Lessons from my mentor, Chris Dale – Sales Management Powerhouse

Everyone stands on the shoulders of the people around them that have shared their wisdom, guidance, and care as we develop.

I’m no different, and neither is my mentor, Chris Dale, a man who has built and scaled dozens of successful sales teams in the IT staffing world. In this article, I’m going to share the principles and tactics I learned from Chris about

    •    How to quickly identify the intangibles in a sales hire
    •    A trick to find out if your sales candidate is motivated or not
    •    The difference between motivation and inspiration and why you should never motivate people
    •    How to define and understand your job as a sales manager
    •    When to part ways with a struggling salesperson
    •    Perseverance and mindset over matter
    •    How to get out of a personal slump

Let’s dig right in.

How to quickly identify the intangibles in a sales hire – Personality & Presence

The best sales hires don’t necessarily have a long track record of success. 

In fact, only looking for people with a track record of success is going to cost you more money and make you miss out on some huge opportunities to take a strong, motivated person and turn them into a key player on your team—someone who becomes skilled and dedicated to you in the long haul. By hiring someone inexperienced, you can also take advantage of a clean slate—an unformed lump of clay that you can lead and mold into exactly the kind of player you’re looking for. 

When you hire an experienced salesperson, they will inevitably bring with them habits and mental positions that may or may not align with what you need. Often, their already developed habits and positions are the reason why experienced sales people command a higher value in the market, but believe me when I tell you, and when Chris Dale tells you, that if you know the secret to making great entry level sales hires, you know the secret to building and scaling massively successful sales teams.

So how do you make that perfect, entry-level sales hire? You look for the winning formula that is a combination of personality and presence. 

This is something you feel with your heart and your gut more than something you can identify logically with your brain, although there are some questions that will help you decide if the interviewee has those intangible qualities of personality and presence. 

Each person’s personality is something that is built over their entire life up to the point you meet them. It comes from a combination of genetics, their childhood, their experiences, and their beliefs. If a person has already spent 20-30 years building their personality, how do you expect to change that in the time you have for training? It’s impossible! 

I don’t care how much you like a person, if their personality isn’t right—if they just don’t naturally connect with people on a personal level—then they will never be the rockstar seller you’re looking for. 

Don’t take me wrong here, people can be molded to some degree. Think of the personality as a rough metal blade just cooled and hardened out of a forge. If it’s already shaped in a way that fits the job—and with sales that job is connecting with people—then you can sharpen it up and smooth the rough edges to make a useful cutting tool. With that image, if you need a blade and the rough metal—the personality—of the candidate is the shape of an anchor, you’ll never sharpen that into the right shape for the job.

A person’s presence is how they project their personality into a room and how they listen. The best salespeople not only have a friendly personality that connects quickly with people, they have a presence you can feel that makes you want to connect with them. 

Again, this is an intangible quality that doesn’t show up on a resume or a test score—this is something you can sense intuitively. We all know in our subconscious mind if someone is really listening to what we’re saying, and we get the best intuitive connection with those people that listen deep enough to really understand.

Here are some questions to help you identify if a candidate for a sales position has the winning combination of personality and presence:

  • Can they carry on a conversation? 
  • Can they tell a good story? 
  • Are they good listeners? 
  • Are they just flat-out enjoyable to spend 15 minutes with?

If you’re uneasy or hesitant answering any of the above questions, you should be uneasy or hesitant about hiring that salesperson.

A trick to find out if your sales candidate is motivated or not – Free Time Analysis

The winning combination of personality and presence is a requirement for a successful sales hire, but that’s not all you should look for. 

In fact, my biggest mistakes in sales hires in the past were people who had incredible personality and presence—they instantly connected with me and made me love them—but I found out later that they had no motivation. 

You cannot motivate a person. 

Go back and read that sentence again. 

This is something I’ve written about before, and I talk about all the time because it’s so darned important, and it’s such a stumbling block for most business owners and sales leaders. 

We know we’re pumped up as leaders, we know we have extra energy that we can spread around, we know we’re incredible cheerleaders—so why can’t we motivate people? 

