alex petralia
2025-02-03 management

Training and Onboarding: The First 90 Days

When I think of one of the many “productivity boosters” we as workers have at our disposal, delegating tasks ranks near the top of the list. Other forms of leverage exist, such as writing code to automate complex workflows, but at the end of the day you still need a person to build and use the tools. If someone doesn’t know what problem to work on or who to go for information, it doesn’t matter what tools you give them. You must train people to be productive with the tools at their disposal.

When it comes to individual productivity, I’ve generally found Andy Grove’s maxim to be relevant: “either they can’t, or they won’t”. Issues related to productivity generally stem from (a) a lack of competence or (b) a lack of motivation.

When someone first joins a company, they do not yet have enough familiarity with the job, the organization, the firm and the industry to be productive on day 1. And while most new hires do begin a new job with a certain optimism and eagerness, that goodwill can quickly erode by week 1 or 2 after a few mishaps during onboarding. 

Therefore, I see the first 90 days for a new hire as particularly important in giving them all the context they need to be productive, as well as ensuring they have a positive experience with the company so that they remain motivated to perform.

Competence #

The first screen of competence is during the hiring process. Ideally you design the interview process in such a way as to accurately assess someone’s raw abilities.

But even after finding and hiring qualified people in general, you must train them to be competent in this particular role. Common frictions when adjusting to a new role include:

The goal of onboarding then is to take someone’s raw abilities and “fill in the gaps” with the knowledge and skill sets relevant to this particular role.

Many managers do not perform training. They expect new hires to pick it up on their own without any work on the manager’s part. These managers do not assemble relevant materials or teach on relevant tooling, and perhaps most importantly, they do not set aside time for training. If you do not explicitly allocate time for training, then the only alternative is time for working.

The work that untrained employees produce is simply substandard work. Like in an apprenticeship, the entire point of training is to produce “work to standard”. Without training, there is no concept of what good work looks like and what bad work looks like. Instead, untrained employees simply produce “stuff”, as producing something is better than nothing. But what is delivered is often hard to follow, ignores standard conventions, prioritizes the wrong things, looks bad, runs bad, and solves the problem the hard way instead of the easy way. Whenever I see a lot of subpar work in an organization, I end up instead noticing a systematic lack of training.

The longer people go untrained, the more likely they are to remain untrained. That’s because the longer you’re at a company, the more you’re expected to know. Asking a “dumb question” after 6 months or a year would expose one’s lack of knowledge, so instead people opt to stay quiet, resigned to a state of ignorance. But rather than wondering: “Why do I not know this?”, one must instead ask: “Why was I not trained on this?”

By the end of training, new hires should have a good sense of what work is valuable, who to ask when they have questions, what kind of communication is expected, how to use the tools at their disposal, and how to navigate the organizational landscape. They know what the standard of work quality is because they’ve seen it all around them, and further, they’ve been trained on how to build things the same way. 

For new hires I often put together a mini-orientation to familiarize them with our industry and organization, the outline of which roughly follows:

Generally, I dedicate about 1 hour a day to lecturing on these topics, getting as far as I can in each within the allotted hour. Sometimes it takes a week to go through the orientation, sometimes two. I realize this does not “scale well” - recordings would be much more efficient - but I think it’s important to signal active investment into your new hires and adapt each training individually to them.

For the technology portion, I like the training to be more hands-on. You can only learn so much from listening to someone else speak; sometimes you need to watch them work (shadowing) or play with things for yourself. 

As a result, I will often, separate from the lectures, share the entirety of my screen for about an hour a day. This way, new hires can see where my eyes go, what I click on, how I flip between email and chat apps and my IDE, what shortcuts I use, how I approach certain problems, how I behave in meetings, and so on. Often as a new hire, you don’t really know how the sausage gets made, but if you can literally see everything that goes on on my screen, you will know.

Motivation #

Once new hires are trained to be productive in their role, there is no guarantee they will actually be productive. That’s because it’s easy to become checked out at work if you don’t have a positive experience with the company. Enormous amounts of productivity are lost by businesses each year, not because workers are incapable, but because they are unmotivated.

Although keeping your team motivated never ends, the first impression for how you treat others as a manager is certainly solidified during the first 90 days. When someone starts on their first day, I always ask: “What really drives this person? What would keep them motivated?”

Many a book have proposed motivators - money, flexibility, ownership, autonomy, mission, impact, balance, stability, talented colleagues, learning - and all of these are good. To find out which of these are most motivating for someone, I typically ask a bunch of questions:

Although my job is to build a personal relationship with every new hire, I also want them to build “lateral connections” with their team members. After about 3-4 direct reports, I don’t want everyone asking me individually for everything. Instead I want them asking each other. To facilitate this, I’ll schedule a series of events for new hires to build relationships, not just with me, but with the broader team, such as:

Finally, I’ll schedule 30-, 60- and 90-day check-ins to follow up on how their experience with the firm is progressing.

Conclusion #

To me, the first 90 days for a new hire are not about the work. Any work here must necessarily be inconsequential, otherwise the firm is placing mission-critical work on untrained hires, which reflects a much larger problem.

Taking an interest in what allows employees to be their most productive and their most content goes a long way. I find that regularly revisiting the questions of “how can I train and motivate better” pays long-term dividends in how people perform on the job.

The job of training is to shrink the productivity gap between the most experienced (tenured employees) and the least experienced (new hires). If this does not lessen over time - if new employees remain trapped in the mire of unproductivity - this points to a lack of training. The goal of the first 90 days then is to be a force multiplier in taking one’s original, raw productivity and leveling it up to that of existing staff.