How to Coach Today’s Multi-generational Workforce

By Ty Bello


There is significant data available to prove that coaching actually works, and within the past few years, coaching has emerged as a top priority in businesses. As a professional coach, we have seen countless businesses change their entire approach toward leadership and management of their team through coaching.

Most leaders want to coach, and most team members want to be coached. Sales organizations are struggling with how to make this happen and change the way they do business.

In this article, I will share the steps that your business must take to adopt and implement a coaching platform. I will address and provide tools to:

  1. Understand what sales coaching really is
  2. Overcome coaching obstacles
  3. Develop a coaching process for your business and your team
  4. Start coaching for success

But before I dive into coaching and the methodology, I need to address why this is so important in a business of multiple generations. Never before have there been this many generations in the workforce at one time.

The following is a snapshot of the generations that are in the workforce:

  • Boomers: Born between 1946 and 1964, 76 million
  • Generation X: Born between 1965 and 1977, 44 million
  • Millennials or Generation Y: Born between 1978/80 and 1994/95, 100 million
  • Generation Z (Homeland Gen, Post-Millennials): Born between 1995 and 2010, 76 million

What is coaching?

So, what is coaching, and why does it impact the team? The answer lies within the person being coached. A generational paradigm has taken place, and the paradigm is that the people in sales today are very different from the old guard.

Lightly put, the newest generations in the workforce – Gen X, Millennials and Gen Z – have been coached throughout their entire life, and the last thing they want is a boss. For the old guard (Boomers), coaching is refreshing, and they actually embrace both the approach and outcome. Although many would say, “You can’t teach an old dog a new trick,” when it comes to coaching, the “old dog” likes it.

Sales coaching is the secret of sales success, because it improves the performance of your sales team, and the coach. Coaches not only encourage their team, but also take a shared ownership in their team members’ successes.


Overcoming coaching obstacles

There are three obstacles that can get in the way of coaching

  • Directing and not collaborating
  • Not enough time
  • Talking and not listening

As stated, there is a fine line between managing and coaching. Coaching does less directing and more collaborating.

By directing a team member, you will miss the chance to see where they are in the motivational and/or learning curve. You will also miss the opportunity of knowing how they see a certain situation, and what they would do in that situation. Directing voids almost all interaction, because you are busy directing and not listening and probing. If you think coaching sounds a lot like sales, you are correct.

Another coaching obstacle is making the time for your team member without interruptions. Team members need to know that they are some of the most important people in your day. You need to give them your presence right then and there. You also need to provide a solid foundation of follow up – and not just general calls or e-mails checking in to see how they are doing.

Also, doing all of the talking and not really listening to your team members may move your agenda ahead, but does little to engage them for sustained growth both personally and professionally. All leaders have an agenda. There are quotas to hit, goals to achieve, and a boss to report to. It is when this gets in the way, as opposed to making this a part of coaching, that you negate any true growth.

Coaching is a culture that must envelop the entire organization. Coaches themselves need to be coached.


Develop a coaching process for your business and your team

To begin your coaching process, you must understand the five steps of coaching:


Step 1: Connect with the team member

  • Pay attention to the relationship between you and the team member. This will make everyone more comfortable.
  • Establish rapport. Let the team member know you are there to help – not just evaluate. Always open by building rapport. This is where you will be working together to improve the situation.
  • Be hard on the issues, not on the people. Coach people, manage processes.

Step 2: Compare perceptions

  • They talk first.
  • 65 percent of all managers open their coaching sessions by asking a question.
  • By asking questions, you will: Learn where the team member is at; discover their insights, skills and judgment; be able to give specific feedback and direct your coaching.

Step 3: Consider obstacles

  • Get the team members’ perceptions of the obstacle, and talk about your perception of the obstacle. (Spend up to 30 percent of the coaching on these two actions.)
  • Once the perceptions are on the table and an agreement is made about the need for change, help the team member consider what is blocking his/her progress to the desired behavior.
  • Continue to use the “they talk first” strategy, and ask the team member to identify the obstacle.

Step 4: Construct or remove the obstacle

  • The team member removes the obstacle, based on dialogue from step 3.
  • You add value and encourage the decision on the table.

Step 5: Commit to action

  • Action steps – what needs to be done? Put some detail into this, as it will be the map for the success of the team member.
  • Summarize the plan.


In the retail setting, coaching must become more intentional. Carve out time with each team member over a monthly period. Use the five-step process for coaching, and you and your team will see greater growth, completion of tasks, and success.

So, what is stopping you from coaching today? You have the basic tools you need to develop your plan and stick to it. Your team will be overwhelmed in a positive way, and your business culture will be changed forever.

How you choose to use the time in your day is entirely up to you. The investment of your time in coaching your team will be a deposit into the future success of your business.


Ty Bello, RCC is the president and founder of Team@Work, LLC. He is an author, communicator and registered coach. The team at T@W has more than 50 years of combined experience in assessing, developing, and coaching sole proprietorships, sales teams, C-suite executives, individuals and teams in a variety of industry settings. Contact Ty at for your sales, customer call center, and management coaching needs. Or visit for more information.


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