5 Steps to Develop Customer Onboarding Project Managers


Have you ever been in this situation? I had to hire a new customer onboarding project manager for my team and interviewed multiple candidates, and while many have some of the skills needed, no one was that golden unicorn. Now things are starting to get a bit hectic, and I need someone in the role sooner than later. What should I do? I find the best of the available candidates, hire them and hope they grow into the role. 

Well, at least that’s what I’ve seen happen time and again. If we want to deliver an outstanding experience for our clients, we must do better than this. We need to think beyond the now and determine how we can develop our customer onboarding project managers so they are able to grow within our organization and become that golden unicorn. How do we do that? Well, I’m glad you asked.

I’ve been trained in numerous methods of developing individuals over the years and have found a simple five-step process works best for me.


Evaluate skills


Understand their long-term goals


Build a plan


Find opportunities


Close the loop

Let’s see what this looks like with the employee. 

1. Evaluate The Skills to be a Successful Project Manager

Objectively evaluating skills and abilities is the foundation of building a successful development plan. Your requirements for an onboarding project manager may be different than mine and will even change over time, however there are some core skills that every client facing PM must have to be successful.

Scheduling & time management

Internal communication

External communication

Technical expertise

Problem solving



Risk management

Best practices of each of these can be a blog post in and of themselves so I’m not going to go deep into them, however you want to evaluate how well the employee meets your specific requirements in this role. You don’t need to build a complex grading schema but can simply identify their skill set as basic, intermediate, and advanced. The key to evaluation is objectivity.

  • Look at how well they are meeting each item. 
  • Do they struggle keeping up with due dates and deliverables?
  • Is risk communicated proactively?
  • Does the employee clearly articulate their message in a way their audience understands with the appropriate length and content. 

I can go on, but you get the picture.

One thing I can’t stress enough is to provide open and honest feedback to the employee so they understand where they are excelling and what their areas of risk are. That is the part no one likes to do, but mutual understanding with real-world examples helps you and the employee be on the same page. Just remember to give feedback on their skills so the two of you are on the same page. Once you understand their skill set, you have a solid foundation to help them grow, but you also need to take the time to understand their long-term goals.

2. Understand Their Long-Term Goals

Wait, why do I need to understand an employee’s long-term goals? I thought I was developing a client onboarding project manager, why does it matter what they want to be when they grows up?

A key part of helping your team grow is understanding their long-term goals. If you only focus on your needs, you are likely to see them look for opportunities elsewhere. Taking the time to learn and support their career aspirations is a significant part of developing someone. Finding a balance between the needs of the role and their goals will help them remain invested in their development and work towards both sets of requirements.

When you have your one-on-ones with the employee, get to know their plans.

– Do they want to grow as a PM? 

– Are they interested in becoming a people leader?

Does the employee want to change to a completely different role? 

There is a lot of value in learning each person’s goals, but for me it comes down to building connections and understanding the differences of each person. You can take this knowledge and use it to balance their goals against their skill set. 

  • How well are they positioned for their goals? 
  • Are they lacking key skills? 
  • Do they understand the requirements to grow to their desired path?

You will need to ask some probing questions along the way to ensure that the employee understands what their goals require. You might not have all the answers but gaining that foundational knowledge will enable you to help them see the gaps between their current skill set and where they want to go.

woman climbing guide with rope hanging around her neck

What if the employee doesn’t know what they want to do in the future? That’s okay, too.

When you find yourself in this situation, have the employee think about the portions of their current and previous roles and what energizes them. 

  • What gets them excited and want to do more? 
  • Also have them think about the things they do or have done that drain them or they loathe.
  • What do they push off to complete last because they just don’t like doing them? 

Some tasks or responsibilities will be easily identifiable, and others may take time. As the employee builds that list it will help, and you, identify growth paths for their future. Gaining this foundational knowledge is going to help you as you move into the building phase of this process.

3. Build a Development Plan For Your Project Manager

Building the development plan is the fun part for me. By this point I’ve gotten to know the employee pretty well and we’ve built a rapport and working together to help them grow is extremely gratifying. The best part about it is it’s not me telling the employee what they need to do. It is working together and helping them drive the process. I can tell the employee what to do until I’m blue in the face, but that won’t drive results. Having them be the driver and determine the next steps with my support is the key to success.

To build a good plan you will take all the conversations around the employee’s skill set and aspirations and focus on the areas of greatest impact. Let them identify what they think is of most value and provide feedback on the areas you feel they may be missing.

As you look at the overall list it may become overwhelming for the employee, so remind them you are going to break it up in segments so it can be more focused and achievable.

hand drawing on window with red and black markers

Once you have agreed on the areas, you and the employee will need to prioritize. What’s going to bring the most value? Are there any quick wins? Prioritize what you are going to focus on so you can build a timeline for the short term and longer-term goals. As you build the goals follow the SMART methodology (Specific, Measurable, Achievable, Relevant, and Time-Bound), which will allow both you and the employee to be able to easily track progress.

Keep the Development Goals Tied to a Schedule

You will find the best method will be to have a mix of short- and long-term goals. Set targets to be achieved in 30 days, 90, and longer. Having a realistic and achievable time frame with smaller gains along the way will keep the employee (and you) motivated. Build in checkpoints so you track progress, provide feedback, and adjustment goals as needed.

I’m also a huge fan of finding a mentor that can help them continue their growth. I especially try to get someone who is outside of the employee’s normal interaction group because the outside perspective can really help them see things differently. With your focus on their current role and organization and the mentor bringing a unique perspective, the different views can make a significant impact on the employee’s development.

One thing to remember, not everyone will need a mentor. This is a tool you must evaluate and apply for the right person at the right time.

As you continue to meet with the employee and make course corrections to their targets, goals, and timeline, you should keep an eye open for opportunities to support their growth.

4. Find Growth Opportunities

Opportunities for growth can come in a variety of forms. Some come naturally and others may need to be cultivated. Think about things like stretch assignments, observation, or job shadowing, and even delegating something you do down to the employee.

Stretch assignments can pop up as a normal part of doing business, but sometimes you need to search them out. It can be something as simple as learning a technical aspect of a role, managing a project outside their normal responsibilities, building a new process, or something else. Our default is always to give those opportunities to the person best suited to complete them but sometimes we need to take a chance and pass it on to someone who is growing and give them the guidance and support to be successful.

man and woman smiling looking at computer

Setting up observation and job shadowing is a wonderful way to help the employee determine if those are areas they want to pursue. Observation is simply having them sit with a SME on the team and building skills or understanding how a task is done. Shadowing is a bit more in depth and allows the employee to follow someone in another role to see what it entails. We always think we know what another role does but when you get to see a “day in the life of” you learn so much more. Maybe it is something that will intrigue them but perhaps they’ll learn it’s a role they don’t want to pursue.

A final opportunity would be to pass on something you do on a recurring basis so the employee can learn next level skills. It can be something like reporting, data analysis, training, or another task that you are able to help them understand. This is one of the hardest things for a leader to do because we know how it should be done and we want it done right the first time. If we don’t take the time to show others so they can build their skills, then we are limiting the growth of our team.

Finally, as we go through each of these steps we must make sure we close the loop.

5. Closing the Communication Loop

Closing the loop is a critical piece of development and if you miss that step then the whole plan is at risk. Closing the loop isn’t difficult, it really just comes down to communication. Both you and the employee need to communicate on what’s working and what isn’t. You will continue to observe their progress and let them know where they need to adjust, what’s going well, and what’s not. Ask questions during this time to see how self-aware they are. Do they have a good view of their progress? Sometimes they’ll surprise you and identify things you may have missed. Let the employee drive the path to solutions with you being the sounding board and guiding voice. The more they own the path, the more successful the employee will be.

Take time during your recurring one-on-ones to give feedback. Keep it honest and objective with concrete examples so they can really understand. If you find yourself using soft words or phrases like “it appears”, “feels like”, or “seems” you aren’t doing them justice.

All this feedback is going to allow the two of you to amend the plan to drive further growth, move to new goals as others are completed, and reevaluate the path as needed. This is a very cyclical process, and as goals change you will need to reevaluate and continue to build.

Remember that feedback is a two-way street. Make sure the employee is identifying what’s working for them and what’s not. What are the challenges they are facing and how are they overcoming them? Make sure the employee tells you if they need additional support in a specific area.

A Real-World Project Manager Success Story

Several years ago I was starting a role with a new company. I was in the process of evaluating the team to better understand each person’s skills and knowledge and had been repeatedly told that one of the team members, let’s call her Carla, was “adequate” and really didn’t have the potential to grow beyond her role. This feedback was accepted but didn’t really align with what I was seeing. One day we had senior leadership on-site as we conducted a client journey mapping exercise and I needed someone to join me with additional details since I was new and didn’t know all the answers. We sat in the room and every question that was directed to implementation, this woman answered quickly. I sat, watched, and listened and tried to understand how this person who was called adequate was able to help successfully work through the process, albeit nervously.

One day shortly after our office had returned to normal I had a one-on-one with Carla. I let her know how well she did during the journey mapping and that I was proud of the effort she put forth. I started probing and trying to understand where she wanted to go in her career. Carla had self-confidence issues, but I was beginning to see significant potential in her. She and I talked over the next couple of months as I evaluated her skills and abilities and I came to understand that she loved what she did, wanted to move up in implementation, but really wasn’t interested in managing people.

Carla was the only level one on the team, and standard practice was to hire new team-members as level two. She and I started working on a development plan that would allow her to work on increasingly complex implementations, build her confidence, and allow her to share her best practices with others on the team.

man and woman meeting with laptops

I had some conversations with other leaders and one of the senior salespeople in the organization offered to be a mentor for Carla. He loved working with her and like me saw her potential. He met with her and gave her feedback, constructive criticism, and helped her see her strengths. I also gave Carla opportunities to work on other areas that she hadn’t before, conducting QAs on other projects, training, and one-off projects.

She and I met monthly to discuss progress, make corrections, add new goals, and ensure everything was working as well as it could. As we closed the loop I was able to tie feedback directly back to key client activities, NPS survey results, internal feedback, and KPIs and other metrics. Throughout this process she listened and helped craft the overall plan and cycle. I helped by offering feedback and making things available to her but she drove the development cycle and was ultimately responsible.

In the end, I led Carla and the team for about six years and during that time she was promoted from a level one almost annually to a level four and finally to become the team lead, a non-managerial leader of the team. I am extremely proud of Carla and the effort she put forth to overcome the preconceived notions of others and succeed based on her own abilities and the willingness to accept the coaching and guidance.

In summary, I’ve put a lot of words on your screen and some will resonate with you and others will not. It’s up to you to figure out the practice that works best for you but at the core it comes down to understanding, evaluating, planning, and communicating with the employee to help them grow, be successful, and transform into the golden unicorn.

Leo Rondeau

About the Author: Leo Rondeau is the senior director of implementation delivery at Spiff. He is an experienced leader having served 20 years in the U.S. Air Force and transitioned to a successful career in SaaS and Services companies. Leo has a passion for developing people and helping them grow into their full potential. 

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