The New Leader's Guide to Managing More Experienced Employees

So, you're in charge, but they've got more experience? Here's everything new leaders need to know about managing more experienced employees.

Managing someone with more experience than you? Take heart, PYT, you are not alone.

The US Bureau of Labor says, by 2020, 32% of people aged 65 to 74 will still be working.

First-time managers and younger leaders should take this statistic for what it is - a strong signal that even early on in their managerial careers, they're likely to find themselves “the boss" of someone with more experience.

So, if you happen to be a new manager grappling with how to lead more tenured direct reports, you’re in the right place. In this post, we're tackling the six most common challenges of managing more experienced employees.

In a hurry? Skim through the six common challenges listed in the next section and click on the "How to Deal" button to be whisked away to the topic you think will be most helpful to you. 

Want to make sure you've got all your bases are covered? Simply read on.

Common challenges of managing more experienced employees

Managing more tenured employees presents a spectrum of "interesting" (read: uncool) challenges for a new leader.

While you are no doubt more familiar than you'd like to be with whichever issue(s) your more experienced direct report presents you with, being aware of the challenges other new leaders are facing will help you better anticipate – and proactively address – minor 'situations' before they become major problems.

So, in the spirit of being prepared for anything, let's start with a look at six of the most common challenges of leading employees with more experience.

Challenge 1

My more-experienced employee’s knowledge and experience intimidate me.

They know their stuff. You know "some" stuff. 

Challenge 2

Because my more-experienced employee has been at my company longer than me, s/he has tighter relationships with co-workers.

Your happy hour invite keeps getting lost in the (e)mail.

Challenge 3

Our clients and customers seem to prefer to work with my more-experienced employee.​​​​​

You can't get a returned phone call to save your life, but your direct report is on speed dial.

Challenge 4

My more-experienced employee thinks and acts like s/he knows it all.

Everything you can do, she can do better, faster, and typo-free.

Challenge 5

My more-experienced employee doesn’t support my new ideas or policies.

Every party has a pooh-pooh-er. At this one, it's your direct report.

Challenge 6

My more-experienced co-worker openly disrespects me.

When your co-worker acts like a co-wanker.

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4 secrets of managing more experienced employees

As much fun as alllllll of that sounds, you, new leader, have goals to set, strategic plans to lay, and projects and programs to successfully manage.

To spare you the time and stress these challenges can bring, the remainder of this post details four tried-and-true strategies for winning over direct reports with more experience and how to convert their expertise from team "morale liability" into the asset it is.

Secret No. 1. Investigate the 'true root' of work issues.

What does this mean?

Here's what I mean by this: the management challenges you are facing could very well be rooted in your more experienced employee’s undesirable behavior(s), but it’s also possible that they are rooted elsewhere.

In you, for example.

What, exactly, am I implying here?

Let me explain with a few examples.

Common challenges of managing more experienced employees, parts 1-3

To help illustrate Secret No. 1 Investigate the "true root" of work issues, we're going to revisit our list of common challenges again, this time narrowing our focus to just the first three challenges.

Those are:

  1. 1
    My more-experienced employee’s knowledge and experience intimidate me.
  2. 2
    Because my more-experienced employee has been at my company longer than me, s/he has tighter relationships with co-workers.
  3. 3
    Our clients and customers seem to prefer to work with my more-experienced employee.

Read each of these closely, maybe even out loud. (I'll give you a minute.)

Now, while it is entirely possible that these types of management challenges are deeply-rooted in reality, i.e., your clients really do prefer working with your more experienced employee...'s just as often the case that these challenges stem from how YOU are perceiving the situation.

A new leadership role means bigger challenges and higher expectations.

These added pressures make it easy to fall into the habit of viewing reality through a hyper self-conscious lens.

In other words, your new role can have you playing serious mind games...with yourself.

I've got both bad news and good news on this perception vs. reality concept.

THE BAD NEWS: hyper self-conscious lenses can lead to self-destructive perceptions.

The good news: if you can practice exercising self-control, reality comes into a clearer focus and the issues highlighted here can resolve quite quickly.

Like, instantly.

So, how can you as a new leader, practice self-control and keep self-destructive perceptions in check?

For practicing self-control in uncomfortable people management situations, we like using the acronym ABC. 

The ABCs of practicing self-control and avoiding self-destructive perceptions

Here's what ABC stands for and how to integrate it into your managerial approach.

