
You know your business better than anyone: your strategy, priorities, and business risks. But you don’t know what you don’t know. To help you make better informed high-stakes decisions, INFORMED DECISIONS shares new ideas, been-there-before advice, and sometimes, a reality check. Each episode focuses on one pressing leadership or strategy topic. In 30-60 minutes, gain strategic perspective, along with practical (and tactical) ideas that can help. Informed Decisions with Randall Craig is not “just another podcast” – go behind the scenes and listen in for yourself what it’s like working with a proven business growth coach, serial entrepreneur, and Hall of Fame speaker.
Episodes
2 days ago
2 days ago
27 min
How we show up as leaders is always top of mind for us as part of how we coach leaders and leadership teams. The focus of this session is specifically how to show up at a leadership retreat because it’s a high-investment event where leaders can’t get the exposure from other team’s retreats, as they are behind closed doors. So we’ll tell you how it’s done!
Topics include:
↳ The impact of CEO as facilitator
↳ How can the senior leaders know they have played their part well at their leadership retreat?
↳ What does the CEO have to do to prepare for their team’s leadership retreat?
Aug 18, 2026
Aug 18, 2026
28 min
More for marketing leaders, aspiring marketing leaders.
Topics include:
↳ CMO role in setting business strategy
↳ The CEO / CMO relationship
↳ AI Innovation for CMOs
Aug 11, 2026
Aug 11, 2026
31 min
A session for CMOs and anyone on the marketing team: how to remain relevant, career plan, and continue to make an impact in a time of significant change?
Topics include:
↳ CMOs as executors vs CMOs as executives
↳ Career paths for CMOs?
↳ And why is it that marketers are often the butt of the joke… is it deserved?
Aug 7, 2026
Aug 7, 2026
34 min
Continuing the conversation with more on board performance: board compensation, board composition, the role of board consultants, the interplay with CEO performance, and much more.
Topics include:
↳ How can board member compensation be structured to incentivize board performance?
↳ If the board has identified that the CEO is underperforming, what role has the board played in their underperformance?
↳ What would a 1, 3, and 5 year board professional development plan look like?
Jul 28, 2026
Jul 28, 2026
30 min
💥Board Governance, Board Development Part 1
Hello board members! This leadership session recording is being share for you! What is your board doing as a whole to keep your governance skills sharp, and your minds ready to identify your next opportunities? Let’s talk about how to build more effective boards with practical thinking on board governance and board development.
Topics include:
↳ What are the formal avenues to allow boards to talk about their governance practices and intensify professional development needs?
↳ Should boards be learning the same materials and having the same training vs each board member seek out individual learning opportunities?
↳ Using generative AI to prepare for board meetings
Jul 21, 2026
Jul 21, 2026
33 min
Topics include:
↳ When leadership team members are resistant to new ideas and feedback: can pre-retreat coaching for inflexible leaders help retreat outcomes?
↳ How do you handle retreat participants who take a long time to come around to ideas?
↳ How can we get everyone on the team to understand and sync up with the organizational strategy?
Jul 14, 2026
Jul 14, 2026
30 min
💥Making change stick: Post-retreat momentum and accountability Part 1
There’s the retreat that comes and goes, and then there is everything that has to be done afterwards. Let’s talk about how to integrate the ideas and ahas from the retreat into your organization’s culture and processes post retreat.
Topics include:
↳ Best practices to create post-retreat accountability
↳ Post-retreat accountability issues… or more general issue of the culture of accountability in an organization?
↳ The impact of having the CEO or other internal team members facilitate vs having an external facilitator (ego… vs role modeling to your team)?
Jul 7, 2026
Jul 7, 2026
29 min
💥Beyond Numbers: Business Leadership for CFOs Part 2
Finishing up our recommendations to CFOs who are career planning, or succession planning. As always, the meta program here is learning how to think like a leader, and the concepts discussed are applicable to senior leaders in any role.
Topics include:
↳ How to get the experiences to be an expert and influential CFO
↳ Opportunities for collaboration between CFO and marketing
↳ What can a CFO do to be more successful?
Jun 30, 2026
Jun 30, 2026
29 min
This session is for CFOs planning their next career moves, however the career strategy tips discussed here are applicable to any senior leader looking to reflect on their next career move, or succession planning for their organization.
