Red Sail Advisors LLC

Consulting to Mission Driven Organizations

What Exactly is a Mission Driven Organization Anyways?

I know that I throw around the term “mission driven organization” with a seeming reckless abandon. The expression mission driven is too frequently used without context and in a wildly wide range of scenarios… so much so that it has lost its meaning and impact. I myself consult to mission driven organizations and, if pressed,…

When Optimism Becomes Denial

It’s human nature. More specifically, it’s the leader’s nature… to be upbeat, to see the positive, to look forward and into the future with optimism. This is not a universal truth, but in my experience people tend to gravitate toward those leaders who see the good and who exhibit strong virtues… and so when times…

Sell… sell… sell, baby… sell!

I have a lot of respect for those who professionally sell and for leaders who can design effective marketing and business development processes that demonstrate a reliable return on investment for such activities. This is important to the success of most modern enterprises – even mission driven not-for-profits. But it all starts and ends with…

Running Through a Tunnel of Fire

In my book, Saving Organizations That Matter, I talk about the notion of leaders and staff “running through a tunnel of fire”… together. Sometimes, groups will do so. Sometimes, they won’t… to the ultimate detriment of their organization and future prospects. Here is a direct excerpt from the chapter entitled Tunnels of Fire. Here I…

You have to have A system!

I learned early on in my career (and probably before that, while in school) that a major determinant of success is “the system”. This is the methodology and associated tools that a person uses to remember stuff. To track details. To know when something is due. To ensure you get back to people when you…

We all have blind spots

I have blind spots. You have blind spots. It’s part of our nature because we learn from our distinct experiences, are constantly shaped over the course of our lives, adopt or discard beliefs, and experience both joy and pain. The practice of leadership benefits from tools and methodologies for sure, but it is a distinctly…

Make sure you know what your Board really wants. Really, really wants.

Sometimes, when organizations are struggling, trustees will hope to bring in a new CEO who can stir things up a bit, make change, and alter the trajectory of that organization. As someone who has sat on not-for-profit boards, who has consulted to such groups, and who has served as CEO for mission driven organizations, I…

How to Storytell the Mission

Every CEO, most board members, and many executives need to be able to describe the work of their organization in compelling, even emotionally stirring terms. This is vitally important to that organization’s success, though I sometimes encounter some within such organizations who do not recognize this fact. Fundraising, securing and building the workforce and culture,…

What I Learned About Racism Working at an Inner City Health Center

This is a topic I could write, and write, and write about… because I learned a lot. A lot. So, this will very likely be the first of many posts on this topic. I’m committed to keeping the Mission Leader’s Journal Blog pithy and to the point and in honor Martin Luther King, I thought…

“You lied to me”: The Perils of M&A

I have been involved in a number of mergers and acquisitions during my career. Most have gone quite well, after a number of ups and downs (mostly downs at first), but a few have not been successful. M&A, as I’ve written about on these pages in the past, is a tricky business. This is true…

Why Resolutions Don’t Stick

Many of us make New Year’s Resolutions. Some of us succeed. Many of us don’t. Lots of us have tried so many times and failed that we don’t bother any more. We can become jaded like that. Companies can view strategic planning in much the same way. Leaders may go through the motions of setting…

Where does DEI “Belong” When Creating Your Strategic Plan?

Awareness, concern, and motivation have never been higher when it comes to diversity, equity, inclusion, and belonging within corporations across the United States. Thankfully. There’s much room for more progress and no one should declare victory just yet, but I do detect forward motion in this regard within the organizations I support. That said, as…

What The Beatles and Alec Baldwin Can Teach Us About Management

Inspiration can – and often does – come from the most unexpected places. For example, I have been watching the “Get Back” documentary about the waning days of the Beatles as they recorded “Let It Be” and prepared for their first live performance in years. I also recently listened to an interview with Alec Baldwin…

Calling All Cows and Elephants

Sacred cows and elephants in the room – those issues that no one likes to talk about, or has the courage to bring up, for fear of awkwardness, repercussions, or conflict. These are the things that lie off to the periphery and remain in the shadows… and which linger, sometimes to the detriment of the…

What’s Your Strategic Disposition?

