We interviewed business coach Peter Shepherd

We interviewed business coach Peter Shepherd

Recently, Jess had the awesome opportunity to interview business coach Peter Shepherd, the owner of Human Periscope and head coach of altMBA. Peter coaches people from all industries - his clients have performed on Broadway, written best-selling books and been nominated for numerous awards. Jess and Peter had a fantastic chat and covered all sorts of ground, including life philosophies, the importance of reframing thinking, favourite authors, journaling tips, strategies for self-improvement and heaps more.

Please note that this interview has been condensed & edited for clarity. Enjoy!

Jess: Alright, I’m going to kick off with a difficult question - if you had to follow the philosophy of one book, which book would you choose?

Peter Shepherd: I’m glad I got this question up front so that I have time to think about it! [laughs]. I think I’ll have to go with The Art of Possibility by Rosamund Stone Zander and Benjamin Zander. The reason why is that there are at least four key concepts from that book that I remember really well and think about at least one a week - they could be books of their own. The first concept is the idea of ‘rule number six’, which is about not taking yourself too seriously. It’s something that I try and remember every day. 

The second concept is about ‘giving yourself an A’. There’s this brilliant story in the book about taking a class of students at the start of semester, and saying ‘what if you wrote yourself a letter now on why you got an A at the end of this class?’. As humans, we strive for something at the end of the road - an A grade, a tick, a start sticker - whatever affirmation it may be. So what if you read this letter, and went ahead, followed your own advice, and got the A? I love that concept.

The next concept is centred around the idea that everything is invented. This concept plays into so much of the work I do, and what I’ve observed in others during my coaching. The stories we tell ourselves are often just invented based on our past experiences. It’s a really interesting, juicy concept. 

Finally, the fourth concept is called ‘how fascinating’. It’s a phrase that’s designed to be used when things go wrong. What if, instead of panicking and throwing yourself into a state of anxiety you simply thought ‘how fascinating’ when things go wrong. Kick start your mindset from a place of fascination and curiosity. I do this often, especially when things get hard or chaotic - but I also think it when things go well.

And that’s why I would pick this book to be my philosophy!

Jess: That's an awesome choice. I’ve read it as well, it’s a brilliant book. I remember reading it and thinking about the ‘number six’ philosophy - I was trying to work out how I could keep that lesson at the forefront of my mind. I often wear rings on my fingers that represent important things to me - maybe I should designate a ‘number six’ ring. What do you do to keep these lessons at the forefront of your mind?

Peter Shepherd: Love this question. I have a white board that sits on my desk - I'm obsessed with white boarding. When I feel inspired, I put certain things on the whiteboard. One of the phrases that has been there for three years - I think it's probably the longest lasting phrase on my whiteboard - is ‘don't forget rule number six’. I feel like the way I trick myself into my memory is I stare at it almost every day. There was a period of time when I also had the words ‘rule number six’ as the screensaver on my iPhone. That was another way I tried to hack it. I literally try and put these reminders in front of my eyes as much as possible. 

Jess: That makes sense! Can I ask what else is on Peter Shepherd's whiteboard?

Peter Shepherd: Sure. I also have a note on there that just says, ‘it's not about you’. Often, we think that everything in the world is a reflection of us, a result of us, or a message to us - but really, what’s happening in the world is rarely about you. So I find that reminder really helpful. ‘It’s not about you’. I also have the Simon Sinek Circle on there, which is about finding your ideal purpose, process and result. It’s designed to help people see things more clearly, so that they can change their corner of the world. 

Jess: Awesome. That's really cool. I like getting a little window into the things that people are holding up as a priority. 

Peter Shepherd: It's so interesting because when I have people over, sometimes I look at my whiteboard and wonder, do I need to rub some of this off? [laughs].

Jess: Yeah, it's kind of a weird tension, especially when it's people you don't know that well, who haven't gotten used to your weirdness. It’s like, ‘hi, nice to meet you, yes I have framed inspirational quotes all over my house’ [laughs]. 

So, you like to journal - how do you incorporate the principles that you follow and want to live by into your journaling practice? 

