Charity leadership is harder than ever. COVID-19’s lasting impact, economic fallout, and global uncertainties with no clear end in sight have made the best plans and practices fall apart around us. The leadership approaches we were trained in can’t answer all the questions we have to ask now. On top of that, many of the ways we’ve developed leaders in the past are now impossible.

Whether it's by choice, by retirement, or by termination, too few leaders show their best selves on the way out. This pattern holds true across industries and the costs of it are deeply damaging.

In a time and culture where there can be a lot of affirmation for posting or saying things that dismiss or demean others in search of a clever mic drop moment I sometimes struggle. The thing is, I can be highly judgmental and I'm quick witted enough to craft some pretty clever tweets that could probably earn me some kudos from those on my side.

But that's not what I deeply want.

Too often we tolerate people who's attitudes, behaviour, or relational failings are negatively impacting the entire group. It's so tempting to keep trying to nudge them into line or justify the need to wait just a little longer before making the move, especially if they are otherwise productive. Some blend of compassion, confusion, and cowardice extends the situation and increases the damage.

What if we reframe the dynamic?

For some people, moving any block from the stable tower (even if the tower is becoming outdated and declining in results) puts the whole tower at risk. They can't discern which pieces are load bearing and they are afraid everything that has been accomplished could be destroyed by moving the wrong block.

Understanding that healthy is not truly a binary reality: neither leaders nor organizations can be fairly typed as definitively healthy or unhealthy; there are still some strong tendencies that are worth considering.

It's funny and fascinating to me that the entire planet has somehow agreed that finishing first, second, or third is deserving of a precious medal and historic acclaim, but fourth is essentially meaningless. It's interesting that the current system didn't start at the first modern Olympics in 1896, but eight years later. I can't find any explanation of why there are three winners instead of just one, or four, or seven. And yet it's absolutely ingrained into the collective conscious of humanity.

I've had several coaching sessions in recent weeks where we talked through specific, current situations where no matter what path a leader or organization chooses there are sure to be some stakeholders who are not going to be able to agree. There is no fully peaceful path.

So what does a wise leader do?

Offend on purpose.

Maybe your experience is less dramatic, but most of us can relate to the sense of our identity being too closely tied to our performance and the approval of others. If we don't get a handle on that insecurity it can all too easily lead us astray; with potentially devastating effects.

The thing about loyalty (as I've written before) is that it comes at the cost of trust and time, and must be earned, not imposed.

Loyalty to any country, cause, creed, organization, or individual should involve a degree of critical assessment, an unflinching reality check to see the best and worst of what it offers. Blind or compelled loyalty is at best idealistic and always dangerous.

Turning weaknesses into strengths takes a huge effort and rarely pays off. Ignoring weaknesses to prioritize strengths leaves dangerous vulnerabilities. So instead let's figure out what level of development we need to achieve so that our weaknesses don't undermine the things our strengths (along with hard work, team, and luck) otherwise make possible.

If every decision requires your personal approval.

If you find yourself redoing your subordinates assignments.

If you've been accused of micromanaging.

If in your heart you secretly feel like it would all collapse without you.

If you can't take a day off, let alone a two week vacation, without checking in frequently and worrying the whole time.

You have a trust issue.

I am grateful for those leaders who are gifted and committed to building healthy organizations that are ready to thrive after they move on. But I have a growing appreciation for the reality that there are other ways to succeed as a leader. The failure comes when we misunderstand or never explore what we really care about.

I often share the phrase 'Anything worth doing is worth doing poorly" as a reminder to myself and others that the important things in life are rarely east from the beginning. We need to be willing to do things at which we aren't particularly talented alongside our areas of uncommon skill. Sometimes it leads to discovery of an untapped excellence, but often it may simply be a pleasant curiosity that gives us some perspective and fun.

In a conversation with a skilled spiritual director I described the feeling of helplessness I can experience when I can't handle the variety and weight of need I'm exposed to. With compassionate wisdom she encouraged me to sit with that sense of helplessness and see if there's a lesson for me in it.

I think there is.

In healthy organizations the mission is understood to flow between departments as information, resources, and support is exchanged. That kind of flexibility and priority adaptation makes for a highly productive and engaged staff. We can evaluate teams, but the standard is how they contribute to the overall goals of the bucket, not how they're doing on their own.

It seems like a dramatic shift is happening in the charitable sector in how we tell stories. No too many years ago I remember hearing advice about finding the most heartrending images to use in fundraising efforts because they bring in the most money. That may still be true, but those increased donations come at a cost to the dignity and privacy of people who may never have the opportunity Gavin had to call me out on breaking his trust.

In typical years we can manage our energy with varying amounts of effort. We can seamlessly shift from a comfortable, sustainable pace to something just a little more intense for a limited time to accomplish a particular goal and then ease off a little. We usually have all kinds of range between just getting by and going full out. But that's not the case right now.