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In-Advance Staff Transition Roadmap


Everyone will leave your organization. (But that’s OK!) 

At some point, whether it is tomorrow or thirty years from now, every single person will leave. By denying this reality, we too often set ourselves up for frustration, confusion, or poor performance.  By embracing the reality that every role and every organization is a step along a path for the people who work there, we can create structures and expectations that maintain stability, peace, and confidence during staff transitions.  Even in ideal situations, the departure of a staff member requires the emotional cost of change, but if you prioritize making plans in advance, then you can focus on the human impact of a transition because organizational operations themselves are already handled.

Taking a set of In-Advance Staff Transition Actions helps people plan for change far before it happens and feel confident they know what to do when a departure is announced.  When the transition begins or a departure is announced, these set the stage for In-the-Moment Actions.

In Advance Actions create positive work environments and cultivate smooth transitions. Map out a succession plan for each role. Consistently record your staff's duties and processes. Review each role’s job duties and responsibilities to highlight which items could overlap with a co-worker’s knowledge. Set times with your staff to train in overlapping responsibilities.  Create a positive work environment throughout the transition. Review your employees’ tasks and processes, adding how long they can theoretically take.  Invest in apprenticeship, internship, or training programs. Offer intentional professional development for current employees.

Action 1: Create a list of knowledge, skills, and relationships for each role.

Succession planning in its fullest form is organization-wide and focuses on each individual's ‘portfolio diversification.’ An organizational succession plan includes having a clear and regularly updated view of all the knowledge, skills, and relationships necessary for the work and for your organization to move forward. Then, if only one person holds essential information, skills, or relationships, those can be shared through training, sharing, or relationship building. The objective is to reach a situation where if any individual were suddenly gone, the rest of the team would have all the knowledge, skills, and relationships to continue without collapse.

Assumptions: systemic challenges we are not addressing in this piece. To some degree, your organization has the standard power structure: Board of Directors, Management, Staff, Independent Contractors, and Volunteers.   There are certain social and systemic constructs we cannot address in detail or try to fix in this piece, i.e. capitalism, health insurance, labor laws, etc.   Many organizations still work under systemic white supremacist principles.  To some degree, your organization has the standard power structure: Board of Directors, Management, Staff, Independent Contractors, and Volunteers.   There are certain social and systemic constructs we cannot address in detail or try to fix in this piece, i.e. capitalism, health insurance, labor laws, etc.   Many organizations still work under systemic white supremacist principles. To some degree, your organization has the standard power structure: Board of Directors, Management, Staff, Independent Contractors, and Volunteers.   There are certain social and systemic constructs we cannot address in detail or try to fix in this piece, i.e. capitalism, health insurance, labor laws, etc.   Many organizations still work under systemic white supremacist principles.

It may be that a particular skill is so specialized that it exists with only one person, and it does not make sense

for another individual in your organization to learn that skill. In this case, making a very intentional plan of how to replace that skill quickly in the event of a departure is crucial. This may mean identifying partners, consultants, retired employees, board members, or others who could step in for that particular need in the short term but at a moment’s notice. Building relationships with those support players in advance takes specific intentionality, so there is less of a mad scramble to fulfill a crucial need in your organization.

Action 2: Consistently record duties and processes.

As people do their jobs, they develop processes and procedures; they learn what works well and what doesn’t . This happens at both the micro level (ex. It’s important to order the supplies on Thursday, not Friday, to get them in time for the usual Wednesday events,) and the macro level (ex. We have tried seven different major promotional strategies and this appears to be why the one we use now is most effective to generate customers). Because most employees focus on doing the work today, and the assumption is that no one is leaving, these details are often only kept in individuals’ minds and not shared with anyone else. When someone announces their departure, there is sometimes a race to write down everything or train someone on everything before they leave. This is never fully effective, either due to the time remaining to do so, the motivation of the departing individual, or the reality that the number and specificity of details are so vast that it’s impossible to do all at once. Instead, organizations can make a consistent habit for all employees of recording how they do things and what they are learning on the job. This works best when 1) there is a provided format (like a company manual) that people can use, 2) time is intentionally allotted for doing so regularly, and 3) there are rewards or acknowledgments for continuing to add to the record consistently. As a bonus, having these consistently updated work manuals can encourage employees to reflect on their processes. Some employees will make more process improvements in how they do their jobs by consistently reflecting on what they are doing, what is working, and what could work better. In addition, when an employee transitions out, this record will help immeasurably when beginning a hiring process for someone new.

