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How Millennial Sales Leaders Manage their Peers

· Jeremy Boudinet · 13 Minute Read

My first post for the Ambition Blog is written in the spirit of our newly-launched #SaveTheMillennials campaign. The purpose of the campaign is to proactively solve issues pertaining to managing a Millennial workforce. 

So I thought it would be appropriate to poll 3 close acquaintances who manage teams comprised primarily of Millennials. The twist: They're Millennials, too.

Q&A with 3 Millennial Managers

Millennial Workforce

​Almost exclusively, the conversations I hear about Millennial management discuss the supervisory role from the lens of a Gex-X member or Baby Boomer. 

Not so, here. As you'll see in the Q&A below, Millennial managers are not immune from the challenges our older generations have faced in wrangling our full potential. 

Meet the Managers

Millennial Manager #1. Grant H.

My name is Grant and I lead a software sales team of passionate, hospitality nerds across Northern Europe and a bit of Africa.  I'm a graduate of the University of Tennessee - started my career in sales in D.C., moved to Seattle and now grinding in Europe. As far as interests go, I'm definitely a travel junkie. Also an avid reader, aspiring history buff and lover of a good TV series.

Millennial Manager #2. Kevin B.

I work for an advertising sales agency that's heavy on cold calls, up to 200 per day. I did so well as a rep that my company tabbed me to open its Atlanta branch. I'm a big sports guy, originally from Philly and graduated from University of Tampa.

Millennial Manager #3. Jake U.

I graduated from Emory with a B.A. in Environmental Studies in 2011. After holding a full-time internship at an advertising agency for my senior year, I went to work full time the day after graduation on a major telecommunications client. In 2012, I switched agencies to do marketing analytics for a major airline.

There, I was quickly promoted to Senior Analyst and then Manager, managing four Millennials, after forming strong relationships with my client and excelling over my peers through hard work and determination. I have recently switched jobs to go client side to the major airline, developing an analytics process for their Revenue Management department while managing a team of 6.

1. All three of you ascended to manager status faster than most Millennials. What got you that success, and what advice do you have for Millennials looking to become managers?

Grant H. Off the bat: I don’t hold higher status than my team members.  I’m no better than them. I’m no more gifted than they are. I resent any manager that leads in any context other than we chose to do a different job. We chose to lead rather than individually contribute. Our success is through our team’s success. 

If you take hot air balloon view of how I reached my position relatively quickly can be attributed to a couple of specific factors: timing and risk.  I’ve heard from people you can’t influence timing. I don’t necessarily think they’re wrong but I’d argue that they aren’t right. At a minimum, they’re only painting half the picture.

While you might not be able to speed up or slow down events to suit your whimsical fancy, you can certainly position yourself to benefit with the structure you’re presented. For example, in my case, I saw the business potential for our products in EMEA and I pushed to move here before others noticed the trend.

Or, if they noticed it too, I acted. That kind of, “if you can’t be better, be first” mentality. So, having that type of foresight can help you manage your timing constraints. However, it should be noted that the acquisition of our startup is something that I had no control of whatsoever.

If that voids my previous statements: whatever – do well and good things will happen to you. The risk is I went the startup route. Startups have less stability but the payoffs are higher if they’re successful. You typically move a bit faster in startups as well because they’re all about the meritocracy model. That “get shit done” mentality. 

I think as Millennials we are a bit more risk acceptant – we have this inherent notion that nothing can really hurt us.** So, the thought of moving abroad was a bit more palatable for me. Because, why not?

I suppose the best advice I could give a Millennials who want to become managers would be to go all in. Leaders appreciate conviction and certainty. It’s extremely rare to be “tapped on the shoulder.”  

Management is a choice, not a reward. If you want to advance, be clear about your intentions to your management and set realistic goals with a proper time frame to achieve it. Look at each meeting as your opportunity to prove your worth as a thought leader. Leave the half measures and indecision to the underperformers.

*Sidebar 1 – Another factor to be mentioned is my industry. I’m in software sales. Sales orgs promote pretty quickly. If I was an accountant I’d have a harder time being a fast mover.

**Sidebar 2 – I’ve noticed that this is a much more American attitude than European. The amount of opportunity (specifically around technology companies) is just so much richer in the US that we worry less about job stability.

Many of my similarly aged colleagues across Europe have a deep seeded fear of economic instability - much more than the same peer group in the States simply because of their job landscapes and small country-specific economies. Basically we can move to SF, Seattle, or NYC with no issue whatsoever. They need hard to come by visas.  

Kevin B.  Since I began working at this company, I've kind of developed two personal mottos, all of which were absolutely critical for my success and led to me getting my promotion. Motto number one: "Keep an old-school mindset -- do not to act like most Millennials." As in, I'm keeping my nose to the grindstone and refusing to let distractions get in the way of my success.

Motto number two: "I'm focused on my own lawn and have no idea what the grass looks like on the other side." In other words, I don't have one foot out the door and I'm staying completely focused on maximizing my opportunity at my current company. To extrapolate on those and turn them into some actionable advice - foremost, don't get caught up in social media, watching some viral video or so forth. 

