Your Team Member Wants to Take a Second Job? Read This First.

When a team member requests information about their second job options at their same place of work, you’ll probably be ecstatic. After all, you already like them, are impressed with their work ethic and want to see them succeed in a different role. Plus, you don’t have to spend time finding another outside hire who may or may not fit your company culture.

However, providing the right advice for transitioning into a second job can be challenging. Since you’re interested in developing their skills, you’ll need to research their implications for career development, what onboarding will consist of, and if your employee can handle the workload.

While they may need extra training and a bit of guidance at first, your team member is sure to succeed if you coach them thoroughly. Consider the following ways you can help guide your employee through the process of obtaining, getting trained for, and settling into their new position.

Learning stage: what a second job really means

In this stage, you’ll start to understand why your team member wants to transition into a second job. You’ll place focus on the attitudes surrounding their position, why they require a new role, and whether or not they can stay committed for the period or length discussed.

Pre-Hire: Why do you need a second job?

While it sounds like prying, you’re actually just inquiring why they want to be placed in this role.

If it’s money, ask if they can give up their weekends for this role and how this will interact with their work-life balance. While you’re at it, discuss the number of pay periods in a year they’re likely to receive during their employment period in this second job. It could incentivize your team members to explore new options or press further.
If it’s skill development, suggest other ways they can still learn skills without sacrificing a large portion of their free time. Some examples include paid training in their current role, online courses directed by HR or yourself, or transitioning permanently into a different position. The last thing you want for your employees is burnout!
If it’s overtime pay specifically, coach them on how this works in their state and if management is willing to place themselves in that pay bracket. While all U.S. non-exempt employees receive overtime pay if they exceed 40 hours of work per week, Californians also earn extra pay if they exceed 8 hours in the day. Depending on the state, overtime is more worth it for the employee but less fruitful for the employer.

Don’t come across as being pushy or nosey. Maybe your team member needs money for a personal problem or experienced severe financial upheaval due to the pandemic. Be gentle here and just inquire about the non-specific reason: money, skills, or overtime. Then, state that you only want to know so you can provide the best option for them going forward.

Be gentle here and just inquire about the non-specific reason: money, skills, or overtime.

First day: Can you commit to this schedule?

Some employees won’t know what they’re really in for until they start working. After the first day on the job, always ask your employee if they can commit to this role for the long-term (if they’re planning to stay in the position) or short-term (for a busy holiday season). Keep checking up on them as they develop in their role throughout the days, weeks, and months.

Most schedule conflicts can be fixed with a bit of switching around, and many of your current team members would appreciate some time off or less demanding work life. Ask around if other senior employees are willing to accommodate the new hire before doing so, or you’ll create more conflict in the workplace. This will only make the situation more uncomfortable.

Training Stage: How to immediately teach applicable knowledge

In this stage, you’ll focus on training and teaching immediately applicable skills, knowledge, and attitudes used for their new job. Training typically focuses on delivering a better performance right now but still plants the seeds that help your team members overcome future changes.

Pre-hire: walkthrough and a quick explanation

Your team member likely has some knowledge of the role they’re transitioning into, but it’s still good practice to initiate a walkthrough of their new environment. Introduce your team members to their new co-workers, where their workstation will be, and what types of duties they’ll perform in their new role. Be as detailed as possible, so they can think more about their decision.

Keep a mental note of how your team member is reacting to various aspects of the job. Notice their body language and change of tone when you speak to them. Are they sighing, tired, or distracted, or are they enthusiastic, interested, and in the right mindset to absorb your training?

It’s normal for your team members to feel nervous or intimidated when they’re experiencing something new, but some of your employees won’t verbally state that to you. It’s essential that you ask the right questions to determine if your team members are suffering from the jitters or aren’t suitable for the job. If it’s the latter option, suggest another option and conclude training.

First day on the job: on-the-job training

On their first day, take your employee through a highly interactive setting that fosters a positive training experience. If it’s possible to conclude training in a single day, try to do this. This way, your team members can ask any clarifying questions about the role before they get started.

