Chester On Point

The Secret to Engaging Millennials is Actually No Secret at All

ruby slippersTo get back to Kansas, Dorothy never had to jump through all the death-defying hoops the Wizard put her through.  She had everything she needed (ruby shoes) from the very beginning. All she lacked was the understanding of how to unlock their magical powers.

Since they began making their way into the workforce in the late 90’s, business leaders, owners, and managers have been trying to figure out how to drive performance from their enigmatic millennial employees. As arduous and mysterious as this challenge has been hyped up to be, the answer is surprisingly simple. To unlock their power, all it takes is a one-to-one relationship with a manager who genuinely cares about them.

Many of my clients employ millennials as their front line workforce and the face of their brand.  These organizations are looking for the keys to engaging millennials to get them to perform up to their remarkable potential. Prior to speaking for their conventions and meetings, I conduct interviews with their front line workforce to help take leaders on a backstage tour inside the minds of those people who keep them up at night.  By getting my subjects to completely relax and let their guard down, these interviews become remarkably revealing about what it is that they truly want from their managers.

This 6-minute video montage features interview clips that I’ve recorded over the past 8 years revealing candid comments from millennial employees in a variety of jobs talking about what they love about their managers, and also what they hate about them. (As you’ll discover, there’s very little middle ground in-between.)

If you ask a millennial to describe their job, inevitably, they will begin telling you about the relationship they have with their manager. This comes before they mention how much they are being paid or what their job responsibilities are. The message is obvious; if you want them to work harder, perform better, and stay longer, focus your time and energy on these 3 crucial relationship-building keys:


1. Get to Know Them – You don’t have to be friends with them, but you do need to be friendly. That requires you take an active interest in who they are outside of work. Ask them about their friends, their family, their opinions, their likes and their pet peeves. Discover where their passions lie, and know what they like to do in their spare time.

2. Help Them to Get Where They Want to Go – You have an agenda and to achieve it, you need them to be on your side. They, too, have an agenda, and they need you on their side. The more you’re able to help them get where they want to go and give them skills that will serve them along their career path – even if their job with you has little resemblance to where they are going – the more likely they are to give you all they have while they are on your payroll. (It’s also the right thing to do.)

3. Pay Attention to the Good Things They Do – While your primary job is to stay on top of problems, you can prevent a lot of little issues from growing into problems by calling attention to those things your people are doing correctly–not just those things they are doing outstanding. Don’t wait for someone to be late to work to remind them about the importance you place on reliability; the time to do that is when they arrive early. Don’t just point out that their last report was incomplete without also complimenting them on the three others they did correctly. Change the focus of your energy and you’ll change the culture of your organization.






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The Best Interview Questions to Determine an Applicant’s Work Ethic

Back in 2006, I published a Special Report titled More than 50 Great Interview Questions to Ask a Gen Y Applicant.  The questions were gathered from hundreds submitted by clients, readers of my books, and HR managers from a wide variety of companies and organizations across multiple industries.

Job InterviewNow that the focus of my work has shifted from Generation Why to developing the 7 essential core work work ethic values that every employer demands, I’m going to replace the existing set of questions to one that lists The 50 Best Interview Questions to Determine an Applicant’s Work Ethic (i.e. their aptitude, habits, and behaviors in those 7 crucial core work ethic areas.)

This will be a crowd-sourced project which means that these questions will again come from those who are actively in-the-trenches, recruiting, interviewing, and hiring employees on a regular basis.  When this project is completed, the resulting Special Report will be available for purchase on my website and via Amazon as a downloadable PDF.  ($29).

However, if you contribute a question(s) that is published in this report, you will receive it for FREE before it is offered to the general public!