At the beginning of any type of strategic assessment or planning project, I like to take some time to try to understand the organization’s “strategic disposition”, that is it’s fundamental personality and tendencies when it comes to self evaluation. Then, I like to apply a bit of pressure to see how deeply held and widespread…

We’ll Fix It With a Reorg!

Sometimes, you need to lay the pieces down on the table, sort and rearrange them, and then reassemble. Organizations change, internal and external pressures intensify, fortunes rise and fall like the tide, and historical approaches should be challenged in the name of innovation, improvement, efficiency, and effectiveness. Such is the case for leaders who wonder…

Why mergers and acquisitions FAIL: They were set up to do just that from the very start!

For many not-for-profit boards, stewardship of the organization’s longstanding mission is job one. They take the enhancement and preservation of the mission quite seriously and frequently that means keeping the structure, operational character, brand, and historical context intact to the greatest extent possible. Anything else would be deemed an abandonment of post, a breakdown, a…

When it’s time to BE MORE DIRECT!

Because I often speak to groups about my book on organizational transformations and ways to manage toxic work cultures, I sometime find myself inadvertently triggering confessions from participants about their particularly difficult personal work situations. I frequently discuss the characteristics of leaders and cultures that can cause an organizational “descent” before I talk about strategies…

Making it Personal by Getting Close

For many who work in mission driven organizations, the mission itself is little more than words touted on the company’s website or documented on posters in conference rooms. It suggests a purpose, an identity, but those words contain little of the essence of the work, of the day-to-day reality, of the meaning. They are, after…

The Valuable Language of Value

There are lots of ways to talk about value. The most straightforward would be to cite the formula: quality divided by cost. This is useful as it demonstrates the relationship between quality and the costs associated with achieving that level of quality. The higher the quality and/or lower the cost, then the higher the value.…

When New Leaders Encounter Toxic Cultures

I have spent a great deal of time working within challenging and toxic organizational cultures, whether as CEO, executive, or consultant, and can say with great confidence that they can prove highly vexing or even fatal for a new leader if he or she does not pursue a deliberate course to tackle that culture head…

The Three Surprising Ways Strategic Planning Can Help Your Organization

Generally speaking, you don’t expect strategic planning exercises to surprise. I mean, what could be so surprising about a process designed to systematically chart a course for your organization? You look at data, you brainstorm, you put together detailed checklists of to dos, and boom, you’re done. No surprises there. But over the past year,…

Mission is the Way Out

“You know that your happiness and suffering depend on the happiness and suffering of others. That insight helps you not to do wrong things that will bring suffering to yourself and to other people.” — Thich Nhat Hanh In many faith traditions, the way forward to enlightenment, knowledge, redemption, and even salvation, can best be…

There is Always a Waterfall

Chaos exists, whether within ourselves, our families, communities, or corporations; it’s just a matter of degree, magnitude, and impact.  The chaos can often be actively managed or suppressed, but sometimes, it breaks free from constraining forces and begins to expand, to dominate.  Once this happens, tamping down on the negative consequences of that chaos becomes a more difficult…

Scaling the “high wall”

No one wants to take on a great challenge for no good reason. You don’t hope for heavy headwinds, rough seas, a high wall to climb over. But life throws these our way sometimes and so we often are confronted with classic fork in the road choices. Do I push through the headwinds, sail across…

The Before and After Consultant

I was incredibly fortunate to have secured a position with Ernst & Whinney (which turned into Ernst & Young while I was there… the first of many mergers in my portfolio) early on in my career. I had worked for the Commonwealth of Massachusetts in a regulatory agency before this and that role was quite…

Welcome to my blog!

I am long-time blogger (based on my outside-of-work interests) and have learned to: (1) write for impact… have something to say and say it well, (2) respect people’s time… get to your point quickly, (3) write often… stale is dead and dead is gone, (4) respect your readers… never spam, annoy or sell, sell, sell,…

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