Some positions require more expensive training, like outdoor management development or experiential activities. Collaborative Learning may also be applicable here, as it can help new employees learn faster if they're directed by other experienced team members.

You’ll still need to coach these skills and mentor them through this process regardless of what method you choose. At the end of the day, you want to give your employee enough independence to take on their role by themselves or with a helper.

Development stage: setting up your team member for long-term goals

In this stage, you’ll focus on long-term development and deepening the current knowledge of your team members. You’ll need to find a development goal that fits your employees' personal needs and future prospects. Their desires need to match up with the goals of the company.

Pre-hire: discuss length of employment

Regardless of how long the employee wishes to stay in this role, it’s important to create a development schedule based on their length of employment. A short-term job role won’t require a long-term strategy or training process, so focus on interactive and job shadowing learning methods. Long-term employment may require simulation games or active discussion.

One of the best ways to determine how long the development stage will last is to recognize potential versus readiness. Although your team members may want to stay in this role long-term or have the potential to see this through, they may not be ready to move into that role right now.

Readiness comes in a variety of forms, skills, experience, or encompassing desire. Their interest in this role may include money to care for their elderly parents, but if the job requires a lot of travel or hours spent away from home, they won’t be able to actively be there for them.

If both you and the team member are okay with this being a temporary role when it was meant to be permanent, that’s great! However, you can likely find a better position for them instead.

First day on the job: Encourage active development

On the first day of the job, encourage active development by specifying their learning objectives. You’ll need to create a training objective based around required active behavior, like meeting a shipment goal or a specific sales figure. Professional learning and management tools can help your employees see their wins in active time, encouraging them to reach for the stars.

Create SMART goals that foster long-term success. You can structure these as follows:

S for Specific: Simple goals are easier to achieve.
M for Measurable: Meaningful goals can help you track progress and stay motivated.
A for Achievable: Attainable goals should stretch your abilities but still be possible.
R for Relevant: Relevant goals can drive you forward because they’re applicable.
T for Time-Bound: Targeted goals take priority in your long-term goals.

An example of a SMART goal for your team member could be something like: John wants to earn the required job-related skills (for example, coding HTML) within 3 months.

Education stage: broaden employee knowledge overtime

In this stage, you’ll focus on a more formal way to broaden your team member's knowledge. Education is often non-specific and applicable over a long time. The education stage is especially relevant when a person has little experience in their new job position.

Pre-hire: Where to start and where to go

Your team members may have experience in this job title, or they may experience a learning curve as they start to understand their role. Some employees will need a more extensive training period, while others can quickly fill in the role with little effort. Regardless of where they start, you need to know how long training will take, as that will affect their start date.

At the same time, some team members may not want to go through the effort of a long training process, which is good to know now. Your team members may fit better in another role, and you can direct them towards a position that will better suit their long-term knowledge goals.

First day on the job: Monitor and evaluate performance

Effective training should result in a change in behavior, but that can sometimes be difficult in a second job. Your team members may have a way of performing tasks that won’t compliment their new role. Instead of coaching away bad habits, try to work around their methods unless they’re dangerous in this new environment (technology in an aircraft, for example).

A good way to tell if a behavioral shift occurred in a timely manner is by testing if they are keeping up with their other employees or mentors in the same position. Don’t just test based on the comparison because not everyone develops in a similar way. Make sure to include and follow their progress from the time they started to now for a more personal evaluation.

Final thoughts

When your employee wants to speak with you about acquiring a second job, they may want to earn back the money they couldn’t earn during the pandemic. On the other hand, they may want to learn specific skills that will benefit you, your employee, and the company for years to come.

Regardless of why your team member is looking to pick up extra shifts, you now have the knowledge necessary to foster life-long success in your employees who want to transition into another position. At the same time, you’ll be able to use your skills to ask questions, provide on-the-job training, and monitor and evaluate their performance in the short and long term.