MSP sales experts swear that hiring college students who were competitive athletes is a good MSP sales strategy.

(Check out this webinar with Kevin Damghani from ITPartners+ who shares how he built a high performing 8 person MSP Sales Team – he talks about hiring athletes!)

Do Elite Athletes Make Better MSP Sales Reps

Playing on a sports team in college is supposed to be an indicator that someone will be a successful MSP sales rep.

One of the things I’ve heard repeatedly is that participation in organized team sports demonstrates an ability to be part of a team, and work together to achive a common goal.  It shows that the potential MSP sales rep has the ability to see things through, and focus on repeatable processes (like training daily) that eventually turn small actions into big MSP sales rep wins.


I never liked team sports much.

I like being athletic.

I like learning new skills.

Mostly, I like to win.  And I don’t like to rely on other people to win things.  

Carrie Simpson practices superman punches

Carrie practices fly punches

I was a great squash player.  I was a good kickboxer.  I’m an okay surfer.

I was a terrible soccer player.  I was a fast, but not particularly strategic ultimate frisbee player.  I didn’t really “take” to any team sports.

The things I’m good at, I obsess over.  I want to be the best at it, even if that’s completely unreasonable.  (You’re not going become a world class surfer when you start surfing at 42).

I had private lessons.  Daily when I could afford it, weekly when I couldn’t.  In squash, kickboxing, and surfing. I traveled to compete, I practiced daily – sometimes multiple times daily.  I cross trained and I spent most of my spare time doing whatever my current obsession happened to be.  (And I lost 100 lbs in the process, by the way…)  I’ve trained with some of the best squash players in the world, I’ve trained with UFC players and coaches.  I moved to Thailand to train.  I waited tables at the squash club I couldn’t afford to be a member of so that I could play there.

Let’s go back to squash, which was the sport I most excelled at.

I moved from a recreational “E” player to a competitive high seed “A” player in under three years.  During this (very sweaty) time in my life, I played league night a few times weekly, which is where this story begins.

Carrie and her opponent on a squash court.

Squash tournament play

Elite Athletes and MSP Sales Strategy

There are two ways to beat your opponent in squash – you can overpower them, or you can out-finesse them.

You power that ball right past them so quickly they can’t get set up for the return, or you place that ball so perfectly that they can’t actually make the return.

I’ve played league night at every club I’ve ever joined, and most league nights are co-ed evenings.  I’m pretty competitive, no matter the stakes. I consistently lost league night games to men that realistically I *should have* been able to beat.  A “B” level player should be able to beat a “D” level player.

Like any good student, I had my coach come out to league night to analyze why this kept happening to me.

I play both a great power game and a great finesse game.  However, after watching a few matches, my coach easily pointed out what I was doing wrong. I was trying to overpower, when I should have been trying to out-finesse.  Play all the power game you want, but as a 5’4″ woman at 130 lbs, I couldn’t out-power a 6’4″ man at 230 lbs.

Here’s what my coach told me:  when you’re playing someone who can only play a power game, you need to stop playing their game and make them play yours.

You need to slow down the play, play with more finesse, and stop hitting the ball so hard.

Good advice.

Want to win?

Stop trying to play their game, and make them play yours.

Do you want to read more sports analogies while you’re learning about MSP sales prospecting? 

Check out this blog post on MSP sales development “Bench Theory”

MSP Sales Strategy 

Picture the squash game now as a managed services sales conversation.

Sometimes, the sales prospect and they and the MSP sales rep will have the same conversational style.

They’re fast both paced, they find the same things funny.  The MSP sales rep gets louder. Then the prospect gets louder, and they are both having fun speaking.  This can be a fantastic MSP sales conversation, but can also lead to both parties speaking overtop of each other.   Using the squash analogy, they are both “power” players.  They both like to hit the ball as hard as they can.

When you’re evenly matched, it’s anyone’s game!

What if both the prospect and your MSP sales rep are soft spoken and less casual?

They both use extremely professional language, and brevity knows them both very well. They are both quite matter-of-fact.  They each speak in a similar soft fashion.  What a gift!

