Blog
Insights, tools, and training straight from the team at Compass Point
BLOG | LEADERSHIP
Are you tolerating toxic productivity?
Toxic productivity. Is this a new term to you? Or did the phrase make you cringe because you KNOW it exists in your organization? While it sounds like an oxymoron, it is more prevalent than most business leaders care to admit. Toxic productivity comes from employees who are a constant source of drama...
Read PostBLOG | PEOPLE / TALENT
Five Years Later: Why We Still Do R5
It has become more than a week on the calendar. It’s part of who we are at Compass Point. It is a reflection of what we believe about people, performance, and long-term success. Learn why we – as a team – step away, recharge, get smarter, and return ready for the second half of the year.
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BLOG | STRATEGY
Technology Is Not an Initiative. It Is the Strategy.
Many boards still discuss technology as a cost to manage rather than a strategic asset to leverage. For family businesses, the question is no longer whether to invest in technology. Is your board governing technology as a support function, OR as a critical driver of the company's future success?
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BLOG | FAMILY DYNAMICS / GOVERNANCE
What Actually Holds a Family Business Together Across Generations?
Family businesses rarely struggle because of strategy alone—they struggle when there is no shared purpose strong enough to unite generations. Long-term continuity depends on more than ownership, succession plans, or governance; it requires a clear reason for the family to work, lead, and build together.
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BLOG | FAMILY DYNAMICS / GOVERNANCE
How Governance Preserves Family Harmony and Reduces Conflict
Stronger governance means stronger families and less family dynamics. Governance helps ground decision-making to navigate love, power and money and reduce conflict in family businesses.
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BLOG | OWNER FINANCIAL GAP
Mind The Gap – Closing Financial Gaps Before They Become Crises
Financial crises in family businesses rarely appear overnight—they develop quietly when expectations about retirement, ownership transitions, and liquidity outpace realistic financial planning. By identifying potential financial gaps early and aligning family needs with the business’s actual cash capacity, owners can avoid rushed decisions and protect both the company and family relationships.
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BLOG | FAMILY DYNAMICS / GOVERNANCE
Talking Business with Tom Garrity: When the Past Shows Up and What Strong Families Do About It
Family business challenges rarely start with strategy—they often stem from inherited patterns of communication, conflict, and identity that have shaped the family for generations. The good news is that while these patterns are powerful, families that intentionally build awareness, resilience, and better governance can break the cycle and prepare the next generation to lead differently.
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BLOG | NEXT CHAPTER
When Your Role Ends But Your Story Doesn’t
When you spend a significant portion of your life building a business, walking away comes with a wide range of emotions. After 13 years building a bakery from the ground up, Angela shares the unexpected identity shift that comes after leaving a business – and what founders can learn about purpose, resilience, and life beyond ownership.
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BLOG | LEGACY / COMMUNITY
Channeling Love into a Family Business Legacy
Marking a very special anniversary, Catherine reflects on how her family turned their loss and love into purpose through a family foundation – and why giving back can become one of the most meaningful parts of a family business legacy.
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BLOG | LEADERSHIP
How Ready Is Your Next Generation for Leadership?
Relying on interest alone can jeopardize family business continuity and legacy. To ensure Next Gen readiness, an owner must move beyond assumptions, and objectively develop and measure leadership progress through proven skills, real-world experience, and structured mentorship.
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BLOG | FAMILY DYNAMICS / GOVERNANCE
Talking Business with Tom Garrity: The Next Generation’s Dilemma
If you want your Next Gen in the family business, read how to make it a place where capable adults can lead, grow and be trusted. Otherwise, they’ll blaze their own trail – and they won’t be wrong to do so.
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BLOG | PEOPLE / TALENT
Are You Planning to Use AI to Solve Problems — or Just to Move Faster?
AI delivers real value when leadership teams focus first on clearly defining the business problems causing friction — not on chasing new tools or moving faster for its own sake. The companies seeing meaningful results use AI to reinforce priorities, improve decision-making, and reduce variability, rather than to amplify unclear goals or inconsistent execution.
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BLOG | EXECUTION
“It Would’ve Been Faster If I Just Did It Myself”– And Other Lies Leaders Tell Themselves
Most leaders have had this thought – often more than once: ‘It would’ve been faster if I just did it myself.’ The hard truth is that skipping the investment in developing others now only builds a business that permanently depends on you.
Read PostWhere Family Businesses Come to Grow & Learn
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