Learners vs Guides: Building Your Leadership Team
Hi! I’m Molly. I write about what it actually takes to lead inside growing, changing companies: the frameworks that help, the honest truth about what it feels like, and the messy work of shaping a career that actually fits.
Lessons is where those ideas live — both the writing and the conversations around it. (If you want to learn more about how Lessons and the community work, you can read more here.)
For more thoughts on how to build and run a strong leadership team in Some Thoughts on Leadership Teams and Lessons on Executive Recruiting.
I've spent a lot of time with founder / CEOs that are struggling with scaling their companies and their businesses. Anytime I talk to a CEO who grew past 50 employees within the last year, I say: “does everything feel like a messy shit show?” And the answer is always the same: yes. Also, “thank god you said that, I thought it was just me!” I wrote a post over here about why I think scaling past 50 employees is so hard. So, this is a post about the single most important thing you can do to make it easier, smoother and more fun to scale past 50 employees (and on to hundreds or thousands).
Here it is:
Have a strong leadership team.
Well that sounds obvious.
Nope.
Let me explain what I mean.
When I say a strong leadership team, I mean a team filled with folks who have seen this rodeo before. And to be clear, I don’t just mean having a leader at the head of each major department, I mean having a team of people around you who have seen scale far beyond your current stage. You need MOST of your leadership team to NOT be overwhelmed by your current stage OR the next stage that is coming.
I call these leaders — the ones who have scaled something before and can see around the corners — “guides” as opposed to folks who are doing it for the first time who I call “learners.”
Btw, as a CEO, you also fit in to one of those two categories — you are either a learner CEO or a guide CEO. You have either seen this rodeo before or this is the first time you have led a team of over XX employees AND managed all these different functions.
The rest of this post is written for the learner CEOs. [I promise I will try to write a post at some point for learner leaders and how to navigate all of this as well.]
The four most common mistakes (in no particular order) that I see learner CEOs make re hiring leaders is
hire “guides” that have seen one step ahead, not 5-10 steps ahead
assume they can scale with a leadership team full of learners
hire their “guides” too late
assume that they can “solve all the problems” with just one hire
[As a side bar, you’ll note that I didn’t include (5) hire the wrong leaders. That is because hiring the wrong leaders is a mistake that both experienced and inexperienced CEOs make. Hiring executives is one of the hardest things you do as a CEO and everyone makes mistakes. There are ways to become better at it (I wrote a blog post about it over here) and I’d argue it’s one of the most important skills a CEO can have (so work on getting good at it!), but regardless of how much experience you have, you are still going to occasionally hire the wrong person. The thing you HAVE to get good at is identifying, ideally as early as possible, that you hired the wrong person and having the courage to fix it (usually meaning firing the person).]
Ok so let’s walk through the four most common mistakes / patterns one by one.
Mistake 1: hire “guides” that have seen one step ahead, not 5-10 steps ahead
This really comes down to “What is the definition of a guide?”
When I say guide, I mean someone that has seen 5-10 steps ahead of where you are today, not 1-2. As an example, if you are 50 employees, you probably need a guide or two who have seen 200-500 employees. If your business is $5m, you should be looking for guides who have built businesses that were $20-50m.