Another big thing I've learned is that work trains you for work more so than grades. A lot of smart people my age graduate with high GPAs, obtain a graduate degree and the like. But truth be told, I've seen a lot of these people fall victim to entitlement - and they're the ones struggling in the workforce right now. Hard work, not grades or academic background, is what breeds success. And entitlement kills motivation.

Last thing: I hear a lot of people tell me they're "determine to succeed" and then work from 9-5 everyday. That's bullshit. In sales -- especially in this day and age -- 9-5 is bullshit, unless you aspire to mediocrity.  You have to put in the long man hours early in your career to accelerate your growth. This is your best opportunity to do so -- don't let it go to waste.

Jake U. I was able to rise quickly through the ranks by utilizing hard work and curiosity. 

Millennials have a tendency to think that rewards will come naturally because they are smart, but this quality alone is not enough.

You really have to put in your time and be willing to raise your hand to take on extra work and have the drive to dig deep and investigate problems and potential solutions. It's this creative thinking that will set you apart from your peers.

2. What have been your most frustrating experiences in managing Millennials? Your most rewarding?

Millennial Management

Grant H. 

I really like how Millennials look at how things could be done. Again, we like to take risks and we don’t focus on our failures.

We love immediate gratification and we have short memories. It’s a blessing without much curse. This lets us try new things and we keep driving forward.  For the very same reasons, we get distracted easily. It’s common for my team to lose focus or to be deflated if there isn’t something shiny in front of them all the time.

Not every week needs to be butterflies-and-rainbow’s appreciation-competition-week. Sometimes I feel that we act like we’re entitled to uproot the status quo just to say we uprooted the status quo.  

Kevin B. 

Most frustrating: People that don't serve their time and leave for a better job because the grass is greener. Rewarding: Recently, enough of my ATL team qualified for the company incentive trip to New Orleans, thus I was able to join them.  My peers, in terms of job title and responsibilities, on the trip were all Gen-X or Baby Boomers.

Quickly upon arrival, I was given the vote of confidence of being in charge of the plans and celebratory festivities for the qualifying reps from across the entire company that were in attendance.

To be recognized and then respected like that by my older peers, while getting to enjoy the spoils with my fellow Millennials - that was truly rewarding. The Millennial colleagues I manage know my work ethic.

I very, very rarely lose my cool, and when I do, it's because that work ethic is disregarded or under-appreciated (mainly from a rep that positioned themselves as a go-getter in their interview but treated the job as a stop-gap and didn't pay their dues). Fortunately, that isn't too often, though it does happen.

Jake U.

The stereotype of Millennials feeling entitled can often ring true in a workplace.

Many Millennials will see how their executives act and think they can get away with it (i.e. taking off early without asking permission), but what they don't realize is they have to earn that right by clawing their way up through the ranks. 

Millennials tend to be very quick learners, however, so it's very rewarding when you teach them something that they then go on to master and become subject matter experts in.

3. You're in a role typically held by baby boomers and members of Gen-X, What advice do you have for them, as a millennial, for getting through to your generational peers?

Millennial Workforce Needs

Grant H. I think there are two camps on this one: Those who want to vocalize the generational gap and those who don’t. I think in either case you need to be aware of it. 

Focus on the things we need and understand why we need them. This isn’t a one-way street.

Help us understand where you’re coming from too. Coach us. Mentor us. Teach us the skills you’ve spent your career honing.

Please manage to my personality before you manage to my generational label. Talk to me about my goals and aspirations and be ready to share your own.  Bottom line – don’t think using colloquialisms like “on fleek” will, in any way, make us relate. Actually, no one, regardless of generation, should use “on fleek”. Ever.

Kevin B.

In so many ways, your professional success is going to be based on appearance. You have to give people what they want. 

Let them see "the good life" and don't be a curmudgeon, or else they won't know you have their back. They will work for you if they know they're on your team and they're also working hard for themselves, too.

Positive people are putting stuff on social media -- it's all new to them. You need to reinforce a positive environment through acknowledgement and, in general, being a positive manager.

Jake U. To the older generations managing Millennials, I would say that we are a very smart, quick learning generation. We have a lot of potential and myriad new, fresh ideas. Don't be afraid of suggestions that we have that deviate from traditional standard practices, but at the same time, keep us in line to make sure we are being bred for our full potential.

Also, please take an interest and mentor us, as we have been used to this type of personal one-on-one relationship growing up and will respond positively to it.

Improving Millennial Sales Leadership 

We Millennials require the help of our wisened Gen-X and Baby Boomer colleagues. With proper support, sales leaders can #SaveTheMillennials.

Please visit and pledge your company to the cause, share a favorite Millennial moment on Twitter or join our Managing Millennials LinkedIn group. There are also some great tech companies on there who can help, so feel free to check them out as well.

Special thanks to our 3 Millennial sales managers for agreeing to participate in this interview and for their candid answers. To our readers, good luck and I and hope you found some new value and insight from these interviews. Thanks for reading and feel free to pass along and comments or questions to

Ambition Drives Millennial Sales Professionals 

Ambition is a sales management platform that syncs every sales organization department, data source, and performance metric on one easy system.

Ambition clarifies and publicizes real-time performance analytics for your entire sales organization. Using a drag-and-drop interface, non-technical sales leaders can build custom scorecards, contests, reports, and TVs.

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