Lessons Learned the Hard Way: The Critical Connection Between Board and CEO

Every board decision assumes the organization can execute the company’s strategy. If the organization fails to achieve the outcomes expected, the root cause is routinely categorized as one of two things: a “failure to execute”, or “insufficient capital to execute”.

Both of those failure modes are typically tied to the leadership and management team, but (in my opinion), the fault is equally divided between the board and the CEO.  

Why?

Because most strategic failures aren’t caused by bad strategies, or even bad execution. They happen because organizations overestimate their ability to execute. Capacity stretches, alignment slips, adoption stalls; by the time the signals show, the capital is already committed or spent.

The board is ultimately responsible, but they typically depend on, and deflect responsibility to, the CEO. The CEO typically operates under the understanding of being empowered to deliver on a mandate of achieving certain objectives, but they can also fall back to the position of “carrying out the wishes of the board” when the results aren’t coming as expected.

I just finished reading the book “Extreme Ownership”, (see my last blog post) so I’m reminded that even when I reported to a board, I still owned the responsibility of the decisions they made. It was my job to provide the best insights and information that I could, and if it still looked like they were arriving at the wrong conclusions and choosing the wrong course, the onus was on me to find a better way to communicate. As one supportive former board member once succinctly put it, “leaders find a way”.

According to Jocko Willink and Leif Babin (the authors of Extreme Ownership), the ultimate leadership metric is the successful execution of the mission; there is no other metric that matters. If the mission is important, leaders find a way, no matter what the obstacles.

CEOs aren’t hired to “carry out the wishes of the board”; they are hired to lead the successful execution of the mission. And although the board hires the CEO, that doesn’t mean they have safely placed the onus of success on the shoulders of the CEO.

I have been in both situations several times – a CEO, and a board member, and I’m also someone that’s been hired to help a CEO. I’ve hired CEOs, fired CEOs, and been a CEO. It’s a complex arrangement, and unless the company simply is maintaining a proven course following its proven strategy in its proven marketplace, it’s critical both sides (CEO and board) know the landscape, the risks and the true ability of the company to execute the strategy.

It’s this last thing (knowing the company’s true ability to execute) that causes most CEO-Board failures – and it’s completely avoidable. In hindsight, I believe it was the primary cause of failure for the last company I was involved with. Strategies can be debated and adjusted as markets and opportunities evolved, ample money can be raised to fund the execution of the strategies, but the failures happen when the board and CEO can’t accurately assess the organization’s true ability to execute the strategy.

And it’s not one thing; it’s not just having the right developers (or enough of them), it’s about being able to execute everything else as well – the marketing, the sales, the growth of the team and the effectiveness of the team as it grows. Customer relations and support, retention, and administrative acumen with a sense for the company’s mission. A true assessment of the company’s abilities - all of it, together. That’s the blind spot. That’s what’s missing. That’s what most companies that failed left to “figuring it out along the way”.

Recently, Mina Johl, founder and CEO of Purple Wins, asked for my perspective on how the language they use lines up with manufacturing CEOs and boards. Their solution to the problem is an AI powered, execution intelligence platform called “NAVETRA”. I’ll be candid: most of the input I’ve given her team is based on my failures, not successes. (Fortunately, there were some successes too, but the biggest lessons were learned from the failures).

Their solution, NAVETRA, introduces a new metric for the board and management to use, “Operating Profit at Risk”, or OPaR. In effect, it identifies and sets a value to execution risk — not project, market or financial risk, but execution risk - before the capital is committed. It’s no longer a matter of “figuring it out along the way”.

It breaks the cycle of “fund, figure-it-out-along-the-way, fail, and then fund-some-more”.

Strategies can change, tactics can change, but the company’s capability and ability to execute doesn’t have to remain an “unknown” or something that becomes evident too late. And it doesn’t have to be (nor should it be) determined by external sources. With the tool that they have developed, Purple Wins make chance-of-execution success visible before the costs are locked in. It uses the information gathered within an organization by the people within the organization, and it provides a quarter-by-quarter metric to keep on course, or an early warning when they are no longer on course.

It’s more than just financial models, strategic plans and an external risk register. It includes and processes relevant input from ten different execution domains. These ten execution domains dive deeper into three broader questions: is the team pointed in the same direction? Does it have the capacity to deliver? And, ultimately, can the team convert the strategy into business results?

For boards, it adds a measurement for execution confidence, organizational readiness, and the aforementioned operating profit at risk metric. For CEOs, it helps keep the board and the executive team informed and aligned and adds a framework that keeps the whole executive team on track, on target, and pulling in the right direction.

It may be just the right tool to help CEOs and Boards share the responsibility and burden for success.

Additional reading and resources:

For more information on the book Extreme Ownership, check out my last block A Book Review: "Extreme Ownership - How U.S. Seals Lead and Win" .

For more information on “OPaR” (Operating Profit at Risk):https://www.purplewins.io/what-is-opar

For information on NAVETRA:https://www.purplewins.io/navetra

For additional information on Execution Risk Governance: https://www.purplewins.io/execution-risk-governance

And here's an invitation from Purple Wins:

Purple Wins is enrolling new cohort members for it’s 2026 Execution Risk Benchmark Study. Each participating organization receives a confidential OPaR range, its three largest contributing execution domains, its sector position, and a leadership-ready report. If you are interested in participating, click here:

https://www.purplewins.io/benchmark-study