Lead With Calm, Deliver With Grit
What Turnarounds Taught Me About Success
I’ve walked into more than one strategy session with a product roadmap in flames, a demoralized team, and a board demanding a plan. These moments are never easy, but they’re also where real leadership begins. Lately, I've seen teams pin their hopes on generative AI to fix broken processes. It most likely will not. But if you know how to build through uncertainty, GenAI can accelerate the rebuild. Here’s what I’ve learned from two decades of turnarounds.
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Culture Is the First Product
I once led a platform rebuild where the engineering lead looked at my initial brief and thought, "This guy has no clue how complex this will be." He was right, but I gave him room to prove it. We had tension, but also trust. That trust turned friction into flow, and what came out of that mess became the company’s most successful product launch.
Key Actions:
Create space for technical leads to challenge assumptions
Prioritize team dynamic over premature alignment
Use early tension to identify cultural gaps before operational ones
GenAI Is Not a Silver Bullet—It’s an Accelerator
Years ago, I helped translate dense healthcare specs into something our teams could actually build. I am not a coder, but I asked the right questions, connected the dots, and kept everyone moving. That project taught me what GenAI makes easier today: turning raw input into usable output. But it still requires judgment, alignment, and lots of editing.
Key Takeaways:
Use GenAI to accelerate workflows, not define strategy
Maintain human oversight for context and quality
Don’t delegate decision-making to the tool—retain accountability
Act Fast, Even With Imperfect Information
I remember building a product integration under ridiculous time pressure. I hadn’t worked in the industry before. I misunderstood parts of the spec. We missed edge cases. And yet, within a month, we had teams across three time zones aligned and delivering.
What Worked:
Pushed code early to staging environments, learned fast
Prioritized cross-time-zone alignment over technical elegance
Focused on progress, not perfection
Liquidity, Customers, and Risk: The Real AI Compass
A few years back, I helped a company fix its sales funnel before acquisition. We didn’t use AI for forecasting or targeting. We just sat with the data, cleaned it up, and made better decisions. At an earlier startup, I worked with a team to reshape its go-to-market plan around one key enterprise client.
Strategic Compass Tactics:
Follow the money: optimize your cash flow and cost centers
Prioritize your best-fit customers: deepen retention before expansion
Identify risk early: from compliance to supplier health
Empower Mid-Level Managers and Emerging Leaders
One of my favorite stories is watching a junior teammate go from unsure analysts to confident product owner in less than a year. I didn’t give her a course. I gave her a shot. She led a GenAI pilot project that was intimidating at first. We worked through it together. She ended up co-presenting to the CEO and it became one of the company’s most successful features.
Leadership Moves that Matter:
Identify emerging talent before they self-identify
Provide hands-on support, not micromanagement
Let teammates speak for the work they own
TLDR
I’ve been through enough turnarounds to know the hardest part isn’t the tech or the strategy. It’s absorbing the pressure without passing it on. I’ve sat through layoffs, client escalations, and board meetings where nothing seemed salvageable. But I’ve also seen what happens when you give people a reason to believe.
Project calm even when pressure is high
Use GenAI as a team member, not a scapegoat
Be transparent, decisive, and grounded—teams will follow
Attribution and Inspiration
Image by Freepik
Good to Great: Why Some Companies Make the Leap...And Others Don't, by Jim Collins
The Power of Small Wins, by Teresa M. Amabile and Steven J. Kramer, Harvard Business Review, May 2011, https://hbr.org/2011/05/the-power-of-small-wins
How to Lead a Successful Turnaround, HBR On Strategy, Episode 103, March 26, 2025
A Guide to Building a Unified Culture After a Merger or Acquisition, by Mina Milosevic, Katherine Rau and Lisa Steelman, Harvard Business Review, April 3, 2025
How to Rescue a Failing Strategy, by George Bene, Jason McDannold and Beth Musumeci, Harvard Business Review, May 23, 2025