Play Along!  Submit a question(s) that help you determine whether or not the applicant being interviewed will:

  • show up to work on time (RELIABILITY)
  • be dressed/groomed and conduct themselves appropriately (PROFESSIONALISM)
  • perform any task asked of them with a positive ‘can do’ attitude (POSITIVITY)
  • give their very best to every assignment and always look to add value (INITIATIVE)
  • comply with your rules and adhere to the authority of their managers (RESPECT)
  • tell the truth and act with honor in all situations (INTEGRITY)
  • go out of their way to provide the kind of service that delights every customer (GRATITUDE)


Tell me about a time when you were given a project at school/work that you didn’t fully understand how to complete, or the teacher/supervisor wasn’t descriptive enough on what was expected. How did you go about making sure the project was completed? (Determines initiative, and attitude.)

We don’t allow employees to have a cell phone with them during their shifts. Do you think this is a reasonable request? How are you going to deal with this policy? (Determines their professionalism and respect for rules/authority).

If a customer were to get in your face and scream at you for something that was not your fault, how would you react? (Determines gratitude/service mentality and positivity.)

The report will also will provide suggestions as to what responses the interviewer should be looking for, and what responses may trigger a concern.

PRIVACY – To protect your identity, we will not publish the source of any of these questions.  (Neither your name or the company you work for will be made public to anyone.)

Submit questions via email to:

It will be exciting to see what results this tremendous community creates!





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Money Can Buy Happiness, but Pride Is Not for Sale

Imagine that you are walking alone across a vacant parking lot on a breezy day, when out of the corner of your eye you notice a crumpled-up bill blowing at your feet. You immediately step on it to keep it from escaping, and then reach down to discover that it’s a $100 bill. No one is within five hundred yards of you, and the wind is swirling leaves and other bits of paper around as far as you can see. You couldn’t find the rightful owner if your life depended on it. The bill is yours to keep.

Drawing only on your emotions as they unfold at that particular moment, answer this very simple question: Are you happy?

Of course you are. Unless you’re allergic to large bills, your response is an enthusiastic “yes!”

So here’s the follow-up question pertaining solely to this $100 cash windfall moment: Are you feeling proud?

Unless you’re overthinking this, you’re probably shaking your head or thinking, “No, not really.” You’re happy about your new riches, but you’re not particularly proud. You didn’t do anything to earn this free money other than burn a calorie or two bending down to pick it up. In this scenario, there was no goal, no effort, no sacrifice, no accomplishment . . . nothing to be proud of.proud

You see, while money, wealth, and possessions can make you happy, they won’t make your chest swell with pride if they’ve blown into your life without achievement. And even though money can buy temporary happiness, it can’t buy the pride of a job well done. And that is the priceless feeling all of us want more than anything. It doesn’t matter how deep an individual’s pockets are, pride can’t be bought, sold, or given away. It has to be earned.

The reason so many billionaires (e.g. Gates, Branson, Buffett, Zuckerburg, etc.) continue to work hard every day is because they are motivated by something much more powerful than money or wealth. They are driven by pride; a burning desire to achieve more, to accomplish more, and to make an even larger contribution.

ACTION IDEA: Build into each weekly meeting a block of time where you randomly call on employees to describe a recent work-related activity or accomplishment that they are proud of. Done consistently over time, your culture will gradually evolve to one where people are encouraging each other to improve and to perform at a higher level.

ON POINT: When we allow our kids, or our students, or our employees to separate effort from reward, we may tell ourselves that we are doing them a favor. In reality, however, we are depriving them of what they need the most and impeding their success in the process.

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Try This Handy Dandy 5-Step Formula to Resolve Conflict with Your Employees

When rules are broken in situFightations that don’t call for immediate termination, gain your composure and think “Open The Front Door Now.” This is the acronym for a simple formula that helps you address—and correct—many of the annoying small issues and problematic behaviors of your employees. Treating these problems according to the OTFDN formula will get them back on your team.

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10 Ways to Encourage Employees to Take Ownership in Their Work

yellow boots on the roadEvery employee who works for you will eventually arrive at a crucial intersection, if they haven’t already.

At that point, you hope they turn right and buy-in to your leadership and the vision and values of your company. Turning that direction means that they see a future for themselves with your organization so they’ll invest themselves fully and go all-in.

Unfortunately, some will turn left and quit on you without actually quitting. They’ll take on the ‘me against the machine’ mindset and begin looking for shortcuts and ways they can do just the MDR (Minimum Daily Requirement) that it takes to fly below the radar and avoid getting called out or fired.

