The Checklist I Use to Choose My Mentors

Jenna Kutcher 

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February 12, 2020


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A mentor is someone who’s been in a similar place that you’re in and has created systems to grow to the next level, figured out how to master their mindset, has more business know-how and experience to share with you. A mentor can help you work around your biggest challenges, blocks and setbacks that you may currently be facing. I’m learning from my mentors now just as much as I did in the early days because there is ALWAYS more room to learn, grow, and understand something new about your biz or industry.

The options are endless for how to approach your own mentorship and growth, but there is some strategy in picking whose advice and teaching you want to follow. In fact, I think through and process 7 key elements before choosing to sign up for a mentor’s program or hire them on as my coach.

This is the framework I use to make these decisions, because they are big decisions! Whether you’re considering signing up for your first mastermind, hiring a one on one business or life coach, buying a digital course or anything in between, make sure you walk through these steps to be certain your money and time investment is the best move for where you’re at, and where you want to go.

What are your biggest gaps?

Think through the holes in your business — what’s really missing? What are your weaknesses, or where do you struggle? Is it planning your time well, figuring out how to scale to the next level? Do you have a hard time focusing on one thing at a time because there is so much happening at once? Is it challenging for you to relinquish control and let others support your business? We all have pain points, gaps and areas that we could work on, so looking to those first can help you determine who best could lead you to find solutions and fill those gaps.

Who do you see crushing it unapologetically in those areas that are tough for you to figure out? Who is your idol when it comes to the list of places you fall short? Who’s brain do you WISH you could pick on the things that are holding back the most?

You don’t want to hire a coach who’s exactly like you, who has the same strengths that you do because that could end up meaning they have similar or even exactly the same weaknesses as you. You want someone who will challenge you, push back, who can pinpoint what steps you need to take in order to make lasting change and improve your approaches or systems.

It doesn’t even necessarily need to be someone in your same industry, most of my mentors are in a similar industry but not in my niche, they have context and understanding but they aren’t on a parallel path to mine.

It’s tempting to pick the person who’s exactly like you but I’d challenge you to instead look at their characteristics, mainly their strong suits because if it aligns with the things you’re struggling with, there’s a good chance they’ll be able to walk you through the steps to getting you to where you want to be. You’ve got to be ready to be challenged if you really want to grow and if I know you, I know you’re up for a challenge.

Who has the same values as you?

There are two kinds of entrepreneurs, ones who are lifestyle based and then there are accomplishment based folks and I want to learn from people who share my same core values: family, faith, impact, community, creating meaning in my life and the lives of others.

If I were to work with someone who didn’t understand that or who encouraged me to just take on all the opportunities to make a million more dollars then their advice wouldn’t be aligned with my bigger vision. And that’s not what we’re looking for in a mentorship situation. You want to feel fully supported to be you and to follow through with your dreams according to what is most important to you, whether that’s freedom, time, money, clout, significance or anything else.

I’ve shared the room with both types of entrepreneurs at masterminds and group events and honestly, it makes me grasp onto my values even harder, like I said, not because wanting to accomplish more is a BAD thing, but because that’s just not where I’m at in this season of business.

While you want to look for someone whose strengths fire up and motivate your weaknesses, you also want to look for shared values in them because if they’re telling you how to become the best in your industry when you’d rather just become the best version of you, then there will be some pushback and you won’t feel fully supported with your overall vision.

Who is an open book?

There’s nothing that grinds my gears more than leaders who only offer up half of the equation and then leave it to you to figure out the rest. I can smell someone with a scarcity mindset from a million miles away and it definitely comes out when you’re an educator who believes there are still “secrets” to success.

When you’re considering a mentor, try to find out whether they’re willing to really show you the whole process because I can promise you, that’s not everyone’s style. Will they give you all the answers you need or will it take an up sell to another program or level of coaching to really get what you’re looking for?

Look, I am all about spending money to get information from people ahead of me in life or business, who know more than I do, but when it isn’t clear that their prerogative is just getting more and more money in exchange for small bites of the answers you need, that’s not a fair setup. I’ve joined masterminds before that has levels of membership where you pay more for the next level and I LOVED that because I knew that going in. The more I paid the more intimate of a setting I was in with the leader and the more one-on-one consulting I got, there’s nothing wrong with that but you want to make sure you understand the full ask before diving in.

Confident coaches hold nothing back. Why? Because they know that you need all the steps and in order for you to be successful you need to implement all the things. I teach a ton of my process for free on this podcast because I know it can help those ready to do the work, but I also realize that very few people will actually do all of the implementation it takes. I share a ton of my best stuff for free online but my courses or masterminds are the exact blueprint so you’re not left to piecemeal something together yourself. You’re exchanging money to get back time and that’s what a lot of mentorship is!

People who pay, pay attention. So when you invest in a coach, be prepared to do the work because a good one will be pushing you, challenging you, and guiding you through the legitimate steps it takes for you to reach the next level.

Paid mentorship makes a difference

There are tons of processes I COULD learn on my own. I mean, I’m self taught in practically everything I’m doing but I am willing to invest big time when it means shortening the amount of time it takes for me to learn something, implement it and see results.

Think about it: you are handing over a renewable resource (money) in exchange for a non-renewable resource, time. Now that was a hard pill for me to swallow when I didn’t have a lot in my bank account. That first $5,000 investment into learning HURT but it taught me that if I am ready to pay AND am confident that I can get myself results, it pays off and saves me so much time in the long run.

The experience of learning from or being in a room (or on the phone) with someone who has spent years figuring out more than I know is invaluable. I could also spend years to figure it out on my own too, or I could put down the money to pay them their rates if I trust it will help me learn and grow and be a worthy investment in order to learn the information they know that I don’t in a way shorter amount of time.