Peter Shepherd: Sometimes I’ll just ask myself directly in my journal, for example, ‘how have I been going with ‘rule number six’ this week?’. This serves as a reminder for myself, and shows me where there’s room for improvement. I ask myself questions all the time when I’m journaling. I write the question at the top of the page, and then do my best to answer it. The hard part is that by asking myself these questions, I’m making things about me - I'm getting caught in the stories I'm telling myself. So I try to be aware of that. I also do free writing sometimes, where I just write one stream of consciousness page in my notebook - it’s often just a brain dump of my thoughts.

Jess: That makes sense. In your coaching work, do you find that the issues you come up against - for example struggling with following a principle, or making things about yourself - are similar to what your clients are struggling with? 

Peter shepherd: For sure, which is why the idea that it's all invented is so important. So many of the hurdles that leaders and change makers have are similar. The stories they tell themselves about what’s possible, what they’re bringing to the world versus what they’re not bringing to the world, what they’re capable of versus what they’re not. Most of the coaching work I do with leaders is about the stories they tell themselves and their team. By reframing their thinking, we can unlock more of their potential. I think that’s the role of a good coach. 

Jess: That makes perfect sense. In your work as a coach, what sort of questions do you ask your clients? Do you have a go-to list? 

Peter Shepherd:  I intentionally try not to have a scripted list of questions because I think so much of coaching is unique to each person, even though their overall struggles might be universal. I don’t find it effective to just ask everyone the same thing - I like to react in the moment, and ask questions that feel relevant, based on my curiosity. Having said that, I do have some general questions that I go back to quite a bit, for example, ‘where's the tension for you right now?’. I think often, people come to a coach because they want to get unstuck or they're trying to navigate a blind spot and they don't know how to. I like to just ask directly - where are you stuck? What is the hard part of this challenge that you're through? 

Jess: If you could only give me one question to ask myself when I'm trying to make a decision, what would you pick?

Peter Shepherd: I think a question that might be useful is - ‘in 12 months time, will this decision matter?’. I think we often exaggerate the significance of our decisions. There are definitely decisions that will and possibly can impact what's going to happen in 12 months time - so it's good to get clear on what those bigger decisions are. It’s all part of the story you tell yourself. Small decisions can feel huge, but you need to evaluate that and figure out if you are over analysing. 

Jess: Thank you, that's a really good one!

Peter Shepherd: If I'm allowed to offer a second question, it would be - ‘what's the worst that can happen?’. I think that's a great question. Again, people catastrophize things, especially the decisions that we make and the impact they can have.

Jess: Yes, for sure. I was listening to your podcast, and you had a funny story about posting an Instagram grid picture that went hilariously wrong - but rather than immediately taking it down in a panic, you decided to leave it on your account. I have a weird habit of posting things and then deleting them. I post something, and then I freak out and delete it. What stopped you from freaking out and pulling the posts down? 

Peter Shepherd: So just to give context - I had an idea to post a banner image on my Instagram of my podcast co-host Jen and I. I’d seen a few companies do this thing where you post nine photos that create a grid, and it looks really cool. So I downloaded an app to do that, picked a photo of Jen and I standing next to each other, and posted it. I didn’t realise that each of the 9 disembodied grid images would be posted individually in my followers’ feeds - showing weird close ups of random body parts. I posted the grid, and didn’t double check it. Then I got in the car and drove 30 minutes to visit a friend. When I got to my friend’s, I opened Slack to check a couple of things and saw that Jen had sent me a bunch of screenshots, saying ‘do you realise what you’ve done?!’. I looked through the posts and had a mild panic attack. I was going to delete the post - it looked so stupid. I decided to check with Jen though, and she said she thought it was hilarious and told me I should leave it. ‘Rule number 6’ is relevant here - I realised I couldn’t take myself too seriously! The posts are still there today, and to lean into the mistake even further, we made a podcast episode about it [laughs]. 

Jess: That makes sense. Getting someone else’s perspective on a problem can really pull you out of the hole of thinking it’s the end of the world!

Now, as well as your one on one and group coaching, you are the head coach of altMBA, which is an online leadership and management workshop. Do you structure your workshops in a similar way to your coaching sessions? 

