Key Steps to a Successful Engagement with a Freelancer

If you have decided to hire a freelancer for your project, you are joining a growing wave of small businesses engaging external resources to help out on as needed basis. Accessing talent on-demand sounds like an excellent idea. Indeed, you can find someone that fits the needs of the project perfectly, has the relevant experience and costs a lot less than a full-time employee.

But before you start a project, it is important to make sure you and the freelancer you are about to hire are clear about expectations. Both parties need to be on the same page about what needs to get done, what good deliverable looks like, timelines, and the way to work. Often deliverables are not easy to define but care must be given to ensure that scope of work is well understood.

This is particularly true if you engage a Baby Boomer as your freelancer. While they can bring a wealth of experience to your project, they may not be most experienced in working on a project basis. It takes some effort to ensure that their experience meet your needs. A few simple steps can help to achieve this.

1. Be Realistic

Needless to say, you as a business owner must make sure that expectations are both clear and realistic. Prior to engagement and contract, it’s a good practice to work with your potential freelancer to understand what can and can’t be done, what are timeframes, what are tradeoffs and dependencies

This is even more critical when it comes to projects that don’t have one specific small deliverable like a logo design or a blog post. It can also take a longer period of time to see results. Longer projects require clear milestones with timelines and payments associated to them.

Through contract negotiations phase it’s essential that you and your freelancer agree on a realistic and achievable deliverables or milestones, set reasonable time frames and establish roles and responsibilities going forward. For example, it’s unreasonable to expect a freelancer to develop a complete marketing plan for a new product that you are launching or training plan for your staff overnight. These types of results just aren’t possible.

Setting expectations is a two-way street. You should be able to rely on your freelancer’s expertise to establish what deliverables will achieve the result you need and what deliverables are possible for your budget and time frame. Baby Boomer freelancers have a lot of experience that helps them to set clear timelines. They also will not over promise and commit to something they won’t be able to deliver. If someone promises something that seems too good to be true, consider asking for more details before getting started or at least ask how the freelancer will drive these results.

2. Start with a Kick Off Meeting

Once you have made your choice and engaged a freelancer, a kickoff meeting is a great way to start the work. This meeting is a great place to reconfirm your expectations and reach an agreement on how to work going forward. If there are other parties that will be working together, a kick off meeting is a great forum to bring everyone together and establish shared goals.

As a manager, you have to discuss what you want out of the project, what the freelancer is going to accomplish, how the rest of your team is going to help. If the project is long-term or ongoing, you should also talk about how often you’ll have check-ins, and be sure to confirm clear—and achievable—milestones that have been committed to during the contract negotiations.

Hiring a Baby Boomer freelancer brings a lot of experience to the team but can also lead to disruptions due to differences in working styles. Kick off meeting is a great way to set the stage for all team members to understand team work norms.

3. Test Things Out

While you may be in a hurry to get going on your large and important project, it may pay to have a trial period. Rather than giving a new freelancer a large, business-critical project, it can be a good idea to start on a smaller test work to assess whether expectations can be met. A test project or a few hours of work can be a great way to make sure it’s a good fit for both of you. You should agree with your freelancer compensation for this test period to make sure they do not feel like they are being asked to do work for free or being cheated. This payment can be counted against the main project if test period works out well and you engage on a longer term basis.

It is also advisable to have several logical milestones defined for the project. Each milestone should result in something that can be demonstrated, shared and assessed. Attaching payment schedule to milestones helps both parties to realize value along the way. On the other hand, milestone deliverable reviews can help to identify any issues and correct them early enough to avoid larger issues down the road.

4. Communicate

Communication is key to a success of any project. This sounds obvious yet many small business owners disregard the importance of frequent communications. When you have someone external on your team, you cannot assume that they have the same understanding of your needs. It is a good idea to set up communication channels at the start of the engagement and to make sure you use them consistently.

Having hired an experienced freelancer, you will benefit from listening to their feedback throughout the engagement. Indeed, you chose them to help you because you value their specific skills. Baby Boomer freelancers have a wealth of experience that could benefit you and your team. They might have ideas for ways to improve the process, streamline communication, or work together more efficiently.

Feedback should flow both ways though and you should not be afraid to share your feedback with them throughout the time that you work together. They would benefit from understanding better how to work with you and your team, what to adjust and how to unlock their potential for your project.

Ready to test out working with Baby Boomer freelancers? Almarelo platform provides tools necessary to put all these ideas and tips to use.

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