Onboarding

Mike Peluso
11 min readJan 22, 2024

A Family member called me up. They wanted to talk about their new job. It was a great opportunity with a very good company. It was a big change for them. Not the company, they had been at big companies before. The change was in the type of job they were doing. They moved from sales and marketing to something aligned, but different enough to where it was a completely new type of job. They called to vent. They were frustrated. They felt clueless about the new job. That’s not surprising, everyone feels a little clueless. What surprised me is that they claimed that they had no template for how to do the job. Since it was a senior position they didn’t want to ask for help as they felt like they would look ignorant and / or unqualified. Jumping to another job quickly was out of the question as they had made some big financial commitments as part of taking the job. I felt for them, the idea of feeling lost in a new job was familiar to me. It brought on that feeling of déjà vu and not just because I had been in that situation myself a few times.

It wasn’t the first time I’ve gotten a call like that. In fact it wasn’t even the first time that month. Before my family member called I had several very long calls with my friend Mark who also just got a new job. Unfortunately for Mark, when he got there, the person who left was already gone and nobody knew how to do the job of the former person who Mark replaced. Mark’s new position was for a quasi-government related organization that was staffed by mostly former government employees. That meant they maintained the worst practices of government. Everything was siloed right down to the individual job. Nobody was cross-trained on anything. Even the manager two levels up from Mark was leaving their position shortly. Not that it mattered, due to the siloing culture, they didn’t have much information to share with Mark.

Mark would call me every day and talk, really he was venting, about how they have to hunt down every answer. He hated that his daily search and rescue mission slowed his productivity down to a crawl. He knew he was reinventing the wheel for every solution he was able to put together to do his job. To Mark’s credit, he talked to me about creating a toolkit for the position. He didn’t want this to happen to anyone else if and when he left the organization. That part was also déjà vu for me as well. Again, I had been in a situation just like that, even to the point of creating a comprehensive how-to document for the job I left so my experience wouldn’t happen to anyone else.

Just based upon the feedback I had received from others over the years, I know very few people who had the luxury of a job manual or toolkit when they started a new position. I created one for the same reason Mark did, my onboarding experience at my last job was lacking to say the least. I had gotten a job doing business outreach with my local workforce board. Business outreach, if you don’t know, is a bit like sales. On my first day my Boss handed me a basket of goodies and sent me to my office, which importantly for this conversation was separated from everyone else who all had offices in a main suite. The separation was better for me at least if I wanted my privacy. It wasn’t so good if I wanted to learn even the tertiary things related to my job through osmosis. I didn’t get much help from my boss, mostly because she was a director of a government grant program, i.e. a professional bureaucrat. She had no idea about the culture of business, let alone the unique needs of business outreach. Well to be more precise I would say that she wasn’t experienced and never seemed motivated by the subject in any way. To her credit she understood the basic concepts of my job even if she couldn’t train me on it. Thankfully one of my colleagues gave me the idea of shadowing one of my counterparts from another area. I reached out and got to spend a couple of days with a much more seasoned individual who was in the business outreach role for her board. We clicked and that person eventually became a friend. The experience was obviously pleasant, but at that early stage it still didn’t really explain what I was supposed to be doing. She took me through a couple of days but didn’t have an overarching template. In truth, I don’t think many people could have explained it. The system was so complicated it took me years and years to really understand it myself. Part of that problem was that the majority of the people holding positions of power, like my former boss, didn’t understand the business outreach functions much either. You could almost say that the system in general didn’t understand what it was supposed to be doing as it related to businesses. Some of the larger boards figured it out out of necessity, but there was no real understanding in place of how to integrate serving businesses, at least not for the organizations like my own where I was an office one one.

Thankfully, as I alluded to, eventually I figured it out. The elevator pitch is that I was basically an economic developer with some highly limited grant dollars related to training workers on the job. A functional description of a business outreach professional in the workforce world isn’t as important as knowing that it’s complicated and training someone in the job is very difficult. That’s why, like Mark, when it was time to leave, I didn’t want anyone else to go through what I did. I built a massive onboarding toolkit. I spent a couple of days walking my replacement through it. Unfortunately, from what I could tell, it was mostly ignored. I think if I was still on staff in a different role, I could have helped him out more. Giving someone a textbook, which is what a job tool kit essentially is, is easy. Textbooks really only work when there is a teacher around who is using the textbook as a guide through the whole course. Since he rarely called, I was not able to guide him. Sadly much of what I built up in my role was ignored and ultimately disappeared.