Peter Shepherd: Yeah I do. The cool thing about the coaching community is that the course coaches get just as much out of the workshops as the students do. I love coaching the workshops, it’s almost like being a student again, but with a different lens. As a head coach, I get to help the students and the coaches, to make sure they all get as much out of it as possible. The coaches aren’t just helping the students through the program - they’re developing themselves as people. Everything is full circle, everyone is practising what they are preaching, everyone is committed to growth. 

Jess: That makes sense. Do you categorize or group the students at all? For example, by personality or learning type? 

Peter Shepherd: Not really. We try to engage with people on an individual level. We check in with everyone regularly and see how they are going and what we can do to help. Sometimes I compare it to improv comedy - it’s not about grouping people and expecting certain things. It’s about everyone, students and coaches alike, showing up mindfully in the present and working together. 

Jess: I get that, I suppose categorization could take away some of the curiosity and collaboration? 

Peter Shepherd: Yeah, exactly. 

Jess: You’re running the altMBA course online at the moment - have you noticed many limitations from this?

Peter Shepherd:  I want to say no, but I guess everything has certain limitations. We have students and coaches from all over the world, which is awesome, but it also means that we can’t be in a physical office together. We can’t work in the same time zone and environment, have cool in-person conversations, or grab coffee together. I love the beautiful global community that we have though. A lot of businesses have struggled during Covid, because they’ve been lacking that in-person interaction. Everything has pros and cons. 

Jess: I’ve noticed that Zoom sort of eliminates the intuition that comes with regular conversations. You know how sometimes you get a gut instinct that someone is uncomfortable, or didn’t like what you just asked, that sort of thing? I find it hard to vibe exactly what’s going on with people when I talk to them online. 

Peter Shepherd: Yeah that’s true. I think a good way to make space for that awkwardness is to just ask, ‘how are you feeling right now?’ or even ‘what is it like to be you as a human being right now?’. Asking questions like this takes away the need to intuit, and allows people to just be upfront. 

Jess:  Yeah, that's beautiful. There would be fewer assumptions about how people are feeling too. 

Peter Shepherd:  Yeah, without information, we create stories. So instead of me trying to create a story in my head about how Jess is feeling right now based on my observations, what if I just directly ask her and we have a conversation about it?

Jess: Yeah, I love that. 

Peter Shepherd: I coach a lot of people from different time zones, and something I do like about the online space - especially online messaging platforms like Slack - is that they sort of encourage people to be proactive and answer their own questions because of the delayed response. There’s something called the lamp post effect, and the point of it is that sometimes people just need to speak their question, concern or thought out loud - they need to hear themselves think. Imagine walking up to a lamp post and talking to it about what’s in your head - if you spoke for long enough, you'd probably come away with some answers and solutions. Because of our asynchronous coaching, there can be a delay in our answers to questions - which gives students the chance to come up with their own solution. It’s about holding space. 

Jess: Yeah I completely get that. That kind of brings me to journaling, and the concept of holding space for yourself. What is your reflective practice not just in journaling, but in general? 

Peter Shepherd: I have a few regular practices. I mentioned the morning pages, where I write one page every morning. Often, it's a reflection on how I'm feeling or a question that I've got in mind. I would consider that a reflective process. The other thing I do after that is I use the five minute journal, which is a really cool product that I've used for five or six years that has three or four questions that you ask yourself in the morning, then a few that you ask at night. One of them is ‘what were three things that happened today?’. Another one is ‘what could I have done today to make it a better day?’. To me, that's a reflective process that you can do literally every single day.

The other way that I like to reflect is through this idea of reflection script, or reflection summary, which I have built into relationships and collaborations that I have with people like Jen, my podcast co-host. We have a rule that whenever we do a workshop or give a keynote or do something new, we have to send one another a voicemail reflective summary. We structure it around three key questions. First, ‘what are your overall thoughts?’. Then, ‘what specifically went well?’. And finally ‘what specifically would you do differently next time?’. It’s a great way to prompt reflection, and to hold yourself accountable. It doesn’t even matter if the other person doesn’t listen to the voicemail - what’s important is that you send it. 