It’s always great to connect with someone who communicates the same way that you do!

The drawback to multiple-introvert MSP sales conversations is often when two soft-spoken introverts are chatting there can be great awkward pauses. The parties don’t bully or rush each other, they both politely wait a little longer than usual for it to be their  turn to speak, and they both spend time composing deliberate responses.

This is a finesse game – you don’t waste energy and you don’t rush (leads to unforced errors).  The MSP sales rep will make a plan and follow a plan.

What happens when your MSP sales rep is the exact opposite of your prospect?

Most MSP sales reps will find this scenario challenging.  If they are a “power” rep, they are probably overwhelming their “finesse” counterpart.  If they are a “finesse” rep, they may always be trying to regain control of the sales conversation.

MSP Sales Strategy: “Mirroring” 

Mirroring is a sales skill has been taught for ages. When your prospect leans in, you lean in.  When they lean back, you lean back.  On the phone, this usually means matching your pace and tone to the pace and tone of your prospect.  (2021 update:  you can mirror your prospect in virtual sales meetings using both body language and tonality!)

Good MSP sales reps can mirror their prospects.  When necessary they can get excitable, and when it makes more sense to be soft spoken and straightforward, they can do that, too.

On some  sales calls, mirroring just isn’t helpful – it doesn’t give you your desired outcome.  Remember the earlier story about two power players?

Two power players in one game can lead to a lot of aggression.

Two finesse players can make for a lot of frustration.

Great MSP sales reps can do more than mirror – they can identify when mirroring isn’t moving the process along, and completely change the pace of the conversation.

Remember – if you can only play one way, you can only win one way.

Can you mix up your style to get more wins, more often?

There are several things your MSP sales rep can try to change the pace of a conversation.  Adjusting their storytelling, for example.

If  they normally would paint a picture for a prospect using a practiced and gregarious tale about a customer that was experiencing X and is now experiencing Y – that might work to bring a quiet, introverted prospect along for the ride.  If your prospect is equally gregarious, they will want to dominate the conversation; they won’t want to listen to the MSP sales rep or their well-practiced tale – they will want to tell a tale of their own.

Instead of launching into that story without breaks or pauses, have the MSP sales rep break the story into shorter pieces and then ask your prospect to comment or compare their experience to them in between the important highlights.  You want your MSP sales rep to share how they went from A (client was in trouble) to B (we made it amazing), but you also want them to hold your prospect’s attention the whole time.

Regular intentional pauses and invitations to contribute make for a slower and more deliberate conversation when both the MSP sales rep and the prospect want to run the show.

Here are some other things your MSP sales rep can try during sales prospecting calls to change up the pace:

  1.  Whenever the prospect finishes speaking, have the MSP sales rep silently count to five before they begin speaking.  This invites the prospect to expand on their thought if they wish (you’d be amazed at how silence can help you win more deals) and also allows some time for the MSP sales rep to consider their response.
  2.  Have your MSP sales rep use “Tell me more about that” and similar questions as often as they can.  Have them encourage introverted prospects to talk more instead of dominating the call.
  3.  If  your MSP sale rep is speaking with someone who dominates the conversation, coach them to speak slowly, evenly and quietly when it’s their turn to do so.
  4. Try to find the buttons that make introverts  “light up”!  Have your MSP sales rep ask the prospect questions about their family, their pets, or sports – if they can get them excited about anything at all, your MSP sales rep can harness that excitement as they present their sales pitch.

You’re not going to win them all, but practice changing up the pace of your sales conversations and you’ll soon find that you’re winning more often!  (Just like I did!)

surf practice

Surfing La Lancha in Riviera Nayarit

Want a little more help with your MSP sales strategy?

You can download our  outbound calling script here:

If you’re interested in outsourcing your MSP sales prospecting, and working with our amazing team of MSP sales reps, we’d love to chat with you!

Fill in this form, or call us at (844) 466-2624!

  • This field is for validation purposes and should be left unchanged.