Here’s Our Onboarding Playbook

Earlier this week, I had a candidate ask about 1:1’s -- cadence, agenda, and purpose. I’m guessing my passion in answering a good, but relatively standard question, was surprising. 

It’s something I’ve always taken very seriously. 

Above all else, I feel my job as a manager is to take care of my people. This is something that I have learned through my career and, I think, has improved our teams’ performance. 

Very early in my career, I was told, “your first first team is more important than your first job.”

That’s still one of my favorite pieces of advice. But, I think it extends beyond your first team and your first job. In today’s era of rapid technology innovation, every job changes so quickly. I would argue that throughout your entire career, the team you work with is just as important as the job you work in. The job is going to change,  but the relationships you build with the people on your team will benefit you for years. 

So, I don’t move 1:1’s unless I absolutely have to. And I rarely, if ever, cancel 1:1’s. 

I’m passionate about this time together. 

And I’m equally passionate about onboarding. 

Maybe I’m just passionate about people. 

Onboarding is the first impression for an employee. According to Sapling, employees who have a negative onboarding experience are twice as likely to look for new positions in the near future. Turnover for startups can be a mission-critical problem. 

I don’t have near as much experience in onboarding as I do holding 1:1’s but we are five employees strong and about to add our sixth so it is currently top of mind. 

Like we’ve tried to do in the past with recruiting, writing a user constitution, talking to your persona, Board Meetings, and more, I thought I would share a peak behind-the-scenes at how we’re onboarding our first sales hire. 

Have a Playbook: 

This, of course, is helpful for the employee that you’re onboarding. It should serve as a one stop resource for all things your new employee needs during onboarding. Everything is new so don’t overwhelm them with having to find new things in new places -- keep it condensed to one playbook with links to all of their new resources. 

An even larger, and potentially selfish, motivation for this playbook is that it gives you and your business a historical benchmark. Every time you onboard a new employee, you can refer to previous playbooks. You can remove what hasn’t worked and improve upon what is working. 

This becomes an incredibly valuable artifact for your business. 

Here’s What’s In Our Playbook: 

Our playbook, for now, is made of three major sections: resources, meetings, and technology. Below is what’s inside each section. 


  • 30/60/90 Day Plan: this is an Google Sheets document that lays out each project as a line item with a 30, 60, or 90 day timeline and a low, medium, or high priority associated. Each line item (project) also has key result for what successful completion looks like. Remove as much ambiguity as possible for your new employees! 
  • GTM Resources: this is specific to the role that the playbook is built for. Here are a few links to the resources you need specific to your role -- in this case, sales. 
  • Competitors: share details on competitors, it will help set the playing field for the space your business is in. 
  • Board Presentations: At an early stage, I am a big fan of being transparent to a fault. You’ve poured a ton of effort into Board Meetings with the intent of updating that audience on your business, the wins, and the challenges -- share that with your employees! 
  • Product Details: You guessed it, this is details...on your product. Links to demos, packaging, pricing, etc. 
  • Customer Success: Outline your current customers, use cases, and contracts
  • Marketing/Brand: Send them brand guidelines, messaging, positioning...and as a sidenote, give them some sweet swag. 
  • Recommended Reading: Our team is big on sharing #inspiring-content on Slack. This is a good way to get in the groove with how the team is thinking about your opportunity. 

Meetings: Make sure their calendar is set before Day 1. If you can, give them access to that calendar ahead of Day 1. Again, remove as much mystery as possible. 

  • Onboarding Meetings: these are one-time only meetings as part of onboarding. I do two 90-minute meetings as part of onboarding but we also build-in meet and greets with other team members and functions of the business. 
  • Weekly Team Meetings: Don’t forget to add them to recurring team meetings! 
  • Weekly 1:1 Meetings: have these set ahead of time
  • 30/60/90 Day Check-ins: New employees have always appreciated that we’re already thinking about these check-ins. 

Technology: This is unique for each role but straightforward no matter what -- have their accounts setup  for the tools that they need. Please! 

Is this perfect? Absolutely not. Has it been enjoyed by the team members currently on the team? Yes. 

With every new employee, we will revisit this playbook. We’ll ask for feedback at the end of onboarding and adjust accordingly. 

I hope that this helps other entrepreneurs. But don’t take my word for it. High Alpha has an incredible HR team. Lindsay Boone, who has onboarded nearly 200 employees shared her insights on their blog earlier this week. If you’re looking for a good resource, give this a read: 

4 Lessons From My Experience Onboarding 176 Employees at High-Growth Startups

And as always, if you have questions, reach out to our team. We’re changing the content marketing space but we also want to help our fellow entrepreneurs. Onward, upward, and onboarded!

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