How To Hire A Sales Coach

by Paul Castain on June 14, 2011

By way of confession, I used to hate “singers” back when I played in bands.

I hated the “singers” because there were many who didn’t have an ounce of talent, couldn’t sing worth a damn and when push came to shove they figured “Oh well, I guess I’ll sing!”

Fast forward a few decades and a lot less hair later, I find myself of a similar opinion of many “sales coaches” so I thought I’d share with you a few tips on how to select someone who can truly help you get to that next level!


How many years have they been a sales professional?

I don’t think that every sales coach needs a kazillion years of experience to be an effective coach but I do want to warn you that there are some people out there with little to no actual sales experience.

What was their track record as a sales rep?

Although I’ve always been a Top 20 performer, I don’t think you have to be the top dog in order to coach others to do it but I do believe you need to know a thing or two about performing consistently.

What is their level of experience in the areas where you wish to improve?

When I say “level of experience” I don’t mean just coaching others . . . I mean actual, hands on, “I did this and/or are doing this myself” type of experience.

Are they still involved in actual selling?

The business world is moving at the speed of light these days. What was relevant, appropriate and spot on a few years ago, might be outdated and antiquated today.

If you want sales coaching that is up to date and relevant . . . you’ll want to hire someone who is still actively in the trenches!

What products or services have they sold?

While good sales skills can apply to numerous industries, it’s important that this component aligns with what you wish to accomplish.

For example: If you’re selling a big ticket item, with a lengthy sales cycle, a sales coach who was involved in transactional type sales probably won’t be a good fit.

What types of things challenged them as a sales professional?

I don’t care how good someone claims to be, there has to be something, at some point, that challenged them.

Since part of your time with this coach will be spent discussing your challenges, wouldn’t it be interesting to see how they handled their own sales challenges?

As a bonus, it might be refreshing to know that they’re human enough to have struggled!

In what ways do they dedicate themselves to continued and never ending improvement?

I think its not only important that a coach is dedicated to continually improving, I think it’s the best way to lead by (or perhaps even coach by) example.

Bonus points if they believe enough in the coaching mindset that they have their own coach!

What prompted them to become a coach?

If you ever want to know how passionate someone is about their livelihood, ask them point blank what made them do what they do.

General Sales Philosophy

It’s critical that your philosophies align with those of your coach’s or you will quickly find yourself in a situation where you aren’t being true to yourself.

There are actually people out there coaching philosophies such as “buyers are liars” or approaches that are over the top aggressive . . . run away, very fast dude!

Additionally, you will need to know where they stand on traditional selling methods vs. the newer “Sales 2.0” methodologies.

Let me put this another way; there are some who feel the cold call is dead and believe generating business through Linkedin, Facebook, Twitter etc is the way to go while there are others who believe in “smiling and dialing”.

It’s my humble opinion that all these cool things can live quite nicely together and that it should never be an “either or” choice!

Note: Make every effort to ensure that your potential coach is “living” their sales philosophies and not just talking about them.

Example: A self proclaimed “Cold Calling Guru” wanted to sell me a cold calling training program for a team I was managing. She left me two messages (that were extremely weak) and then gave up.

Coaching Program

How long is each session?

How many times per month do we have sessions?

Do they offer before or after hours scheduling options?

What does a typical session look like?

Important: There are some coaches who believe in leading you on a path of self discovery by asking you questions and offering zero guidance. You need to decide if that’s good enough or if you would prefer someone who will offer you some gems of wisdom as well!

Are there action items and is there accountability?

No coaching session is complete without getting “the action verbs going” otherwise you have no opportunity to try your new distinctions on for size!

What happens between sessions and are you available to me during this time should I have questions?

Let’s face it, sometimes things come up that are too pressing to wait for the next session. Will your coach be available or are they only available when the meter is running?


This may sound like an obvious question to ask, but there are many coaches who don’t charge per session, they charge you upfront for the entire program.


Do you need to sign a contract and if so, how do you call it a day for any reason, at any time?

So there you have it, several tips to help you select the sales coach that’s right for you.

For a free handy/dandy PDF with all these tips, click here!

To visit Paul’s new coaching page . . . click here!

  • LA Palamar

    Fabulous criteria Paul.  What’s with the “Fee’s” heading…you going somewhere with that?  Just curious – ever the student, I am!

  • LA Palamar

    Oh…and btw, I always thought the lame, no-talent person was the one on the tambourine! haha (ps. am desparately hoping that wasn’t you in your Rock Star days!)