Jess: That's brilliant. I love the idea of facilitating reflection between you and someone else. That's a neat little trick. When you’re forced to consolidate things verbally, or to write them down, it points out the gaps in your thinking.

Peter Shepherd: Yeah, reflecting on your mind or what you’re learning, or on something that has happened sort of closes the loop and finishes that chapter. If you don’t reflect, you don’t get feedback, and you don’t get closure. 

Jess: Yeah, having a little reflection as a prompt at the end of every project would make us all so much better at what we do, including faciliating collaborative coaching.

Peter Shepherd: Sometimes the changes that we need to make are minor, but if we never call them out and reflect on them, we will probably carry them over to our next project and not make the change necessary. 

Jess: Yes that's true. It isn't always these giant changes that need to be made - we can make small, consistent changes, and gradually learn and improve. Is there anything in particular that triggers you into a state of reflection, aside from your morning and night journaling?

 Peter Shepherd: Yeah, a new project does that for me, especially something collaborative, where I’m held accountable. 

Jess: How do you feel about people working alone? Do you think that it works? 

Peter Shepherd: I collaborate with people like Jen and the team at altMBA, but largely I work alone and it's hard. I think it’s important to have people around that you can lean on, whether they’re your coach, friend or collaborator. Your chosen family. You can work alone and still have a community of freelancers around you. 

Jess: It’s been particularly hard to find that community during Covid. Do you have any days where you just didn't want to get up, or days when you're in a massive slump?

Peter Shepherd: Yeah, I have definitely had unproductive days, where I’ve just sat on the couch and watched a documentary. Usually on those days, I’ll just think, ‘you know what? Today is not my day. But that’s perfectly okay.’. I give myself permission to not be productive all the time. I know that I show up when I need to. I show up for my clients, and for whatever I have scheduled. During Covid, I was less inspired to create and build new things though, because I felt like I didn’t have the creative juices left in my brain to sit and create something. I think it was because of the stagnant environment. When we lack input, our output suffers. I’m comfortable with knowing that I will show up when I need to though. 

Jess: Yes, for sure. It’s ironic, because we’ve had so much free time. Just think of all the things we could make! But when your environment changes so dramatically, you lose all these sparks for creativity that you usually have. It’s strange. 

Peter Shepherd: Yeah, it is. Even the input of just going to get a coffee and sitting in a cafe for 10 minutes can be so helpful.

Jess: Yes. A hundred percent. What did you do to try and spark creativity during this time? 

Peter Shepherd: Getting fresh air was very important. I’m lucky to live near the bay in Melbourne, so I’d go there regularly, have a swim and freshen up. That would reset me mentally and physically, and prompt me to think a bit more creatively. Getting out every day, or at least as much as I could, helped me.

Jess: I heard you on The Daily Talk Show podcast, and you spoke about having a quarter-life crisis. I’ve totally been there.

Peter Shepherd: Yeah, the good old quarter-life crisis.

Jess: I’m curious about what helped to shake you up and out of this slump, and to create change?

Peter Shepherd: My quarter-life crisis was related to me expecting other people to create opportunities for me. I was working for a startup, and then we got bought out by a big corporation. For a while, I was given all these new and exciting roles and projects. I was bouncing around, doing really cool things, and I got used to that cadence. Then, I got to a point after five or six years, where I feel like no one was giving me new opportunities. I kept wondering where my next opportunity was. It was a very unhealthy state of mind, just waiting around for someone else. At some point, I started thinking about doing an MBA, and I realised that I needed to figure out a way to meet other people, and to find a new business to collaborate with. Then I found Seth Godin's altMBA. Four weeks and $4,000, as opposed to two years and $100,000. It felt like a no brainer. What a cool experiment! The tipping point for me was realising that there was something that I could try for four weeks that might help me to get unstuck and to find new opportunities. I needed something else. I needed to start letting go of other people and start creating those opportunities myself.

Jess: That's really cool. Is that when you first started using all these tools around reframing your thinking and becoming fascinated with asking yourself questions? 