The answer is simple—no one works for free. In the sales world, the money you make is usually directly connected to your level of energy, motivation, and success. If someone isn’t motivated to go out and make money, then they’ll never be motivated to go out and sell, and there’s no amount of cajoling, encouraging, specialized training, or red-faced yelling you can do to really instill motivation. 

You might have felt like you motivated some people in an exciting meeting before, but do you expect that motivational energy to stick with those people through the long week, the rejections, the letdowns, and the constant daily grind? 

I don’t care if you’re a lightning bolt, you don’t have the energy to motivate people in the long term if they don’t already have it within themselves.

So, since you can’t motivate people, you have to hire people that are already motivated. You need someone who’s already naturally hungry, and who is going to stay that way. 

Now, you may feel someone is motivated because they need to pay off some debt or they’ve just had a child, but will they still be motivated once they’ve gotten a couple of big commission checks? Will they check out in the 4th quarter when their quota is reached? 

Long-term motivation is what we’re looking for, and to find it, we have to dig back into the past and analyze a person’s free time. People don’t fundamentally change all that much in their lives, and let’s face it, some people are great salespeople and some aren’t, which is fine because it takes all kinds. 

When interviewing a potential sales hire, especially an entry-level hire, the future rockstars are the ones who were active in their free time in school or college. They were self-starters who took on extra work or activities—maybe because they wanted money or recognition or whatever, it doesn’t matter. 

What matters is that these people have an underlying energy that propels them into the world to do things. Some people have it, many people don’t. We’re looking for those internally motivated people with friendly personalities and presence that we can then train in the sales processes that we know work.

““You can help teach people to be genuine. Part of that and is in yourself being genuine and being vulnerable. I think if you set the example as the sales manager that you’re humble, you’re always learning yourself, you’re showing that you’ve got coaches and you’ve got mentors, I think that sets the tone for the team that they can be vulnerable and lead and help shape that likability factor.””


Here are some questions to help you identify if a candidate for a sales position has real, long-term, internal motivation:

  • What did they do on their summers off and after school in high school? If they worked, played sports, or were otherwise involved in things that’s a good sign. Generally, people who had to work because their families were poor are motivated to do better than that situation, but people who came from wealthier families who did not have to work can be motivated as well, which usually shows up as some voluntary activity or projects during free time.
  • What did they do in college besides school work? If they only did school work, was it above and beyond in any way? (double major in challenging fields, for example)
  • Why did they do those things in their free tme? Just having done them is a good sign of motivation, but if they can articulate their reasoning then that can give you some great insight.

Remember, it’s not your job to motivate, it’s your job to inspire.

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How to define and understand your job as a sales manager – 3 Responsibilities

We’ve already covered in detail your first job as a sales manager, which is to identify and hire people with the intangible qualities that make a great salesperson, but what’s a sales manager to do in the bulk of their day-to-day time? According to my mentor, Chris Dale, and according to my subsequent experience, it all boils down to three basic things:
    1.    Set crystal clear expectations
    2.    Teach and train people in how to hit those expectations
    3.    Hold them accountable

Everything else in a sales manager’s role follows on one of these three basic things. 

The expectations you set should be reachable so that people don’t become discouraged, but they should also be challenging enough to push the team to feel that strong sense of accomplishment that comes after overcoming an obstacle. 

You know you’ve set crystal clear expectations when each person on your team is able to clearly and quickly state their expected goals if you ask them, in words that you would use, without memorizing anything. If they struggle to define the specific expectations well, or if they ramble on with multiple objectives that aren’t the primary expectation, you should spend more time simplifying and communicating your expectations and the reasons behind them.

Now that your team understands what’s expected of them, it’s time to teach and train them in how to achieve those goals. 

You should have a defined and proven process for selling to share, otherwise, your salespeople are just wandering in the dark. 

A note of caution here though, avoid paralysis by analysis, there’s nothing worse than a sales team that sits around re-mapping territories, trying to find the single best account to attack or other over-planning distractions. 

Once you have a process for attacking the target, it’s time to get out there and get to work, pick up the phone and make some calls. 

