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Choosing a Retreat Facilitator–10 Tough Questions to Ask

Quite unfortunately, there is no shortage of people who claim to be experts in business growth, marketing, and strategy. How do you choose the best one for your conference, meeting, or virtual event? The best way is to ask some questions – here are ten to get you started

  • How much do you really know about strategy? And leadership?

    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 podcasts. 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.

  • What did you do before? How long ago was that?

    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.

  • What else do you do? Besides lead retreats?

    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 board members, 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.

  • Are you really a thought leader?

    The retreat leader should not just be a facilitator, but also a thought leader who can inject new insights into the 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 podcasts 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. (I never call myself a thought leader, but others have: Think- ers360 has ranked me a “Top 50 Global Thought Leader” on Business Strategy, and also a “Top 50 Global Thought Leader” on Marketing.)

  • Who are your best-fit retreat clients?

    Facilitation is important, but domain knowledge is equally important: you certainly don’t want the leader learning your industry or sector on the job.

    We have deep experience with service or knowledge-based organizations: agencies, professional services, financial services, tech, healthcare, and associations. Our leadership retreat clients have ranged from scrappy start-ups, to North American agencies, to global financial institutions. We only accept engagements where we know we can make a difference, and where we enjoy working with each other.

  • What is your approach to facilitation?

    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.

  • What are your requirements of us, before the meeting?

    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 in- complete 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 de- sign the agenda and work with you to fine-tune it. Finally, we’ll develop any training modules and facilitation notes, and review them 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.

  • What do others say?

    Read through the facilitator’s testimonials, and ask for their credentials. Is their client list filled with credible names?
    Then 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.

  • How have you been recognized for your impact?

    Experts are recognized by their peers – not 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 Griner award by the CSAE for my impact on the association/not-for profit sector in Canada. Check out my LinkedIn recommendations for feedback from my clients.

  • How do you make sure that what happens at the retreat sticks?

    Dig deeper, because the answer to this question starts well before the session 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 or team meeting 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 facilitator.

    We do all of the above, and more. Post event, we can collaborate closely with internal resources, and if required, we can supplement existing internal resources with coaching, functional training, ongoing professional development, and resources from our Leadership Intelligence Center.

  • Sylvia Link, APR

    Sylvia Link, APR

    Director of Marketing & Communication Retired Teachers of Ontario

    Randall's expertise and experience in all areas of strategic communication, marketing, web and social media is remarkable in its breadth and depth.

  • Sylvia Plester-Silk

    Sylvia Plester-Silk

    Catalyst On Purpose Transformation

    Randall has a gift of being able to take complex processes and make them understandable and applicable. Our participants raved about the incredible quality and clarity of his message.

  • Donald Cooper

    Donald Cooper

    MBA, CSP Canadian Speakers Hall of Fame

    Randall Craig has that rare combination of subject matter expertise and performance excellence. He is authentic on stage, smart, and makes the complicated simple. He made effective use of the "Hot Seat" - something only a real expert should even attempt… and he qualifies in spades. Highly recommended.

  • Sylvia Link, APR

    Sylvia Link, APR

    Director of Marketing & Communication Retired Teachers of Ontario

    Randall's expertise and experience in all areas of strategic communication, marketing, web and social media is remarkable in its breadth and depth.

  • Sylvia Plester-Silk

    Sylvia Plester-Silk

    Catalyst On Purpose Transformation

    Randall has a gift of being able to take complex processes and make them understandable and applicable. Our participants raved about the incredible quality and clarity of his message.

  • Donald Cooper

    Donald Cooper

    MBA, CSP Canadian Speakers Hall of Fame

    Randall Craig has that rare combination of subject matter expertise and performance excellence. He is authentic on stage, smart, and makes the complicated simple. He made effective use of the "Hot Seat" - something only a real expert should even attempt… and he qualifies in spades. Highly recommended.

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