Is Your Team Prepared?
Written By: Cheron Smalls | HR Director | Warren Whitney
Is Your Team Prepared?
As you plan for next year, consider what your people need to carry those plans forward.
If your most reliable employee were out for six weeks, what would stop? The answer says a lot about how ready your team is for next year.
I once worked with a technology director who knew an organization’s systems inside and out. He was a founding employee and built many of those systems himself. Two junior employees worked alongside him, but he still held much of the knowledge.
As part of business continuity planning, the organization identified that gap. The director documented key processes, trained his colleagues, and gave them opportunities to handle situations independently. About two years later, he left to start his own business. The team was ready. Critical functions continued, and one of the remaining employees moved into a management role.
“It was a disappointment, but it wasn’t a panic.”
That preparation protected the organization. It also gave employees the experience they needed to take the next step in their careers. As you plan for 2027, how prepared is your team for what comes next?
Look at the people behind the plan
Your goals for next year may include growing revenue, expanding a program, or reaching more clients. Each goal will require something from your team. Before you commit, consider who can do the work today and who could learn to do it with the right support. This applies whether you lead a ten-person firm or a large organization.
Leaders often turn to the same reliable team members because they know those employees will deliver. Over time, more knowledge and responsibility can gather in those roles. Other team members have fewer chances to learn, and the organization becomes less agile and more dependent on a handful of individuals.
Ask where that may be happening on your team. Is there work someone else could begin learning? When a new opportunity comes in, could an experienced employee guide a colleague through it instead of taking it on alone? Don’t leave this to chance. Decide with intention that you want knowledge and development spread across the team, and set aside time for teaching, practice, and feedback.
Give employees a future they can see
In a smaller organization, the next job title may not exist yet. An employee can do good work and still wonder where they can go from here. I encourage leaders to go beyond the standard performance review and include career development in their conversations. What do they want to learn? Where would they like more responsibility? What interests them about another part of the organization?
The answers can help you connect individual goals with business needs. An employee could learn a new system, lead a supported project, or join meetings to understand how decisions are made. A colleague could introduce them to important clients, referral partners, or vendors and gradually give them a larger role in those relationships. Many of these opportunities cost little beyond time and trust, yet they show employees what is possible and help the organization build the skills it will need.
Be thoughtful about workload. If someone takes on a development opportunity, discuss what time and support it requires and what may need to come off their plate. As responsibilities grow, revisit whether their role and title still fit, and whether compensation should change with them.
Prepare for the gaps you already know about
A planned vacation can reveal how much an organization depends on one person. So can a retirement conversation or a request for leave or a sabbatical. Start with the essential work. Who processes payroll? Who understands a particular system? Who knows whom to call when something goes wrong?
Then look beyond the task itself. A written procedure may explain the steps, but the person providing coverage also needs access, practice, and enough understanding to answer questions. Relationships deserve the same attention. If an owner or executive director is the only connection to a key partner, begin including someone else in those conversations. Shared knowledge includes knowing the people who help the organization succeed.
Keep learning about your team
Preparation needs to change as employees gain experience. Someone who was new to a type of work last year may now be ready to lead it. Another employee may have earned a certification or developed an interest you have not discussed.
Regular conversations help you make better decisions about assignments and development. They also make it easier to respond when new work arrives or someone becomes unavailable. A plan that sits on a shelf will not help. Revisit it as your people change.
As you look ahead to next year, choose one place to begin. Identify an essential function that needs a backup, a relationship that needs to be shared, or an employee who is ready for a supported next step. Agree on who will be involved, make time for the work, and check progress along the way.
When the technology director left, the organization could say, “It was a disappointment, but it wasn’t a panic.” Aim for that kind of transition.
If you would like a second set of eyes on where to start, we are glad to talk it through.
Are you planning for the future?
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