8 min read

7 Easy Ways to Craft a Great Onboarding Experience for Software Services

Little things done well can create huge value
7 Easy Ways to Craft a Great Onboarding Experience for Software Services

Great onboarding helps clients AND employees yet we tend to undervalue it for both audiences.

Stop right there. Clear your mind then think back to the most recent employee you hired. Would you have known what to expect if you were in their shoes?

  • For the interview process?
  • Leading up to an offer?
  • After accepting an offer?
  • On your first day?
  • For your first 30 days?

Probably not. That’s the bar set by most software services businesses. When you do communicate, it’s haphazard at best, and often days, even weeks, go by with no updates.

I’m not picking on you. I’ve been in this very same boat.

While running my first business, I had strung recruits along for weeks, sometimes months, with little more than the occasional email or phone call to ensure they were still hooked on my fishing line. Never on purpose. Always because I had no process in place and was focused elsewhere.

This became clear to me only after I had sold that business and began coaching other software services leaders. My advice didn’t match what I had done first-hand earlier.

Instead, I now had the benefit of looking at the experience of a potential hire from their vantage point. And it wasn’t pretty.

I was embarrassed. Some of the people I subjected to my broken “process” had been peers earlier in my career. They never called me out but I think it was simply due to super low expectations.

Most businesses lack an explicit onboarding experience.

And it is NOT limited to new hires. The same is true for onboarding new clients. By default, the process is whatever the person assigned to the client decides it will be at that moment.

The good thing is (since the bar is set so low) you don’t have to do much to make massive headway for new employees or clients.

What little things can you do to improve onboarding?

Here are 7 things you can do (in no particular order) to create your first pass at an explicit onboarding experience. The real beauty of these steps is in the fact that they work for both employees and clients alike.

After all, you’re dealing with people here. They have feelings just like you and appreciate small gestures that show you care and see them.

1) Clear and timely communication

When you set expectations upfront and make it crystal clear what has happened, is currently happening, and will happen, your new employee or client no longer has to guess.

I know guessing gives me anxiety. I also know when I’m left in the dark (or feel ignored) that I’ll naturally start to resent the situation. That is no way to start a relationship; especially, one that you hope will last many years.

Action: take time to map out what you want to occur. If you’re just starting out, you have a blank canvas so design what you’d want to see if you were in their shoes. For those of you that have been around awhile, ask your team, compare experiences, and build something consistent from that feedback.

2) Corporate swag and tchotchkes

Who doesn’t like getting free stuff? Especially, when it's from a company (people) that you’ll hopefully be working with for the next several months or years, as the case may be.

These trinkets don’t have to be expensive. The gesture is what matters most. Yet why not take the time to make them meaningful as well as pimp your brand in an attractive way. If your merch is cool, people will use it — and every person that sees it, could be another new hire or client waiting to happen.

Action: start simple with pens or t-shirts and put your name on them. Don’t cheap out here. Make sure they are high quality so people will actually use them all the time.

There are so many corporate swag businesses out there. I used Merchology years ago because they were easy to work with, had a great selection of brands that my employees and clients appreciated, and didn’t require me to buy in massive quantities. I paid more but gained flexibility.

3) Structured first few days

I know you’ve been here. You started a job and, on the first day, you were given time to set up your equipment, only to be seemingly forgotten about right afterward. You didn’t want to be the person that didn’t know what to do next so you faked it by looking involved.

How about instead, you create a simple schedule so your new hire knows how they will spend their first day. Even better would be a schedule for the first few days so they know what to expect during week one.

This works for new clients as well. Unless you’re coming to see them or they’ve traveled to see you, the agenda would likely pertain to a specific meeting. I’m hoping it wouldn’t be more than 90 minutes because that’s about when I tune out or need to hit the restroom.

Action: map out what is typically helpful for a new hire to be exposed to in week one and create a high-level agenda. Share who they will work with and some approximate timings. Be sure to leave time in the day for your new hire to digest all the information.

For clients, this will likely be when you’re starting your first project together so the initial meeting should be scheduled as early as reasonable. Share who is attending, their roles, and how to reach them when needed. I’d also go so far as to set up recurring check-ins so you establish a cadence right out of the gate. Good communication can typically head off disaster before it sets in.

