 have to try to grow ourselves. Our job as leaders is to grow people but we also have to grow ourselves. If we think at Lessonly, one of your core values of putting learners first, how do you focus on your own growth as a COO? What have you focused on growing your skillset over the years?
There’s a few that come to mind. One of them for me has been, and this is the last core value I left out, we have difficult conversations. It’s part of my going back to PI, the high extra version which is me tends to drive. I’ve had to work out the kinks of myself drawing satisfaction, energy from the acceptance of someone else. Difficult conversations have always been tough for me because it’s like, “I’d rather just work around this and not address it directly. I don’t want the person to feel bad.” That type of mentality has been something. My development tactics, a lot of them have been in partnership with Max. We have the type of relationship where we can tell each other things from our perspective of, “This area you need to focus on.” That’s the one he’s challenged me on and I’ve tried to get better at.
It’s hard for a lot of CEOs to find the second in command that they have that implicit trust. You were lucky that you had that relationship before you started working together.
I don’t know what I’d do. My view on second in command stuff, that CEO job is so tough for so many reasons. I got some advice from some of the folks at OpenView. At the end of the day if you sit in a seat like mine or like yours, a lot of ways you got to dive your own ego. You got to ask yourself, “How am I useful to the CEO, to this business?” Let the rest take care of itself. That type of mentality is one where at the end of the day, the people in the business who know the business are going to recognize the impact you’re having.
My mindset coming in every day is like, “How can I help him make that job a little bit easier? What can I be thinking about day-to-day that takes some of those concerns and worries off of Max’s plate in this case?” Over time you build the respect of each other. What Max and I got into, the driving motivation I think for both of us we talk a lot about is we have two very different focus in the business. He’s product, I’m revenue. We have a bad revenue quarter, I don’t want to let you down. If we have a great revenue quarter, he’s like, “I don’t want to let you down on the product side.” We need to be serving each other as best we can. That together ultimately makes us both sharper and better. Without that, it wouldn’t be as fun, number one. Number two, I think it would be hard day-to-day if we didn’t have that level of trust.
We were talking about this at the COO Alliance event. The COO’s job is to make the CEO iconic. The CEO’s job is to play behind the scenes to almost support us so the team realizes we’re not jerks. We have to be the ones making all the tough decisions. How do you support each other? Can you give us a specific example of how you might support each other, how you make it iconic and how he supports you as being the operations guy in the business with the rest of the team?
Part of it is focused in attention. A personal passion of Max, or a lifelong goal, was to write a book. I’ve talked about the book already. That took six months. He’s writing this four hours a day. He put a lot of time into this. A tactical example of that was me having trust that, “Six months from now, this book is going to come out. It’s going to be great for the business. It’s going to be great for you personally.” You can imagine in those moments, and Max won’t mind me sharing this, he’s sitting there talking to me about, “I’m almost feeling guilty for doing that.” The book came out six months later and he’s on fire about it because it worked. It was trust that that would work. That’s me trying to do the things behind, which is run the business, keep all the revenue thing, all the stuff that keeps the business running. He doesn’t have to worry about it. He’s writing a book. It’s how to make that the iconic side.
What Max has a gift for when it comes to reciprocating that back to me in this case is just appreciation. That’s all I need. Whether that’s a text that says, “I recognize you did a great job here.” That’s what Max will do is occasionally write a note to our board and recognize something I’ve been doing. That’s all I need. Make sure you don’t lose sight of the tough work we’re doing here. I save those things because he’s great at giving specific compliments that make you feel in those moments where you’re like, “Can I do this job well?” You go back to those things and it helps you keep known that the person you’re working with day-to-day, your partner has trust in you. That’s how he reciprocates it.
Hiring The Right People: What you’re doing may seem insignificant, but the important thing is that you do it.
You have done the Predictive Index profile with each other. Did you do your love languages as well? Is one of your love languages words of affirmation?
It is. I think we both did it. We’re both the same in that.
We’ve started doing personality profiles not just with our COOs in the COO Alliance but also the CEOs and then with their teams. The love language is a bizarre one. When you do it for your team members and you understand their love languages, you understand how to either praise them, give them a hug, give them a little gift. The next one is they also came up with one reason. They call it the apology language. How do people like to be apologized to? How do they like to be either shown or told that someone feels bad about something? That’s an interesting one inside the company too. Lessonly clearly is one of these top, big emerging software companies. What do you as a company see as some of the top software platforms out there that the entrepreneurial mid-sized company should be using? What software tools do you use that are accelerating the business from recruiting, interviewing, selection, onboarding, culture training, operations?
On the sales side, I’m a bit biased here, there’s a tool called Doodly. It’s a tool for salespeople. It started as a way for salespeople to take notes and get them in Salesforce which sounds simple but is amazing. It’s evolved to updating everything you need to in Salesforce in a simpler, easier to use interface so that our sales reps don’t spend day-to-day in Salesforce and are getting accurate forecasts and stuff like that. That’s on the sales side. On the product side, there’s a company here in Indianapolis called Woven. What they do is an engineering type, recruiting platform that I’m not well-versed in. I know the team has been super pumped about the speed at which it helps them hire and get through engineering tests. As well on the product side, our product leader loves a tool called Officevibe. It’s a polls-type tool for employee sentiment. It does it in an interesting way. Those would be three that come to mind.
Are you Salesforce partner?
Yup, we are. Salesforce launched a competing offering. It’s been years in the making like most of their new products. That’s not a dig. They did launch a competing offering called Trailhead, but we’re still a Salesforce partner because sales and service reps spend a lot of their day in Salesforce.
What’s a good sales contact manager that works that you don’t spend hundreds of thousands of dollars trying to get work?
For the first four years of the business, we use one called Pipedrive that I think a lot of people know. We had this ceremony, fake funeral the day we had the CD rom. We put it in a coffin and buried it. It’s the day we had to get rid of Pipedrive because it was a sad day for us.
Why did you have to get rid of it?
Mainly reporting, honestly. If they could have given us more reporting, Salesforce, as we’ve grown in sales operations and gotten sophisticated with stuff, wasn’t cutting it.
Final question, if you’re to go back to your 21-year-old self because we would never listen to our parents or anybody else when we’re 21, but if you could listen to yourself back then, what word of advice would you give yourself now that you now know to be true as a leader? What would you have wished you’d known earlier?
One of the lessons I’ve learned, I’m a big fly fisherman. It’s coined in the fly fishing world, but it’s called river hours. River hours is this idea that I’m going to walk out on to a stream. I’m going to spend eight hours fishing. I may not catch a single fish, but if you take a mindset of those eight hours were river