Topics include:
↳ The lifecycle of CFO: Average CFO tenure, and what can a CFO expect from their career
↳ Managing the CEO/CFO relationship
↳ Removing barriers that prevent CFOs from operating at full capacity
Jun 23, 2026
Jun 23, 2026
32 min
💥Leadership Retreats: Mistakes to Avoid Part 2💥
Learn from the mistakes of others and have your most productive leadership retreats yet. Stand on the shoulders of our best leadership retreat suggestions.
Topics include:
↳ Using an internal facilitator vs an external facilitator
↳ What leaders need to change about their perspective on leadership retreats?
↳ The impact of alcohol on retreat success: Should drinking be part of the agenda?
Jun 16, 2026
Jun 16, 2026
33 min
💥Leadership Retreats: Mistakes to Avoid Part 1
For a deeper dive into how to plan and structure your executive offsites and team development for max impact, we are sharing here the recording of our very popular opening-the-kimono knowledge share Q&A session on leadership retreats mistakes to avoid.
Topics include:
↳ Corporate Values: Being strategic to highlight and reinforce desired corporate values and behaviors into the retreat design
↳ Addressing the elephant in the room
↳ Team building activities vs relationship building activities
Jun 9, 2026
Jun 9, 2026
35 min
💥Who's Running Your Company: Achieving High Employee Engagement Part 2
Closing out this important topic on the core leadership skill of engaging our employees. We are all moving at high speed; let’s take this half hour to try to get into the heads of our employees to help them do their best for you and your organization, and vice versa.
Topics include:
↳ How does an eager, motivated, capable, resourceful new employee end up checked out, burned out, and disengaged…?
↳ Making the business case for a budgets for employee engagement investments such as training, retreats, etc.
↳ How to give our employees the space to recommit to the organization and reengage.
Jun 2, 2026
Jun 2, 2026
36 min
💥Who's Running Your Company?: Achieving High Employee Engagement Part 1
Understanding how to develop a loyal, diligent, and high-performing team is a key leadership skill… and yet, all the stats point to the same thing: Employees have become disengaged from their work in record numbers. If this is true at your shop… who’s running your company??
Topics include:
↳ Is 100% employee engagement even possible?
↳ How can leaders and managers know they have done enough to support, motivate, incentivize their employees to engage them?
↳ Evaluating employee engagement at the individual level vs the staff as as a whole.
May 26, 2026
May 26, 2026
30 min
💥Succession Planning: Future-Proofing Your Organization: Part 2
In part 2 on this topic, we close up talking about the tight connection between employee engagement and succession planning, as well as personal brand development of key employees as part of succession strategies.
Topics include:
↳ How long does it take to bring someone up to the executive level?
↳ When boards succession plans: How to get boards on side?
↳ Personal brand development as part of succession planning strategies
May 19, 2026
May 19, 2026
28 min
💥Succession Planning: Future-Proofing Your Organization: Part 1
Even if an AI bot is your planned successor, any succession plan is better than no succession plan. Succession planning should not be scary; it’s good for business. In this two-parter, we share key considerations for successful succession planning.
Topics include:
↳ Normalizing succession planning when leaders may feel replaceable.
↳ Fear of “putting all your eggs in one basket”: Training employees when they can leave at any time.
↳ Specifying long-term notice in employee contracts.
May 12, 2026
May 12, 2026
27 min
💥Member Value, Non-Dues Revenue, and New Association Business Models: Part 3
This part 3 wraps up our conversation for association and nonprofit staff by tackling the tensions that exist in the industry: saturated markets, attitudes towards sponsorships, the new member vs long-time member experience gap, and more.
Topics include:
↳ Associations often offer perks to new members, but what about their existing loyal members? Where should the balance be?
↳ How can we do sponsorships differently to avoid the tension between members and sponsors?
↳ Associations are often operating in a saturated market; what considerations should be made for M&A and competitive analysis?
May 5, 2026
May 5, 2026
28 min
💥Member Value, Non-Dues Revenue, and New Association Business Models: Part 2
In this part 2 we reach deep to ask the existential question: Is transformation in the association space really possible? What would it take to see a new business model? And are there really new ways to drive non-dues revenue?
Topics include:
↳ Is transformation possible for association given the current culture?
↳ How can we persuade current association staff to see the benefits of running their associations like a business?
↳ Are there really new ideas for non-dues revenue?