4) Message from your CEO

Who doesn’t like hearing from the CEO? Don’t remember feeling super important when they made the time to talk to you? The message or encounter doesn’t need to be elaborate. Just acknowledging their presence can make a huge difference in how you and your business will be perceived early on.

Action: write an email welcoming the new hire or client and add a personal touch to it so it doesn’t feel contrived and pre-written. Send it yourself (assuming you’re the CEO). The time it takes to do this is insignificant but makes a big difference to that person.

As a bonus, sign it and mail it to them. I know I’d see this as elaborate and unique given all I ever receive nowadays is bulk marketing and bills.

5) Training for success

I know. Training sounds expensive and super time-consuming. But it doesn’t have to be. You can record much of it with video. After all, pictures are worth a 1000-words so videos have to be even better. Plus, you can do it from your iPhone or laptop. Why overthink it?

Action: take out your phone and share your knowledge with a video. Or open your laptop and record your screen while you talk. The software is simple now and the very act of hitting the record button is the hardest part. Don’t believe me? Just ask Google and you’ll find a ton of ways to get started. Pick one.

This will be your first version and likely will be short-lived. The really cool thing here is to have your team make future versions. After you’ve taken the first step, most of the pressure is off. As your processes evolve, your team now has a baseline to work from — they include what is still relevant from the prior version and reference what is new.

Please don’t write this stuff done and tuck it away in a binder. You will have wasted precious time and no one will read it. Video is your play here.

6) Feedback loop

The key to any great experience is the feedback that helped it go from okay (maybe even terrible) to outstanding. As a starting point, you don’t need surveys or polls, you just need to ask a couple of simple questions.

  • What did you like about our onboarding experience?
  • Where was it confusing?
  • Is our experience better than your last (employer or provider)?

Action: encourage your new hires and clients to provide feedback by using questions similar to my examples above. Take notes, share them with your team, and look for patterns to see where you should focus on improvement.

7) 30-, 60-, and 90-day plans

Before you groan too loudly, I’m talking about broad strokes here. You don’t need to craft a play-by-day agenda for these plans. You’d be wrong anyways and not flexible enough to roll with the inevitable punches headed your way.

Instead, work backward. What makes sense at 90-days will inform what you should help them achieve at each of the earlier timeframes.

Action: Ask yourself a few questions like the following.

  • Where do you want your new hire or new client’s project to be at 90-days?
  • What must have taken place to get them there?

Tada. You just created their 90-day plan. Sounds simple but it doesn’t have to be elaborate. I’ve tricked myself here many times.

From there you work towards the next earlier plan.

At 30-days, you can likely add a bit more detail but keep it at a weekly level. Don’t pack their days with activities that don’t truly matter. Focus on what will help them achieve the future plan.

If doing XYZ won’t benefit them in 60- or 90-days, why even bother focusing on it in the first 30-days. Trash it. Give everyone involved their time back.


Few people like to read all the nitty-gritty so here are the 7 things you could do to create a great onboarding experience right now. And remember, you don’t have to do all of these at first. Start somewhere and iterate.

Just starting to explicitly invest in your onboarding experience will put you ahead of most software services firms. The bar is really that low.

  1. Communicate clearly and often. Let people know what to expect, when to expect it, and from whom to expect it. Put yourself in their shoes and try to be as transparent as practical.
  2. Everyone loves free stuff. Invest in some swag for your brand and share it with new hires and clients. If you ensure it’s high quality, they’ll use it and help you also build further awareness for your brand. Win-win.
  3. An agenda for week one. Let your new hires and clients know what to expect once they come aboard. Take the mystery out of it and help them make the most of those first few days.
  4. The CEO shoutout. Everyone loves to hear from your CEO and it largely doesn’t matter what is said. Keep it simple, sincere, and personable. If you’re not allergic to snail mail, send it old school.
  5. Teach people to succeed. Share how you work and what to do to be an effective employee or client. Do me a favor — don’t write out a tedious procedure and stick it in a binder. No one will ever read it. Instead, use video to capture important visuals while you talk about what matters.
  6. Ask how you can improve. Feedback is key to a great experience so be sure to ask consistent questions that require an open-ended answer. Share what you learn and look for patterns to prioritize improvements.
  7. Plan for the first quarter, one month at a time. Work backward from what you need to have achieved after 90-days. Use that to inform how you prepare your new hires or clients one month at a time. If a task is not relevant at 90-days, don’t put it on your 30- or 60-day plan — unless you have a great reason.

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