Unfortunately, the onboarding challenges I experienced in my workforce job wasn’t the only time I was in that situation. In defense of the workforce system and the people who worked in it, my lack of onboarding, and similar experiences I witnessed of others who were in business outreach rolls, were based in a systemic ignorance. My other experience wasn’t ignorance, crappy onboarding was actually by design. The company in question, a chemical manufacturer, had a sales philosophy of throwing shit against the wall and seeing if it sticks. They would hire dozens of people in different parts of the country regularly, give them a manual, some very basic training, i.e. a day or two, and release them. The job paid straight commission. The ones who survived ran their areas like little businesses and had nearly complete autonomy. They would make hundreds of thousands of dollars each year and would naturally stick with the company for their entire career. The company would find one of that sort of person out of one or two hundred hires. It was luck of the draw and even the VP of sales would tell a story of how he was one day away from getting fired when he walked into the right place at the right time and landed a big account. The tradition of purposefully negative onboarding started with the founder of the company in the 1920’s when he would buy a luxurious gift for a new sales rep’s wife and then charge it to the new rep’s account. This started the new rep in red with the company and they had no option but to hustle to get in some sales or tell their wife to give back the nice gift. Poor onboarding because of incompetence is one thing, poor onboarding as a business philosophy is, at best, an antiquated notion and at worse, pure evil.

I’m sure some companies have fantastic onboarding, but in my experience most don’t. These stories of lackluster onboarding from my friends and family, not to mention my own experiences, align well to the experiences most other professionals I know have had.

To be fair there is some validity in job immersion, i.e. the concept of throwing someone into a job and they have to sink or swim. It forces learning and there are clearly some cost savings related to not having to spend the resources to develop a comprehensive onboarding program. I don’t think it’s the best option even if it seems to be the one chosen by most organizations. We can’t forget that there is often stress associated with not knowing what to do when starting a new job, sometimes it’s a substantial amount of stress. This stress has caused some new employees to leave or at the very least consider leaving. My family member I talked about at the beginning of this article, although somewhat anchored by financial commitments, did consider jumping simply because of the stress from the lack of onboarding.

Without a good onboarding program, short sighted management usually feels that what’s lost in a slower ramp up and commensurate limited productivity of new hires is far less than what’s lost by investing in weeks of intensive training. This is arguably true in organizations with high potential for churn. For most other organizations, the ones where people stay in the job for years, It just causes people tons of grief. I don’t think this is a little problem, this lack of proper onboarding to professional jobs. Remember, the average tenure on a job is 4yrs so professionals will go through this onboarding challenge an average of 10 times in a typical 40 year career.

So how can we mitigate this if the majority of the jobs we get have limited to no substantial onboarding? Well I do have some tips.

The first tip, well it’s almost a rule for any job, is that activity equals knowledge. This is the brute force attack to onboarding. It looks like following up on every little thing you don’t know. No matter what the task is, make sure you truly understand every aspect of it to the best of your ability. This is more challenging than you’d think as you have to be savvy about how you do this. Don’t rely on just one person to ask all your questions. Usually they have their own workload and over time you’ll annoy them. I have always felt that to be successful is to spread your questions around to as many knowledgeable people as you can. I’d even suggest rotating them.

You’ll also want to read everything available. Internal policies and procedures are a start, if they exist. There are always tons of industry journals and websites. There may even be podcasts. All of these media sources can be tremendously helpful. Consuming all of this information does take time, yet there is no question that the more you absorb about your position the better you are.

The biggest and best thing you can do is to network like crazy. Look for a local industry affinity group. Find someone, preferably multiple people, in an adjacent organization or division with similar roles. You could even start this research before you start on day one. Most people want to help others just starting out. A call to a professional in an aligned position with the question: “I just got a job, is there anything you would suggest I do on the first day” would probably get more help than not. Once you make that first call, you may wind up starting the process of continually engaging in a community of people who do what you do. At that point the question “How do you go about… ” becomes as much of a bonding effort amongst colleagues as it is a request for information.

As you start to build your network, and your answers, you’ll need to keep some sort of reference document or documents. This helps with both long term and short term tasks. Many professional jobs have intermittent tasks, things you only do every six months or once a year. In my experience you’ll forget much of what you learn about these intermittent things between the times it takes to do them. That means for the first few years, every time that intermittent task comes around, you’ll find yourself asking.. How did I do that again? If you made the cheat sheets, then you don’t have to worry about that. Also, they can assist the next person if you move on.

In a perfect world, everyone would come onto a new job and get extensive and well prepared training and reference materials. On top of that, they would have access to a highly experienced mentor who has allocated a good amount of time to work with the new hire. Obviously, in our hyper focused world, this is not realistic. It’s not just because of budget / resource issues. It’s also not realistic because of the way the world operates. These resources simply may not exist because there are more jobs that are highly specialized to an organization or industry. Often the person before you was the only person who knew how to do the job.

Unfortunately, for those that don’t jump jobs every two years, and have become desensitized to this reality, there is a tendency to be shocked that onboarding is generally very weak or non-existent. I believe that if you expect a near complete lack of onboarding before you start a new job, then you can be mentally and emotionally prepared. That’s the point of this whole article. I wish I could get everyone I know jumping jobs to read or listen to it. Maybe, just maybe, if everyone I knew did that, my next call won’t start with someone saying “I am so stressed because I don’t know what i’m doing and there is nobody here who knows either” to “There was nobody to help me get up and running, as usual, thankfully I was ready for it”.

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Mike Peluso

Mike Peluso writes is about the collision between the professional world and life. Read more at www.pelusopresents.com or listen to the Peluso Presents Podcast