When I invest in learning, I have that added motivation to kick my butt into gear to implement and make the cost worth it by using what I learn and scaling or creating a new course or utilizing a mindset hack to be able to be more productive or successful with my business decisions.

Whether it’s an online course or a more formal mentorship, the main reason I’m signing up and handing over my credit card info is to shorten my learning curve and save myself the time and frustration on something complex that would take me years to learn and a lot of trial and failure. What is an actual system or process that would be really hard to Google to discover and learn? Find who teaches it really really well, gets results for themselves, their students or followers, and pay for that.

Look outside of your industry

The first mastermind I joined was Lewis Howes, he’s now like a brother to me, but I joined it because there was no one else like me in there. It was 90% health and fitness people and I wanted to see what was working in other industries and challenge myself to figure out how to apply their teachings to my world.

It was so fun to learn from people who were crushing the business world and to take what was working for them and creatively apply it to my industry, helping me blaze a trail that wasn’t like anyone else. I loved bringing my own gifts to the table without feeling fear of sharing, because we all were in different lanes serving different audiences.

It was awesome because I wasn’t competing with anyone else and was much more open to learning, sharing and discerning what could work for me. If you’re a little bit competitive by nature or aren’t sure you want to share your hard earned trial and error tricks of the trade, then joining something outside your industry could be especially beneficial for you in a mastermind or group coaching setting. You can pick up an even more diverse array of ideas and find out of the box ways to inject those into your own tasks and processes.

Who has a different perspective?

I want a different perspective, one that I wouldn’t normally find comes naturally to me. I want to learn from someone with a different childhood or career path or life experiences. I choose people to follow who think differently than I do and approach problems in ways I probably wouldn’t even consider. This is probably the top reason why I’ve chosen mainly men to lead me as my mentors, coaches, and mastermind leaders.

I don’t want to generalize but I think we can all admit that many men, especially in the business and marketing world, have this unapologetic way of being who they are without even considering they might be too much, not enough, selling too hard, talking about themselves too loudly, creating an uproar, pushing some people away. All these things that I can catch myself wondering about and double checking that I don’t step on anyone’s toes? They don’t even register for so many men and I LOVE that. I need that reminder to not overthink every single thing.

As women, we’re naturally nurturers, and I know for me, I can become very in tune with and even obsessed with what people might be thinking of how I act, speak, or portray myself and my business. A man generally don’t think twice and so it’s been important and really helpful for me to learn from them, to lean into that masculine energy.

I know this might sound odd and I know there are certainly powerful women who can speak their minds and truth without a second thought, but that was never my natural stance as a small town introvert who kind of stumbled into this big business world in a way I didn’t expect. It’s been a trip for me to take control of my voice and lean into the power and dominance that I can possess, and I think learning from men for me personally has truly been a big part of that.

For me, the heart stuff comes naturally, easy really. I’ve got the passion and the drive, but what I want when I have a mentor is to get the processes, the head side of things. I feel like a lot of women naturally lead with the heart stuff and I LOVE that, I am that way, so when I choose mentors, I want to learn and glean that head stuff that doesn’t come as naturally to me. Make sense?

I don’t want to imitate everyone else that’s ahead of me, I want to stay in my own lane, so getting a fresh set of eyes on my world and my work and being pushed out of my comfort zone helps me grow more than having someone agree with me.

I don’t want a perfect mentor

I don’t ever want to follow in the footsteps of someone who acts like life’s sunshine and roses and who portrays a message that they’ve never messed up or faced serious hardship.

I don’t have to agree with every decision my mentor has made or see that they have a perfect track record and have waltzed through this business world with ease. That’s like the LAST thing I want in a mentor, actually, because it’s just not realistic. We’ve all made mistakes; we’ve all fell on our faces. That’s being a human being and guess what, I’m an imperfect leader, too! Give me someone who can talk about those fails and missteps and then share where they’ve learned, how they’ve grown, and what they’re doing differently now.

I don’t know about you but I usually learn more when I mess up and so if someone can be honest to me about those seasons of entrepreneurship, perhaps I can learn from them and not make those same mistakes.

Imperfect leadership is real leadership. Because we all mess up but I want someone who cares enough to keep showing up. I respect that so much more than someone who only shows the perfect and the polish because that’s not life.

And y’all know exactly what I’m talking about — we’ve all seen the people who can spout advice and tips and knowledge for days and only show their highlight reel. That’s not the leadership for me. It’s just not real, and it sorta goes back to my values again. I value authenticity and imperfection because we ALL have that in us, so why not share the tough stuff that made us stronger and help others avoid the mess ups we’ve made along the way?

The Big Picture

Finding mentors who align with your vision and values and also challenge you to be better can be absolutely everything in growing your business and even making your life and mission feel more holistic in many ways. I hope that you feel like you have a blueprint or the questions to ask yourself to feel equipped to seek out a mentor, mastermind, or online course that helps to fill in your gaps, gives you new insight and perspective, and takes you to the next level.

We don’t have to do this business thing or this life thing alone. There are ample opportunities to come alongside like-minded people who WANT to help you, who want your dreams to come true. It just takes a little bit of digging to find out who fits your lifestyle and values and who can bring out the best in you so that you can achieve all that’s on your mind and heart, without the years and years of going it alone and struggling to get there. Let those who are just ahead of you guide you, coach you, and support you along the way. I can promise you that it’s worth the money and it’s been a blessing in my own life every time I’ve made the leap to take on a new mentor.



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  1. […] Find a Mentor that you can talk to a few days a week as you return to work . Share your thoughts and feelings and ask them to help you define boundaries around work and family and to pinpoint priorities in your life. Outer accountability and big picture view from a mentor is invaluable. I loved this checklist Jenna Kutcher uses to choose a mentor. […]


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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