Accept the situation you are in

Avoiding destructive perceptions begins with the following very simple reality check:

You are a new manager.

By definition, for the next – gulp – several years, you will be presented with tasks you don’t know how to complete and situations you don’t know what to do about.

Make no mistake, a new manager's role is a learning role. The quicker you accept this and settle willingly into the role of the learner, the less frustrating the ride will be for you…and for everyone on your team.

You are new. 

Respect this.

And, yes, others know more than you and have known one another longer than you. 

Respect this, too.

Instead of being intimidated by the knowledge, experience, and relationships of your more tenured direct reports, learn about them so that you can leverage them to make your team and client relationships better.

Be the manager, not the subject matter expert

Too many first-time leaders confuse being a manager with being a subject matter expert.

You are a manager, not a subject matter expert.

​It is NOT, in fact, your job to know everything about everything. It’s your job to know who on your team knows 'all the things' and how to organize their skills and talents in such a way that, as a team, you continually drop banger-after-banger on your company.

The role of a manager is comparable to that of a conductor.

A modern symphony orchestra has something like 100 players. Violinists, cellists, bassists, flutists, bassoonists, trumpet players, tuba players, trombone players, percussionists, harpists, etc.

The conductor isn’t at the helm because s/he is a virtuoso at every single instrument.

She's up front because she knows the strengths and talents of each team member and how to employ them ‘in concert’ such that the team produces an undeniably beautiful sound.

Check your ego at the door

Here's the deal - our first concepts, Accept the situation you are in and Be the manager, not the subject matter expert are easier to write (and read) about then to do in real life.

So, to help turn this advice you are reading into something you are actually doing in real life, I’m going to ask that you start a very simple, very actionable daily habit.

And that is this:

Each day when you arrive at the office, mentally check your ego at the door.

Need a visual? Visually check your ego like it’s a coat at a fancy-ass wedding reception where you’re fixing to get turnt.

Need a reason why you should do this? Like coats, egos are stifling and restrictive. They straitjacket our performance. 

If you keep it on, the dance (read: office) floor won’t ever see your best moves.

PIN IT: Managing self-destructive perceptions

Yes, your people management woes might be stemming from a difficult direct report, but they might also be self-inflicted wounds. New leaders can practice self-control and keep self-destructive perceptions in check by remembering the acronym ABC.

Accept the situation you are in

Be the manager, not the subject matter expert

Check your ego at the door

That said, never ever forget this: They picked you.

Someone with decision-making authority identified YOU as THE ONE with the brains, the talent and the no-guts, no-glory work ethic to take on a leadership role. Somebody believes in you. 

Don't let one person distract you from what you've got to do to when someone believes in you.

And you know what the best thing to do with somebody's belief in you is, don't you?

The best thing to do with someone's belief in you

Over the next few months, you will need to demonstrate why you were picked to a wide audience - your boss, your customers, yourself, and, yes, your direct reports.

All of your direct reports. Your more experienced team member is not holding some VIP ticket to this show. 

If anyone is holding such a ticket, it’s your boss, and, at least to some degree, you’ve already got their buy-in. If you let your need to prove something to someone influence your actions, you’ll never ever earn either.

Now, what if your perception is aligning just fine with reality and that the ‘root’ of the problem is your more experienced employee’s attitude and/or behavior?

Well, then...

Secret No. 2. Create productive outlets for unproductive behavior.

What does this mean?

Yes, it is 100% possible that your ego is properly checked and that you are, in fact, facing the tough reality of dealing with an experienced employee sporting a wanker-y attitude.

That it is them.

Let's revisit our list of common challenges again. This time, we highlight three scenarios that could indicate your experienced employee is genuinely NOT psyched about working for a less-tenured supervisor.

Common challenges of managing more experienced employees, parts 4-6

To illustrate the creating productive outlets for unproductive behavior, we take a look at our list of common challenges once more, with a focus on the last three challenges.

  1. 4
    My more-experienced employee thinks and acts like s/he knows it all.
  2. 5
    My more-experienced employee doesn’t support my new ideas or policies.
  3. 6
    My more-experienced co-worker openly disrespects me.​​​​​

Facing one of these situations? Don't sweat it! We're about to break down an approach for handling each of them.

Scenario No. 4. My more-experienced employee thinks (and acts) like s/he knows it all

Here’s your two-part approach to managing the Know-it-All:

Know-it-All Management Part 1. Provide an opportunity to share their expertise.

