Peak Performance Selling

The Mental Game of Prospecting & Leadership

Episode Summary

Prospecting and cold outreach is challenging, especially to sustain successfully without burning out. Jason Bay, CPO @ Blissful Prospecting works with B2B sales teams to master the art of effective prospecting. Listen in on how he works with leaders to get buy in from their teams, how to prospect effectively and the mental game to play to make it easy.

Episode Notes

Jason Bay is Chief Prospecting Officer at Blissful Prospecting. He helps reps and sales teams who love landing big meetings with prospects—but hate not getting responses to their cold emails or feeling confident making cold calls.


Cold outreach is such a scary things for reps to do.  Getting your team bought-in to cold outreach.  So much of that comes down to your mindset, so you can feel confident in your outreach, knowing you’re actually adding value and reaching quality prospective buyers. 

Prospecting is a hard thing to get over regardless of where you’re at in your sales career. 

How did you get to this point? And how do we help people get in the right mindset to be comfortable prospecting? 



Emails you don’t know where it goes or what happens. 

Cold calling 95% of the time people don’t pick up! 

Started sales journey selling house painting services door to door. 

18 - college - studying to become forensic scientist- lots of CSI

Had a friend that intro’ed him to College Painting Business

SURPRISE → you’re going door to door

I didn’t know what sales was

I ended up being really good at it but never struggled, I was really nervous to go door to door, I had never painted a house before.

Was in hometown of Brookings OR had 120-130 people to sign up for estimates first weekend 

Closed $10K in paint jobs first week and found out I LOVE sales

Got into sales by accident, but didn’t really struggle with it much at first. 

Where I struggled was at teaching people how to do it



As you grew into teaching people about sales, where did you find early sellers struggled the most?



Becoming a manager and many of these college students had no interest in actually being in sales. Many used this as an internship to get experience for a future job.

The toughest thing at first; Let’s talk about What Sales Is & What it isn't?

The fear of being pushy, talking a lot, making them uncomfortable


You have to convince the new sellers, just because someone doesn’t SEE they need something, doesn’t mean if presented different evidence, they may realize there’s a problem.

What’s the difference between pointing out a problem and HELPING PEOPLE 

  1. trying to be a super hard closer?

We are going to tell this person they don’t need our service and if they want to buy, that’s on them!

Companies with fresh BDRs & SDRs that think it sounds so cool being in sales

Let’s talk about what sales is and understand the mental game where you get hung up, because you feel like you’re doing something dirty. 


JB: That story you tell yourself is so important to sustaining in sales over the long-term. Where do managers struggle to get their reps to prospect?



Anytime you’re teaching/coaching someone to do something, your blind spots will be those things that come naturally to you. 

If you were good at building pipeline and prospecting, you’re probably not going to focus on that. 

  1. Getting managers to see their biggest strengths will probably be their biggest weaknesses across the team
  2. SDR managers who don’t know how to cold call, they are trying to get their team to buy into something that they don’t know how to do

The player/coach thing doesn’t work out too well. Most managers don’t even have time to coach. Make cold calls with your team. 

Get on a Zoom call and make cold calls with the team to train them!

As a manager, you don’t need to be the best prospector on your team, but you need to be proficient at the job. 

The best thing I did between my first and second year - was sometimes me going 0/3, then 2nd year I went ahead to CRUSH it. If I don’t show them success, they won’t believe it can work. I am going to show them success so they see what it looks like and they believe it!


JB: It is easy for managers to get so far away from the job and many managers struggle to allocate their time to coaching reps. Getting reps to have that power of belief is so critical. 


How do you balance showing someone what to do and being a super rep vs. letting the leash out for them?



Confidence is 80% of the game in sales, especially prospecting. If the prospect doesn’t hear the conviction and belief. That conviction that I can help you and if nothing else I know you can spend 20-30 minutes with me and it’ll be worth the prospect's time. 

Some people may say you rob them of their learning, but they need to see success.

Coaching is not an all or nothing thing. 

Why? What? How?

Why- theory, psychology behind it, old way vs. new way -- Maybe with your intro we need the prospect talking within the first 10-15 seconds because the sooner they are engaged, the better

WHAT? Use a permission based contract early on

HOW? Maybe doing a couple quick examples for them.  Sales can be compartmentalized. Could look at Starting a demo call, set an agenda and purpose. Now you can be looking for the part that we’ve identified and they can be ready for it


You can still do stuff for people and make it a coaching moment, but you’ve got to give them the WHY, WHAT & HOW! 

Salespeople are incredibly resourceful, if you never tell them why it works, you are robbing the system from any possible improvement. 

Sometimes too many people focused on the WHY - but no HOW to actually do it. 

Individualized for the rep and doesn't have to be all or nothing!