Action 3: Cross-training or job-sharing can strengthen resiliency, team collaboration and creativity.

Sometimes, an organization is large enough that multiple people operate in the same departments with significant overlap with their roles and experience sets. (ex. Three people in a marketing department who handle different communication or promotional channels.) This can make it easier to have multiple individuals fully learn each other’s roles and intentionally swap back and forth responsibilities regularly. This sacrifices some level of efficiency or specialization for benefits in resiliency, teamwork, and creativity, as people can deeply understand and collaborate on their shared collective responsibilities.

This is naturally much more difficult in small organizations or departments with higher levels of training and specialization for each role.

graphics of coworkers working with calendars and clocks

Action 4: Find opportunities to practice sharing responsibilities.

Allow staff to (truly) take a vacation from work and call in sick without needing to check in or answer questions.

Telling someone how to do something differs from giving someone the actual experience. As an organization implements information sharing, skill building, or cross-training, resilience is built by allowing backup staff to try the tasks independently. One way to do this is to emphasize real vacations, where staff members take off and are truly ‘out of the office’ and unavailable. This makes the responsibility more real, giving staff members the confidence to handle tasks in their absence, and also builds the experience that will pay off if and when that staff member leaves permanently.

Because this allows practicing with lower stakes for short-term coverage, it also provides the opportunity for multiple staff to work together on the tasks while the main staff member is ‘out,’ so one person isn’t tossed in the deep end all alone.

Action 5: Consider 'transition bonuses' and make people aware of them.

Despite all the contracts and norms we may have in our organizations, most employment is practically at-will. Opportunities arise, relationships deteriorate, life intervenes, illness strikes – any number of things can cause an employee to decide it’s time to leave an organization. Depending on the role and the advance preparation, giving ‘two weeks' notice’ may be fine or traumatic for your organization and the rest of the team. Sometimes, people may choose to leave immediately, and sometimes, people may give ‘general notice’ that they intend to step down in the next year but can be flexible about it as needed or as other opportunities arise. Organizations can’t fully control how much notice an employee gives. However, there is an option to incentivize longer notice periods through ‘transition bonuses.’ For example, an organization's policy can be that if someone gives their notice to depart with eight weeks' notice, they get some additional payment beyond their last paycheck and any paid time off cash-out when they fulfill the eight weeks. A secondary advantage of these ‘long-transition’ bonuses is that they set up positive energy between the employer and departing employee, where the employee transitioning slowly and helping the rest of the team is seen positively and is appreciated in a concrete form by all. This contrasts with the ‘guilt pressure’ and ‘abandonment’ feelings that often spring up on both sides when someone announces their departure. It may be that having a longer transition for an outgoing employee saves more money (in overtime for other employees, customer disruption, etc.) than the ‘transition bonus’ costs. This strategy may be cheaper and calmer for everyone, depending on the specific situation. It is imperative, however, that if an organization implements transition bonuses that the employees are aware of the policy and can plan to engage with it when they decide its time to leave. Springing the idea on someone who already has given their notice is much less likely to be effective.

Action 6: Make consistent space in the schedule for transitions or disruptions.

Staff departures will happen. Even in the most attractive and robust organization, people will come and go. In addition, there will always be organizational disruptions of many kinds – a difficult customer, a natural disaster, a sudden shift in competition, an injury – any number of real-life issues arise. Organizations often operate by ‘maximizing productivity’, requiring its employees to use every moment of their time and every bit of their energy for the normal day-to-day. This approach ignores the reality of expected disruptions, leaving no cushion of capacity for dealing with issues that arise.

