How I Train New Hires Over and Over Again Without Losing My Mind

Coaching in the Workplace: How We Do It as a Distributed Team

When you’re part of a rapidly developing SaaS startup, constant scaling is a fact of life. It naturally entails an unending need for building processes – and to hire new people who have to run these processes.

But teaching people new skills in a demanding and dynamic work environment can be a challenge.

Following simple but strict rules has helped me as a manager and coach on Hubstaff’s team to get a hold of our processes. This has allowed me to optimize the experience for both myself and the team members I’m in charge of coaching.

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The start of my coaching experience

At a fast growing startup like Hubstaff, we all wear many hats. My responsibilities are to take care of two important marketing channels: search marketing and integrations. But besides these responsibilities, I had to quickly fill in the role of a coach when we started hiring new team members.

With the first new hire, the coaching experience was truly enjoyable. While onboarding the person, I answered each question happily and took every little bit of time I had to train them. And I was fine with correcting the mistakes that inevitably happen while people are learning something new – but that quickly changed.

With the second hire, the training turned into frustration from day one. I had to repeat all the training sessions and set aside a significant amount of time in my week for these activities. And after three weeks, the person ended up not being a right fit for our team. This meant new interview rounds and – surprise, surprise – a new round of coaching.

The story repeated itself: Walkthroughs. Questions. Answers. All over again. And I wasn’t even sure if the people would end up staying with us. I felt stuck, like I was reliving days over and over again – like Tom Cruise in Edge of Tomorrow.

While following this inefficient “non-strategy” of repeating myself over and over again, I was falling behind on my own work and goals. This resulted in stress and busy weekends. You could even say I had become bitter toward coaching. So before trying to figure out how to improve my approach to coaching, I had to reflect on the value of coaching. I needed to remind myself that coaching was important.

What helped me in this process was realizing that I owed a lot of what I know today to the people who have coached me in the previous years.

Dave, our co-founder at Hubstaff, has personally invested time in teaching me a ton of important skills since Day 1. Before Dave, I had several other mentors who helped me grow as an individual and I’m deeply grateful to them.

Why did all these people take the time to train me? Because that’s the only way for new hires to grow and for the company to evolve. You learn and then you contribute. You need to pass your learning to someone less experienced than you – even if you have to do it repeatedly.

In fact, this is how humanity functions: We rely on our predecessors’ patience to train the future generations.

In vain have you acquired knowledge if you have not imparted it to others – Deuteronomy Rabbah

But how can we make coaching and sharing knowledge easier? How can we ensure our tasks don’t get put on the back burner while we’re training new team members? How can we smartly train someone?

I have three actionable tips from my own experience that you might find useful as a coach and manager yourself.

Follow the 20-30-50 rule

This is a way to handle your own time while coaching other team members.

My formula is that I will spend 20% of my time during the week in training overall. In a 40-hour work week, this means between eight and ten hours of training. If it seems insufficient, I’ll work on improving my training method rather than increasing the training time.

I’ll spend another 30% learning and the remaining 50% contributing to the work on my team.

Pie chart for how to distribute your time across learning, training, and contributing

You can apply this rule yourself by dividing your tasks into three categories:

  1. Training
  2. Learning
  3. Contribution

Take note of how much time you are dedicating to each of the categories. You can use a time tracking tool like our very own Hubstaff to record your time, plus a task timer like NowDoThis or TaskTimer to enforce a countdown timer on each task of the day.

If you exceed the time allocated for the task, you don’t do it. That’s the rule. The logic is the following: If you’re spending a lot of time on training someone, then you’re ignoring your other tasks and diminishing your potential to learn and contribute.

I learned this from our co-founder and my mentor Dave.

With him I have monthly review calls to discuss our quarterly goals progress. If we would exceed the time allotted for the call, Dave would end the call. The rest would be discussed in our project management software. This is a good example of sticking to the 20-30-50 rule and being smart about how you fit your goals in the dedicated time.

Create a detailed training manual

The next useful tip that I learned from my own coaching experience is that you need a detailed training manual. This will replace endless calls and chats with new team members.

Think about it – all major software products and services have a support documentation center with articles, videos, and FAQs. They were created to decrease the load on their support teams. You should treat your coaching the same way.

After my numerous frustrations of having to repeat my training sessions, I created training videos answering every major question that comes up when a new hire starts the onboarding process.

training manual for coaching

I made the training videos using SRecorder, but you can also use Monosnap. Then I organized the videos in a folder in our team’s Google Drive. I also made sure that our process documentation was as thorough as possible but also succinct so that people are not overwhelmed.

This approach saves countless numbers of my hours in training new people and keeping the 20-30-50 rule in proportion. No matter how many people need to get trained, I only have to share this folder with them to get them started on the process.

This approach also helps me judge a new hire’s ability to solve problems on their own. Once the training material and the process documents have been handed over to them, do they still ask the same questions? Do they still need their hand held through the process?

If yes, they’re most likely not a right fit for the team.

Use a project management tool for communication

My last tip is to drop email as a communication tool in your training.

How many times have you starred an email from a team member, so you can reply to it later, but you ended up forgetting to answer? It keeps happening to me and it just creates utter chaos in my inbox. Plus, email is highly inconvenient for keeping track of the discussion on a particular task. I would have to search through my entire email history to find one line of text.

On the other hand, a project management tool allows you to discuss everything that is task-related on the task card itself. That’s how you can document all the task communication in one place. So if a new team member is to take up that task, they can just read the communication history to get up to date.

This saves time for both you as a coach and the new team member who needs to catch up fast.

use a project management tool for coaching

Over to you

We are where we are in our careers because of people who have coached us. And those we are teaching today will pass on their knowledge. Keeping this in mind will help you overcome any frustration associated with training.

What can also help is reading the short book The Coaching Habit for further tips on how to optimize your training process. This book completely transformed the way I coach today.

What are your biggest challenges in coaching other team members? What are your best hacks in handling training people?

We’d love to hear from you in the comments.

  • Awesome post! Content amplification can be a fully fledged blog post!

  • Rhea Gultian

    Thanks for this great post. Surely this is helpful for me starting my own agency,

  • fieldd

    Madhav, I want to be you when I grow up! My goal is to gather up all our processes one place, but I haven’t found that tool! What project management tool do you use? Thanks again for the post. Jess

    • Wow, I’m flattered Jess! For project management, we use an internal tool called Hubstaff Projects which should be out in 2017 for y’all to use. 🙂

      You can gather up all your processes in a Google Drive or Dropbox. The basic requirement is a process document (that’s incredibly easy to understand), a folder full of training videos and a reporting spreadsheet. Here is a related article of mine, if you’re interested to know more – http://blog.hubstaff.com/developing-marketing-strategies/

      When you speak about a tool to gather up all your processes, what do you exactly mean? What would you want in such a tool?

  • MichaelBungayStanier

    Thanks for the shout out, Madhav!