  • paulcastain

    Ha . . . you’re onto me :)

  • paulcastain

    I bet I could have written more there but it was just a reminder to ask about fees.

    I’m actually going to circle back now and add something.

    Thanks LA!

  • TJ

    Great post, Paul. I used to run into the same problem in theater…entirely too many people who said to themselves “so, this acting thing isn’t really going anywhere for me, I guess I’ll just direct…” If more people asked themselves and their peers the questions you provide here (replacing sales coach with director, of course), the world wouldn’t be quite so irritating.

    Keep up the awesome work!

  • Angie Carciofini

    Great blog, Paul. I wanted to share a quick story. Hired a sales coach several years ago for over $5k. He used to work for a world-reknown motivational speaker (who I love). But he decided it would be cool to call me at my house at 4:30am! Needless to say, the husband at the time didn’t really appreciate that. I fired him and got most of my money back (besides being totally creeped out). But it’s important to ask these questions that you’ve posted because you never know what you’re getting.

  • paulcastain

    I think I like your Director example better TJ . . .well stated!

    Thanks for stopping by!

  • paulcastain

    Yikes Angie . . . I’m creeped out just reading that!

    I’m telling you right now that if I ever have to call someone at 4:30 am, I’m charging more than $5k :)

    Seriously, there are some odd folks out there!

    Thanks for sharing that!

  • LA Palamar

    Ah, okey dokey – and same re: contracts? Just a reminder to generate a solid contract?  Have to tell you I’m doing some coaching with NO contract. Not very smart of me I think.  

  • Wim @ Sales Sells

    This post reminds me of the time when I was a junior account manager and we had weekly meetings with a sales coach. All he did was yell a bit and pump fists.

    Now don’t get me wrong, I like a good motivational session, but that guy got paid $300 for jumping around like a fool for an hour or so. I mean, I would have been happy to do that for just a drink :)


  • paulcastain

    Don’t get me started on these types Wim.

    This is my biggest issue with some (not all) “Motivational Speakers”. They put on a great show and at the end of the day, all they gave you was a Red Bull Adrenaline rush with the debilitating crash . . . because they were all fluff and no substance.

    And to your final point . . . I often do that and drive others to drink :)

    Thanks for stopping by Wim . . . I always appreciate your insight!

  • paulcastain

    You know it’s funny LA. I haven’t used contracts simply because I want to have to “sing for my supper” every time we have a session.

    Now having said that, I do think there are things that need to be put in writing especially confidentiality, the fact that people aren’t hiring us to offer psychological advice etc so I might implement this shortly.

    If I do, there will be no commitment in terms of my clients having to do x amount of sessions. It just isn’t my style.

    We will have to compare notes on this one LA for sure!

  • Adam

    Paul since reading some of you previous comments on here, LinkedIn, etc. I’ve been more aware of these self-appointed “gurus” and “experts” out there, who offer little or no relative value. Thanks for sharing a plan that helps weed through the mud.

    I notice in your Playbook group many people who have great advice and approaches to sales who don’t anoint themselves leaders but I value their opinion more than many of the self-appointed types.

  • paulcastain

    I’m happy to hear that you made that observation Adam.

    The people who you just described are the true “gurus” because you have in essence “bought” them without ever having been “sold”.

    Chances are you have probably shared their information with others and given them some Positive Word of Mouth Advertising in your own network.

    But most importantly Adam, even if you didn’t say great things about them, they are giving in ways that increases everyone’s online real estate :)

    Thanks for stopping by Adam and also for being one of the people who continually gives to our Linkedin group!

    Much respect and appreciation! 

  • Don Romine

    We used to say they had LSD…

    Lead Singer Disease 

    Great post Paul!

  • paulcastain

    That’s freakin awesome Don “LSD” 

    Rock on!

  • Daniel Wood

    If you are too coach you need to know the subject.
    You don’t necessarily have to have been a good sales personl. Selling and teaching selling are two different things.
    But you need to know the subject.

    Just look at Tony Larussa, he was never a star baseball player but he is one of the best managers in baseball.
    He knows the sport, he knows everything there is to know and he is a great teacher.

    That is what it takes in my opinion.

  • paulcastain

    I agree Daniel and you’re right about the sports world filled with great examples like the ones you provided!

    I remember as a young guitar player studying with some teachers who were incredible players but fell short when it came time to transfer those skills!

    Thank you for stopping by Daniel!

Previous post:

Next post: