As a CEO or executive in Calgary, we know you have a packed calendar and no interest in wasting time on a strategic planning retreat that goes nowhere. We get it. The truth is that the success of your retreat depends on what you prepare before anyone enters the room.
This guide gives you the essentials so you can focus on what matters. With a few smart steps up front, you can save time, keep your Calgary team aligned, and set the stage for a strategic session that produces real results.
Let’s make this as simple as possible and get into it.
Location Can Make or Break Focus
Your environment sets the tone and choosing the right space makes a big difference. You want a room that helps your team think, not a room full of distractions and day-to-day garbage. Calgary has plenty of great off site options: Hotel Arts, Kananaskis and more. Regardless of the venue, your goal should be the same. Choose a venue that is offsite, somewhere neutral, comfortable, and free from the constant pull of office interruptions.
Speaking of distractions, unless your team is literally a group of STARS Air Ambulance pilots or ER doctors at the Foothills Hospital, most urgent emails are not actually urgent. A neutral space communicates one message. This time matters.
Give Your Team the Gift of Time
Speaking of time once again (notice a trend yet?) Trying to squeeze strategy into half a day is a guaranteed way to waste everyone’s time. You are bringing your best thinkers and most expensive talent together. Give the process room to breathe.
If you are a small not for profit updating an existing plan, one well designed day can work. For most Calgary organizations though, two to three days produces far better results. Overnight breaks matter. People connect dots when they step away. The best ideas often arrive on a run, in traffic on Deerfoot (seriously), or somewhere between shampoo and conditioner. That space is part of the process, so make sure to build it in. Honestly, the importance of this point can’t be understated. We know you’re busy. We know your team can feel overwhelmed. If you want to do strategic planning right give it the time it deserves.
Be Clear About How You as CEO Will Participate
Like it or not, your presence as a CEO can shift the tone in a room. If you plan to participate as a team member and not be the final word, say it clearly and follow through. If you have a different plan – and that’s a-ok – communicate what that plan will be. When CEOs stay vague, people hesitate and stop communicating naturally, regardless of how cool and liable (whoops, likeable) you are.
Therefore, spend some time thinking ahead. Communicate with your team about how you intend to engage and participate. Then be consistent and stick to it. You’ll be rewarded with a far more authentic conversation. If you don’t, you’ll lose credibility and create a world of silent (read: behind your back) frustration with your leadership team. Don’t do that. If you are looking to improve your executive presence or how you show up for your team, learn more about our executive coaching options.
Give Your Facilitator Insight Into Friction Points
Speaking of credibility, you can go a long way in setting us up as your facilitator for success. Every leadership team has tension somewhere. Maybe it is a disagreement on priorities. Maybe it is a personality clash. Or it could be a pattern of avoiding tough conversations.
Share these friction points with your facilitator before the retreat. The more they know, the better they can guide the conversation and keep it productive. You do not need to solve every issue. You just need to flag the hotspots so your facilitator can steer the session effectively.
Facilitator Access is Critical
This step is often skipped, yet it makes a huge difference! Make your team available (as a priority) for short one-on-one conversations with the facilitator before the retreat. This helps us as facilitators to understand personalities, pressures, concerns, and expectations before the session starts.
More importantly, these meetings allow us to learn what everyone’s top priorities and personal agendas are. With that knowledge, we can save hours of debate about what your team already agrees on.
At Wilkins Creative Insights, we conduct one-on-one conversations with every participant as a rule. By the time we step into the room, we have gained trust, context, and rapport. This way your team spends the retreat doing real strategic work, not icebreakers, trust falls, or warm up activities that senior leaders do not need. You are investing in strategy, not summer camp. Start strong.
Plan for the Resources You Will Commit After the Retreat
It is easy to create a plan in the room. It is harder to execute that plan once everyone goes back to business as usual.
A resource plan is your reality check. Before your retreat, think about what support you are actually willing to provide. Time. Budget. People. Technology. Whatever it takes to make follow through possible.
Ask yourself:
• What budget is available to execute the plan?
• Are you going to test the waters with your plan or jump right in? (And are you communicating your approach effectively with the team?)
• How can leaders take on these priorities?
• What timeline is realistic for your organization?
We will help your team create a plan you believe in. Your job is to make sure that plan is not a wish list. When the room knows how priorities will be supported, your discussion becomes more focused and the outcomes become far more powerful.
Final Thoughts
If you’ve read this far, you know it will take a bit of planning to get your strategic planning workshop in Calgary off the ground. However, preparing for a strategic planning retreat is not about adding more work to your plate. It is about reducing the risk of wasted time and maximizing the impact of the investment you are already making.
Choose the right space. Give yourself enough time. Decide your role. Equip your facilitator. Listen to your team. And back your strategy with real resources. Boom.
If you want a retreat that moves your business forward and strengthens your Calgary leadership team, these steps will help you get there. If you want the expertise to make your workshop come alive, hire us.
Ready to set up your strategic planning retreat?
If you want a facilitated session that is structured, efficient, and actually leads to action and accountability, reach out today.
