Issue #8 - Why First Impressions Matter

Onboarding new hires well is critical to the long term success of your business and those employees, a story to reinforce that perspective, and solutions to help you go from zero to hero in no time

Welcome back to Better Outcomes, a weekly advice column for service business operators that are fed up with the status quo. Contrarian insights and a Q&A for subscriber questions. As well as a healthy dose of storytelling from my (mis)adventures in building businesses.

This is the first issue of the new year. So long 2020, you won’t be missed. With a new year and a new job, I’m optimistic about the future. Probably not saying much given I tend to see the good everywhere I look—even if I’m skeptical of the default narrative.

Today we focus on employee onboarding. A subject that doesn’t get the attention it deserves in most businesses yet can have a profound virtuous effect on your success.

The outline for today’s issue of Better Outcomes newsletter:

  • Question — No Q&A, today I’m asking you a question

  • Storytelling — Two examples of opposite onboarding experiences

  • Commentary — What you should take away from this

  • Books & Products — Practical solutions to help your business grow

  • And, One More Thing

Need Help? I’ll let you in on a little secret — someone else has the very same questions but is anxious about speaking up. Help them while also helping yourself.

All you have to do is reply to this email or message me on Twitter or LinkedIn. And I will keep everything anonymous unless you give me permission otherwise.

Until next time,
Casey Winans

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Q: What do you recall when you think back to your first days at each new job you’ve had over your career?

Yeah; that's a loaded question. Like me, you've probably had both good and bad experiences. The good ones stand out yet so do the bad—with others lost in the mix.

This is especially important today. In the world of WFH that was thrust upon many of us last (almost said 'this') year due to the pandemic sweeping the globe. Now more than ever, great onboarding is even more critical to ensure remote employees feel like they are part of a community and know how their work will impact your business.

This is your homework for today. Ponder the following question and share your feedback in the comments. What stood out that was great (or at least good) and what scarred you?

Leave a comment

Check out the Books & Products section below for promising solutions that you can rollout to your business and become a digital-first onboarding company.

📘 Storytelling

I want to share some recent onboarding stories. These examples offer experiences that are almost polar opposites. The businesses both offer services to customers in the form of project-based engagements yet the work and industries have no overlap.

A Tale of Two Opposites

I just returned to work. The kind of work where I have a boss and a paycheck. So a J-O-B. Never thought I'd do that again after starting my entrepreneurial journey a decade ago, but the planets aligned and the gig was too good to pass up. Now I do from-within what I used to do from-outside businesses.

The onboarding process knocked my socks off. Thoughtful and consistent throughout, with every piece executed digitally. The only part that was "offline" was stopping by HQ to grab my laptop and an unexpected bag 'o swag. 🎁 Plus I took the opportunity to chat with one of my favorite people (Lori). 👋

I knew exactly what to expect on Day One, with meetings, agendas, and a virtual catered lunch. Consider me a fan. The swag was so good that I had to threaten my wife and kids so they wouldn't pillage all my newfound loot. 🏴‍☠️

Is there room for improvement? Sure. Nothing is perfect so there is always something to be tweaked, expanded, or omitted. The best businesses never rest on their laurels. They seek out feedback and strive to exceed expectations.

Now let's contrast this with my friend's recent experience. If I were lazy, I'd just say his experience was nearly the opposite. But that's not entirely true and won't help you so I'll elaborate. Gosh!

I want to call out some major differences before I share the short-comings of this other business. It has 25-30 people while mine has nearly 90 people. That can make a huge difference given the larger business has dedicated people for each role. The smaller business has its employees wearing multiple hats.

While the other business may be smaller, it has chosen to stick with out-dated, manual processes driven haphazardly by people. And I want to call-out my use of "chosen" because this is a choice. Lack of attention is a choice.

This means things can fall between the cracks and simple tasks can go sideways. None of the paperwork could be digitally executed. Instead, this meant he ran around town to find a notary that would sign documents stating he was who he claimed to be. And he also had to print, sign, scan, and mail dozens of forms.

I also want to call out that Day One and Week One are ambiguous at best. It will likely involve Slack and some phone calls, but it's safe to say the sense of an introduction to the company will be haphazard.

Could you see how the two businesses differed? If you said 'no', we need to have an intervention. And you may need to stop smoking crack.


Manual onboarding and massive ambiguity hurt everyone. Even though onboarding is a process each employee only does once at your business, that doesn't mean it's not critical. In fact, it's the opposite. You can't afford NOT to invest in a comprehensive system of onboarding. Not if you want people to do their best work.

But all is not lost. There are easy things to do that can radically improve how new employees perceive their first days and ensure your team is consistent and thorough. Yep; I’m talking about the proliferation of cloud-based SaaS solutions that are flooding the market with value (and other shiny things).

Today there is no excuse for manual. The business I sold was even doing this years ago so anyone can do it now. What are these solutions you ask? Here goes:

📚 Books & Products 💻

Disclaimer: I do *not* currently use affiliate links. I make no money here. I just think the books and products are promising. If I ever go the affiliate route, I’ll be upfront about it.

  1. Delivering Happiness (Amazon) by (the late) Tony Hsieh
    This is a great book that I’m still actively reading. It’s a wealth of knowledge in how to treat customers, with long-term thinking and contrarian insights. Just the sort of book that fits the thesis for this newsletter.

  2. Namely — People Operations (I have personal experience with this one)
    This is a SaaS solution that helps you manage your pipeline of applicants and the people that you invite to join your business. It covers things like onboarding, benefits, engagement, compliance, and managed options. It’s a great way to go from manual to exceptional. The entire onboarding process can be digital so your new employees do it correctly and quickly.

  3. Rippling — Employee Management Software
    Rippling lets you manage and automate all of your people operations in one place—onboarding, offboarding, and everything in between. It even touts onboarding new hires within 90 seconds — talk about fast! It offers automation and workflows and boasts 400+ integrations. According to their website, the average implementation time is 2.5 weeks; who can’t find that kind of time?

  4. Gusto — Human Resource Information System
    Just like Namely and Rippling, here is a third option that has been popular. Hire, onboard, and nurture your incredible team. It boasts of custom workflows, check-lists, and the ability to send customized offer letters in seconds.

One More Thing…

❤️ I’d love your support. Please forward to friends and share on social media.

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🔍 If this is your first issue, 👋. You can check out all the past issues here.

Better Outcomes is written and curated by Casey Winans. Follow me on Twitter, Medium, and LinkedIn. Want to work with me? Send me an e-mail. Or maybe just buy me a beer?