads. She’s the kind of leader who treats discomfort like a compass: a signal of where growth lives.
Whether she’s guiding a product team through a multi-year transformation or racing on unstable terrain, Melissa embodies Rule #10 of my 12 Rules for Finance Leadership:
If it’s hard and everyone’s avoiding it, it’s probably worth doing.
In our conversation, Melissa shared powerful stories and tactical insights for anyone leading through change, building cross-functional partnerships, or trying to future-proof their team.
Here are five lessons that stuck with me, and why they matter now more than ever.
1. Translate Value Across the Aisle
Melissa started her career working with rocket scientists at Honeywell. Literally. That’s where she learned one of the most underrated leadership skills: translation.
Engineers tend to think from the inside out, details first, conclusions later. Finance professionals think the opposite: top-down. Bridging that communication gap takes more than reporting. It takes humility, patience, and pattern recognition.
“The best finance leaders,” Melissa said, “don’t just crunch numbers, they learn the language of the teams they support.”
Action Step: In your next cross-functional meeting, practice restating a key insight in both technical and financial language. Be the translator in the room.
2. Clean, Consolidate, and Consistent: Your AI Readiness Starts with Data
Before AI can transform your workflow, your data has to be worth feeding it. Melissa and I call out a painful truth:
Most companies’ data, regardless of size, is garbage.
That’s why she focuses on the Three Cs:
Clean: Remove noise, duplication, and irrelevant information.
Consistent: Standardize formats and definitions.
Consolidated: Eliminate data silos and disconnected spreadsheets.
It’s not glamorous. But if your data isn’t usable, no AI system will save you. The cost of ignoring this will only compound.
Action Step: Choose one critical dataset or reporting workflow this week. Audit it for cleanliness, consistency, and source reliability. Build a roadmap for improvement.
3. Run Toward Discomfort, Not Away From It
Melissa didn’t come from a background in semiconductors, aerospace, or enterprise software. But she stepped into each of those roles anyway and figured it out. She didn’t wait until she "deserved" the job. She led by doing.
Whether she was leading SOX implementation during its first year or joining a newly spun-out startup from Motorola, her bias was always the same: act first, learn fast.
“You’re stronger than you think,” she told me. “Stretching yourself is how you build confidence. It’s not something you have; it’s something you earn.”
Mindset Shift: What’s one challenge you’re avoiding because it feels unfamiliar? That might be your next growth edge.
4. Align Culture Before Compensation
Early in her career, Melissa chased opportunities based on scope and pay. But now, her non-negotiable is cultural alignment.
“You don’t do anything meaningful alone,” she said. “And if your values don’t match the team, it’s not going to work, no matter how strong your resume is.”
She’s turned down lucrative roles when they didn’t align with her values and walked away when the cultural reality didn’t match the sales pitch. Today, she knows what matters: people, purpose, and long-term alignment.
Action Step: Before your next big move, write down your top three cultural must-haves. Ask explicit questions in interviews to vet for alignment.
5. Invest in Yourself to De-Risk the Future
With AI and automation accelerating every week, many finance leaders feel behind. Melissa’s response?
“You’re not behind. You’re just not engaged yet.”
She’s enrolled in free AI and cybersecurity courses, taken cloud certifications, and kept herself sharp, not out of fear, but out of strategic preparation. She’s building her readiness for whatever comes next.
If a global finance exec can find the time to do this, and run 51 marathons, what's your excuse?
Action Step: Block time to complete one course, certification, or hands-on training this quarter. And if you manage a team, carve out space for them to do the same.
🧭 Final Reflection: Pain Is Temporary. Value Is Compounding.
Melissa reminded me of something I’ve seen across every high-performing leader I’ve worked with:
They don’t chase comfort. They chase clarity and growth.
They know that the hardest things, whether running a marathon on a melting ice sheet or leading a cloud migration with 100 stakeholders, are the ones that shape your legacy.
So ask yourself:
What’s the hard thing you’ve been avoiding because it feels uncertain?
What would it look like to move toward it this week, on purpose?
And if you’re wondering if I’ve had my own version of this, leaving a prestigious role at Google to pursue a more aligned life was mine. I didn’t feel fully ready. But I knew the path would teach me. And it has.
12 Rules of Finance Leadership - Refresh
Build Leaders, Not Puppets: Don’t train people to escalate, train them to think. Delegation without decision-making authority creates dependency, not leadership.
Don’t Let Systems Become Bigger Problems Than the Ones They’re Meant to Solve: If your process is slower than the decision it supports, it’s time to kill it or redesign it.
Don’t Say No - Educate and Offer Alternatives: Saying “no” shuts down trust. Explaining why not, and offering what could work, builds influence.
Scope Is for Projects, Not for People: People grow when they stretch. Don’t confine them to job descriptions. Empower them to solve real problems.
If You Do Something More Than Twice, Build a Process, or Stop Doing It: Repeat tasks signal either inefficiency or a system waiting to be built. Automate or eliminate.
If You See Something Broken, Fix It: The best teams don't wait for permission. Ownership is earned by action, not title.
Learn from Bad Examples: Some of your best mentors will be the ones who showed you exactly what not to do.
High-Performance Teams Don’t Rely on High Performers Alone: High performance gets you started, but a team of high performers will fall into a natural hierarchy, which results in churn and career dissatisfaction. Organizations need to attract all types of people to scale.
Always Choose People Over Processes: The right process should enable people, not replace them. If collaboration is clunky, fix the communication, not just the workflow.
If It’s Hard and Everyone Is Avoiding It, It’s Probably Worth Doing: The highest-leverage work is often the work everyone is silently avoiding. Find the friction and lean in.
You Don’t Need the Title to Do the Job: Leadership, ownership, and value creation are earned through action. If you want the job, don’t wait for the title to start doing it.
Lead Like an Athlete, Not Like a Machine: Sustainable high performance means knowing when to sprint, when to recover, and how to make progress through downtime.
🎥 Watch the full episode on YouTube: Here
🎧 Listen on Spotify: Here
If this sparked something, I’d love to hear from you. Message me or drop a comment:
What’s your “North Pole” moment, and what rule are you leading by?
Devon Coombs, CPA, MBA
Founder & Host, Ambition Aligned
Fractional CFO & Strategic Advisor | Ex-Google & Deloitte
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I help senior finance leaders build AI strategy, navigate complex transactions, and develop high-performing teams.