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Why Millennial Managers are the Most Perplexed Demographic in America

I’ve been writing and speaking about millennials since they first made their way into the workplace as teenagers in 1998. Since then, I’ve interacted with thousands of mature business owners and leaders who’ve confessed their struggles and frustrations in managing this enigmatic generation.

Today, more than half of all millennials (born 1980-2000) are 25 and older, and the part-time teen workers of 1998 are now 35 years old. They hate being lumped into a generational heap that’s been branded and widely criticized for being inherently lazy and entitled. This is especially true for those overachieving millennials who are anything but lazy and entitled.

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How Today's Political Attack Ads Diminish Tomorrow's Leaders

Negative Ads

Even though the midterm elections are months away, I’ve already maxed-out on the amount of negative political ads my mind can tolerate without imploding.

The rough and tumble game of political campaigning has always involved an element of truth-twisting, scandal-mongering, and mudslinging. However, politics of late has become so ugly that most ads on TV should be preceded by a parental warning and shown only on late night cable.

The overwhelming majority of these ads are determined to destroy the credibility of the candidates running for public office. Campaigners spend untold fortunes and use all means possible to make their opponents look more like creeps and convicts than willing, trust-worthy servants. And all parties are equally culpable.

It’s sad that we’ve allowed our election campaigning to become so heavily polluted with 30-second, tightly spun character assassinations. It’s naive to think that this ubiquitous negativity doesn’t affect our own attitudes and perceptions about, well just about everything. What’s even more alarming is how this ever-deteriorating campaign process is value-imprinting our next generation of voters—and anyone who aspires to positions of public service or any position of leadership.


At home, school, and church, we teach and preach lessons of civility, honesty, decency, and tolerance. We say to our children, “If you can’t say something nice about someone, don’t say anything at all.”  Then every two years, they are subjected to elections where the outcomes are determined not on the basis of who has the best ideas and leadership abilities, but rather on which candidates exposed the worst in their opponents. It’s the epitome of hypocrisy.

When I was young, my mom used to tell me that if I dreamed big, lived clean, and worked hard, I could grow up to be President of the United States. Try to convince kids today that being elected President is something they should dream about. They know all too well that those who dare run for office—any office—instantly place a giant target on their backs. And the higher the office, the bigger the target.

Even when candidates manage to survive the storm and get elected, they set themselves up as punch lines for comedians and punching bags of talk show hosts. What kid in today’s world wants to dream big, live clean, and work hard for that?

If you don’t see how all of this can ultimately poison the culture in your organization, think again.

The only way to grow your business is to grow your people and harvest their talents and capture their passion and ideas. To stay competitive, you have to continually develop young leaders who are willing to think big, act bold, make sacrifices, risk failure, and make difficult and perhaps unpopular decisions. However, if those in your new crop of talent fear that they, or their ideas, might get shot down and they’ll lose face or be ridiculed, you’ll never realize the true potential of the resources in your ranks.


The ultimate winner on Donald Trump‘s popular reality show The Apprentice is not the best and the brightest, but rather the individual who is able to use any means necessary to survive the heat in the boardroom and get the other contestants fired. While this makes for an interesting reality show, any resemblance to it will destroy an organization’s culture and impede the development of its talent.

Studies prove that people function at a much higher level when they work in an environment that is free from gossip and infighting.

Whether you employ ten or ten thousand, it’s imperative that you strive to make your culture one that values innovative thinking, celebrates character, and rewards risks. That requires leaders at every level to consistently acknowledge, recognize, and reward individuals who are positive and encouraging and who go out of their way to help their coworkers.

ON POINT – The best way to counter the negativity that abounds throughout this–and every campaign season — is to continually shine the brightest spotlight on those people who are modeling the character, the values, and the leadership your organization espouses.  And if you’re not doing this with the same intentionality, fervor, and frequency that is on display by today’s mean-spirited political campaigners, it’s going to extract a toll on your workforce, and your culture.

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