
“Above all, it is essential you have an honest sense of your abilities…” - Seneca
Overconfidence often leads to overpromising and underdelivering, a definite recipe for disappointment.
True growth starts with an honest self-assessment. Know your strengths, recognize your limitations, and focus on steady improvement.
In sales, the best performers aren’t the ones who believe they can close every deal but those who understand their abilities and use that insight to build trust and deliver value.
Take time to reflect regularly, whether through tools like Mark Manson’s life assessments or a simple self-check.
The clearer your view of yourself, the stronger your foundation for success.
Actionable tips:
- Assess your skills regularly and reflect on recent sales calls or deals. Where did you fall short? What could you have done better? Keep track of recurring challenges.
- Ask a colleague or mentor to give you an honest review. Outside perspectives can highlight blind spots you might be missing.
- Don’t aim to close every deal; instead, focus on realistic, achievable targets that stretch your abilities without overwhelming you.
Remember you will die.
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Disclaimer:
The Sales Stoic draws inspiration from the profound wisdom of Stoicism as presented in Ryan Holiday's "The Daily Stoic." As avid readers & fans, we deeply respect the work of Ryan Holiday, and acknowledge the significant impact of Stoic philosophy on our own approach to sales and life.
While The Sales Stoic applies the core principles of Stoicism to the unique challenges and opportunities faced by salespeople, it is an original work with its own distinct voice and focus. We aim to build upon the timeless wisdom of Stoicism to empower sales professionals with practical guidance and actionable insights for success in their careers and personal lives.
Jack Frimston
Co-Founder at We Have a Meeting
Zac Thompson
Co-Founder at We Have a Meeting
It's March the bloody second. Excuse me. The days are rolling, rolling, rolling, rolling, rolling. I've got one for you. All right, mate. It's my favorite Stoic philosopher. Epic T is No, it's Seneca. Above all, it is necessary for a person to have a true self-estimate, but we commonly think we can do more than we really can. That's good.
Wow. That is really good. are you taking from that then? We commonly think we can do more than we really can. The first thing that springs to mind with that is we overestimate what we can do in a year and we underestimate what we can do in three or five or 10 years, which I think is a great one. You think, oh, this year I'm going to achieve X, Y and Z. Whereas there is, there's a study with Parkinson's law I was listening to that actually, so Parkinson's law is you
feel whatever time is set to do the task, you will feel that time to complete the task. It's typically what happens. So if you have one hour to complete it, you're doing one hour, but if you had five hours, you take five hours. And there was also a piece of data attached to it that whatever you predict, what your prediction of how long something will take, it will always take double that or triple that. But even if you try to predict that it will take double that or triple that,
you'll probably, you'll still be offered it'll be double that or triple that. So when you hear Elon Musk talking about, we're going to be in Mars in 10 years or next year, he's probably said it so ambitiously because he knows it will take longer. Yeah. But that's the thing is being like, I'm going to do that. So that's the first thing that I think of, is people overestimate what can be done, but then they also underestimate. like deep time is great. If you put the work in day in, day out, you'll see the results eventually. Everybody wants.
something now. I also think about this self-assessment. A lot of people would do things like this. If you listen to Modern Wisdom, The Satellite are giving a those kind of podcasts every year in December. Why are you smiling? Satellite are not giving a ****. Yeah, but I give a ****. The Satellite are giving a ****. They'll send out like a questionnaire that you can ask yourself questions every year to say,
Who am I? So the self assessment, have this self awareness. But I also think that you don't need to necessarily like wait until the start of the year. You can do these self assessments throughout the year. So who am I? What do I stand for? What are my beliefs? What is something that I'm afraid to admit? What am I, what, what my skill set is lacking? What can I improve? And it's about having those honest questions with yourself to kind of unearth some home truth. So what can't
What questions are what questions could sales people at home ask themselves that get them the realization that they might be looking for? Well, what are they trying to find? Maybe. No, no, that was the first question. Oh, I did that. They allowed my straight down the camera guys. We'll see at the BAFTAs. We'll see the BAFTAs. Yeah. First of all, what are you trying to find? Why am I here? What do I want to achieve? When do I want to achieve it by?
Who do I become if I do achieve it? Who do I become if I don't? Understanding all lanes, all eventualities, but certainly understanding the intrinsic. Why am I here? Why am I doing it? And what is it for? Why? One of the questions I ask new people to write down when they start is why do I do the things that I do? Which is just, it's a big open question, but you you're trying to get to that. Why?
You used to say that when you were hungover sometimes, embarrassed. Why do I do the things that I do? Yeah. Yes, I did. Also, I think really good for self-awareness is reaching out to a friend or a mentor. So it could be a sales leader. could be somebody that you admire in the sales space. It could be a friend who's done things ahead of you, whatever, but just getting a honest opinion on your blind spots.
is really, really interesting because you might go through it and think, you might go through life and think, I'm very generous. Then all of a sudden you ask, well, okay, what are my biggest flaws? I'm really trying to improve. You tell me your my biggest flaws and I'll just say, thank you. And you might say, well, listen, when we go out for dinner, I feel like I always pay. So I feel like you might be a bit tight. And I go, no, I'm so, I'm so generous. Like I always, if you call me, I spend my time and I do whatever.
But actually maybe there is a piece of that. So it's all about like finding out what your flaws are and what your weak spots are. And I think that's great in a sales environment. Yes, I do as well. Had a thought that came to me then in, sorry to make this about Jiu Jitsu again, but in Jiu Jitsu, when you first start out and you ask him for advice, often the advice you get is stop trying so hard, stop trying to be so strong in certain positions.
There's a thing that Bruce Lee said about martial arts. said, be like water. That was his belief. The water changes, doesn't it? Based on where it's put. If it's in the cup, it becomes the cup. If it's free flowing, it's free flowing. It becomes whatever it's doing. And that's the, that's the thing to think about in those moments. I think how do I be like water? Wow. I can imagine you in a cup. I want to talk to you about.
closing deals. So you've come to the right man. Typically most salespeople will have a conversion rate. If I sit down with X amount of people, I will close this, this amount of deals. say your conversion rate is one in five, you know, based on facts, yeah, you're going to be working for a better conversion rate. Yeah, you're working. That's what you're improving your skillset, but you know that you're probably not going to close four out of five of those deals. Yeah. Don't aim to close every single deal. Go into those and think, okay,
I know that four of them probably won't. What can I learn? How do I practice in these scenarios? How do I get better? What feedback can I get just before I let you go? Could I get some feedback? Do you mean I'm trying to learn? I'm always trying to learn and people love, love, love to keep dance with their father. Yeah. Um, they love to give their opinion on things. Don't they? People love to jump in and give their opinion. So asking somebody for their opinion is definitely a bit of a power move as well to get people to open up and give.
their truth. Yes. An audit of deals won and deals lost is an interesting exercise. If you can get older and say, look, can I maybe learn for next time why you decided not to go in and see what I can learn, but also asking people who did go with you, why they decide to go with us. Because the reasons that you've told yourself, if they really liked me, they'd love the sales approach might actually be.
You were the only one who could do this thing to be honest with you. So we just went with you and you even gave us a little bit of a discount. So, yeah. Oh, I thought it was because of me and my sparkling personality. It's great. It's great for feedback. I think that's great advice. Like the wins and the losses, the war room is an amazing place to be like where you dissect things and only when you dissect them can you learn. So if you're a salesperson listening to this, which I assume you are, go out to your customers, go out to those lost opportunities and say, why did I lose you?
and why did I win you? I've been Jack Frimston. I've been Zach Thompson. Remember you will die. Call that a kickflip?