JB: Without bringing the WHY to the coaching and selling, it gets really boring after awhile. 



Personal trainer - more like a coach - I show you what it looks like then ask you to correct your own form by looking in the mirror. It’s pretty common sense when we start talking about it. 

We make it a lot more complicated than it actually needs to be. 

Managers probably weren’t taught how to teach or how to coach. 


JB: How do you coach or train reps to bounce back after the tough days or weeks?




What can you control? What can’t you control?

Personal Trainer example- how do you wrap up your self-esteem in the things you can drive success towards and find victories in. 

You want your self-esteem wrapped more around doing the things you said you were going to do vs. looking at the skill. 

Focus on the habits. If I do the right things the result will happen at some point

Dis-attach yourself from the result and the outcome

Psychology technique- Pattern Interruption- hear about it a lot in sales, but this is to do it to yourself

4 Parts - Upper Left - IDENTIFY THE PATTERN (I make cold calls, don’t set meetings and get bummed) Upper Right - PINPOINT THE TRIGGER (get really specific here, block of cold calls for an hour, bummed out. What environment am I in? What do you feel physically? The story you tell yourself?)  DERAIL AND REPLACE (How I feel is that I’m not good at this thing.  Diffusion is not to ignore it, and acknowledge it) PRACTICE & REPEAT - make it a habit!

John Jones- UFC/MMA - was lightweight champion - was fighting at 205lbs now going to 265lbs, HUGE jump. Wants to fight Francis Nganno - this guy is a human Hulk.  Ask John, Are you scared?  YES I AM scared, I am comfortable with the worst case scenario he, might knock me out or break my jaw.  

Take the worst case scenario and become really comfortable with it. Then you can derail the negative talk, have some RADICAL Acceptance for the worst case scenario. 

Maybe make the calls from outside the office, do it somewhere else, shake it up and do something totally different. 


What am I telling myself when I’m struggling?


JB: How do you manage Mental health in sales?



Atomic Habits- James Clear

The #1 thing you can do is change your identity and who you are up stairs mentally

Smoking cigarettes- someone offers you a cigarette - “I’m trying to quit” = that story is you are a smoker vs. “I don’t smoke” changes your identity

You have to realize how I feel about stuff is important and how you think about it and identify as a mentally healthy person

Studies of Blue Zones - where people live to 90-100+ years. One of the biggest things is they have a strong community with a sense of purpose! Longevity studies point to the mental part of the community is what helps them live longer

You are taking YEARS off your life if you don’t take care of your mental health

In sales, the only thing you can control is the inputs. 

At the end of the day the prospect is the one that gets to decide if they take the meeting or make the purchase

Mental health needs to be part of your identity, 

Jim Rohn- You are the product of the 5 people you spend the most time with we are chameleons 

Find people talking about mental health in sales


JB: Mental health in sales is a struggle and challenge. I’ve been going to see my therapist more to give me space to talk out loud about my own shit. The downward spiral is the easy place to be and it takes some real effort to break out of that.



If you don’t prioritize something in your life, and prioritize people that prioritize the same things you do, it’s going to be a struggle. 

Crabs in a bucket- when one crab is getting close to getting out of the bucket the other crabs pull it down. 

The one hack, if you want to make something more of a priority, surround yourself with more people that value that same thing. It makes it easy. 

Biggest key with habit building, lots of people talk about discipline. 

Discipline to me isn’t about making the “right” choice in the moment, it’s about REMOVING CHOICES and making it HARD TO DO THE WRONG THING.

If you can remove the bad decisions so they aren’t easy because you only have so much will power

How do I make it easy to do the right thing? How do I orchestrate my life and my workflow so doing the right thing is easier than doing the hard thing. 


JB: This is the stuff I wasn’t trained on in school and making it an identity of the type of person I am and clear your environment of the things you want to avoid, it makes it so much easier!

Top traits and characteristics in sales leaders you’ve worked with?



Empathy, not just talking about it but really sit in their reps feelings and take a chance to empathize

Empathy is #1 skill in sales and leadership!

Empathy is a skill that you can work on and build. I didn’t have a lot of it until I started going to therapy


JB: It’s very hard to empathize with anyone else if you hadn’t dug into your own stuff. 

Do you Love winning or hate losing more?



I love winning! I can get over losing pretty quickly, but making that $$, getting some cheddar.  I love that!


JB: What does success mean to you?



I think it’s totally different to everyone with their own definition of success

It starts with understanding. What do I value in life?

Work/life balance. I don't’ want to work more than ~40 hours a week

Can we make the income that we want and do something that I enjoy and spend quality time with my family wife and dog, parents, brother, sister, in-laws. 

Not about the hustle porn

I love what I do for work



JB: Joseph Campbell: “Follow Your Bliss”

Blissful Prospecting


Follow Jason Bay on LinkedIn