8 Lessons To Build Your Executive Team

What's up, everyone? Welcome back to another episode of The Crazy Ones. First off, I just want to say one thing. This podcast is on fire right now. The audience has grown 50% month over month, and we have heard from hundreds, literally hundreds of listeners just in the last week as I'm recording this, looking at my packed inbox. And I just want to call out a few of you who wrote into the show. Isaac Roberts, Jordan Cohen, Tasha Cherian, Alyssa McGinn, Ari Hershberg, Mackenzie Alameda, and so many more of you. I just wanted to say thank you. Keep writing in at thecrazyones@morningbrew.com. Let's keep building this movement. Let's get a lot more crazies listening to the show. But let's switch to the episode and do the damn thing. Today I am talking about senior leaders. During my time building and running Morning Brew, I had the opportunity to hire, manage, and work with a number of senior leaders. And I consider senior leaders to be anyone who is on your company's senior leadership team. Sometimes that's SVPs and EVPs, other times it's VPs. It depends on how you title people in your company. And senior leaders can make or break your company. That's why I'm talking about this episode today. They can be rocket fuel or they can be quicksand, and rarely is it anything in between. I'm going to share my biggest lessons hiring and managing senior people to increase the odds of your senior people turning into rocket fuel. Let's hop into it. What's up, everyone? I'm Alex Lieberman. Yo, this is Jesse Pujji. And this is The Crazy Ones. Lesson number 1, know the game you're playing. Some senior leaders are built to get you where you want to be 12 to 24 months from now, and that's okay. Others are built for the long haul. Either choice you make is not necessarily right or wrong. You just have to know the game you're playing and decide the tradeoffs that you are okay with as a leader. If you're hiring for the short-term executive, someone who I consider to be more of a mercenary, Optimize for experience and pattern matching, meaning them taking their previous experience and applying those lessons to their current experience. Look for someone who has done the job, operated at your scale, but ideally at a bigger scale, and someone who will be able to pattern match their way into a successful tenure of a year to 2 years. If you are hiring for the long-term exec, optimize for passion for your brand, critical thinking, open-mindedness, and a history of winning in different contexts at different jobs. Lesson number 2, focus on their words, not on their delivery. Let me explain what I mean. The more senior the employee, the more confident that they likely are in the things that they say to you. Sometimes confidence in delivery can be misconstrued as ability and understanding in what they're doing. That is why when you're interviewing a senior leader or managing them directly, you should pay super close attention to what they say and how clearly they're thinking versus how they are saying the things they're saying and how clearly they're speaking. Focus on the substance of their words more than how they are delivering their words. And this is especially true of senior marketers and senior salespeople. And that's because senior marketers or senior salespeople by nature are great storytellers, and it's a great trait for them to have. But But it also means that it can be very, very easy for you to fall into the trap of being convinced by their delivery over their actual substance. Lesson number 3, open-mindedness and humility is a must. It is very common for senior people to have egos and a view of how the world should be in their eyes. You know, society rewards strong points of view, and these people have clearly done something right in their mind to be promoted to the point of seniority. And so for some, it leads to them thinking that they know everything. But having an ego, having strong points of view that can't be changed, it breaks down very quickly when senior leaders join new companies. Every business and every role is different. And if your senior leader is not willing to change their views or learn based on a new set of information or a new context, they are going to try and pattern match your business into oblivion. Lesson number 4, senior people are multipliers or divisors. A great senior leader leapfrogs your business 1 to 2 years in the future. A bad senior leader holds back your business 1 to 2 years in the past. Why? A great leader brings knowledge, strategy, and people that would have taken you 1 to 2 years minimum to figure out as a founder. And so by hiring them, you just get to skip the mistakes and the misuse of time By having them do their thing. On the other hand, a bad leader sets the wrong strategy that you end up trusting for some period of time, because inevitably when you hire senior people, you do have to place some level of trust in them because you're not going to micromanage your entire senior leadership team. But also senior leaders inevitably hire teams under them. And if your senior leader is, let's just say, a B-minus, the odds are that they're