How CEOs think about loyalty, side gigs, and their successors
How we think about employee loyalty, why some side projects are okay and others we don’t want to know about, and how to become the trusted one.
👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.
Sometimes finding product market fit means being able to predict what your customers want – like when we pick the topics to write about each week. And sometimes it means just asking your customers what they want – so this week, we’re answering your questions.
You submitted questions a few weeks ago, and today we’re answering five. Let us know if you like this format, and submit any new questions this post sparks.
– Greg
Your questions answered
1. Is loyalty important? Do CEOs want their employees to stay with them long term or are they more than happy for them to venture into other things?
In my experience, CEOs value relentless commitment, especially in hard or less exciting times. It’s easy to be happy and committed when the business is doing well. But when things get hard (sales slow, layoffs, clients are unreasonable, the CEO is unreasonable, etc.) most people’s commitment fades.
CEOs reward this type of relentless commitment with money (when they can), time (mentorship), opportunities, and connections – in the current business and long after you’re gone. There are three execs I’ve worked with who I know if I called, would do everything they could to help me. But to get those benefits, I had to work long hours, on hard projects, in tough times.
– Taylor
If you’ve been a great employee in one of my companies for a couple years, you’ll get a good reference and a bit of help in the future – and you shouldn’t expect much more. But if you work side-by-side with me with relentless commitment for 3+ years, particularly in hard times, you’ve earned a lot. That creates a bond that survives long after the current gig.
So I value blind loyalty less than relentless commitment and accountability to the shared outcome, over multiple years. I know it won’t last forever (I might need to lay them off, they will find better opportunities etc.) but that shared experience is not forgotten. These are the people I want to work with again and again – and if I can’t, I will at least continue to offer mentorship and connections where I can.
– Greg
2. Are you okay with employees working on side projects? What if they turn them into full time?
Honestly, my kneejerk reaction is no. I don’t think most people have enough mental energy to obsess over more than one large project or problem, and as CEO I want you to be obsessed with my (the company’s) problems. So I’d rather not know you have a side hustle.
I also think that if you have ambitions inside the company, you are going to be competing with others who do not have a side hustle – and they are pouring all their energy into their day job. So you might be at a disadvantage – assuming you actually want the promotion.
Based on my own experience with Personal Math, I do see the value in projects that develop your skills, your POV, and your profile, whether it be writing or coding. So I would encourage anyone on my team to take on those kinds of projects. But be warned – it’s not easy (though that’s another post).
However, if you are cutting out of work at 2pm to drive your food truck, don’t tell me and quit as soon as you can make a living slinging your fried chicken.
– Greg
3. Are you looking for your successor? If so, what traits are you looking out for?
I’m looking for a business partner more than a successor – someone who can drive the business forward and compliment my weaknesses. For me, that’s a COO-like leader who can prioritize and bring to life ideas that create enterprise value. Like Taylor.
I’m also always looking for people who I think have the potential to be like me (a better version, not hard) – high-output generalists, who work high-low, and can also focus 24 months out. I don’t need many of them, but these people are like the 10X engineer, so valuable to the business and to me personally:
I just enjoy working with and mentoring these people. Usually, they’re missing that ability to develop medium to long term strategy. So, if I can help them with that, they can be CEO one day.
I want to be able to walk away from the business at any moment – for personal or professional reasons. But I take my commitment to a company really seriously, so having more of these people in the business gives me a sense of personal freedom.
So it’s not an active search, but if there’s a crisis or a planned exit, I do want to know I have people who can step in and not fall on their face.
– Greg
4. How do you engender enough trust with the CEO that you are called upon to solve his/her toughest challenges?
I want to work with people who can hold a project or task in the right context of the business – e.g. the value of the project to me (why I personally want it to happen) and why it matters to the business. The faster I feel like someone grasps the context of my request, the easier I can breathe knowing they will do the right amount of work given that context.
Too often employees over invest in a project or idea that won’t matter, or fail to pursue an idea because they can’t see the second- or third-order ways it could impact the business. So I give my toughest projects to people I feel like have great context on the business and/or ask me the right questions to get that context.
– Greg
The unspoken reality of gaining the trust of the CEO is you have to make things happen that the CEO wants to happen – sometimes even if the data or evidence doesn’t clearly support that thing. It’s easy to execute the CEO’s idea when all the signs point to doing it, you agree with the idea, or there is already evidence it’s going to work. But CEOs trust people who also make progress on projects that are based on their hunches or personal experience.
Sometimes these are big things, like exploring a seemingly crazy big idea. Sometimes they’re small things, like trying a new marketing email template style they like. As someone in this position, I’m constantly making judgement calls on the places where I can bring the CEO’s crazy idea to life, vs. what I want to ignore or push back on based on data, insight, or information I have.
– Taylor
5. How can I accurately estimate the amount of time needed to deliver a project while ensuring it meets expected quality standards? For example, if I am asked to develop an onboarding program for new employees, I might complete it in one week, one month, or three months. What factors should I consider to determine the optimal timeframe that balances efficiency with quality?
I like when employees quickly (within 48 hours) give me the small, medium, and large. When I first make a request like this, I’m often not explicit (to others or myself) about the level of effort and investment I’m willing to tolerate to get the output. So when employees come back to me with small, medium, and large options that include the time they’ll spend, rough budget, and pros and cons of each, it’s easier for me to react to and point them in the right direction.
I don’t need the budget or time spent to be exact – just ranges that are directionally accurate so we can align quickly on how much investment we should make for what output. For example, here’s how you might create small, medium, and large options for your onboarding scenario.
– Greg
*Note: Large option only makes sense if we plan to revamp hiring or have a large class of new employees joining the company.
Let us know if you like this format – and submit any other questions here.
Have a great week,
Greg & Taylor