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3 Common Statements Entrepreneurs Say During a Coach/Mentor Session

Being vulnerable creates a better Coach/Mentor relationship

When working with coaching clients I tend to use the personal trainer analogy as to how I approach working with them…my job (as your coach/mentor) is to push you and challenge you into doing work that’s hard and outside your comfort zone.

By: Heather Wentler – StartingBlock Madison Entrepreneur in Residence

Read Time: 6 minutes

Having a business coach or mentor is what levels you up along your entrepreneurial journey. When working with coaching clients I tend to use the personal trainer analogy as to how I approach working with them. Most people want to feel good about their bodies when they look in the mirror, and it’s important that they get to determine what “feel good” looks like. Your gym trainer is going to make you use muscles you didn’t know you had and you’re going to feel the change before you see the change in the mirror. When you hire a coach or work with mentor(s), their job is to push you and challenge you into doing work that’s hard and outside your comfort zone. Here are three myths I hear a lot when I first start working with clients.

  1. No one knows what I’m going through

While part of this is true, because everyone has a different lived experience, if you have been an entrepreneur in any sector, everyone has gone through a version of what you’re going through right now.

What we don’t do enough of is talk about it. We don’t like to talk about our challenges, failures, or being vulnerable to people. These stories aren’t buzz-worthy in the news, and it’s like the pile of stuff we throw in closets when company comes over, we don’t want anyone to see it. Once a client and I start talking about their experience as an entrepreneur, the challenges they’re facing and the obstacles that have got them where they are today, we can start making the experience feel like something you’re not in all alone and that others have gone through it. Many times I’m also able to connect you with others who are willing to talk about how they overcame similar problems and a peer relationship can form.

Entrepreneurship, leadership, management within ventures, and every employee role can feel isolating and lonely at times. But a good coach or mentor is there to help uncover the roots of why you’re feeling this way and support you in creating plans to move you out of these spaces and also connect you with others to support your development and confidence.

  1. I’ve read the books and articles, so why isn’t this working?

I hope I’m not bursting anyone’s bubble when I say this, but you’re not Elon Musk, or Mark Zuckerburg, or Sara Blakely, or Oprah. What I mean by this is that all of those articles that say “5 things Mark Cuban does before 5 AM” doesn’t mean it’s going to work for you.

You are YOU and that’s pretty damn awesome! What’s usually missing from those top anything lists is the personal lived experience, connections, and failures these people have to be where they’re at.

I actually loathe articles that have top anything lists…BUT even I use these clickbait titles sometimes because they’re a great marketing tool and get people’s attention. Why? Because we’re all looking for a magic bullet or “do this and you’ll see results” scenarios.

I’m going to tell you a secret…No one has a secret potion that if you drink you’ll instantly be successful. No one does 5 things every day and gets to have a 4 hour work week. What everyone does do to become successful is a lot of unseen work and sacrifices in a lot of other areas in their lives to reach the level of success they want. It takes years sometimes to get to where they want to be. And many times they have to adapt or do things they never thought they’d be doing within their careers to be able to continue to grow and reach success.

In case you need to hear it, I grant you permission to not get up at 5 AM, not do active journaling before 7 AM, not get in a grueling cardio workout before breakfast, and you don’t need to send a minimum of 100 emails a day, or any of the other things that Entrepreneur and Forbes publications tell you is required to be successful. I also give you permission to figure out what works best for you for workflow, check your emails as much as you feel comfortable with, never stop learning and adapting rules and routines as things change, and set boundaries around work and personal life.

  1. I only want to talk about this one specific thing

When I give feedback I always start with “You’re welcome to take my feedback with a grain of salt or reject it. My feedback is based on the information you tell me and you know your venture better than I ever am going to”. I don’t require people to complete tasks or milestones before we meet again, and I let them set the expectations and guide the conversation.

I recently was meeting an entrepreneur who said “I’m very coachable but I don’t take feedback on how to change well”. I had to pause for a second and then asked them to clarify that because part of coaching is hearing different ideas and strategies to try and find new ways to approach a problem you’re encountering. I also like to use stories from my own or other people I’ve worked with (never revealing their names/ventures) to try and relate or highlight what was done to make change happen. They said they didn’t want to hear those either. While part of me was thinking this relationship isn’t going to work for either of us I started asking more questions to try and get to the root of why they said these things.

What came out was that they were feeling very overwhelmed, burned out, and like a failure because they kept spinning and not gaining traction. They had tried many new ideas and none of them had worked and “I don’t have time to try I need results”. There were also other things adding into their state of feeling overwhelmed. My feedback on ways to change things felt like me adding on to their to do list vs. them feeling like they had already checked this off their list. Once I knew this we could take a few steps back and have a better conversation as to how we could best communicate with each other going forward and how I can better support them.

In general, you’re not always going to agree with your coach/mentor. They should be 100% ok with that, and willing to hear the feedback as to why you don’t agree with them and do their best to adjust their approach, context, or further explain why they said certain things. They should also understand that there are many stressors impacting your daily life. Sometimes when someone becomes defensive or not open to feedback it’s not because of anything the coach/mentor said but, it may be the breaking point for you.

Your job, as the person receiving the coaching, is to call out when things aren’t working for you and also giving your coach/mentor all of the relevant information they need. If someone asks you “How are you doing?” don’t say the typical “Fine” and tell us what’s actually going on. We can’t help unless we know how you want us to help and have all of the context to give our best. Want to talk more about working with a coach/mentor and how to create a successful coach/mentor + entrepreneur relationship? Or to talk about anything else related to running and working for a startup venture? Schedule an Office Hour with me.


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