Advice to a CEO Leading a Transformational Turnaround

On Our Radar

For the past 25 or so years, I’ve had the chance to help countless businesses — many of them retailers — get unstuck, reimagine themselves, and accelerate value creation.

Along the way, I created Jackman, a purpose-built reinvention firm focused on alignment — of strategies, action plans, and, most importantly, of leadership teams themselves. We now practice internationally, having had the good fortune of helping over 100 companies around the world get back to growth and relevance fast.

Some of those companies needed help because they had run out of growth yet had no real plan for renewal. Others were still growing yet losing their competitive position — they needed an answer to market shifts and disruption. The remainder were, for lack of a better term, flat-out broken: brands that were great once but now failing, lost and in need of a transformational turnaround.

Almost all our work with businesses in that third, “broken” bucket has been shoulder-to-shoulder with CEOs and leadership teams in a tough spot. We’ve seen firsthand what it takes to navigate high stakes change from the top and see it through to execution. It’s a high wire act, and it’s from these learnings that we can now offer humble advice to any CEO walking it. Perhaps it’s an epilogue to three decades learning what works (and what doesn’t) in transformational turnarounds.

Think Fast

First, let’s be clear: Transformational turnarounds are hard.

Before getting to the advice part, it’s helpful to acknowledge the stark realities which make it particularly hard for leaders dealing with a transformational turnaround:

Reality #1: You have no choice but to fix the business while you change it.

It isn’t possible to get an old model to sustainably deliver growth and then transform it, because what didn’t work before won’t work now (or later). Equally, it isn’t possible to transform the business and then drive for growth, because you’ll lose stakeholder support and run out of cash. Both thrusts must run in parallel, not in sequence.

Reality #2: You must demonstrate bold thinking and action.

Playing it safe leads to failure. Your job is to substantially and dramatically change the business, so you must accept that the time for incrementality has passed and get on with being bold. (I recall something about rearranging the deck chairs on the Titanic—it probably felt good for a while.) The hard fact is you have no choice but to push for truly brand-defining action that will change the value proposition, business model, and the outcome.

Reality #3: You’re in a race against time, and you need to move fast to win.

As time passes, disruptors gain further traction and market share, legacy rivals sense weakness and outpace you, and tired assets (like older stores and yesterday’s technology) erode performance. When performance and confidence diminish, access to capital—the lifeblood of transformation—becomes scarce, and top talent leaves to join winning teams. The antidote is to move fast, faster than those around you are comfortable with, and make progressively bigger bets without lengthy validation.

Reality #4: You must think about and manage risk differently.

On the topic of making bets, the greatest risk isn’t making the wrong bets—it’s not making any at all. Your reality as a transformational CEO can be summed up as “Change or Die,” requiring you to weigh the relative risk of any bold move against the deadly risk of doing nothing or too little. You then de-risk by taking a different approach to executing change (more on that below).

Reality #5: You face much greater pressure to keep teams focused and aligned.

By its nature this is polarizing, challenging work. The risks are greater than they are for incremental change, and burnout or disillusionment are real threats. In these circumstances, functional leaders will actively seek out ways to do less, go slower, stray from strategy, or bail entirely. Success requires you to not let any of this happen.

Action + Scale

Now, as promised, onto the advice part.

For a CEO leading a transformational turnaround, faced with the difficult realities described above, here are eight pieces of advice that will increase the odds of your success:

1. You need talent on your team.

Normal situations call for solid talent; transformational ones have a higher bar. Don’t settle for anything less than what you need. Act fast to fill gaps or trade out weak links—like really fast. Do whatever it takes to inspire and incentivize your team, so they stay in their seats for the bumpy yet fun ride ahead.

2. You need a clear North Star and a focused plan.

Your North Star is the reason your business exists beyond just creating shareholder value. Much more than a slogan, a strongly articulated North Star becomes a lens through which to evaluate all decisions. Once it has been set, your job as CEO is to hold everyone accountable to relentlessly execute on it. So, keep it simple and motivating and make it pervasively present. Write it on the walls of your HQ and make it everyone’s screensaver. Keep it alive in Town Halls and how you measure progress. If you don’t actively insist that everything is tied back to strategy—now, 6 months from now, 18 months from now—no one else will either. For more detail on crafting and rallying around a North Star, read our guide here.

3. All your direct reports must be on the exact same page.

Leadership that is aligned, bought in, and leaning in together is an unfair competitive advantage. Transformation is a team sport with zero room for rogue players and behaviour, so anyone not onside should be first taken to the woodshed and next shown the door. I highlight this as it’s common in transformational situations to see leaders misaligned and executing their own plans by function. You need one aligned team executing one plan. For further reading on how to forge alignment in times of constant change, read our guide here.

4. How you execute is everything.

The best way to mitigate risk when executing change is to adopt a “prove and move” approach. For any strategic hypothesis, start with rapid “Test & Learns”: low- or no-capital customer experience shifts that can be executed and measured quickly to gain insights. Then, use what you’ve learned to implement progressive iterations of the value proposition, customer experience improvement, or brand messaging. From there, accelerate into full-scale execution while building evidenced business cases that earn increasingly greater Opex and/or Capex investment. If you work in this way, you’ll never feel like you’re making a “big bet” again.

5. Transformational turnarounds can and should be self-funded.

The key is to create what we at Jackman call a transformational growth model—a flywheel between “sweating the assets” of the old business to generate cash, then investing said cash in the emergent business to spin off even more funding. When you get this flywheel going, your odds of success go up substantially.

6. You need active management and centralized governance.

Transformational turnarounds are difficult to manage, not only because they are complex and multi-dimensional, but because they are “horizontal” in nature—meaning they touch everything and everyone across the company. And yet companies are organized vertically, by function, so they’re often unaccustomed to working across siloes. You need to go beyond traditional PMO functionality, and ensure continued executive focus, cross-functional coordination, centralized measurement and calibration, and a rigorous connecting of customer-facing dots sooner than would otherwise be the case.

7. Keep your entire organization informed and inspired.

In transformational situations, what you want is your people, from admin and the DCs to the sales folks or store floor, to say, “We’re doing this together. It’s hard but incredibly rewarding.” It’s that simple, and you achieve it in three ways: explain and connect every action to strategy; constantly share and show progress; and celebrate your heroes. When you do all of that, you put an incredibly powerful force at your side: culture.

8. Most importantly, there is only one leader capable of owning a transformational turnaround, and that is you.

To be clear, I don’t mean to take anything away from functional leaders and the critical role each must play in transformation. But the truth is only the CEO can own that transformation. Why? Because only the CEO can see the full picture, connect all the dots, and make it a reality. Only the CEO can look beyond the inherent biases of functional leaders (sorry, but it’s true—when your weapon is a hammer everything tends to look like a nail), resolve inevitable trade-offs, and relentlessly demand that all pieces and parts add up to the most valuable whole. And crucially, only the CEO wields the power (and has the ultimate responsibility) to keep all stakeholders on the same side and supportive of the transformational turnaround. Of all the advice given, this is the most important.

Yes, transformation is hard. But irrelevance is harder.

Being a transformational CEO in a turnaround situation isn’t easy, but someone has to do it. For those lucky enough to assume such a courageous and pivotal position, the rewards are almost always worth it. Think about it. If it works, you are hailed as a hero and can enjoy the spoils. If it fails, you gain something much more valuable: experience.

Hopefully the advice shared will help a leader in a tough spot. Jackman is always available for advice in challenging times—after all, that’s been our job for 25 years or so.