Part of a series on leadership transition.

No leader will lead forever. We all eventually move on to new opportunities. Or die. Or relocate.

This is a consistent and inevitable fact. It’s perplexing that many leaders, who normally pride themselves for vision and foresight, avoid facing it. It’s not that transition isn’t thought about. In fact, for many leaders, it may be a consuming thought. But, like poor health, many people prefer to spend their time and energy worrying instead of changing habits.

Leadership is the opportunity to build. We can build lives, organizations, and value. People thrive when they are nurtured and cared for. The time of transition is one of the greatest opportunities for a leader to demonstrate their best leadership. But, there are challenges which must be faced.

The Challenges

Buyer’s Market

It’s a demographic problem. There are more Baby Boomers than there are Generation Xers (remember us?) The ever-fascinating Millennials are mostly not ready for many executive positions. So, for the time being, it’s mostly going to be Gen X picking up the slack (remember when we were called “Slackers?”).

Other relevant demographic factoids: Boomers are demonstrating a hesitation to leave senior leadership roles. This is, in part, resulting in Gen X and Millennials, who are dramatically more entrepreneurial, being more likely to be self-employed and less interested in a corporate ladder.

Many Baby Boomers needed to compete, climb the ladder, dog-eat-dog it up to their positions in leadership. However, the economics of leadership has changed. There are now more leadership positions available than successors. The demand is greater than supply.

The best successors can pick and choose. The best may not need to climb your ladder, wait in the wings or jump through your hoops.  Your position, your organization may need to become attractive to them.

Last demographic factoid: For both Gen X and Millennials, compensation packages aren’t the primary motivators in job choice. Things like quality of life, work/life balance, connection to mission, the opportunity to make a difference may be more important for a candidate. This means smaller organizations can easily compete with larger ones – just by being better places to work.

If you are having a tough time finding good leadership successor candidates – you might need to brace yourself and ask, “Is it us?”

Has your organization answered this question: What are we doing to attract the best leadership possible? Are we going to need to settle?

Self-Identity

For many leaders, our job and our role is our identity. We have authority, influence, and perks. Who are we without our job? It’s nice to have a title (even if we made it up) that says, “I am someone.” For most people, it’s never quite as exciting to say, “I was someone.”

It’s fundamentally critical for leaders looking at a transition to answer the question, “Who do I want to become in this next phase of life?”

For some of us, the answer is, “I want to start or lead something new.” Totally fine. For others, this is, “I want to fully enjoy my time as a Grandparent.” Also, fine. Some want to find a way to do the “fun stuff” of their previous job without the responsibilities – volunteer and board positions often make this possible.

The point is, we need to re-create who we are and who we want to become. This shifts the transition process from, “What am I leaving?” to “I’m excited about where I’m going!”

Who do you want to become? What do you want the next phase of your life to be about? What remains to be accomplished or experienced?

Not Prepared Financially

Not being prepared financially is a very common reason for delaying the transition. It might be embarrassing for some – so it isn’t often talked about.  However, high-earning leaders in executive positions often tell me, “I’d like to retire now but I’m not financially able.” Many of them are also married to high-earners. These are people whose incomes are in the top 5%-10% of the country.

It isn’t as if turning 60 (or whatever our individual magic number is) suddenly sneaks up on us. It takes us 60 years to get there. Deep down, we know, we could see this coming.

This is anecdotal, but in my experience executives who’ve built their own businesses seem to be financially ready to retire sooner than others. It’s the executives who were hired into their positions who seem the least ready. The lesson from this is that their boards would be wise to start a transition planning conversation with their CEO’s earlier rather than later.

Have you (and your spouse or partner) created a clear picture of how you want to experience life in this next chapter? Do you know what it will take? What professionals can you talk to who can help guide you? What mentors or friends, who have transitioned well, would be willing to share their experiences with you?

No Bench

I once worked with a client whose executive got hit by a truck. Really. Fortunately, he’s ok now. But his recovery took some time. The accident threw the organization into a state of panic. No one was lined up or prepared to step in for him. There was no bench. He made all the key decisions, handled the tough staff issues and carried the key strategies internally.

I value this story. Nearly all the executives I tell it to hate it. It demonstrates a very difficult reality: Everything is not within our control. The unexpected happens. We’ll leave our positions prepared or not.

Many of us haven’t developed our bench. Perhaps we’ve built a team of great 2nds. “Doers” who are great at supporting and implementing our work as leaders. They may not be motivated, creative or driven to function well as key leaders. Sometimes this is due to their individual personality or backgrounds. Sometimes they’ve been conditioned, by us, to not take active leadership roles. Often we’ve selected or hired people to be implementers and put limited effort into helping them develop their executive capacities.

It takes time & effort to develop a bench. However, with focused effort, it rarely takes as long as many imagine. If done well, the effort becomes self-sustaining. An organization that learns to build capable leaders – keeps doing that. It’s a matter of values and culture. The best leaders naturally build more leaders.

How deep is your bench? Who can step in and take over key functions? What are you doing to actively cultivate your bench?

Trust

Many leaders find it difficult to let go and trust others to carry on, particularly those in a Founder or Legend type role. (There are people who fundamentally shaped the culture, purpose, and direction of the organization.) There are a number of common reasons for this. Some of which are directly tied to why we may not have developed a sufficient bench.

Some of the challenges is in how we define trust. The kind of trust I’m referring to has been earned. “Trust but verify,” Ronald Reagan said. The best leaders create opportunities for their trust in others to be offered, earned and built. They actively invest in helping others learn the skills, character, mindsets, and maturity needed to carry trust. They don’t leave trust to chance.

They see trust as a relationship dynamic they helped build.

Trust is a deep and important issue for leaders. Our level of trust determines our ability to rise. This isn’t as compared to others. Just as compared to ourselves. Leaders with lower levels of trust don’t accomplish as much as they could. They struggle to handover their organizations. They do damage to their legacy.

Do what you need to do to start building trust. Entrust small things before big things. Learn how to interpret other’s mistakes. Many mistakes are a normal part of the learning process. If you believe your trust issues run deeper than a specific workplace context – counseling might be one of your best business investments.

What is one way that you can extend trust to someone on your team? What do you need to do to set them up for success? What do you feel you need to see before you believe you can offer more trust? Are your expectations responsible for holding you back?

To Conclude

Take this opportunity to prepare to transition well. Set your team and your organization up for the best possible success. Engage ideal successors while they are available. (If they are good enough to be “ideal” they have options and don’t need to wait for you.) Prepare for what’s next. Preserve the legacy of what you’ve built by performing a flawless handover.

Contact me if you’d like to explore how to set your organization up for a successful leadership transition.