Peter Shepherd: Yes, totally. One of the things I realized while taking the altMBA was that we had coaches - as opposed to teachers - who were there to help guide us through the workshop and get the most out of it. Prior to that, I don't have much experience with coaches. Once I looked into it and got familiar with it and I was asked to come back and coach the altMBA, I realised that the work that I'd been doing was coaching - I just didn't call it that. I was one of the senior account managers in a company, and we were building culture-based recognition and incentive programs for a bunch of blue chips in Australia. My job, essentially, was to help leaders be better leaders. I’d help a lot of my clients to solve problems by asking them questions and holding space, and I didn’t know this was a useful set of school skills for a coach. Eventually, I got really curious about coaching, and decided to quit my job and start coaching on my own. 

Jess: What has being a coach taught you about yourself?

Peter Shepherd:  So many things. One of the main things is that there is an infinite number of blind spots that we have as individuals, and we are so good at finding hiding spots for ourselves. When I was coaching others, I would so often see myself in their stories, struggles and roadblocks. I’m a work in progress just like everybody else. We’re all scared, we all feel like imposters. No one has a clue what they’re doing. 

Jess: People talk about ‘wearing many hats’. I find that really relevant as a small business owner, but sometimes I find it hard to step out of one role into another, and to adjust my thinking and framing accordingly. For example, I rarely look at my business from an accountant's perspective - I always look at it from a creative’s perspective. Do you have any tricks for hopping into different framings?

Peter Shepherd: A lot of freelancers are great at doing the actual work - the work is our craft, it’s what we love - the thing we suck at is the business side, things like financing, seeking out new opportunities and collaborators, all that. I think it’s really important to carve out time each day, even if it’s just for 10 minutes, to work on the business side of things. I have a reminder in my calendar to do that each day. If I can just stick to this routine, I know my business will be so much better off. 

Jess: It’s a relief to hear that someone else needs prompting for these sides of their business! Do you spend much time on email or on social media, responding to comments and questions?

Peter Shepherd: I don't actually spend much time on email. Most of my communication happens through Slack, which takes up a pretty significant chunk to my day. I would say that I have an unhealthy habit, with how often I check Slack - but then again it’s an important aspect of my business. Sometimes I’ll spend an hour to two responding to clients on Slack, then pause to get a coffee, and I catch myself feeling like I haven’t done much that day. That I haven’t accomplished much. But in reality, responding to emails from clients is an important facet of my job - I have to make sure to remember that. 

Jess: Yeah, I fall into that pattern of thinking too! What's your approach to social media, in terms of that taking up time and what you're doing with that? 

Peter Shepherd: I have a love/hate relationship with social media. I have Facebook and Twitter but I don’t use them much. Instagram is the one that I catch myself mindlessly scrolling sometimes. I don't use it that effectively in terms of putting out content. I've been told that I should use it better. Sometimes I want to, sometimes I can't be bothered. I just have a very ad hoc, messy, sometimes anxiety-inducing relationship with Instagram.

Jess: Yeah it hooks you like that!

Peter Shepherd: It’s been described as a slot machine, because you pull it down and then you wait for a bunch of things to change, and then you do that over and over again. So I can see how I'm addicted to it. On the other hand, I do follow a bunch of people that I get a lot of value from, so there’s a weird tension there. 

Jess: I've got two phones at the moment. One phone has no apps on it, so I have my SIM card in that phone for most of the day. Then I switch the SIM into the other phone and spend a few hours dealing with emails and social media. If I used the phone with apps all the time, I’d constantly be opening them. It's like Pandora's Box, and you can’t live with it, but you can’t live without it.

Peter Shepherd: Yeah, exactly.

Jess: Okay my final question - sometimes when I’m reading or thinking, I imagine someone else other than me narrating. If you could have a little mini author sitting on your shoulder and gently narrating whatever it is that you’re doing, who would you pick?

Peter Shepherd: Good question. I recently listened to Michelle Obama narrate her own book and her narration was phenomenal. I want to say that my little author voice would be Michelle Obama!

Jess:  Nice, that’s an awesome choice. Thanks so much for chatting with me today, I’ve learned so many brilliant lessons that I’ll carry from this pandemic back into actual life again. 

Peter Shepherd: Happy to help!


We hope you learned as much as we did from this interview. We better head off now, we've got to run some thoughts by a lamp post. 

Thanks for reading!
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