Apr 28, 2026
Apr 28, 2026
27 min
💥Member Value, Non-Dues Revenue, and New Association Business Models: Part 1
This one is for our clients and colleagues in the association and not for profit space, but the conversation around value to clients and being brave enough to change the status quo remains relevant across industries. There was so much to talk about this became 3 episodes!
Topics include:
↳ Why don’t we see more significant “transformation” and reinvention in the association industry?
↳ If an association relies on non-dues revenue (eg. products and services) to survive, what is the distinction between running an “association” and a “business”?
↳ What pressing challenges is the association industry facing?
Apr 21, 2026
Apr 21, 2026
26 min
💥Digital vs Transformation: A Leadership Discussion Part 2💥
Closing up our conversation and Q&A on digital transformation with more perspective, strategy, and practical tactics.
Topics include:
↳ Planning vs Action i.e. speed of decision making: How important is a robust planning and research phase vs speed to implementation or speed to market?
↳ Does “digital transformation” have to be all encompassing? Can’t modernization and digitization or automation be enough? , and
↳ Digital transformation: Investing in technology or investing in people?
Apr 14, 2026
Apr 14, 2026
30 min
💥Digital vs Transformation: A Leadership Discussion Part 1💥
This session is for anyone who feels their organization may have outgrown their current tech stack. Let's answer the questions: Is the prospective digital change really strategic? Is it really transformative? And what management practices need to be updated?
Topics include:
↳ Understanding the difference between having a ‘strategy’ and having a ‘plan’ (and why it’s important).
↳ If 50% of organizational transformation projects fail… what aren’t we learning from the mistakes of others?
↳ How can we use AI in our digital transformation?
Apr 7, 2026
Apr 7, 2026
30 min
Rounding out this three-part series on leadership retreat success strategies. This part 3 dives into addressing more challenges you may encounter without the proper forethought, communication, and expectation setting.
Topics include:
↳ Addressing the financial optics in tight economic times
↳ The impact of a work-from-home and hybrid team on leadership retreat planning; and
↳ When employees see a leadership retreat as an inconvenience
Mar 31, 2026
Mar 31, 2026
32 min
💥Powerful Leadership Retreats Part 2💥
Getting into some leadership retreat whoopsie scenarios in part 2 of this topic. WWRRD: What would Randall and Ronja do??
Topics include:
↳ Managing poor attitudes and conflict going into a leadership retreat.
↳ When the most senior leadership doesn't think they need to change; and
↳ When leaders don't have 100% confidence in team members who are at the retreat.
Mar 24, 2026
Mar 24, 2026
32 min
💥Powerful Leadership Retreats Part 1💥
Sharing here the recording of our original live session on what goes into organizing a truly impactful retreats that propel your organization to the next level of growth. We covered so much we got three episodes out of it!
Topics include:
↳ What challenges can a leadership retreat solve (and what problems can it not solve)?
↳ Moving from alignment to implementation and accountability when the retreat is done. , and
↳ Why do leadership retreats fall flat? (And how to avoid this from happening)?
Mar 17, 2026
Mar 17, 2026
31 min
💥Hiring a Keynote Speaker: 10 Great Questions to Ask Part 2💥
You’re on your way to being expert at sourcing the right fit speakers for your retreats and events after this!
Topics include:
↳ If all professional speakers get the same certifications and learning, is it the same quality across the board?
↳ Creative negotiations in lieu of speaker rates? , and
↳ What's it like working with TOP speakers…
Mar 10, 2026
Mar 10, 2026
30 min
💥Hiring a Keynote Speaker: 10 Great Questions to Ask, Part 1
When clients knock on our door to speak, we make sure it’s a good fit for both sides. In this episode we shed light on the business of speaking, and share the questions you should ask any speaker you are considering.
↳ The speaker selection process
↳ How to identify real quality speakers, and
↳ Speaker budget vs budget speakers: Do you get that much more for paying that much more…?

About Randall Craig
Randall has held a long-time position at KPMG, was an executive at an American public company, and founded (and exited) two of his own companies. He has served over 100 organizations as an advisor or board member, leads the Braintrust Professional Institute, and is a venture partner at a VC. Randall has written 8 books and has built a library with over 1100 resources. Randall delivers C-suite coaching, facilitates high-stakes meetings, and speaks at leadership retreats.
Randall has been inducted into the Professional Speaking Hall of Fame, and earned a Black Belt in Karate. He holds an FCMC, CFA, MBA, CSP, and is a certified Basadur Simplexity facilitator.