Training and Learning


One aspect of taking the lead on a sales or customer success team is that of a trainer, facilitator, and mentor. Your department is only as good as its training system. Without a flexible system for standardized training, the department will not achieve its goals. 

 Training needs to be meaningful, practical, and useful. 

Meaningful training sticks with the person and resonates much more profoundly. One example of this is role-playing sales calls. If your team deals with regular sales calls, role plays can help each team member improve as they are made aware of their strengths and areas for improvement. Studies have shown that learning is best with engaging and interactive scenarios. 

Training should also be practical in that a team member should be able to use these skills and tactics on a real phone call. It’s always good to add some theoretical sections to a training session; however, there should always be a takeaway to use as soon as they start their next call. One example of practical training could be writing out scripts for your product/service and role-play different sides. At the end of the session, they will have had an opportunity to practice, get feedback, and fine-tune a script. 

If training is not adequate, meaning it cannot yield results, don’t waste anyone’s time. The takeaway here should come from a well-thought-out hypothesis that’s ready to be tested or a proven strategy. 

Look for training opportunities.

You’ve noticed that one of your sales reps is doing quite well this month, and the other members are barely reaching their KPIs. What is the difference between these reps? That is the question to answer.

One way to diagnose the problem without creating more work for yourself is to call a team meeting. Give them at least 24 hours to prepare something useful to share. Each rep should share their screen and talk through their workflow. Look from every angle to find a glaring difference or even a subtle one. Now discuss what you discovered with the team, look for patterns, discrepancies, similarities, strengths, and weaknesses. 

No one wants their time wasted. Get to the point, make sure everyone participates, are engaged, make sure reps can apply it right away, and ensure it has the promise to improve performance. 

How to test what works?

What if you notice that all of your sales reps are struggling to reach their KPIs for the month. How can you apply the impromptu training to diagnose the team issue? It’s more or less the same, but testing your system is required. 

Don’t create a new system if it was working before.

If your system was working fine before, don’t throw the baby out with the bathwater. Decide with your team one point in your process that you want to change. Some of these changes may seem trivial, but you won’t know until you test them. Here are some things to check:

  • Font and size of the font
  • Signature- too many links? Maybe add a link?
  • Subject lines- ensure they are clear and consistent
  • Too many links in your body? 
  • The follow-up content? 

At the end of the day, if your team is not reaching their KPIs, you, as their team lead, are to blame. Look for ways to help them improve their sales process. If they are the right fit for the role, they will eagerly seek a solution to optimize their sales process, especially if it will add money to their pocket.  


One of Ray Dalio’s principles I’m quite fond of is ‘Evolve or Die.’ We all need to evolve as fathers, employees, and citizens, and the best way to grow as an individual is to learn. 

What if your team moans about learning? If you follow the steps above in the Training section, you should have no problem getting them to pick up a book. However, if they are averse to picking up books, then you’ll have a hard time in an evolving industry. Make this point salient.

If you want to learn something, read the book like you have to teach the content to someone else. You don’t need to read every single word in every single book to become learned. You need to be able to extract what you need to teach this topic to others. The best way to learn something is to explain it to others. 

When I first started out teaching ESL in Vietnam, my English grammar knowledge was subpar. Teaching requires you to clearly explain the meaning, form, and pronunciation of various grammar points. I was motivated to improve to help my students, so I sought resources to help me understand the complex grammar points. After a couple of horrible classroom experiences, I began to understand the nuances of challenging grammar and my ability to explain it to a full classroom.

Never let the gaps in your knowledge hold you back. If you lack expertise in an area, seek out the answers on your own. There are no excuses for not improving yourself. The volume of free content available on your phone is limitless. 

Online training

The problem I hear most from HR managers is that their employees don’t complete online training on time. Now that this is the new normal, remote employees and managers need new tactics to improve their skills and be accountable.  

Establishing clear guidance on the training process is critical. For example, if you have recorded a training video and posted it in your Slack channel for viewing and comments, make it very clear verbally and in writing. 

Hi team

Here’s a short video about some of my findings while going over your workflows. Watch and answer the questions to the best of your ability. Complete this task by the end of Friday, June 22nd. Thank you. 


Don’t mince words or be vague. Speak in imperatives, but be as polite as you can. You may come across as being a bit short, but there should be no reason for misinterpreting the message. If an employee is unable to complete this task, they should have the ability, without any repercussions, to ask for an extension to the deadline. Extensions should be requested well in advance, and the reason should be excusable. 

What if they don’t do the training?

Some team members can shrug off training until the last minute, and there is nothing to do about that without creating more of a burden on the trainer (require them to submit their plan for your viewing 24 hours before the meeting). When a team member does not give advanced notice of completing the task, what should be the necessary actions? 

Read the situations below and choose one that you think should be the first step.

  1. Confront the absentee team member once they are back in the office. Choose a public area to set an example.
  2. Call them on the phone and ask them to explain their actions. 
  3. Wait until you see them again and ask them if everything is ok. 
  4. Write them up and send it to HR posthaste! 

It can be infuriating if someone doesn’t complete your training. Don’t take it personally. Remember, your colleagues have lives too and should never be chastised about their inability to ask for an extension to complete the training. Here’s how I would approach it:

Me: Hi Chris, I noticed you didn’t get a chance to complete this week’s training. Is everything ok? 

Employee: Oh, yeah. I’m sorry. I’ve been working on this other project, and my 6-week old daughter is keeping me busy. 

Me: I understand. I hope you’re getting enough rest. Let me know if I can take anything off your plate. Get to the training by next Wednesday, and just let me know in advance if you are too busy. It’s an excellent session, and I think it can help you because it’s on Time Management. 

Employee: Thanks. I’ll give you advanced notice if I can’t complete the training. 

By asking if everything is ok, you show that you are genuinely concerned about their health and well-being, which allows them to open up a bit more. The ones who care about their tenure with your company will become more proactive in asking for extensions or learn to make time for the training. Those who cannot make these changes can be managed out of the department or, more likely, the company.   

What do you do if an employee does not do the training and asks him if everything was ok twice already? 

It’s time for The Talk.