hiring B-minuses to C-minuses, and that creates a ton of organizational debt that you have to undo. Lesson number 5, senior leaders always cost more money than you think. When you're hiring a senior employee, you're not just paying for their all-in comp, which is typically some combination of salary, bonus, and equity. You're paying for their team, which is the people that they want to hire under them, which inevitably they will want to do. You're paying for their growth plan, as in the budget that they ask you to give them in order to test out their strategy that they want to execute on. And you're paying for their playbook, meaning the software, the agencies, the consultants that they used in previous businesses and they want to use again. You have to be super explicit about what a senior leader's budget is ahead of them taking a job and holding them accountable to it, unless you're down for them to just spend way more money than you anticipated in the first place. Lesson number 6, trust is earned, not assumed. Your time spent with a senior leader should look like a series of S-curves. And here's what I mean by that. You spend lots of time with them in the beginning as you're ramping them up, as you're working on their 30, 60, 90-day plan, as you're orienting them to the nuances of your business. And then as you gain trust in them, it drops off in terms of your time spent as they take on a new challenge that's maybe outside of their circle of competence. You dedicate a bit more time to them again, to make sure they are thinking through things critically. And then what happens is it drops off again once they've kind of reearned trust in a new area of expertise. The reason you manage senior people in S-curves and not just manage them a lot in the beginning and then don't spend a lot of time with them in the future is because extrapolated trust can be a really dangerous thing with senior people. Just because you trust them in one domain of expertise where maybe they've spent the last 15 years of your career, it does not mean that you can or should trust them fully in a domain of non-expertise. In any area of non-expertise, they have to re-earn trust with you before you give it to them. Lesson 7: Make the interview process as real as possible. A senior person is a huge investment that has huge implications for your business. You don't want to be surprised by how a senior leader thinks, how they work, or where their blind spots are when you hire them. And the best way to avoid surprise is to simulate actual work as closely as possible. And so at minimum, you should be doing a working session after work one day where you're talking through a current issue in the business that the person would be handling if they were in the role. And you should be going through this with them and troubleshooting with them for at least a few hours. That's at minimum. At best, especially if it's a senior leader who's in between jobs and they have, you know, an abundance of free time, you should actually pay this person as a contractor or a consultant first to tackle the problems that you're experiencing in your business that they would be handling if they were full-time. And based on how their trial goes, you make a very informed decision of whether to bring them on full-time. The worst-case scenario here is that you pay them as a consultant, It didn't work out. And by the way, you've saved a boatload of money because you didn't make the mistake of hiring them. And finally, lesson number eight: references can actually be really helpful. And I will say, I will be the first to say, I've gone back and forth on reference checks. I've in the past said that they're not helpful at all. But here's my current stance: 95% of the time, I don't think reference checks will actually change whether or not you will hire someone. I think ultimately you will end up going with. Whatever you thought the decision was going to be before you talked to references. But I do think reference checks will give you valuable information on how to manage a senior leader once you inevitably hire them. Said differently, when you are talking to references, you should explicitly ask the following question: Where can I coach so-and-so person such that if I help them in this area, they will be unstoppable in their career and with our business? And this is a way for you to get real weaknesses out of references who have a vested interest in the potential employee's career without them feeling defensive and that you'll hold their feedback against the candidate. And so those are my 8 lessons from hiring and managing senior leaders over the last 8 years. Now, I would love to hear from you outside of this topic. What is one very timely, very significant challenge that you are currently navigating in in your career or your business. It's a challenge that is taking up a lot of mental real estate that if you could get clarity, it would be absolutely amazing. Those are the types of topics we want to talk about on upcoming episodes. So let us know at thecrazyones@morningbrew.com. I look forward to hearing from many of you, and I'll catch you all next episode.