Making space for these short-term issues also sets the team up for success. In more concrete terms, structuring workloads so that employees who work 40 hours a week can consistently complete their day-to-day tasks in 32-35 hours leaves space for all these other resiliency and contingency activities – or to maintain their own morale and energy levels to keep a consistent quality of work.

graphic of people hanging gears onto a a robotic brain.

Action 7: Invest in apprenticeships, internships, or training.

Understand how training entry-level individuals may not bring an immediate benefit but fosters a stronger ecosystem and support for your organization.

Another strategy to minimize the impact of transition is to consistently train people long before they are needed to fill the role. Apprenticeships, internships, or other training programs can build an available workforce for an organization or industry in an overall community. They can also help fast-track a new hire if someone has already been learning the organization's culture and the required skills. Usually someone in training can’t be promised a full-time job (except in large organizations). This means that the organization needs to see benefits in training entry-level individuals without a direct, immediate benefit to the organization. Instead, the investment in the people is the purpose: to build a stronger ecosystem that helps the organization and its people down the road.

This is often hard for managers to embrace because if they can’t offer a trained apprentice or intern a job immediately, they may see that person go work for a competitor or in a different industry, which may feel like a ‘waste.’ The investment in people and professional development has long-term benefits, however, that set you up for future success. Investing in people, not just the short-term needs of the organization, builds partnerships, industry reputation and the ability to hire more quickly to fill a position when needed.

This strategy also can address ‘pipeline issues’ where there are desires to consider candidates for a role who are from particular communities or geographies but where finding a targeted candidate like that on short notice is nearly impossible. Because bringing in trainees is not as time-sensitive, those individuals can be recruited over time and build a pool of future candidates for hiring that is different from whatever workforce recruitment pool may already exist for the organization.

Action 8: Offer career-oriented professional development for current employees.

Similar to trainee programs, investing in professional development and training for current employees can have significant long term benefits. In a multi-tiered organization, replacing a departing employee by promoting or transferring internally can be easier than hiring a new person from the outside. To strengthen the ability for promotions, taking an active stance in both professional development and career building with current employees is very helpful and builds more employee loyalty and enthusiasm. Again, some business leaders resist professional development or career-building work with their employees because it may encourage employees to leave their organization and take advantage of opportunities for upward mobility. But as with entry-level trainees, investing in your workforce pool and the industry ecosystem results in maintaining positive relationships over time, easier hiring later, and a stronger organizational reputation. Internally, it increases the chances of addressing a transition through promotions and entry-level hires, instead of more expensive and risky searching for new people in roles with more responsibility.


Organizations that do some or all of the above steps in advance will find staff transition much easier for everyone involved, including the other members of the team. Many organizations do not pursue these strategies either because they are over-pursuing productivity, or because they are attached to the 'no one will ever leave' mythology.

Small businesses, with so few employees that people are already wearing ‘multiple hats,’ may not be able to spend the time or energy to implement all of these strategies. That's completely understandable. Be judicious. Applying even one of these action steps can still take incremental pressure off of whoever will be responsible when a transition occurs.

In addition to these In-Advance Staff Transition Actions, organizations can prepare to take a set of In-the-Moment Staff Transition Actions as well, to handle the transition itself calmly, and effectively.

Creative Evolutions uses these principles regularly to support staff culture and hiring work for a variety of creative organizations. For information on how our team can work with you, or for more about this process and other ways you can approach staffing, contact Creative Evolutions!

Read More: In-the-Moment Staff Transition Roadmap by Douglas Clayton and Calida Jones

Calida N. Jones is an accomplished musician, social justice advocate, and educator with more than 25 years of experience in performance planning, workshop and curriculum development, volunteerism, project management, and teaching in  private and public institutions.

Douglas brings more than 25 years of experience in the arts and culture industry, specifically within opera, theater, and arts service organizations. Passionate about innovative business models in the arts and culture sector, his driving purpose is to create more equitable and effective ways for talented and committed people to be creative and successful in our society.

Image Credit: Canva, Douglas Clayton, Calida Jones

Work Cited:

Special Thanks for Supporting this Roadmap: Cindy Jenkins, Donald Holmes

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