Step back to leap forward: Why your next off-site could supercharge your growth

Here’s a brutal truth: whilst you’ve been firefighting your way through another quarter, your competitors have been quietly building the one thing that scales—culture. They’ve stepped away from the chaos, gathered their leadership teams, and invested in the strategic thinking that actually moves the needle. The cost of staying stuck in day-to-day operations? Research from Gallup shows that companies with engaged leadership teams are 2.3 times more likely to outperform their peers on revenue growth. Yet most founders I meet haven’t run a proper management off-site in over a year.

The firefighting trap is killing your scale-up

If you feel too busy for an off-site, that’s exactly why you need one. It’s tempting for founders to stay glued to daily operations—it feels productive, and let’s face it, you’re probably a bit of a control freak. Most entrepreneurs are.

I see it everywhere. Brilliant founders who’ve built something remarkable, then find themselves drowning in operational quicksand. Every day becomes about putting out fires rather than preventing them. Every meeting becomes about what’s urgent, not what’s important.

Sound familiar?

The irony is painful. You started this business to build something bigger than yourself, but now you’re the bottleneck. Your team looks to you for direction, but you’re too busy managing crises to provide it. The quarterly cadence that scales becomes impossible when you’re living week-to-week.

I’ve seen this from both sides of the divide – as a company leader myself at Rackspace and Peer 1, and from running dozens of off-site strategy sessions for my mentoring clients. Here’s what I’ve learned: stepping back isn’t a luxury. It’s survival.

When you remove your team from the daily distractions—no Slack notifications, no “can I just run something past you”, no operational emergencies—something magical happens. They start thinking like leaders again instead of reactive managers.

As Jeff Hoffman – founder of booking.com – told me on a podcast, the biggest barrier to scaling a business is often you, the founder. “You can’t scale until you can get out of the way. And you can’t get out of the way until you can trust people.”

Off-site retreats force you to delegate. You can’t step back to brainstorm strategy if you’re still micro-managing back at base. By stepping aside and giving others more responsibility, you’re not abandoning the ship—you’re enabling it to go further.

What separates great off-sites from expensive talking shops

Not all off-sites are created equal. I’ve seen leadership teams spend two days in a boutique hotel achieving precisely nothing except a lighter bank balance and heavier cynicism.

The difference? Purpose and process.

Great off-sites have three non-negotiables. First, they’re designed around outcomes, not activities. Just because your top team all enjoy a kayaking trip doesn’t mean that it will deliver what you need. What decisions need making? What alignment needs creating? What behaviours need shifting? If you can’t answer these questions before you book the venue, don’t bother going.

Second, they balance strategic thinking with cultural reinforcement. Strategy without culture is just wishful thinking. Culture without strategy is just a nice place to work whilst you slowly go out of business. Why culture eats strategy for breakfast isn’t just a catchy phrase—it’s operational reality.

Third, they create psychological safety for real conversations. As I often say, “Culture is what happens when the boss leaves the room.” But what happens when the boss is in the room, setting the tone for difficult discussions about performance, priorities, and the future?

The compound effect of stepping back

Still not convinced stepping away is worth it? Consider the ROI of a well-run off-site.

When done right, strategy retreats drive alignment and better decisions. They yank the leadership team out of firefighting mode and get everyone aligned on long-term goals. By carefully designing these sessions, companies ensure discussions are candid, productive, and focused on what’s truly critical.

There’s a reason we bake quarterly off-sites into the leadership rhythm of the companies we coach. A regular cadence of stepping back has a compound effect. As I’ve observed, introducing a discipline of daily huddles, weekly check-ins, monthly reviews and quarterly off-sites dramatically improves execution.

The payoff is alignment and clarity cascading down the organisation, instead of chaos.

Think of off-sites as preventative maintenance for your business. Skip them, and misalignment creeps in. Invest in them, and you keep the machine running smoothly.

Culture shows up when no-one is watching

Company culture gets reinforced at off-sites. Culture isn’t ping-pong tables and beer Fridays—it’s the shared values, behaviours and norms that drive performance. But those values can fade from memory if you never discuss them.

Use off-site days to shine a spotlight on your purpose and values. Are we truly living our values in our decisions and policies? What needs to change to be the company we say we want to be?

These are the conversations that often get squeezed out by quarterly targets. An off-site gives them the stage they deserve. The business value is obvious: a company with a strong, lived culture will outperform one with a glossy values poster nobody actually follows.

And let’s not forget morale and retention. High-growth phases are stressful. People risk burnout when it’s go-go-go every week. An off-site can re-energise the team—a chance to celebrate wins, acknowledge hard work, and have a bit of fun together.

Companies that invest in regular leadership alignment are five times more likely to be high-performing organisations, according to a PwC Global CEO Survey. That’s a powerful mandate for getting this done.

Planning your retreat for maximum impact

Alright, you’re sold on doing an off-site. How do you actually make it happen successfully?

Get it in the diary and make it non-negotiable. Schedule your off-site well in advance and secure full buy-in from your leadership team. Then commit to doing this regularly—many teams do quarterly.

Yes, everyone is busy. Yes, two days feels like a lot. Do it anyway. As I tell sceptical CEOs, you just have to carve it out and set it in stone. If you wait until you’re “less busy,” you’ll wait forever.

Choose an inspiring, distraction-free venue. Environment matters more than you think. The whole point is to remove the usual office distractions and trigger fresh thinking. Big ideas need breathing space.

Many companies go off-site to a country hotel or dedicated retreat space. When leadership teams visit our Management Lab, something magic happens. The complete change of environment really works. Free from ringing phones and constant connectivity, people become fully present.

Be clear on purpose and agenda. What do you want to achieve? Is it to realign on strategy? Solve a specific big problem? Improve team cohesion? Set two or three clear objectives and design an agenda around them.

A common pitfall is trying to cover everything in two days. That’s a recipe for a meandering talk-fest. Instead, focus on what matters most. Every session should tie back to your off-site goals.

Establish a “no tech at the table” ground rule. Ask everyone to ditch their devices during sessions. It’s amazing how one furtive glance at email can derail the flow. You’ve all cleared two days to be here—make it count.

What to focus on: culture first, strategy second

Here’s the blueprint that works for most leadership teams:

Start with culture and big-picture vision. Begin your off-site with the foundations—why your company exists, what you stand for, and where you’re heading. Discuss purpose, core values, and long-term vision before diving into this year’s targets.

By leading with discussions about mission, values, and your Big Hairy Audacious Goal, you set an aspirational tone. It energises the team and creates context for all other strategic choices.

If your values aren’t clearly defined, an off-site is a great place to do a “Mission to Mars” exercise. Ask: who are the exemplars of our values in action? Figure out the behaviours you want to see and not see.

Inject storytelling and recognition. A powerful culture agenda item is sharing “heroes and legends” from your company. Ask each leader to recount a story of someone who really lived the values. This turns abstract ideas into concrete examples and creates folklore that binds the team.

Tackle the strategic deep-dive. With cultural context set, transition into the strategic meat. Focus on a few core strategic questions or decisions. For an annual off-site, this might be a SWOT analysis, identifying your biggest obstacles to hitting long-term goals, or revisiting your value proposition.

Keep these sessions interactive. Use frameworks to structure thinking—revisit your One Page Strategic Plan, do a “pre-mortem” to surface lurking issues, or map out external trends.

Prioritise tough discussions. An off-site is your chance to put elephants on the table. Have that debate about whether to kill a pet project, or address silos between departments. Successful off-sites hinge on the quality of conversation—you want genuine engagement and even constructive conflict, not polite agreement.

Making it stick: from insights to action

The final sessions should answer: what are our top priorities going forward? After debating many ideas, it’s time to narrow them down. Use voting or dot-sticking to quickly gauge what the team finds most critical.

Aim to leave with a short list of key strategic priorities that everyone commits to. Assign owners for each priority so accountability is clear. Sketch out a rough action plan—who will do what by when—so momentum isn’t lost when you’re back to daily work.

Finally, agree on how you’ll communicate outcomes to the rest of the company. The whole organisation knows the leadership team has been away. Don’t keep them in the dark. Plan to cascade the top three messages within 72 hours of returning.

The power of making it a habit

An off-site isn’t a one-and-done silver bullet. The real power comes when you make reflective retreats a regular rhythm. Many CEOs I work with commit to quarterly off-sites as part of their operating system.

The business value of this commitment is huge. By regularly stepping away to recalibrate, you catch issues early, adjust strategy to new information, and ensure culture evolves intentionally as you scale.

Each off-site builds on the last. If you set quarterly priorities at one retreat, the next can start by reviewing progress before tackling new challenges. This creates a powerful loop of plan-execute-review-plan that keeps execution aligned with strategy.

Companies that embrace this habit find decisions get made faster and with more buy-in. Everyone knows there’s a forum to hash things out thoroughly every few months. It reduces frantic strategy meetings and endless email debates.

Don’t forget the human element

An off-site for serious strategy talk is great—but if you make it all work and no play, you’re missing a huge opportunity. Bringing fun and camaraderie into the mix energises your team and creates lasting memories.

Schedule social time and shared meals. Eating and relaxing together is one of the best team bonding activities. Schedule a team dinner where work-talk is banned after the first drink. Executive teams rarely spend time together socially, so this is a golden opportunity.

Include team-building activities. Incorporate something that gets people moving and collaborating in a different context. This could be outdoors—anything from a short hike to structured team challenges. Break the routine, get fresh air, and let colleagues interact in a non-work setting.

Consider vulnerability exercises. For deeper team cohesion, try guided exercises that encourage openness. Going around the room with vulnerability-based questions can lead to amazingly candid sharing. When leaders allow themselves to be vulnerable, it builds intense trust and empathy.

The signal you send as a leader

Don’t underestimate the message you convey when you prioritise off-sites. It shows your team that working on the business is important. You’re effectively saying strategy and culture aren’t afterthoughts—they’re top priority.

When the CEO leads by stepping away from daily operations to invest in team development, it sets the tone for a culture of continuous improvement. By championing off-sites and personal development, you encourage others to do the same.

Over time, you’ll see a ripple effect: a learning-oriented, aligned leadership team creates a motivated company behind them.

Ready to step back and scale up?

In the whirlwind of scaling a business, stepping away can feel indulgent. It’s not. Taking time out to work on culture and strategy is one of the smartest moves a growth-stage CEO can make.

An off-site is where you plant the seeds for your company’s next stage of success—seeds of clarity, alignment, and renewed purpose. The returns come in sharper strategic direction, stronger culture that drives performance, and a leadership team pulling in the same direction.

The best time to have done this was yesterday. The second best time is now.

If you’re ready to work on your business instead of just in it, our Management Lab in Wiltshire has hosted hundreds of leadership teams through breakthrough conversations that shape their next chapter of growth. Sometimes the most important work happens when you stop working and start thinking.

Your only regret will be that you didn’t do it sooner.

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Written by business coach and leadership coaching expert Dominic Monkhouse. Contact him to schedule a call here. You can order your free copy of his book, Mind Your F**king Business here.