On one of the occasions where your team member is positioning themselves as an expert, listen closely to the topics s/he seems to take the most pride in their expert knowledge on.

Is it a technical skill?

A people skill?

Product or process knowledge?

When you’ve zeroed in on a subject, approach your team member with both an acknowledgement of their expertise and an ask for sharing it.

Here’s an example script of what this conversation might sound like:

"Morning, Gwen. During our meetings, I’ve picked up on the fact that you’re quite knowledgeable on creating sales funnels. I believe our entire team can benefit from your experience, so I’d like to assign you a project. Can you put together a brief training for the team outlining your winning approach to funneling and present it to us?"

After you’ve acknowledged the team member’s know-how and assigned them an “I’m the expert on this” task, it’s time to move into phase two.

Know-it-All Management Part 2. Challenge this team member to expand their skills and experience.

While your team member might be a bonafide expert on a certain subject or two, they aren’t on all subjects.

Your next move is to encourage this team member to expand themselves professionally by tasking them with a new learning experience. 

If you are aware of a particular deficiency this team member has, you can choose the topic for them and frame it as a general team need OR you can give them a little autonomy by asking them what they’d like to learn about and assign them the task of finding and completing a course or workshop.

This approach indicates to your team member that you’re aware of and appreciate their existing talent and skills, but also of their potential.

Scenario No. 5. My more-experienced employee doesn’t support my new ideas or policies

The crux of the "management of change" challenge is to create a happy balance between respecting tradition and encouraging innovation.

Let’s say you’ve got an employee who has a tight grip on past programs and policies and that this behavior is preventing you from furthering your vision for the team.

Your go-to strategy here looks this:

Managing More Experienced Employees - Change Resistant Employee Strategy

The true value of this strategy is in the dialogue exchange.

By giving your team member part ownership of the policy development process, you are forcing them to articulate a thought process to you. 

Instead of simply stonewalling, they’ll have to offer a rationale for their hang ups. If they can’t, it will be clear to all parties that s/he is being difficult for difficulty’s sake.

So, how do you get that rich, give-and-take dialogue flowing? 

By asking questions like:

“What do you foresee to be the biggest constraint this policy will put on our team?”

“What resources does the team need to follow this policy? New training? A new tool?”

“My understanding is that our goals for this policy are X, Y, and Z. Would you agree?”

Sometimes, you have to “go first” when demonstrating that you are a team player. This signals to your team member that it’s safe (and best) to reciprocate.

Scenario No. 6. My more-experienced co-worker openly disrespects me

If your more experienced employee is on the super salty side, they might act passive-aggressively or aggressive-aggressively in meetings, side conversations, emails, etc.

This situation is entirely inappropriate. And it also has the potential to drain both team morale and productivity quickly. 

It needs to be nipped now and with clear, calm, and specific language from you.

If verbal (including tone), written, or body language ever approaches disrespectful, here’s your go-to phrase:

"My expectations are that everyone on this team feels respected at all times. At this particular moment, my expectations are not being met. [Name the offender], I believe you and I should spare our team members this discomfort and continue this conversation together with our [Name your HR director]."

Have this meeting with your employee and the HR director immediately to signal that you aren’t messing around.

Younger than your direct reports? Here's how to handle three uncomfortable, "but, I'm the boss" situations. #leadershipskills #howtomanagepeople

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Secret No. 3. Have a clear management vision - and plan.

What does this mean?

In the early months of your leadership role, there are two concrete ways to do this and, ultimately, earn confidence and trust from your team.

Let's dig into each of them.

2 ways first-time managers can build confidence and trust with more experienced employees

Confidence and Trust Builder No.1. Follow-up

If you say you are going to be somewhere or do something, be there or do it.

If you have no real plans to be somewhere or do something, don’t say that you are going to be there or do it.

Concepts don’t get simpler.

And, yet, most managers - and human beings in general – can’t seem to execute this play.

Is this sad reality of the human condition? Yes, but it’s also a tremendous advantage for you.

Because most people don’t follow through, those that do end up looking like rock star managers and human beings.

Confidence and Trust Builder No.2. Have a plan

People trust and have confidence in leaders who know where they are going and have an idea of how to get there.

If you don’t know where you are taking your team and/or have no real idea how to get there, you will struggle to earn their trust and confidence.

You want a management plan.

You need a management plan.

Why? Because a thoughtful, carefully-crafted management plan is a first-time managers best friend, their road map for success.

