Many people claim to be experts at facilitating leadership and board retreats. But how do you know who might be best qualified for you? The best way is to ask some questions – here are ten to get you started.
A tough question, but if the answer is “read all of my books, review my (published) research, listen to my podcasts, and here are example advisory clients”, then the person may have the expertise. But is it proven? Have they built their own strategies at the organizations they’ve led? And helped their clients do so too? And what is the scale of the organizations that they have led (or advised)? And what is the size of the organizations whose retreats they have led? Feel free to read all eight of my books, and listen to my podcast; happy to share my list of advisory clients as well. I have decades executing strategy as a leader, decades advising senior leadership on strategy, and decades as a master facilitator. I’ve advised (and led retreats for) global multinationals, start-ups, and associations. And I’ve built three companies myself.
It’s very hard to get up in front of a group of leaders if you haven’t been in their shoes. And it’s hard unless you have worked with many leadership teams, across different sectors, helping solve their toughest challenges. Just because you can speak or facilitate, doesn’t mean you have the depth to run an effective retreat. My early career was with KPMG, and left them in the 1990s to become a (3X) serial entrepreneur. I have also spent three years as a senior exec at an American public company, and have long sat on corporate and not-for-profit boards. I’ve helped 100+ well-known organizations address their key issues.
Is the facilitator committed to leading retreats, or is it just a sideline? And if they do other things, do these enhance the value of the retreat experience, or do they distract from it? We exclusively focus on helping organizations build alignment, solve tough problems, and grow. Core to our successful retreats is the value we bring from our three other activities: executive coaching, training leaders, and writing/speaking. I also sit on a public company board and am a venture partner in a VC, which brings another important dimension to many of our retreats.
The retreat leader should not just be a facilitator, but also a thought leader who can inject new insights into the retreat conversation. The problem is how to prove that they actually “are” one. A strong indicator is a long history of creating new intellectual property. If they don’t demonstrate their thinking outside of the retreat, then it’s unlikely they will bring new insights or add unique value at the retreat. Pay attention to their podcast and blog, but also LinkedIn, Facebook, YouTube, X/Twitter, etc. Google them, see how often they come up, and where they appear. Beyond my weekly blog and weekly podcast, I have 700+ thoughtful articles, 70+ white papers, and hundreds of hours online of me being interviewed (and me being an interviewer). Check out my LinkedIn profile, the Braintrust and the Randall Craig websites, and Google. Check out my LinkedIn profile, my speaker website and the Braintrust Professional Institute website. Try searching me on Google. Or try Googling “Choosing a leadership retreat facilitator“, and see how I rank. (I never call myself a thought leader, but others have: Thinkers360 has ranked me a “Top 50 Global Thought Leader” on Business Strategy, and also a “Top 50 Global Thought Leader” on Marketing.)
Fit is important: you certainly don’t want them learning your industry or sector “on the job”. We have deep experience with service or knowledge-based organizations: professional services, financial services, agencies, tech, and associations. Our leadership retreat clients have ranged from scrappy start-ups, to global financial institutions. We only accept engagements where we know we can make a difference, and where we enjoy working with each other.
“The answer is in the room” is the hallmark of an excellent facilitator, but it is rarely the hallmark of an excellent retreat. Retreats are rarely just pure facilitation, and the best ones also include components of small group work, training, coaching, group dynamics, social time, and a linkage to other resources. While each of our engagements is unique, they all share a common foundation: to explore the knowledge in the room, extend it by introducing new shared vocabulary, and build alignment toward common goals. We use a variety of techniques – including the ones cited above – to make sure that we get the most from each and every participant, and that the retreat goal is achieved.
Too often, retreat facilitators bring a canned presentation or process, and ask perfunctory questions for “customization”. The benefit of this is that there is little time impact for you beforehand; you show up, participate in “the process”, and then go back to the usual day-to-day. The downside: no deep customization, little alignment, and incomplete buy-in. There must be participant engagement with the facilitator beforehand: this is the “raw material” that the facilitator uses to fully customize the agenda, develop the materials, and interact effectively. We meet with the leader to understand the objectives, then interview each attendee to understand their challenges, and the dynamics at play. We listen for themes, then design the agenda and work with you to fine-tune it. Finally, we’ll develop any training modules and facilitation notes, and review then with you. And if needed, we’ll also do some micro-coaching to maximize your effectiveness at the retreat. The goal of the retreat isn’t a retreat – it’s to achieve a specific outcome: this can only happen when everyone is engaged, right from the start.
Read through the facilitator’s testimonials, and ask for their credentials. Is their client list filled with credible names? Satisfy yourself with their references, either through online testimonials, or by asking for the reference’s contact info. Check out my LinkedIn recommendations for feedback from my clients, or ask me for references – happy to help.
Experts are recognized by their peers – not by themselves – for the impact of their work. Beyond their certifications, ask about their national-level awards. I am the only person who has been named a Fellow of the management consulting profession (FCMC), and also been inducted into the Canadian Speaking Hall of Fame. And I am one of only 27 people awarded the CSAE Griner award for my impact on the association/not-for-profit sector in Canada.
Dig deeper, because the answer to this question starts well before the retreat itself: what conversations and interviews take place beforehand? How is the agenda set up? What pre-reading and/or pre-work is expected of attendees? And then within the retreat itself: What accountability processes are set-up? What commitments are made by each attendee, and by the group as a whole? Finally, what follow-up is built into the post-retreat processes, both by the most senior leader, and potentially by the retreat facilitator. We do all of the above, and more. Post retreat, we can collaborate closely with internal resources, and if required, we can supplement with coaching, functional training, ongoing professional development, and resources from our Leadership Intelligence Center.
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Includes 4 Questions for planning a knockout retreat, 7 retreat planning mistakes, CEO Retreat opening remarks blueprint, and our credentials.
Randall is a perceptive, highly innovative thinker with an acute awareness of the fundamental principles of business and a sincere curiosity in the promise of technology and how it can improve the human condition.
A top number one communicator and visionary with excellent skills and technical knowledge. I can recommend Randall without reservation.
Randall is simply one of the brightest people I know. He is gifted in seeing things from both the 50,000 foot level and sea level at the same time, and snatching -- seemingly from thin air -- the one piece of the puzzle that will make the entire strategy work