The way people work has changed dramatically. Gone are the days of large, stable organizations and strict 9-to-5, Monday through Friday schedules. Now, people work anywhere they have Wi-Fi. A series of evolutionary trends have forced employees to shift not only their hours and expectations, but their mindset. They must be agile and open to new opportunities in order to keep pace and stay employed. More and more, they expect that growth and global economic shifts may require them to look elsewhere for opportunities.

With these factors at play, the assumption is leaders’ mentality and skill set have kept pace. But according to recent research from Deloitte, only 28 percent of millennials feel their organization is making good use of their skills. Millennials have made it clear: they want to spend more time discussing new ideas/ways of working, developing leadership skills, and receiving coaching. Unfortunately, leaders are unsure how to coach this new breed of worker to keep them feeling valued and engaged.

The good news is that it IS possible to not only manage, but actually mentor today’s employee. The solution lies in recognizing the forces affecting employees and their work, now and in the future, and empowering leaders to adopt a new mindset and set of coaching behaviors to counteract them.

Five Converging Forces

It’s easy to see that the cadence of work is different.  As a result, flextime, remote, part-time, and contract schedules are the norm. According to the 2017 Deloitte Millennial survey, two-thirds of employees born after 1982 are working some type of flextime schedule.

These are the effects, but how did we get here? What caused this rapid shift? The changing landscape of work can be traced back to five factors.

  1. Technology: In 2018, barriers to groundbreaking technology are non-existent. Anyone with internet access and a credit card can take advantage of cloud-based deployment to find solutions that fit their needs.
  2. New Behaviors: The influx of new technology leads to new behaviors. Employees are more open and transparent and accustomed to collaboration. In addition, employees at all levels of the organization are sharing what they know on Twitter, LinkedIn, and Slack. Thought leadership no longer comes from the C-suite; anyone can be an influencer with the right ideas.
  3. Globalization: Boundaries no longer exist and business is the great equalizer. We are all taking part in a global economy and the language you speak and the currency you use matter less and less.
  4. Millennials: According to a 2016 study in Forbes magazine, millennials will comprise more than one of three adult Americans by 2020 and 75 percent of the workforce by 2025. This demographic shift has forced everyone to adapt.
  5. Mobility: Today’s employee can work anytime, anywhere, on any device, forcing employers and leaders to adjust expectations and renegotiate what “urgent” means.     

But the More Things Change…

While almost every aspect of work has radically shifted, there is one thing that hasn’t changed: people! In spite of dramatic economic and societal shifts, people’s innate need to belong, feel good about their work, and contribute in a meaningful way is more important than ever. Unfortunately, it’s harder and harder to do as evolutionary forces continue to place demands on employees’ ability to stay engaged with and loyal to an employer over time.

The Game Changer: Coaching Conversations

So, what’s the solution? Will employees’ needs continue to outpace leaders’ ability to adapt? One solution is increasing the sheer number of conversations leaders hold. According to Gallup, employees whose managers hold regular meetings with them are three times more likely to be engaged. It’s also been shown that a culture of frequent conversations yields higher productivity and team function.

Unfortunately, a growing divide still exists despite countless conversations between leaders and their direct reports. As it turns out, it’s not the number of the conversations leaders conduct, but the quality of the interaction. A typical conversation between employee and supervisor is often not as focused, and therefore not as effective as it could be. Ineffective conversations become even more of a “miss” when you consider leaders tend to have fewer conversations because of time and place restrictions.

Conversations become a game changer when they are not just conversations, but coaching conversations. What’s the difference? A regular conversation meanders across a variety of topics with no stated agenda. In contrast, a coaching conversation features a structured framework that a leader employs to impact the decisions and actions of the employee.

Leaders can make the limited interactions they have more important and impactful by bringing a framework to conversations they’re already holding. In fact, it’s as simple as asking questions and listening more.

Exploring a New Mindset

Typically, leaders approach coaching their teams in one of two ways. The most common is with an outside-in mindset. This approach is characterized by lots of advice-giving and “telling,” or in other words, a one-way sharing of knowledge. There is nothing wrong with this approach and it’s absolutely necessary during onboarding or when an employee is learning a new software program, for example. However, it’s not the most effective way to lead people to make decisions on their own.

An InsideOut mindset produces better results. It focuses more on getting existing knowledge out of the employee and less on the manager sharing their knowledge. A leader approaches a conversation with the goal of asking questions rather than giving direction. This creates employees who are empowered to own outcomes, make faster decisions, and offer up new ideas more frequently.

Three Conversations with Today’s Employee

A new mindset is just the beginning. It’s critical for leaders to begin engaging in conversations that move both the day-to-day work and the manager/employee relationship forward.

There are three types of coaching conversations that great leaders should hold with their teams: breakthrough conversations, check-ins and feedback, and alignment conversations. It’s important that leaders are adept at which conversation to hold when and how to conduct each one effectively.

Breakthrough Conversations

What: A conversation initiated by a manager or employee when the employee has a goal.

When: Held when an employee asks for help, shares a challenge, or asks for perspective.

How: The GROW Model.  

The GROW Model is a coaching process and decision-making model co-developed by Alan Fine that helps people gain focus and speed their decision making. It features four distinct phases in which the leader asks the employee a series of several questions to streamline their thinking.

For example:

  1. Goal: What do you want from this discussion?
  2. Reality: What have you tried so far?
  3. Options: If anything were possible, what might you do?
  4. Way Forward: What and when is the next step?

Check-Ins and Feedback

What: A conversation initiated by a manager to assess progress and provide feedback.

When: Held regularly to hold employees accountable and to keep people aware, informed and on track.


  • Keep it brief: Don’t interrupt the flow of work.
  • Ask open-ended questions: Avoid asking questions that can be answered with a simple “yes” or “no.”
  • Let the other person talk first and more often.

Alignment Conversation:

What: A conversation initiated by a manager to gain alignment and agreement.

When: Held when someone is unaware of an issue, doesn’t know or agree with direction, or refuses to cooperate.

How: Alignment conversations are tough conversations charged with emotion, so it’s important leaders practice the three “P’s” prior to holding them.

  1. Prepare: Get clear on the goal, the reality and the options if alignment is not possible.
  2. Plan: Write down a map of the conversation and anticipated responses.
  3. Practice: Discuss the plan and practice until it becomes second nature.

Work in 2018 looks nothing like it did even 20 years ago. While employees have adjusted to this new reality, it’s clear leaders’ communication skills have fallen a bit behind. But it’s not too late for them to catch up! If leaders bring the right mindset to every interaction and practice holding three types of conversations more effectively, they can quickly get up to speed and more closely align their coaching to what employees want and need. The result? Employees who feel valued and heard and commit to a long-term relationship not just with their manager, but with the company as well.