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According to a recent report from LinkedIn, almost one-third of professionals state that they would prefer to work more 6 hours each week than to seek help in the workplace. And if you think that the number of people who needed help at the office and didn’t ask for it was almost 85%, this turns things even worst.

One of the things that was also possible to see in this report is that many time, employees simply talk to their colleagues but they hardly ever turn into their bosses.

The reality is that, for most people, approaching the boss for a difficult conversation no matter if it is to start a new project, ask for a raise, say that you are pregnant, ask for feedback or that you made a mistake is incredibly hard.

So, before you start shaking just by thinking about the idea of talking to your boss, there are some things that you should keep in mind.

Prepare Yourself Mentally

Before you head the meeting with your boss (he probably needed to schedule it for you), you should take a couple of minutes for yourself, to put your ideas and thoughts in place.

Here are some things you can do:

• Take a couple of deep breaths since they will allow you to be more focused and less nervous.

• Write down the main points that you want to cover in the meeting. Notice that you should try to make a script, just a list of the main points so that you can easily remember them all.

• Change your mindset: this is only a conversation or meeting with your boss. Don’t see it as a difficult conversation but as an opportunity that you have to open up.

How To Prepare Difficult Conversations With Your Boss

While you may be tempted to talk to your boss about your problem when he is just passing through or near the coffee machine, you should avoid it. The truth is that you need to realize that everyone has their own tasks to do and that your boss may be late for one. So, instead of “trapping” him, it is always better and wiser to ask for an appointment or a meeting. You should also stat that it won’t take too long and that you will be available at any time.

As soon as you agreed on the time and place for the meeting, you want to ensure that you are there on time. Besides, there are other aspects to keep in mind:

#1: Explain Both The Situation And Context:

One of things that many people tend to do when they are having a difficult conversation with the boss is to start divagating. However, as you know, time is money. So, you should try to get to the point as you can. Notice that this doesn’t mean to be aggressive. Simply explain to your boss the situation that is affecting you and the overall context.

#2: Be Clear, Direct, And Unemotional:

While we understand that this is easier said than done, we also know that you can do your best to control your emotions. As we mentioned above, it is important that you enter in the meeting with your boss with the right mindset. After all, this isn’t a conversation where your life is at stake. On the other hand, you should make an emphasis that with this meeting, you will be able to solve a problem that has been tormenting you for quite some time.

Your boss is just a human being like you. So, you want to make sure that you keep to the facts and that you are upfront and direct. One of the things to keep in mind is that you don’t need to provide your boss with all the details. Just explain to him the overall situation and its context.

#3: Ask For Your Boss Perspective:

Ultimately, you are having a conversation. So, it is normal to ask the other person for their perspective over the situation, even if we are talking about your boss.

Maybe he saw the situation or was aware of a part of it. You never know if you don’t ask.

#4: Arrive At A Mutual Understanding / Resolution:

After you explain to your boss your point of view and after you listen to his feedback, you will probably agree on some aspects and disagree on others. SO, it is important that there are no questions remaining without answer and that you both understand each one’s points of view.

Bottom Line

Conversations with your boss don’t need to be hard and you don’t need to get all nervous. No matter what is on your mind, it is always better to clarify the situation before it gets worse.

The goal is to change your mindset and not assume that the talk will be hard. Above all, be honest, straight to the point, and avoid showing your emotion

A Bit More About Millennials

According to Gordon Tredgold, founder and CEO of Leadership Principles, there is some interesting data that is worth to be mentioned so you can better understand how Millennials think:

  • More than 60% of Millennials state that they prefer to earn less at a job than earning more at a job they don’t like. 
  • Almost 90% of Millennials prefer to work in a place where there is collaboration instead of competition.
  • About 80% of Millennials prefer to get direct feedback
  • Millennials tend to stay longer in the same job than Gen-X.

While there are some differences between Millennials and other workers, the reality is that it is important to keep in mind that there are also some similarities. After all, they share the same passion for their careers. 

So, What’s The Challenge?

One of the main difficulties that have been shared by many senior sales leaders is concerned about how to train and develop Millennial salespeople. And the numbers don’t lie. After all, it is very expensive to hire a new employee. And this becomes even more evident for those companies who prefer a more traditional approach to training. These companies tend to provide all kinds of training to new employees in a traditional classroom. 

In addition to all this, most experts believe that by 2025, about 75% of the global workforce will be in the hands of millennials. So, you need to take some measures to ensure that your staff is well trained. 

5 Tips To Train And Develop A Millennial Sales Force

#1: Use Video:

There’s no question that Millennials love video. After all, just think that they include their mobile apps on everything they do. So, with this in mind, instead of keeping your sales training in a classroom using the old Powerpoint presentations, you can come up with different training methods using videos instead. Millennials will think the training will be a lot more fun and they will definitely be more engaged.

#2: Keep Track Results & Give Feedback Directly:

As we mentioned above, Millennials prefer to get their feedback directly and not get a written report, for example. So, one of the things you can consider doing is to implement the “test to teach” approach. 

Since millennials like to get regular feedback, you don’t need to wait until the end of the year to do it. Besides, this ends up being better for companies as well. After well, when they get your feedback, they will know what they are doing right and what they need to improve. So, you will be seeing an evolution throughout the entire year. 

#3: Make Sure That The Sales Training Is A Constant:

One of the best things about working with Millennials is that they are always eager to learn. Besides, millennials also appreciate having the time to be with their families as well a to pursue their personal goals. So, more flexibility in terms of the training you provide is definitely a plus. 

#4: Allow Them To Learn From Their Peers:

One of the things that we mentioned above is that millennials prefer collaboration over competition. This means that they prefer to work with their peers instead of with the sales manager, for example. After all, thy don’t like being told what to do. 

And this goes for training as well. So, whenever possible, you should make sure that the sales training that you provide your employees with should be given by a peer. In addition, Millennials love to see things in action and they are more willing to watch and listen to one of their peers demonstrate a skill than a manager. This is often called social learning. 

#5: Use Gamification To Engage Your Millennials:

As we already mentioned and you probably already know, Millennials are great fans of using technology into their favor. This is why they always try to use apps to keep up with their goals. So, gamification makes total sense here. After all, they will be completely engaged when trying to “hack the system” or “find the back stairs to the next level”. You will be enticing their imagination and creativity to look not only for problems but for the solutions to those same problems. So, they will get the reward. 

Bottom Line

Training and developing a Millennial sales force doesn’t need to be hard or impossible. All you need to do, as a business owner, is to put yourself into their shoes and see the things they prefer and their values. Since by 2025 about 75% of the global workforce will be in the hands of millennials, you need to ensure that you can engage them the best way you can. And with the 5 different ways that we showed you, we are sure that both your company and your employees will benefit from the change. 

anthony p garcia

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