My friend and regular co-facilitator Pam shared a reflection the other night as we debriefed our latest strategic planning event. She said that, while sometimes our sessions go according to our design and produce solid plans, the sessions that evoke concerns among participants that “we’ll never get to alignment” are the ones that result in the most insightful and effective strategic plans in terms of navigating incredible opportunities or choppy waters. I’ve been thinking about that statement since she said it; it may not be comfortable to experience a messy session, but she’s absolutely right.

Last Friday and Saturday, Pam and I led an intense planning session with the provincial/territorial board members and executives from CPHR Canada – the organization that represents Chartered Professional Human Resources professionals across our country. The session couldn’t have come at a better time, with the first five days of the new U.S. President’s mandate sweeping through HR circles with the same intensity as the fires that have been burning in central California for the past few weeks. While Canadian HR practitioners are generally not directly influenced by U.S. policy, the anti-DEI stance of the new government, paired with potential tariffs on Canadian businesses, represents an unavoidable threat. HR professionals may be faced with coordinating layoffs, modifying Canadian DEI policies, and supporting fearful colleagues and team members through a time of massive instability. In other words, they are feeling a lot of pressure about what is coming their way.

As we always do, we prepared a detailed session plan for the two-day event. We mapped the anticipated energy of the participants, planned a series of our favorite tried-and-true exercises, and designed an approach that would support the participation of all of the diverse voices in the room. We added in some creative modes of delivery – including the use of Lego and artistic design – to spark creativity and challenge the linear thinkers in the room to tap into abstract thinking. And then we sat back and considered what might happen if things didn’t go as planned. Based on our assessment, we planned for expansion and shrinkage of the agenda, disruptions, and other typical risks.

Managing the voices and perspectives of 20+ smart, passionate, and committed professionals is a challenge most days. But this event was particularly complex. CPHR operates as a federation, with the national body responsible for governance and the HR designation, while provincial/territorial member associations are responsible for member support and experience. A federated organization requires a balance between respecting the national body’s role and acknowledging each jurisdiction’s unique perspectives, priorities, and challenges. The added complexity of the profession’s current challenges made it clear this session was going to get spicy.

The Best Laid Plans

We started the day with a journey map exercise, pulling everyone out of their seats to contribute to a massive storytelling wall, tracking CPHR Canada’s recent history and immediate future within the context of national, provincial, and global forces. By the time we finished this first warm-up activity, we knew this was not going to be an easy-peasy-lemon-squeezy kind of day. The conversation had a seriousness to it that we don’t always see. This room of leaders knew they had a short window to have some hard conversations to build a strategic plan that would be an asset in this time of massive disruption...and they were going to take that opportunity.

By the first break, Pam and I were already conferring on potential shifts to the agenda. It was obvious that we weren’t going to breeze through anything. There was a need for the group to challenge assumptions, explore potential pathways, and engage in some important debate about the future of the organization. Our job was to create space for healthy conflict in a safe and respectful environment (though to be fair, these are HR rockstars—they didn’t actually need our help in being respectful, just in guiding and balancing the conversations).

While I like to think of time as a social construct during our sessions, the reality is that our society lives by the clock. And while there are many ways to build a strategic plan, I typically like to ensure that by the end of day one, we have the bones of a plan in place. That way, participants leave feeling energized knowing that the end is in sight. Plus, this approach leaves day two to add detail and refine the essence of the plan. But with this workshop, their discussions were so critical that we had to end the day in the messy middle. Of course, we still wrapped up in a good way—reassuring them that they were almost done with the hard work, and that tomorrow would be easier. Then, the group retired for the evening, connecting over a dinner gathering at the hotel restaurant. [As an aside, if you are looking for a wonderful venue to host an offsite session in the Montreal area, we highly recommend the Château Vaudreuil. The space, the team, and their attention to detail to ensure the venue supported our work was exceptional, and we would love the opportunity to facilitate there again.]

Escaping the Messy Middle

Given the ticking clock and the work left to do, Pam and I met that evening to map out a revised plan for day two. We knew there were still gaps that needed to be filled, but also some concerns that had to be aired. We created a new session plan (thankfully, Session Lab helps us manage our catalogue of favorite exercises and easily adapt them). Then later at dinner, we continued gathering intel about what else needed to be surfaced before we could achieve alignment.

The following morning, the group arrived knowing they still had a lot of work ahead. But Pam and I have been through enough of these sessions to know what needed to happen next. Incidentally, one of my favorite prompts for sessions is the same prompt I use for myself when heading into a situation I can’t fully control: If nothing else... In this case, we knew that if nothing else, we had to achieve agreement on the key pillars of the plan and their importance—and capture the essence of the Vision and Mission statement (because wordsmithing in a group of 20 smart and passionate people is a recipe for chaos).

As if on cue, in the last two hours, clarity reigned. The conversations had done their work. The room moved from uncertainty to focused collaboration, and the solutions came together quickly. As Einstein once  said, "If I had an hour to solve a problem, I’d spend 55 minutes thinking about the problem and 5 minutes thinking about solutions." This session proved that when the right (and often, messy) discussions happen first, alignment follows naturally.

The Takeaway for Leaders

If you’re leading a complex organization, building a strategic plan will never be as simple as following a pre-set template. The world shifts, new information emerges, and real strategy requires adaptability. That’s why investing in the right facilitation matters. A great facilitator ensures that even when the process feels uncertain, the outcome is never in doubt. 

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I regularly write about the real-world challenges of strategy and leadership, sharing insights from working with mission-driven organizations, member associations, and government-related bodies. If these topics resonate with you, sign up to receive my next strategy blog post straight to your inbox.