“Dream job” is referenced these days ubiquitously. It’s among the most corrosive world-of-work ideas that have surfaced over the last decade.

Here’s my issue: the notion that we all should have, or be pursuing, our own “dream job” puts a social media perfection filter on something that is not an end state.

When it comes to keeping staff engaged, it’s never been a more fragile time to be a leader.

We judge our staff by what they have recently accomplished—in other words, by what they have already done.

But our employees judge themselves by what they believe they are capable of doing, one day.

During a recent coaching call, a client and I talked about this very thing, about how important it is to close this mindset gap, especially if we want to keep good staff during the so-called “great resignation.”

We are all replaceable at work. Eventually, every person leaves but the show goes on. The work continues. The brand endures.

Think about a longstanding organization over the course of fifty years. It brings to mind the Ship of Theseus. Does an organization which has had all of its people replaced many times over, remain fundamentally the same thing?

All leaders have at least one or two special attributes. Things for which they are known, that they can do which are especially valued. You’ll still be replaced, no problem. But, it’s good to know: what sets you apart?

I like to have those leaders I coach ask themselves:

• What one thing am I better placed to do than other leaders around me?

• What skill or competency do I have those others seem to lack?

• I can certainly be replaced, and when I go, it’ll be very hard for them to find another leader with ?”

Knowing what differentiates you from others helps you position yourself, and clearly articulate your value…

I like to have folks ask themselves: “why must I do this work?” It still gets to a person’s purpose, but it uses the back door. Encased within this question is an imperative. It whispers to us, what might happen if I quit…if I ceased to do it? What would I miss most or how would I feel if I simply stopped?

So, instead of struggling with: what is my purpose? Ask instead, why must I do this work? See where it leads you and what it stirs up. You might be surprised.

Interesting things arise from witnessing others be coached—as much as it does when you're being coached personally. Group coaching is a safe, affordable, and energizing way to accelerate through your most pressing issues and ideas, with other progressive leaders who “get it”.

Video conversation between Jonathan Bennett and Danielle Rocheleau on succession planning, and why executive coaching is the next move for Jonathan

Today, I’m excited to announce that I’m launching a coaching practice under a brand-new banner, ClearlyThen Inc. I’m coaching leaders of progressive businesses and organizations whose purpose is to make a big difference in the world.

I believe coaching is a tonic. It is an expansive and inherently creative act. I’ll be there, for when purpose-driven leaders feel like the whole world is resting on their shoulders, or when they are ready to enact change and push hard for what’s next.

Draw an org chart for the organization that you would re-build from scratch. Ask yourself:

How can there be as few levels as possible between the CEO and the front line staff?

How can I maximize the span of control (people, size of budget) of each manager?

How can I design this to minimize program, department, or service silos?

What functions might I outsource, or cost-share with partners?

What measures (KPIs) could I use to show how this new structure improves client service, and streamlines work flow for our staff and volunteers?

Congratulations! You’ve just started some thinking on which you can begin to build an organizational review.

Imagine if all your management team members had high levels competency. How would that change your organization for the better? What would you be emboldened to try? What could the team achieve together? How would clients / patients / participants ultimately benefit? Build a professional development and training plan for your management team.

Build a re-branding project. Here are some powerful questions: If asked, our clients or customers would describe the impact of our work on their lives as… If a staff member or supplier was trying to convince a professional acquaintance to apply for an open position at our organization, they would attempt to persuade them by talking about how much we… When thinking about the impact we make, it’s because our organization is the only one that can…

Find your organization’s articles of incorporation and bylaws. Print them….As you read, and annotate, ask the following questions: Do they properly describe your organization as it operates today? Is there anything in there that is inconsistent with your board policies or practices, or your operational policies and procedures? Do you know if they are compliant with the governing acts in your jurisdiction?

Analyze organizational risks. Use the following quadrants: High likelihood, low impact. Low likelihood, low impact. High likelihood, high impact. Low likelihood, high impact.

Ask, what worries you most about the organization Brainstorm a list of the top 10 things that keep you up at night (finances, IT dependability, staffing, quality of service, lawsuits, etc.) Plot them on the grid. Do you have a contingency or mitigation plan for each?

Stop mindlessly scanning job ads. Instead, ready your organization for your safe departure. Who is the person that would step up and fill your role in the short term due to an emergency? Does this person know I think they will be filling this role? What do they need (training, supports) to be ready should the need arise?Is there an up to date job description for my role? Does the organization have a succession plan for its leadership? Has the Board discussed its plans to ensure a stable transition to a new leader, and its approach to recruitment? Build a leadership succession plan.

What are three reasons why your organization should be doing strategic planning now? (old plan is ending, new pressures, COVID-19 impacts, other changes in the environment.) Give three consequences that may occur if you fail to craft a new plan.

Write down what you would like the legacy of this planning process to be? (bold new vision, deeper connect to stakeholders through meaningful engagement in shaping the plan, etc.)

What do we need to make decisions? (evidence, stakeholder feedback, data, new business models, etc.), and who do we need to help us shape this plan, when and why?