I still remember all the excitement of my first day working in tech. This job was a big upgrade for me. My first role after college was Director of a tutoring center. I taught kids between 4 and 14 how to read, write, and do math. I didn’t realize when I signed on that “Director” was code for teacher, janitor, marketer, and sales person. I did it all. I loved the teaching aspect, and hated all the rest. Cleaning kid bathrooms is not for weak stomachs.
I was grateful for every little thing that was different about this job, especially the schedule. My tutoring job hours were Tuesday - Saturday, 10 to 8. That schedule stopped me from spending any time traveling or with the people I loved that worked Monday - Friday. When I prepared for the first day, I didn’t have Sunday scaries. I felt free walking into work knowing that Friday I’d be done.
There was one other thing that was different. At the tutoring center, everything for training was set up when I got there. This was a corporate company and they had a program for onboarding. There was a computer, a phone, a check list. But when I arrived on day one at the small tech startup that promised fast paced learning and growth, my desk was empty. I didn’t even have a computer. This was back when we didn’t have the internet on our phones so I just sat there waiting for three days until one of the co-founders took me to Best Buy. Once I got started, I didn’t have a boss so I just did work. Good work? Ehhh…
Expectation Debt: prepare to be shocked at this number
If you’ve gone to enough conferences and webinars, you might believe that the corporate job was doing more right simply because they applied structure, but the emotional cost of both of these scenarios was the same: expectations didn’t align with reality. The cost? Trust. In the first job, I made it out of the entire interview process without knowing what I would do every day. I had no idea I’d be making sales calls each morning or that I’d have to scrub kid pee off every corner of the bathroom. That’s why I left less than 2 years into the job despite the great onboarding experience. The same thing happened in the startup role, the mistrust just started adding up earlier. I didn’t know what I would do each day. Once I realized it was more cold calling, I was done. Fortunately, they offered me a social media role and that was the beginning of my career in marketing with HR tech companies.
The fact that people still show up to empty desks and misunderstandings about what the job really entails almost 20 years later with all the “advancements” we’ve made in the workplace really blows my mind. The amount it’s costing them? That research hurt my brain. Ready for this? According to Gallup research, poor employee retention costs US businesses an estimated $1 trillion annually. If I were presenting that stat from stage, I’d say it one more time because that number is outrageous. That’s $1 trillion dollars of money spent advertising jobs, training, and onboarding. But it doesn’t end at the balance sheet. There are indirect costs, too, of lost productivity, less internal knowledge, and toxic team cultures.
My hypothesis is that this expectation debt is a consequence of a world of work that grew really fast. Before the internet, jobs were pretty standardized. We could post a job title and a 50 word ad in the newspaper and the right person would show up. There was a more universal language to work. In the 1990s, companies got bigger, technology became more pervasive, and job titles got more creative. Naturally, the consequence was a lot more misunderstandings of what work each job aligned to. I mean, at one point my job called me a “social media ninja.” *eyebrow raise* But in the current economy, no one can afford more candidate experience misunderstandings that cost them the talent they spent money to hire in the first place.
Save Money Setting Better candidate expectations: Every Day Tasks
You can skip the cost of setting bad expectations. Save your budget to hire people instead of pouring into this trillion dollar trust deficit. I’d start with making sure that every job posting you share has a section called “every day tasks.” None of that “collaborate with the team,” either. I want that list to be as specific as a theatre cue sheet. Every detail of the scope and scale should be included. When you write “work with a team,” explain which team and how many people are on the team. If you wrote “clear messy areas,” be explicit about if that includes toilets and children’s aim.
Bonus: you can use the every day requirements to ensure the mandatory requirements are real. The golden rule of removing bias from requirements is this: if you can’t align it to something it prepares you to do every day or a goal for the role, it’s probably not required. I’m looking at you, unnecessary college degree requirements.
Next, create a day 1 readiness checklist. This should include all of the steps that happen before the first day, on the first day, and over the first 3 months to not just set expectations but check in with your new teammate to confirm their understanding. Comprehension and what you consider comprehensive aren’t one size fits all. It’s always worth asking if someone understands. Bonus: you might even get some free advice on how to make the systems you’re already working with better if you ask for feedback. Automate surveys to new hires post-onboarding to ask: “Did your first day go as expected?” Use the % of yes answers to track improvement over time. Another great benchmark? Fewer tickets and requests for computers after day one.