Your plan will also protect you from flailing under the stress and insecurity that so many new leaders experience during their first few months (okay, year) in a new management role. It will help you better enjoy your work experience.

So, what's in a thoughtful, carefully-crafted management plan? 

At the very least, a management plan should contain detailed strategies for the following topics:

Managing More Experienced Employees - Management Plan Details

As you can imagine, developing a management plan that does all of these things can be a time-consuming process.

And, because it's a time-consuming process, most managers don't take the time to develop one.

This is a mistake.

Developing a strong management plan is hands-down the most effective way for you to quickly get a grip on your new leadership role and to find confidence and success in it. 

If you have experience creating management plans or 30-60-90 day plans as they're sometimes called, excellent. Consider this a not-so-subtle reminder that now more than ever, you need one.

If you DO NOT have experience creating management plans, that's okay. 

We've written a handful of extremely useful posts on how to create powerful 30-60-90 day plans.

We've also created a 30-60-90 Day Plan template to help you build out your personal plan.

That template? It's totally FREE. Just enter your details in the box below to tell us where to send it.

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That clear vision and management plan of yours?

It’s also going to help you institute the fourth and final secret to successfully managing more experienced employees.

Secret No. 4. Be consistent.

What does this mean?

Saving the most legally significant recommendation for last here.

You want to know how to manage an employee with more experience than you?

Hold them to the same expectations and systems as everyone else.

Here's why - and how - to do it.

Why - and how - to hold your team accountable to the same standards and systems

By law, you cannot treat employees - or prospective employees - differently because of their age.

The Age Discrimination in Employment Act of 1967 protects applicants and employees 40 years of age and older from discrimination on the basis of age in hiring, promotion, discharge, compensation, or terms, conditions or privileges of employment.

The US Equal Employment Opportunity Commission puts it like this:

the law prohibits discrimination in any aspect of employment, including hiring, firing, pay, job assignments, promotions, layoff, training, benefits, and any other term or condition of employment.

Do not adjust your managerial approach based on age. Base it on behavior. 

How can you make sure you base your managerial approach on behavior and not age?

Start to demonstrate clear, consistent management patterns now.

Demonstrating clear, consistent managerial practices can be a struggle for first-time managers because, well, they are new.

You, for example, probably haven’t had the opportunity to make enough ‘calls’ to demonstrate a clear, consistent pattern to your team just yet. That’s completely understandable.

As you move forward, you’ve got to be cognizant of your decision-making pattern - or lack thereof - and work to be as consistent as possible.


Because a track record of consistent decision-making signals the following to your team members:

  • Whether or not I like the outcome, my manager does rely on referenceable logic and rationale in her decision-making process.
  • My manager applies a similar standard to all situations, making the outcomes more predictable and fair.
  • Because of past outcomes, I have an idea of how my ideas, suggestions and performance will be evaluated ahead of time. This enables me to better position myself for success.

Even if you’re only a handful of weeks into your new role, it’s likely you’ll have at least a few helpful resources available that can help you jump-start your efforts at establishing that consistency.

  • Company policies
  • Standard operating procedures
  • Performance evaluation matrices
  • Risk analyses or SWOT analyses completed by your predecessor
  • Vendor/supplier qualifications
  • Your team

The availability and quality of these resources will depend on the formality of your organization and, honestly, how much your predecessor cared.

If a collection of these things already exist, great! Study and revise them. 

If they don’t, you will need to start creating them.

And, hey, wouldn’t this be an awesome opportunity to loop in your know-it-all or I-don’t-like-new-ideas team members?

Overview: The crux of managing more experienced employees

It’s no secret that the US work force demographic is “maturing”.

By 2020, it’s expected that 32% of people aged 65 to 74 will be in the workforce.

This statistic means the likelihood that new managers will supervise more experienced employees is high.

We just shared four secrets to managing more-experienced team members that first-time managers can use to overcome potential challenges. You’ve now got actionable strategies for integrating each into your managerial approach. The infographic below was created to help you keep them top of mind. 

Feel free to download and print it out, save it to Pinterest, or embed it on your own website using the code below!


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Hello! My name is Morgan. I created to help new managers quickly find confidence and success in their first leadership role. Here you'll find programs, tools, and guides designed to fast-track your journey from first-time manager to confident, creative leader. The best place to start? Our 10-Day Leadership Skills challenge where you'll learn how to leap over the five biggest hurdles that keep most new managers from finding their footing in their first year. Sign up below, its free!

Morgan Greenwood


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