One of the best ways to teach and train your people is by role-playing. Role-playing gives each person a tight, instant feedback loop that naturally conditions their brain to trigger actions and reactions that are appropriate. 

You’ll never know that something you say doesn’t make sense, or that your body language when you walk in the room gives off a lack of confidence, unless someone tells you. 

Role-playing is completely underutilized by salespeople today because it’s uncomfortable and embarrassing and awkward. Get over it. Set the scenarios, play the roles, and be real. 

There’s a prevalent mood in modern society to be soft, and that seeps into the business world like a plague. Forget it, be direct and honest with each other with your feedback. If something a salesperson is doing isn’t good, who is it going to help if you don’t address that, or worse, if you sugar coat your feedback so that it’s not entirely direct, honest, and clear. 

I’m not saying be mean and cut people down—I’m saying be 100% honest. Set expectations before you start role-playing that everyone is going to speak their mind and give feedback that, while critical, is meant only to help.

A note of caution and a nugget of wisdom here—do not take your feedback giving lightly!

Chris told me a story of a girl he’d complimented on her effort during a role-playing session early in her career, and how she kept his email to refer back to when things got hard throughout a long and successful career. 

As leaders, remember that there is a huge responsibility on us not only to point out faults in an honest and direct way, but also to build up people whenever you see them do something well. 

The feedback you’re spitting out to different people every day has a huge impact on the life of each individual that you’re dealing with. Again, this doesn’t mean to go soft on your feedback, but it does mean two things:

  1. Be honest and direct without insulting the person. Talk about their actions, not about them as an entity.
  2. Never, never, never miss an opportunity to praise something done well. This is just as important if not more important in training than giving feedback for fixing problems.

Finally, as a sales manager it is your job to be a “professional reminder.” Although you have motivated and trained people on your team, the ultimate responsibility to keep everyone moving in the right direction is you. 

Get involved in your team’s highest priority work and help push it forward. When someone is in a slump, talk through it with them and give them clear and actionable advice on making sure all their activity is the highest priority activity it can be.

One more tip–simplify. Try to keep things as simple as possible, because what we do in the sales industry is not that complicated. You have either your goods, your services, or whatever you’re trying to provide to your customers, and there are people out there who either need it or they don’t. 

In the world we live in today, there are so many choices to be had. Decisions come down to who do they trust and who do they like the most. If we can keep things simple, we can have the competitive edge.

When to part ways with a struggling salesperson

This is one of the hardest part’s of a sales manager’s life—firing a struggling employee. 

You always have this feeling that the person is going to blow up at you, and the conversation will be awkward, which is certainly a possibility. 

More often than not, however, the person you let go knows full well that they’re not in the right place, and they’re miserable. Often parting ways professionally is the best thing for everyone. But there’s always the hard question…

“When do I know when I’ve done enough and it’s time to part ways with a struggling salesperson?”

The answer comes down to these three questions you need to ask yourself, that align with your three responsibilities as a sales manager:

  1. Have I made it clear their top 3 responsibilities and can they clearly state that for me?
  2. Have I taught this person how to execute on the gameplan we’ve agreed upon?
  3. Have I followed up regularly to make sure their activities are the right activities with the right targets? 

If I can look myself in the mirror and answer those three questions knowing I’ve done enough, then it’s time to part ways. If I’m not sure about any of those questions, I’m going to put the work in to know I’ve done all that I can without wasting both of our time.

Personal Perseverance and Mindset

Everything we discussed already I learned directly from Chris, and I hope you’ve learned something from this. 

Beyond just the job of a sales manager, however, Chris taught me a lot about personal perseverance and mindset over matter. I know this is a big topic in the sales and success world, but it deserves another mention here. 

What you think you can do and how you think and tell yourself things are going to be very often become reality. 

Just last year, Chris was diagnosed with congestive heart failure, and given more than one “death sentence” from the doctor. To which he replied, “That’s not how it’s going to go, I’m going to get better.”

Today he’s doing better than ever and loving life—a testament to positive thinking and empowering the people around you.

Have you used these lessons in your sales management experience, or would you like to? Let me know in the comments below and jump on the email list to get more lessons like these in your inbox once per week.

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