When I was pregnant with my oldest daughter, I tried to prepare myself well for what was coming. I read a lot and debated which hospital I should choose to give birth in (we actually went to see three of them in person! I still had free time back then). I took a Lamaze class and bought two CDs with meditative music from my Yoga teacher, who also helped me prepare myself physically for the big event: giving birth to my beautiful baby.

It was only when I was on my way to the hospital that I realized that while I am very prepared for this event that will change my life forever (or as prepared as one can be), I am hardly prepared for what comes next: parenthood. I was terrified when I understood how much time and effort I spent preparing for this important but time-limited event, and no time at all preparing for the life-long change that comes afterward. 

I remembered this feeling when I worked with one of my consulting customers on hiring a new VP Product. It was a long journey. Finding the right person in this nontrivial hiring atmosphere, especially at such a senior level, is not easy. In the end, they found a great person. But then the CEO realized – much like I did – that he is not at all prepared for onboarding a VP! He was never a product leader himself and never even worked with someone at that level before. Building an onboarding plan for the new VP was indeed a tricky task for him. Much like parenthood, it was also a very important one since the CEO really wanted the VP to succeed.

We ended up spending a good amount of time on building the perfect onboarding plan. Here is the structure that we ended up with, and the specific points to keep in mind when planning yours.

Create a Baseline

I hope it goes without saying that you do need an onboarding plan for a new employee. Yes, even if you are a small startup. Take a few minutes to think about what the new employee would need to know in order to be successful. 

Some of these things are technical – a laptop, access to key systems, etc. List them out and make sure they are ready for them (or include guidance as to how to get them). It sounds trivial, but understanding these things in advance will make the onboarding process much smoother and will give the new employee a feeling that they are being taken care of.

Most of the onboarding plan, though, includes the things that the new employee would need to know. I encourage you to start higher up, with as wide a context as you can give. For example, when I hired my new employees, I always started their first day by sharing with them the entire history of my company, how and why I started, and how we got to where we are today. It’s the kind of background that they will most likely never get otherwise.

Some of these things require learning directly from people (for example I doubt this background that I just mentioned is documented anywhere for most companies), but since you are most likely busy, try to think creatively about how they can get the knowledge they need without you teaching them every bit of it. It could be that there are other people who can help with that knowledge – and that learning from them would be a great way to get to know them too – killing two birds with one stone. It could be that you have some reading materials – albeit not perfect, still a great way to gain a good baseline of knowledge. They might need to work with the product to get themselves familiar with how it works.

My recommendation is to create a table with the following columns:

• Topic
• Details about what they need to know about this topic
• How they can learn it (meetings with X and Y, trying the system for themselves, etc.)
• Specific learning materials (recorded lectures, internal documents and presentations with links to each)

Note that you don’t start with a generic list of the people they would need to work with (that can be one of the topics – getting to know them), but instead, you actually ask yourself what is it that you want them to know in order to succeed. Looking at this from this angle will most likely reveal things that you wouldn’t have thought of otherwise. 

The specific learning materials allow them to move at their own pace, in between onboarding sessions. Don’t worry about them hearing the same thing over and over again. In most cases, each person they will talk to will give them a slightly different perspective on a given topic, and anyway, when you learn something new it takes a while to be able to fully grasp it so hearing things over again is not a problem.

The list should be comprehensive but don’t worry too much about making it complete. The next part takes care of this.

The Plan Is a Working Document

Once you give your new employee their onboarding plan, you need to fully hand it over to them to manage. They need to make it their own. It’s perfectly OK that they write on top of it, mark or even delete the parts that they have completed, but also add stuff as they learn that there are things that they need to know that did not appear there.

When they meet people for introductions, these people might think of documents that the new employee can read that maybe you didn’t think about. They should add them to this document. As it often happens, once you start diving deeper into a topic, a whole new list of sub or related topics emerges, often ones that you completely forgot when you originally planned the onboarding. 

Your employee should feel free to add these to the plan. In fact, you need to make it clear that it is your expectation that they manage the plan this way. You can then sit together and give them guidance on the priority of getting into these additional topics. 

In many cases, the onboarding plan is never formally completed. Especially with product people, they will start the work itself before they go through each and every item. But the fact that they have a baseline to come back to, a place with references for self-learning of many relevant topics, can serve them well beyond the initial onboarding itself.

Include Specific Goals

To balance between sitting and learning all day on one hand, and jumping right into work on the other, I recommend adding specific goals to the onboarding plan. These are the things that you want the new employee to achieve during their first time with you, typically 3 months or so. But here is the tricky part: the goals you set should be balanced. 

Generally speaking, there are two types of goals that belong there. The first is goals related to the work that you must have them do. For example, when I started as the VP of Product at Twiggle, the most important thing for the company was to define the product that we would offer to the market. It was an urgent and important task, one that no one else in the company could lead. 

But the onboarding plan should include goals of the second type too – goals that are much smaller and would serve the new employee’s learning as well as the company’s needs.

For example, when Tal, our COO, started, I had one major goal of the first type – I needed her to take ownership of the entire operational side of the CPO Bootcamp before the next batch started. It was a stretch goal to achieve in a few weeks, but the mere fact that I stated it so clearly (plus the fact that Tal is a super talented COO) helped us both focus and nail it.

But Tal’s plan included other, simpler goals as well. For example, I had a bug in one of the automatic processes that sent my monthly accounting report to my CPA. I added to the plan a goal to fix this issue. You might ask yourself why this belongs in an onboarding plan instead of a simple work plan for the new employee. The reason is that it was a learning goal, with a side benefit of getting the work actually done. I wanted Tal to get to know this automatic process in and out. I added some materials as part of the onboarding document I mentioned above. But the best way to learn how a process works is to get your hands dirty and do some work yourself.

Make sure you include goals of both types in the plan. Another way to look at it is to make sure that the set of goals you set well represents the things you want the new employee to know. Think about it as evidence that they master a certain topic. If they have done X and Y then they probably know Z.

Manage the Process

Last but not least, remember that onboarding is a process that needs to be managed. Encourage your new employee to take notes during meetings and list anything they don’t fully understand. Then, make sure they have frequent Q&A sessions with you or another member of the team who can answer all of their questions. 

Manage the onboarding process like you would manage any other project – monitor progress and status, remove blockers – things that your new employee can’t continue without, and make it your point for the onboarding to be successful.

Whether you are a product leader or a CEO, I’m sure that once you adopt this perspective you’ll know what to do to make it work. Good luck and happy onboarding!