Ctrl+Alt+CEO: The May Reboot

Entrepreneur

08-05-2025

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For many, May sits in an awkward middle ground - not quite the urgency of Q1, not yet the intensity of summer. But for a growing number of leaders across industries, this mid-year moment is becoming something else entirely: a deliberate reset. Not a slowdown. Not a break. But a re-evaluation of process, purpose and performance.
"What if a deliberate mid‑year pause could be the single biggest catalyst for your Q3 success?" asks Michael Ryan, founder of digital marketing agency Ink Digital. His question isn't rhetorical - it's tactical. "A strategic 'May Reset' focused on refining processes, shifting leadership mindset, and carving out creative space positions your business to enter summer not just energized, but truly aligned with its goals."
Ryan's agency is using May to overhaul two foundational areas: client onboarding and campaign retrospectives. "We've learned that small inefficiencies in communication and feedback loops compound over months," he says. "So we're using May's natural lull to streamline workflows, accelerate creative turnarounds, and ensure every project kicks off with crystal‑clear objectives."
But if May is about rethinking structure, it's also about rethinking self. "I've transitioned from 'reaction mode', responding to every email and Slack ping, to creating deliberate white‑space in my calendar," Ryan says. "Empowering the team to make autonomous decisions while I focus on big‑picture strategy has turned urgency into intentionality."
One of his most radical resets? A weekly digital detox. "I've instituted a weekly 'creative fast': one full day without meetings or digital interruptions. That silence has sparked our best ideas yet, sharpened my strategic thinking, and given the team space to innovate without distraction."
Across London, another kind of reset is underway - one rooted not in silence, but in technical immersion. "At Faculty, we're re-evaluating how we engage with the very frontiers of AI," says Dr Marc Warner, CEO and co-founder of the artificial intelligence firm. "Back in January, after a visit to San Francisco and subsequent reflections, it was clear that the AI landscape had shifted enough that we needed to re-educate ourselves."
Warner and his Chief Technology Officer spent two intensive weeks revisiting the most cutting-edge models in AI. "That trip was transformational for how I spend my time and how we think about where to focus," he says. "While the outputs are still unfolding, the signal was clear: this is the moment to reset to spring forward." This wasn't just a tech refresh. It was a leadership awakening. "One of the biggest mindset shifts has been doubling down on aligning AI initiatives with core business priorities," Warner says. "After over a decade of building Faculty, we've learned that AI strategy should always be subservient to business strategy."
He's wary of chasing shiny objects. "There's a real temptation to create a laundry list of possible AI applications, pick the easiest to execute, and hope something sticks – but that approach rarely delivers real impact," he explains. "Instead, what works is identifying the organisation's most important priorities and asking: where can AI truly accelerate these?" In Warner's case, recharging doesn't mean stepping back - it means diving deeper. "For me, recharging doesn't mean stepping away; it means leaning into the work that stretches and excites me," he says. "My reset at the beginning of this year - sitting side-by-side with our CTO, digging into the technology – was a prime example. It was energising and reminded me how important it is to carve out time for exploration, not just execution."
But not everyone is using May to pause. For Kateryna Serdiuk, founder of digital art marketplace Subjektiv and former investment banker who once orchestrated $25b in equity transactions, the month is less about reflection and more about acceleration. "This month we're doing the opposite of slowing down. It's full steam ahead," she says. "We're laying foundations for what's next, putting time into product tweaks, new partnerships and customer growth." Her reset? Pre-empting logistical risk, especially in the increasingly complex US market. "We're taking a closer look at how our logistics work in the US," Serdiuk explains. "The tariff war means there's more uncertainty than usual, and rather than waiting for issues to arise, we'd rather pre-empt them."
Subjektiv, built to simplify art acquisition for a new generation of collectors, depends on operational precision. "If friction creeps in, it affects the whole experience," she says. "Our strategy is solid. It's more about making sure the infrastructure can support what we're building, especially as we grow across new markets. The rest is working well, and we want to keep it that way."
For Serdiuk, clarity comes not from stillness, but from execution. "Not a shift, but a strengthening," she says of her mid-year mindset. "If anything, the turbulence around us has made us more certain about what we're doing and why." And like her peers, she knows that success depends on more than ideas. "You can have the best idea in the world, but without the right people to help make it happen, it stays an idea," she says. "We're putting more attention into team culture, shared goals, and finding those who want to grow something meaningful together."
Across the UK, another CEO is using May not just as a moment to reflect - but as a mandate to disrupt. "We transitioned to our unique cashback business model to deliver real, tangible value to our customers," says Cas Paton, CEO of OnBuy.com, the rapidly growing online marketplace. "This commitment drives us, especially at a time when people are feeling the effects of economic uncertainty."
For Paton, May is about dialing up - not dialing down - OnBuy's impact. "We're intensifying our efforts to make sure that our rewards have a significant impact, while also challenging the norms in retail, finance, and traditional cashback industries." But that drive outward is matched by focus inward. "The current economic climate is a challenging one for business. It's at times like these that leadership takes on a whole new meaning," he says. "Teams need to feel stability and positivity in order to perform at their best. That's why we're not taking our foot off the accelerator."
Paton's mid-year mindset? Momentum and clarity. "We're continuing apace with our bold international expansion plans and ensuring that all the exciting signals we're seeing about the success of our strategy are being fed through to our team."
Even his recharge mode is strategic. "Juggling work and life is a challenge, but you have to get off the hamster wheel to be able to step back and plan," he says. "I try and absorb as much calm and family time as I can. It helps me to re-energise, so I can give my all to the success of OnBuy when I'm back at my desk."
So while May may seem like a moment to coast, these four founders see it differently: as a pivot point - a strategic intermission before the pace intensifies again. Because whether it's making space for silent thinking, doubling down on technical learning, challenging market norms, or charging forward while others pause, the May Reset is not about stepping back. It's about choosing how - and where - to leap next.